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!

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!

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!!

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.

Creating content takes time. Time is money. If you enjoy this AD FREE blog, please support it! Become a Patron!

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!

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

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!

Become a Patron!

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.

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. 

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!