Oct 17, 2017

Fighting against the current

We are 3.6 miles from the pickwick lock and damn. We have both engines running (rare) and are only making 4 knots against the current. Not fun! I'm glad we are almost there!

Once through the lock we enter the Tennn-Tom waterway and I think from that point on everything will be going with the current. 

I hope we make some killer time on the ten-tom. I'm ready to be off this blasted river. We have around 450 miles to the Gulf. 

LeeAnn was at the helm for most of the day today. I have the kids baths, made lunch, etc. My biggest challenge of today was getting Hobie to wipe his own bum. 

It's very windy and cold today, which is a nice relief from the heat and humidity of the previous few days. 



Oct 16, 2017

Amazon in the rain

Last night we anchored behind Kelly island. 

It was supposed to be around 10' deep. Ended up being 25'! Luckily the bottom was clay and provided great holding. 

We stopped around 4. It gave me plenty of time to make dinner. Then we sent the boys to their room to watch a PBS show while leeann and I sat outside and enjoyed our dinner in peace. It was WONDERFUL. We talked while the sun went down. Watched an eagle land on the island next to us. It was great. Hope to do it again soon!

They boys were very restless last night. I ended up laying down with them to try to get them back asleep around 3 or 4 am. Charlie kept hitting me and trying to lay on me. By 5am I was getting extremely frustrated... then he started to gag like he was going to puke. 

I swept him up and luckily got to the bathroom in time. 

I stayed up with him the rest of the morning, getting small cat naps here and there. 

We got the boat moving around 9 and traveled 4 hours to Clifton marina where I had shipped some packages from Amazon. 

It started pouring so we hung around the marina until there was a break in the rain. 


Now we are traveling up the river to make a little more progress before stopping for the night. 

Oct 14, 2017

Goodbye Kentucky Lake

We left Kentucky Lake today. I will miss the dramatic landscape and plentiful, well protected anchorages. The landscape reminded me of the North Channel in Canada. Rocky, steep hills. It's been a nice break from the rivers. 

We're now on the Tennessee river and I'm not at all looking forward to the crappy riverside anchorages I assume we will have for the rest of the way to the Gulf of Mexico. 

We have 535 miles to the Gulf. Without taking currents into consideration, and assuming we travel an average of 30 miles a day, we have 17 days before we reach the ocean. We are traveling 40 miles today, so I'm hoping we can make it in 12 days. 

We've been traveling with a group of boats. It's fun to hang out with other people, and we've made some super great friends. But in some weird way it adds pressure and expectations. 

Everyone is rafting up, we will look rude if we don't? Do they hear our kids crying? Is everyone eating together? Will we look rude if we leave before everyone else? The group wants to travel another 10 miles, if we stop now, and then they stop, will we feel guilty for slowing them down?

The friends we've made are so nice, we want to hang out with them until it's time to put the kids to bed. By the time the kids are asleep, we are tired from a day of traveling and want to go to sleep. The next day we get up and do it all over. Leaving no time for LeeAnn and I to talk with each other and work through the emotional roller coaster of turning our lives upside down. Or to just be alone with our own thoughts. 

After a few weeks of this, we started to slump into a depression

Traveling on our own has been really nice. We've taken some really easy days and it has made everyone feel better. We can keep to our own schedule rather than the groups, and when we stop for the night we relax and recharge. 

I had also been really stressed about money, and it was making LeeAnn stressed. Then I spoke with a business acquaintance and he asked "if you could do anything for 8 hours a day, what would you do?" 

I thought about it and realized at best all I have is an hour or two for work right now. 

So I don't have time to work for clients or customers, and worrying about money isn't going to solve anything. It's just going to ruin this once in a lifetime experience I'm having.

As my buddy Jon told me: "Don't worry about money (I know easier said then done).  You'll always have the ability to make enough money.  You won't always have the ability to sail with you wife and kids to the ocean."

LeeAnn and I discussed this, and both agreed to just not worry about it. When we get to Florida we will find a nice place to dock for the winter and I'll figure it out then. 

Between traveling on our own terms and letting go of our worries about money, our onboard happiness guage has gone from empty, to half full and rising!


Sep 26, 2017

Taking A Boat Through Downtown Chicago

We raised our anchor around 8am and headed the short distance from the Play Pen to the lock.

I called the locktender several times on the designated channel. He didn't respond. So I called him on the phone. He told me to go in the lock and then he hung up on me. Had the lock been open, I would have done so, but he didn't open it until after I called him. I reviewed everything I had done and concluded he must just be an asshole. 

We went through the two-foot drop with no issues and then proceeded through downtown. 

There is no permit or any kind of registration to use the locks. They just let us in. It's a little weird. The river is very commercial, and it felt like we were in a place we weren't supposed to be. I kept thinking we were going to get caught. It was like we had wandered into the "staff only" area of a theme park.

So while it was cool to go past all the buildings in Downtown Chicago, I never really relaxed and enjoyed the moment. Before I knew it we were leaving the city behind. It all went much faster than I would have liked. 

The Illinois river system is pretty amazing. The beginning stretch of it is mainly a canal, but unlike the Erie Canal, the Illinois is still a very busy commercial shipping network. The infrastructure along the walls to load and unload barges is totally foreign and captivating. As we moved along, I continued feeling like we had stumbled into a place we weren't supposed to be. 

We made fast progress down the river and made it to Joliet. Our first impression of Joliet was not great. The docks were decent, I mean, they were free and that included the power, so it’s hard to complain (I’m not). But it’s clear that they have not been well maintained by the city. 

There was a broken beer bottle on the concrete pavers and some people who looked like they had made quite a few wrong decisions in life staggered by openly drinking. I questioned our security and looped several of our dock lines back to our boat. We've heard stories of kids untying boats in the night. 

Generally, people won't get on your boat, so looping a line back can be a good deterrent. But on the Erie canal, we met one local couple who actually locked their boat to the dock cleat with a bike lock. Floating in the Erie Canal might result in a scratch boat. Floating down the Illinois could result in being run down by a barge and killed. 

We could see a playground from where we were docked. Across the street was the “Joliet Housing Authority” It looked like a jail and my suspicions were later confirmed. I thought it was funny that they called it the "Housing Authority." At first I wondered if it was a shelter. 

I asked a few of the moms at the park if the area was safe. They gave me an unconvincing “Yeah, it’s ya know, like anywhere.”

You mean it’s like anyplace on the outskirts of Chicago? Like any place in Joliet?” I had no point of reference for her “anywhere” but she wasn’t giving anymore clues. 

We headed back to the boat for dinner, then later a long time friend who works in Chicago drove out to see us and bring me to the grocery store. The next morning his family drove out and we all had breakfast. Then we left the dock and headed down the river.


















Sep 17, 2017

Hangng out on a boat in Chicago



We arrived in Chicago in the small hours of the morning and tied up on an end dock. The next day after the staff arrived, I walked to the dock house to pay for several nights. 

There was one girl in the dock house talking on the phone when I arrived. Two other marina staff members sat outside chatting. Perhaps it was their morning break time. I stood waiting, reading a posting of marina rules. Several more people walked in Two of them walked up to the counter like I wasn’t there. I figured they were “city folk” and didn’t let it bother me, but I stepped up and made it clear the next guy wasn’t going to walk past me. 

The girl finally got off the phone and helped the other two customers. When it came to be my turn, I said: “I arrived early this morning and need to reserve a slip.”

“Do you have a reservation?” She asked.

I said “no.”

She told me “you have to make a reservation using the Dockwa App.”

I didn’t really want to download a freaking app just to pay for a dock, so I asked “there is no way to just do it here?”

“No.”

“Is it okay if I leave me boat where it is while I make the reservation?” I didn’t want to steer the boat on a busy holiday weekend while downloading an app and then using it to make a reservation. 

“I don’t know, where are you?” she asked.

“The end of G dock.”

“What slip?”

“I don’t know, the only one out of the two available.”

“Which one is that?”

I looked around for a map, she stood with an empty look in her eyes, like a robot waiting for some external input to trigger her next algorithmic response. Finally spotted and 8x10 map on the other side of the dock house. Exasperated, I walked over to it, found G dock, ran my finger down along it to the end, found the empty slip and said G-24 (or whatever it was).

She said “That’s someone’s slip. You can’t stay there.”

I’m not a violent person, but at this point I wanted to choke her. 

“okay” I said as I left.

The boys were in the stroller, hitting, kicking, fighting with each other. LeeAnn was anxious about the city, and how impossible it would be with the boys. I suggested we take a walk, find a park away from the water where the boys could run around a bit. 
I wasn’t concerned about making a hasty exit from the slip. The dock girl did nothing to help me, and I wasn’t going to feel bad if I inconvenienced her by being in someones slip when they returned. I was prepared to take my time. 

We found a park and unbuckled the boys. Hobie refused to get out of the stroller. Charlie found a stick and starting whacking it against the stroller which to his delight caused Hobie to scream and throw a fit. 

I searched for “Chicago” at Dockwa.com. Although I was reluctant to use it, I must admit, Dockwa.com was pretty sweet. It made it fairly easy to see the various places to stay and how much each one cost. I saw that staying in the Monroe mooring field was a fraction of the cost of Burnam. $38 per night verses $100 per night. I made a reservation for two nights and we left Burnam Harbor.

Muhaha! I win dock girl! Screw your stupid fancy marina!

Not that she cared. I imagined she sat behind her desk with a line of code repeating in her robot brain:

“waiting for external input….”
“waiting for external input….”
“no external input…entering sleep mode….”

We traveled a mile north, closer to downtown and picked up a mooring ball. Way better in my opinion. Our boat would face into the wind so we would catch the breeze, and rather than paying the $10/night electricity fee at the dock, we could run our generator guilt free. 

My one worry was having to dinghy to shore, but then I learned that Monroe Harbor runs a sweet tender service. They shuttle boaters back and forth using these awesome taxi boats. We loved using the tender service. It was part of the fun of going to shore. 

We spent the next few days exploring the tourist sights right near Monroe harbor. There was PLENTY to do. 

- We went to Shed Aquarium
- The super awesome kids playground across the street from the marina. Hands down the coolest playground we have ever been to. I mean, they had towers and slides that were at least two stories tall. Not to mention the “enchanted forrest”, the interactive fountains, boats, swings, and who knows what else. We definitely didn’t explore the whole playground. 
- The famous “bean” and face fountain.
- Navy Pier, where we rode the ferris wheel, carousel, then got deep dish pizza (which took a regrettable 45 minutes to cook but ended up being worth the wait). 

We didn’t go to the Field Museum which had dinosaur bones that Hobie wanted to see, or the planetarium, which sounded cool. Both of these educational field trips were within visibility and walking distance from the harbor. We also never went to the incredibly cool looking fountain on the edge of the harbor. Who knows what else we missed within easy walking distance. 
After a few days of playing tourist, we made the 10 mile jaunt down to Calument River to drop the mast at Crowly’s. Those guys were awesome. Expensive, but awesome. 

We traveled back up to Chicago the same day, but passed Monroe harbor to anchor in the free “playpen”. This anchorage was a little exposed to the north, which wouldn’t have been a problem except for the northerly cross swell entering the harbor. This is also where the yocal boaters come to… be idiots. Although it was a cold, cloudy, rainy day, there were some college kids swimming from a power boat. This was an attractive sight that didn’t bother me at all 😃

But the dudes doing the wake surfing, I could do with out them. 

Soon the sun set and the anchorage was all ours. The city light up, and we had a beautiful, peaceful night. 


We arrived in Chicago in the small hours of the morning and tied up on an end dock. The next day after the staff arrived, I walked to the dock house to pay for several nights. 

There was one girl in the dock house talking on the phone when I arrived. Two other marina staff members sat outside chatting. Perhaps it was their morning break time. I stood waiting, reading a posting of marina rules. Several more people walked in Two of them walked up to the counter like I wasn’t there. I figured they were “city folk” and didn’t let it bother me, but I stepped up and made it clear the next guy wasn’t going to walk past me. 

The girl finally got off the phone and helped the other two customers. When it came to be my turn, I said: “I arrived early this morning and need to reserve a slip.”

“Do you have a reservation?” She asked.

I said “no.”

She told me “you have to make a reservation using the Dockwa App.”

I didn’t really want to download a freaking app just to pay for a dock, so I asked “there is no way to just do it here?”

“No.”

“Is it okay if I leave me boat where it is while I make the reservation?” I didn’t want to steer the boat on a busy holiday weekend while downloading an app and then using it to make a reservation. 

“I don’t know, where are you?” she asked.

“The end of G dock.”

“What slip?”
“I don’t know, the only one out of the two available.”

“Which one is that?”

I looked around for a map, she stood with an empty look in her eyes, like a robot waiting for some external input to trigger her next algorithmic response. Finally spotted and 8x10 map on the other side of the dock house. Exasperated, I walked over to it, found G dock, ran my finger down along it to the end, found the empty slip and said G-24 (or whatever it was).

She said “That’s someone’s slip. You can’t stay there.”

I’m not a violent person, but at this point I wanted to choke her. 

“okay” I said as I left.

The boys were in the stroller, hitting, kicking, fighting with each other. LeeAnn was anxious about the city, and how impossible it would be with the boys. I suggested we take a walk, find a park away from the water where the boys could run around a bit. 

I wasn’t concerned about making a hasty exit from the slip. The dock girl did nothing to help me, and I wasn’t going to feel bad if I inconvenienced her by being in someones slip when they returned. I was prepared to take my time. 

We found a park and unbuckled the boys. Hobie refused to get out of the stroller. Charlie found a stick and starting whacking it against the stroller which to his delight caused Hobie to scream and throw a fit. 

I searched for “Chicago” at Dockwa.com. Although I was reluctant to use it, I must admit, Dockwa.com was pretty sweet. It made it fairly easy to see the various places to stay and how much each one cost. I saw that staying in the Monroe mooring field was a fraction of the cost of Burnam. $38 per night verses $100 per night. I made a reservation for two nights and we left Burnam Harbor.

Muhaha! I win dock girl! Screw your stupid fancy marina!

Not that she cared. I imagined she sat behind her desk with a line of code repeating in her robot brain:

“waiting for external input….”
“waiting for external input….”
“no external input…entering sleep mode….”

We traveled a mile north, closer to downtown and picked up a mooring ball. Way better in my opinion. Our boat would face into the wind so we would catch the breeze, and rather than paying the $10/night electricity fee at the dock, we could run our generator guilt free. 

My one worry was having to dinghy to shore, but then I learned that Monroe Harbor runs a sweet tender service. They shuttle boaters back and forth using these awesome taxi boats. We loved using the tender service. It was part of the fun of going to shore. 
We spent the next few days exploring the tourist sights right near Monroe harbor. There was PLENTY to do. 

- We went to Shed Aquarium
- The super awesome kids playground across the street from the marina. Hands down the coolest playground we have ever been to. I mean, they had towers and slides that were at least two stories tall. Not to mention the “enchanted forrest”, the interactive fountains, boats, swings, and who knows what else. We definitely didn’t explore the whole playground. 
- The famous “bean” and face fountain.
- Navy Pier, where we rode the ferris wheel, carousel, then got deep dish pizza (which took a regrettable 45 minutes to cook but ended up being worth the wait). 

We didn’t go to the Field Museum which had dinosaur bones that Hobie wanted to see, or the planetarium, which sounded cool. Both of these educational field trips were within visibility and walking distance from the harbor. We also never went to the incredibly cool looking fountain on the edge of the harbor. Who knows what else we missed within easy walking distance. 

After a few days of playing tourist, we made the 10 mile jaunt down to Calument River to drop the mast at Crowly’s. Those guys were awesome. Expensive, but awesome. 
We traveled back up to Chicago the same day, but passed Monroe harbor to anchor in the free “playpen”. This anchorage was a little exposed to the north, which wouldn’t have been a problem except for the northerly cross swell entering the harbor. This is also where the yocal boaters come to… be idiots. Although it was a cold, cloudy, rainy day, there were some college kids swimming from a power boat. This was an attractive sight that didn’t bother me at all 😃

But the dudes doing the wake surfing, I could do with out them. 

Soon the sunset and the anchorage was all ours. The city light up, and we had a beautiful, peaceful night. 
















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Sep 14, 2017

LeeAnn Says Goodbye :(

In our latest video, LeeAnn talks about leaving, sheds a few tears, gets a little upset, but don't worry, it has a happy ending.

Leaving everything behind is hard. It's scary. I think this video does a good job of showing a little part of that.

Patrons get early access. See it now at patreon.com/hobosailor for $1. The video goes FREE to the public next week!


Sep 13, 2017

Saving To Sail Away


Saving money is very responsible, and being responsible is...very boring. As in, you don’t go to concerts, movies, or even on vacations kind of boring. But, you don’t have to spend a lot of money to have fun. 

“Baby I don't need dollar bills to have fun tonight (I love cheap thrills)!” ~Sia

People think saving is boring. Or… maybe people just think I’m boring, because no one ever leaps to talk to me about money. 

But I don’t think it’s me. My sense is that people talk about how to get likes on Instagram more then they discuss financial strategies.

We have this trickery in the United States. Instead of just talking openly about money, we hide wealth and display it abstractly based on the house we live in, the car we drive, the clothes we wear. It is stupid to engage in this game. The truth is that everyone is broke. I know this because everyone goes to work.

Rich people don’t go to work. 

Or… if they are truly rich and still go to work, then they are just emotionally bankrupt. If someone is so rich that they don’t have to go to work, but go anyway because they can’t think of anything better to do… that person is a lost soul. That person should become my patron, because I can think of all sorts of ways to spend their riches. Just look at Steve Jobs. Super rich, and fucked up. 

We all portray these glamorous lifestyles on social media, but the truth is that 99% of us spend the better part of our day working for the man so we can pay off the loan we got to buy shit we couldn’t afford while trying to show off how rich we were.

It’s socially expected, an actual measure of achievement when a person can sell themselves into 30 years of corporate slavery in the form of a home mortgage.

The saying “you live, you work, you die” is just another way of saying “your childhood, your adulthood, your old age.”

Why is that normal? 

I’m sorry, but I’ll pass on “normal.” I don’t want to spend the best years of my life going to work. I don’t care how much you love your job. I had a great job. I was my own boss, I made good money, I worked with cool people and had cool customers. 

I still quit!

Not because I’m rich. Which, I’ll grant you, by many standards I am rich, but I’m no millionaire. I’m able to quit my job and sail away because of the decisions I made. Many of those decisions were financial. 

Whatever your dream is. Sailing away, touring the country in an RV, backpacking through Thailand, if your dream is not “commuting to my 40 hour per week job, 5 days a week, 50 weeks a year.” Then you need to get smart about how you spend your money!

I’m not some bullshit 21-year-old content marketer fresh out of college with 60k in debt creating some bullshit tips compiled from the internet. I’m sitting on a boat right now. Sometime next week I’ll sail 100 miles from Muskegon to Chicago. It will mark the beginning of a vacation, nay, an adventure that will be measured in years rather than weeks. I’m the real deal, the living proof that these tips and tricks actually work. 

They worked when I was 21, exploring Canada’s stunning North Channel, they worked when I was 24, poor but living free in the Exumas, they worked for me when I was 28 and managing an annual corporate budget of nearly a million dollars, and they work for me now, a 33 year old who is debt and job free. 

These tips and tricks have worked for me. 

I hope they work for you.

Purchase the e-book here: 

https://www.patreon.com/hobosailor/



Testimonials and Praise for "Saving to Sail Away":



"I make more money than Chad but he’s more successful than me. I have hopes and dreams for the future. He's already living his.

His ebook gave me insight into the mindset, habits, and, above all, sacrifices, that have allowed him to live his ideal lifestyle – sailing around the world with his beautiful family. Free from the daily grind, making memories, and experiencing the world. It's something so many people wish for, but don't achieve. 

Whether or not your ultimate lifestyle goal is quitting the rat race and sailing the world (mine isn’t), this is a realistic, practical outline of exactly what it takes to make your most ambitious goals a reality – on any size paycheck – if you want it badly enough. 

He doesn’t sugar coat it, he’s brutally honest at times, and what he recommends isn't easy to do. If it were easy, more people would be doing it. If you're considering this lifestyle, the ebook is an excellent introduction to the hard work you should expect to put it in to achieve the same results." ~ Brian Gladu





Sep 3, 2017

Moored in Chicago - Monroe Harbor

We arrived in Chicago this morning around 2:30am.

We were expecting the trip to take about 20 hours, but we had poor wind so we motorsailed. Made great time and finished in around 14 hours.

We first took a dock in Burnham harbor. Then today I went to register at the marina office. The lady told me I needed to make a reservation online before we could get a dock.

When I went to make an online reservation I noticed we could get a mooring ball closer to the city, two nights for $80 vs. $100 a night for a dock. I opted for the mooring so we have more spending money in the city.

There are a lot of weekend boaters out today. Everyone is rushing around in very large high speed boats. They are either crazy, stupid, ignorant, or all of the above. Some boats are  piled with people and I think a lot of them may be going to the "playpen" which sounds like a great party for college kids, but not so good for ... actual kids. We may anchor there in a few days. Can't beat free!

Overall, It's been a stressful few days! All the emotion of leaving home. Then an overnight passage through the middle of the widest part of Lake Michigan, entering Chicago at night, being tired today, but wanting to make the best of our first day on adventure.

Leeann is a pretty anxious personl... so when she gets stressed I get stressed about making whatever is causing her anxiety to go away. I can tell she has been trying hard to stay positive.

The kids are pretty emotional about leaving  but they don't really understand it. They are just acting tired and whiny and demanding a lot of attention. We are trying to give them all the emotional support they need during the transition. Then again, today Hobie asked if we could live in Chicago forever so maybe he is fine about leaving home.

I'm surprised how intuitive Charlie was about leaving. Yesterday he was asking to "go back" which broke my heart.

LeeAnn slept with the boys last night, and once we docked I climbed into bed with them. I always start to second guess myself late at night. I turned my life upside down for this. Sold my company. Left a high paying job. Sold our stuff. Rented out our house. Left our friends and family. I hope it all doesn't turn out to be a big mistake.

Overall, things are good and we are making the best of it, but I'm excited to get a good nights sleep tonight, and into a routine during the next few days.

At least the weather is good! It would be way worse if it were cold and rainy!

Sep 2, 2017

Sailing to Chicago from Muskegon

The boys watching Wall-E while crossing the lake to Chicago.
Passage sounds so dramatic. Like something that should be done on the ocean. But in my book, anything that requires traveling at night is a passage. It means traveling far enough that the weather could change and you will be stuck out in it.  LeeAnn and I also refer to passages as going "offshore" or "making a jump" due to the distance covered.

We take passages pretty seriously. It's not a boat ride, or what most sailors would refer to as a "day sail." We conserve energy (you never know when you're going to need it), nights on passage can be very long, and lacking in sleep. We don't drink. We don't let the kids use the rope swings or do anything that would increase the risk of them getting injured. They are already oblivious to danger, and when you are on a passage just getting to shore can take hours, not to mention getting from a marina to an emergency room. The worst case scenario is a helicopter ride from the coast guard. Something I hope to never experience.

All that being said, I think I've taken passages a little too seriously over the last few years. Granted, LeeAnn and I have had enough terrifying experiences to keep us from ever wanting to leave solid ground again. We have reason to be cautious. But I used to revel in the thrill of taking a boat to sea. I'd pretend I was in a movie, playing the part of a brave adventurer. After seven years of being submissive to customers and employees at work, this adventurous version of myself is what I want to rediscover.

This was the mindset I had as we began our 100-mile passage from Muskegon to Chicago. It would take us 14-20 hours depending on the weather. It was the most ambitious passage we've made in years. Although we've sailed over 1,000 miles on oceans, bays and the Great Lakes since 2014, all of it has been following the coast. This trip to Chicago was still "coastal." At most, we would be 35 miles from shore, but that's far enough to lose sight of land and be 7 hours from help. The route would take us diagonally through the bottom half of Lake Michigan. The widest part.

We were clear of Muskegon's breakwater by 11am. We watched the horizon slowly break apart behind us. It appeared to melt into the water. The boys had fun pretending to not be able to see land. Soon there came a time when they didn't need to pretend.
In the middle of Lake Michigan

By 6pm we were dead center in the middle of Lake with fairly calm winds. The lake was incredibly smooth, which was nice, but it also meant that the motor was on the entire time. Considering we would be dropping the mast in Chicago and motoring all the way to the gulf, I hoped we could sail to Chicago. For a while, we picked up some good wind out of the west and started making about 7knts. It looked like we would arrive in Chicago around 1am. Then the wind died and our speed dropped back to 5 knots. 

Our forecast for the night changed to winds out of the Southwest, 10-15 knots. right on our nose. It's pretty incredible. We had a prediction for winds out of the North. How can the weatherman be so completely wrong?

"North winds tonight. Wait. I mean Southwest. Definitely Southwest."

Being in the middle of the lake, it was kinda too late to turn back. At least there were no thunderstorms in the forecast.

The boys were a little cranky most of the day. Charlie kept saying "go back, go back" which was pretty heartbreaking. 

We grilled steak and some brats for dinner. Then since we were motoring and had plenty of hot water, LeeAnn and I both took showers. I love taking a hot shower while on a passage. It feels mysteriously good.

Then we figured out a watch schedule for the night. With the Southwest winds slowing our progress, I figured we would be on the water most of the night. Mike would take the first watch, then LeeAnn, and finally I would come up to bring us into Chicago.  

Around 7pm Mike spotted something ahead. We thought it was a ship on the horizon, dead ahead. It was far off so I didn’t worry about it at the time. After a little while, it hadn't moved, so I got out the binoculars. At first, I thought it was big racing sailboat with a spinnaker up. Then I noticed the two spears on top, and realized it was the Sears Tower! We were all very excited and surprised to be able to see it so far away. 

A blurry picture of the boys passed out and cuddling together.
By midnight we were 16nm Northeast of Chicago. The winds had clocked around to the Southwest at about 10 knots. Adding our 5 knots of headway made it feel like a stiff 15-knot breeze.

Small choppy waves built up. LeeAnn saw fireworks and a few passing ships on her watch.

I was eager for our cell service to pick back up. I wanted to let my mom know we were okay. She was worried about us taking a b-line across the widest part of Lake Michigan in the middle of the night. 

By 1am the moon was breaking through a patchwork of clouds. The skyline of Chicago brightly lite our way. The wind full in my face. Not warm, but not cold. The waves were building at about the same rate that we were approaching Chicago, so the weather felt balanced. Looking to pass the time quickly on my watch, I started watching episodes of "Silicon Valley". I set a timer to 10 minutes, and each time it went off I went outside to scan the horizon for freighters. 

The approach to Chicago at night was a lot easier than I expected. There weren't any navigation lights for a channel. This reduced confusion, but it was a little unnerving. I was really bummed when I couldn't find my spotlight. When coming into an unfamiliar marina a night, it's extremely handy to have a powerful spotlight. Fortunately, the moon and the city provided plenty of light to see by. 

We found a vacant end dock, tied up, and went to bed!


Chicago on the Horizon

The Moon over the skyline of Chicago



















Cut The Dock Lines And Dump The Weed!



We headed for the fuel dock right after waking up. We needed to top off our fuel, and pump out. I had filled our water tanks the night before.


More people came down to the dock to see us off than I expected. It was a little hectic working with the dock hands to get the boat taken care of while also talking with guests and keeping the kids under control.


The toughest person to say goodbye to was my Mom. When we were ready to go, people slowly made their way off the boat, but my mom lingered. I could tell she didn't want to get off the boat.

I finally walked her to the side. We had to go. She turned to get one last look at the boys, then gave me a long, tight hug. I was glad to be wearing sun glasses.

She stepped off the boat, and for a moment there was an awkward silence. Something was supposed to happen next. Then I remembered. I was supposed to take the helm.

Several people lined up to push the boat off the dock. At least 50% of them were dock hands, and I wish I would have had the sense to instruct the guests to help push us off. Especially my Dad.

I was 20 when LeeAnn and I left on our first sailing trip to Canada. My dad helped push the boat out of the slip, and when he reached the end of the dock, he shook my hand and said: "have a great summer." I felt so proud in that moment.


This time, he stayed back. Perhaps satisfied to watch from a distance, or perhaps snapping photos. I told my Uncle Troy to give the bow a good push, then for a moment, I panicked.

I'm very comfortable maneuvering the boat, but in front of friends and family there to see us off, in front of the marina staff, as we departed on a cross country boat trip, I worried that I would crash. We'd ram the dock in front of us with our bow or hit the gas dock with the stern and everyone would question my ability to take the trip.


Fortunately, it didn't happen. We had a smooth departure out of the marina. Then my dad sent me a text that they were heading to the end of the pier to take pictures and wave goodbye. So... even though there was no wind, I felt like I had to raise all the sails.



As we approached the channel, I remembered something very important I forgot to do. I had a small bag of pot on board that I meant to throw away before leaving the dock. I didn't want to risk going past the Coast Guard station with it, so perhaps more suspiciously, I went to the back of the boat and emptied the bag overboard.

A sad waste, but the coast guard is federal, and being a branch of the military, they need no "probable cause" to search your boat. It's not worth the risk. I also tossed my pipe in the water and sadly watched it sink.


I wondered how long it would be before I smoked again. I thought about the time a group of us bought weed in the Bahamas. The purchase was shady, and I worried the guy we bought it from was going to turn us in to the police for some kind of reward. I suggested we go back to the Norwegian couple's boat to smoke.

It was during a cold front with 20-knot winds uncomfortably rocking the anchorage. The weed hit me hard. So hard that I couldn't understand anything the Norwegians were saying.  For all I knew they were so high they stopped speaking English. I went outside to lay down in the cockpit. The Norwegian girl followed me.

I kept saying "I just need to lay down."

She kept talking to me..."Du må legge deg ned?"

No seriously lady, I don't have a clue what you are saying. I just need to lay down. 

"Du må legge deg ned?"

I think LeeAnn finally got her to leave me alone. Perhaps LeeAnn was so high she could now speak Norwegian: "Han har det bra, han trenger bare å legge seg ned."

After a while, LeeAnn and I stumbled into our friend's tiny inflatable dinghy for the ride back to our boat. We got lost in a universe of anchor lights, high winds, and waves splashing into the boat. We turned around several times, zig zagging through the marina laughing and probably making more of a scene than we realized.

LeeAnn said: "I see my parents!" and I snapped back from my daydream.

They were the first of a few people in the channel to see us off. A short distance later we saw Ken, who has become a good friend. And at the very end, my dad, Aunt Joni, and Uncle Troy.

Without thinking, I turned south, following the shoreline, but our deck hand, Mike, questioned what heading we should be on for Chicago. I checked my route and turned to the Southwest. A course that would steadily leave the coast a Michigan behind us.

LeeAnn and I watched our home port shrink into the distance. We wondered whether our boat would ever come back to Muskegon, and if it did, how many years it would be.








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Ready or not... here we go!


I got up this morning, checked the weather, and found a pretty good report. I went over it with LeeAnn and we decided to go for it.

First we started calling around to see who could help with the sail over to Chicago. It's a long trip through the middle portion of lower Lake Michigan. Having an extra pair of hands and eyes will make life a LOT easier.

Then we rush around, packing up last minute items, going grocery shopping, etc.

I'm exhausted. It's 12:34am on Saturday now. I just finished one last sewing project. The sewing machine isn't coming with us.

It's freaky to think that tomorrow... everything changes. I start a new life. No idea where it will take me.

I've tried very hard to stay calm and centered today. I want to make smart decisions, and anytime I felt myself getting carried away, felt like I was thinking too fast. I just stopped. Sat down. Reminded myself that nearly everything was done, and as for tomorrow all we need to do is get fuel and a pump out. Everything else can be done after we leave the dock.

I need a shower? I can take it under way. I need to secure the dinghy? I can do it underway. This is one of the reasons why we wanted help for this first big leg of the trip. So while the things we forgot to do need to get done, someone can still man the boat, help with the kids, etc.

Here is our forecast for tomorrow:

 SATURDAY
 East winds 10 to 20 kt backing to north 10 to 15
 kt...then becoming variable late in the afternoon. Slight chance
 of showers in the afternoon. Waves 2 to 4 ft.

 SATURDAY NIGHT
 Southwest winds 10 to 15 kt becoming northwest
 10 to 20 kt. Chance of showers in the evening. Waves 1 to 3 ft
 building to 2 to 4 ft.

 SUNDAY
 West winds 10 to 20 kt diminishing to 10 to 15 kt.
 Waves 2 to 4 ft.

The forecast this morning didn't call for any wind out of the south until Sunday. Saturday afternoon with variable winds isn't the best, but I'll happily take it. Saturday night with Southwest winds is a bummer. We will be headed south west and the wind will be right on our nose.

I hope the SW wind will be short lived. We could motor sail as close hauled (into the wind) as possible. Or we could change course and head more west so when the wind switched around to the NW we have a better angle to turn south toward Chicago. I suppose heading west would be better than going east.

I'll check the forecast again before we leave, then make a plan while underway!

Aug 27, 2017

Two weeks before departing on the great loop

Here is a video covering what we are up to.

Two weeks prior to departing on the inland river portion of the great loop!

http://www.patreon.com/posts/14254084

Aug 22, 2017

Thinking About Money

I'm starting to worry about money, which you can probably tell based on this being my second financially related blog post in five days. We're not in a dire situation at the moment, but I'm trying to be proactive and figure things about before the well runs dry. I started a managed wordpress hosting business called wowie.co. It has potential but still needs some work before it will generate income.

I also signed up for a service called Patreon (patreon.com/hobosailor) which helps bloggers get paid for their content. Without Patreon I'd have a hard time justifying the time I spend creating blog posts and videos. Time I could otherwise spend working on Wowie.co. Regardless of Patreon, I'd still create blogs and videos. It's something I enjoy doing. But I don't think I would make it as high of a priority.

To be clear, this post isn't about plugging my two potential sources of income. I simply wanted to be transparent about what I'm thinking and feeling right now as we are less than two weeks away from departure. I also wanted to be clear about the ways I'm hoping to make money to pay for this little adventure.

We have also rented out our house, but 100% of that money will go towards property expenses, health insurance, and our emergency fund. We have not yet started receiving rental income.

At this point we have enough cash to last 4 or 5 months based on the following budget:

Food: $150/week
Based on our transaction history, we spend about $513 a month on groceries or about $128 per week. I'm budgeting $150 because I want to be a little on the high side. Better to plan for the worst case scenario and come out ahead. I figured out past spending habits using Mint.com. A totally awesome service for budgeting that I highly recommended!

Fuel: $50/week
We have 2, 25-gallon fuel tanks. We burn about a half a gallon per hour, which means we can travel for 50 hours per tank. If we only run one engine at a time, which we usually do, then we can stretch the fuel to about 100 hours. We plan to travel about 5 hours a day, 5 days a week. This means we can go about a month before needing to refuel. I'm assuming fuel will cost around $3 per gallon or $150 to fill both tanks. The marina we are at right now is charging $2.52 per gallon, so I feel my assumptions here are on the safe side.

Fun: $100/week
This is a total guess. I don't know how much we will spend per week on sight seeing, but we've taken a number of sailing trips with no budget for fun and it sucks. It's like going to an amusement park and not being able to go on any of the rides.

Repairs and Upkeep: $25/week
I'm probably way under budget on repairs, but it's better than nothing for now.

Dockage: $50/week
We anchor most of the time, but there may instances when there isn't an anchorage isn't available (rare) or when we just need a dock for some reason. I figured it would be better to have it in the budget.

Saving: $0/week
At this point, we are not saving any money for retirement. Scary!

Total: $375/week, $1,500/month


If you enjoyed this post, you might want to check out patreon.com/hobosailor where every month I'll be posting details on our actual income and expenses once we get underway.



Aug 18, 2017

THANK YOU to our first patrons!

Shout outs to Katie, Mike, and Trey. Our newest, first, most coolest Patrons. 
We cannot thank you enough for your support!







Aug 17, 2017

Cruising Income And Expenses?

I'm toying around with the idea of posting our income, expenses, and the balance of our cruising account. Almost everyone asks how we can afford to go cruising. People often wonder how much it really costs.

So, please forgive me while I experiment with format and presentation. If there is something specific you would like to know or see, if there is a certain way you think I should present this information, please email me at Chad@hobosailor.com

You can view the July Income and Expense report here: https://www.patreon.com/posts/income-and-july-13909942

Here are some notes from the report:

Moving out of the house and getting the boat ready to go has been costly. Not in the sense that we spent a lot of money, but in the sense that I really had to focus on packing, moving, and boat work instead of income generating tasks. As a result, I've lost momentum, and lost out on money I could have earned. 

At this point, I'm starting to think about finances again, and I'd be lying if I said I wasn't worried about it. Starting our patreon account is a direct result of that worry. 

We have plenty of money at the moment, but I know we will burn through it quickly without any money coming in and I don't want us to end up in a desperate situation. 

I know it's going to cost about $2,000 to have the mast stepped (taken down) in Chicago, Shipped on a truck, then re-stepped (put back up) when we arrive in Mobile, Alabama.

We have not yet started receiving income from renting out our house. Unfortunately all of that money will have to be saved and put towards:

  • Income tax on rental income
  • Income tax on other income that I know will be taxed but didn't save for
  • House maintenance & repairs
  • Health Insurance

A Bell of a good time!

We went sailing with the Bell family earlier this week. We ended up dropping the sails in the middle of the lake so we could all go swimming. Here's a quick video and a few pictures:



In other news, we are 100% moved out of the house. It feels SO GOOD to have that monumental task completed. A renter has signed a 12-month lease, so if we back out now, we are officially homeless and will need to find somewhere else to live.

Jul 31, 2017

Shakedown Cruise with the Hackers

This weekend my friend Wayne and his three kids, Aiden, Mason, and Nash, joined my boys and me for a weekend adventure aboard Longer Days. Our plan was to head south for the Venetian festival in Saugatuck Michigan. 

I woke up at 6:30 Friday morning, (thanks, Charlie), and started cleaning and organizing the boat so the Hacker’s would have a place for their gear. They arrived at 10:30, tossed bags into rooms, and all the kids proceeded to go berserk with excitement. 

We left the dock around 12:00 with 10-15 knots of wind from the north. Mason (11 years old) helped bring in the fenders, tidy up the dock lines, and then raise the jib. I thought how awesome it would be for my son to someday be old enough to help out like Mason did. 

Jul 25, 2017

Are we living aboard yet?

LeeAnn left for Europe last week Friday, and the boys and I moved onto the boat. So I guess we are officially living aboard, but it doesn't really feel like it.

The house still has a ton of 'stuff' in it. We've been storing, selling, and giving things away for months now. I feel like we should have reached the bottom by now, but we're still digging! It never really felt like we had all that much stuff. But when you start to go through it all... it adds up. 

There are things that are easy to get rid of, the old brown couch we bought for $25 at a yard sale. There are things that are easy to keep, like old photos. 

Then there are things like... cooking spices. I can't bring them all. Half drunk bottles of alcohol. Should I dump them or throw a party?

At what point do I take our shoes off the shoe shelf and sell the shelf? When do I take the magnets off the fridge? 

I guess the answer is 'now', but it's hard because mentally I think I'm still living in the house. Even though the beds are gone.The kitchen table is gone. The decorations are gone from the walls. It's still my house, and in my head, I still live there. 

I've found the best approach to getting things done is to pick a room and clear it out. Within that room, it's helped to take everything off shelves, out of the drawers, out of the closet. Once things are spread out across the floor, no longer in their "place" it's easier to say "ok, now where does this go?"

I've spent so much time dreaming about sailing away, of leaving my house. I never appreciated it much. Now I look at it differently. I'll miss wrestling with my kids on the living room floor. Watching as they launch from the couch and knowing that if they fell, the worst they would get is a hard landing on a carpeted floor.

It's not all bad though. I love the minimalism of living on the boat. it doesn't feel very minimalist with "stuff" pouring out of lockers. but it's the most important stuff. The kid's favorite toys, their favorite books. Many I forgot we even had. Where has "if you give a mouse a cookie" been hiding all this time? We have all our favorite clothes. Our favorite cooking utensils. You get the idea. 

Tomorrow is my third day working on the house. I have the major tasks to accomplish:

1. Get everything packed up, or in the garage to be sold.
2. Organize the garage so people can "shop" through our things. 
3. Organize the storage area in the basement.

Things have been going well at the house, but I hope I can make a bigger dent tomorrow. I still have a lot of work to do on the boat, and a lot of work to get my new company off the ground!










Jul 16, 2017

Books in the bilge!

Getting the boat ready to go has really sucked. So it's a breath of fresh air that packing has been going really smooth. If not better than expected.

We've definitely had to be really picky about what we are bringing. The hardest things to go through were books and toys for the boys. The nice thing though, is we are picking out all the favorite toys, the favorite books.

Jul 12, 2017

Praying for the low point...

The last few days have totally sucked. Everything seems to be going wrong. Everything is difficult. Progress is painfully slow.

Two of the biggest hangups are getting the pressure water and fridge running. Can't really move onto the boat without those two things.

The Battle Of The fridge:

Problem: So I screwed up and left water in the refrigerator cooling line. It cracked the raw water strainer during the winter.

Solution 1: Bought a new strainer. Great. Install it while kids scream and fight... open the seacock (the valve that lets water in from the outside of the boat) and find that the old water hose has stiffened, or just fatigued from multiple strainer replacements and the hose has cracked and is now leaking.

Solution 2: Buy new hose from West Marine, bring it back to the boat to install it while kids beg to go swimming. Forgot my heat gun at home. Can't install. Take kids swimming so LeeAnn can organize the boat.

Solution 3: Bring the heat gun the next day and install the hose. Kids are watching Curious George on the iPad. Add hose clamps... they don't fit because the new hose has thicker walls.

Jul 8, 2017

Moving aboard

The boat is rocking like crazy right now. The marina we are at is exposed to the north, which is the direction the wind is blowing from. We're on the Northernmost dock. The most exposed, so we're taking the brunt of the waves. The dock isn't a breakwall like it probably should be. Just a dock so the waves go right pass it.


We've started moving our things on the boat. We had about 5 boxes and large bins in the basement packed up and ready to go. Everything found its place on the boat fairly quickly. LeeAnn and I kinda looked at each other and thought "well that was easy." We've been struggling to figure out what else we can move aboard before we officially move on.

Jul 2, 2017

Easy to dream, terrifying to do


We're less than five days away from starting our move onto the boat.

I'm full of doubts. I wish I wasn't, but I am. 

We've given away our cats.

Ready for launch!

Finally tied up all the loose ends today. Rudders have 6 coats of Interprotect barrier coat epoxy, 2 solid coats of bottom paint (I might add a third coat) and are back in the boat (thanks Ross!).

The sail drives have been painted with 5 coats of Interprotect, and 3 coats of Trilux 33. I was super freaked out about painting the sail drives. It seems like every article on sail drives shows a picture of one that has been nearly eaten away by galvanic corrosion.

Jun 12, 2017

Rudder Repair

I'm beat. Spent the day working on the boat. I dropped the rudders out of the boat to check the bearing and rudder post. I also had some cracks around the top that I wanted to repair. One of them was really bad.

The boat sits right on the ground, so the only way to drop the rudders was to dig a hole beneath them. Not a fun task. Top layer of gravel. Below that is some kind of bedrock. The best method was to chip away at rocks and then once enough particles were broken loose, scrape them away with the shovel. So really I did more scraping away than digging. 

May 29, 2017

Turn this way?


I've been going to work on the boat every day. It's been a little hard being away from LeeAnn and the boys. By the time I get home for dinner I can tell that everyone is a little on edge. Hobie craves attention and life just goes better when there are two parents around to give it to him.

So for two days we tried packing everyone up and heading to the boat together. This was not very productive, but it was a lot of fun! We packed a cooler of food, brought some games and toys for the boys. 

Charlie was only 1 last year so he probably didn't remember the boat. He isn't talking much yet, but we could clearly understand him as he walked around saying "like boat, like boat." We walked him around the boat, helping him with the three steps down into the hull where he and Hobie will sleep. 

May 22, 2017

Sailing to the Florida Keys

We've been getting a lot of questions from friends and family about what we are up to. So here's a summary, and answers to some common questions:


Where are we going?
We are moving aboard our boat and setting sail for the Florida Keys where we will spend the winter of 2017. We are tentatively heading for Stock Island, where the plan is to get a dock and hang out for the winter.



Apr 4, 2017

Carry That Weight!

LeeAnn just left for the consignment store with her second van load of stuff!



Carrying a heavy box of books up the basement stairs, I considered the weight. Wondered about the mental weight of these books. How heavy do they weigh on my sub-conscious? And how good will it feel when they are gone? One less thing to take care of. One less worry.