We did it!
After months of preparation, our live-aboard journey begins with a serendipitous nod, a slight pivot and a few tears of relief.
Good news for all you tired of reading about boat yard delays - as of last Thursday, Michael, Maisie and I are officially out of the boatyard and on our way!
September 25 will forever live in my memory as a very happy day. That morning, we got word from the boatyard that all the repairs and upgrades on Osprey had been completed, and that we were free to move aboard. To add to the good news, later that afternoon, our property manager informed us that they had secured tenants for our house. What a relief to know we’ll have some rental income! I actually let out an audible gasp and teared up when I read the email. A wave of relief washed over me.
The Plan (and the Pivot)
Our original plan was to take about a week to move onto the boat. There’s a lot involved—bringing aboard everything we’ll need for the year, provisioning with about a month’s worth of food (since we won’t have a car, staying stocked in pantry staples can be easier than finding a way to the store), and finding places to stow everything from clothes and dog food to spare parts and paddleboards.
But on Thursday, we checked the weather—as all good sailors do—and realized that Saturday was the only day in the near future with favorable winds for making progress toward our first destination: Annapolis, Maryland.
For context: it’s a three-hour drive from Deltaville, VA to Annapolis, but about a 17-hour sail. Typically, we’d split that into two days, and we’d need cooperative wind and wave conditions.
So, in true sailor fashion, we adjusted. What was supposed to be a week of moving and provisioning got crammed into a day and a half. By Friday night, we were exhausted. But in that moment of fatigue, we felt grateful for the rest and rejuvenation we’d had in the weeks leading up. I think that will be a recurring lesson on this journey—rest in the quiet moments and be ready for the hard, fast pushes of work that come.
Serendipity on the Dock
Saturday morning, we were up at dawn, getting Osprey ready for her first passage as our full-time home. I was on the foredeck, handling bow lines, when Michael called from the cockpit and pointed toward a boat entering the anchorage.
It was crewed by two sailors we’d met several years ago in one of our favorite Deltaville anchorages—the very first liveaboards we ever met in person. To see their boat glide in just as we were preparing to leave felt serendipitous. A heavenly nod, reassuring us that we were exactly where we were meant to be.
A Perfect Sail
We decided to head to Solomon’s Island, Maryland, about a 10-hour passage, and in the direction of our next major destination: Annapolis. The forecast called for a steady 12–15 knots from the east—perfect. We set our sails and didn’t have to adjust them once.
Maisie was pleased—she prefers when we’re not clambering around adjusting lines. She settled into a long cockpit snooze while Michael and I just grinned at each other, thinking: we are really doing this.
Settling In
Fast forward to today, and we’re working on projects to make the boat feel more like home:
Adding extra foam to our cockpit and salon cushions
Organizing the guest cabin (our garage/closet/attic/basement all in one)
Setting up a projector and screen so we can cheer on the Steelers and Commanders this season
Installing a nifty mesh insert under our mattress that (fingers crossed) will prevent mildew in the humidity of boat life (if you’re thinking “ew, gross!”—don’t get me started on what I found in the storage compartment under the forward cabin bed.)
The updated cushion is perfect for watching our Steelers and Commanders in comfort!
Gratitude and What’s Next
I’ll end with two closing thoughts:
We’re deeply grateful that both Category 5 Hurricane Humberto and Tropical Storm Imelda are forecast to stay out at sea. It looks like the Chesapeake Bay will be blessed with beautiful days ahead.
Once we finish our projects here in Solomon’s Island, our next stop will be Annapolis for the sailboat show. We can’t wait to connect with other cruisers and, hopefully, make new friends to share in the adventure.
😃We hope you enjoyed our first post as full time cruisers! We can’t wait to share more of this journey with you!
Jen, Michael and Maisie
I assume it is mostly Jen writing!! Good on ya! You are very entertaining and informative.
Thanks for the wonderful post! Keep sailing!