Michael and I have spent the last few days packing up our house and getting it ready to rent while we are on the boat. Maisie (the dog) remains oblivious to what lays ahead.
Side note: if you know anyone looking to rent a 4BR house in Richmond, let’s chat.
While we await our official transition to boat life, I thought it would be fun to share a little FAQ post.
When we shared our news with friends and family, we got a lot of really great questions. Below are the 10 most common questions we received.
Where are you going?
How big is your boat? Will you sleep on it?
What will you eat?
What about the dog?
Will you work remotely?
What happens if there is no wind?
What about hurricanes?
How do you get to shore?
What about alone time? Will you get sick of one another?
What are you most looking forward to?
If you’ve been wondering about any of the above, read on to learn a bit more about our soon-to-be life on the water!
Where are you going?
Itineraries on boats are flexible (because weather) but our general plan is to hang out in the Chesapeake Bay until the end of October (see #7), then slowly head south along the Intracoastal Waterway before hopping to the Bahamas for the winter. Sometime in the spring we’ll head north again (again, see #7) and will spend the summer exploring New England and potentially further north.
The current plan is to return to the Chesapeake Bay by next October to regroup and decide what comes next.
How big is your boat? Will you sleep on it or stay in hotels or AirBnBs?
TLDR: We will live full time on the boat, which you can think of as an RV on the water.
Our boat is a 35.5ft sailboat called Osprey. Traditionally, boats are referred to in the feminine, with sailboats taking the preface of S/V (sailing vessel). From hereon out, we’ll refer to our boat as “she”, “S/V Osprey” or “Osprey”.
Think of Osprey as a floating R/V or a tiny house. She has all the comforts of home, they are just smaller. She has two “berths” (bedrooms), one “head” (bathroom), a “salon” or “saloon” (living area) and a “galley” (kitchen). If you haven’t noticed, everything gets a special name on a boat.
She has an incredible electrical system, which Michael will likely share more about later. We power our electronics with solar and by converting engine power via inverter. We can also plug her into shore power at marinas, if we want to run things that draw a large electrical load (mainly air conditioning).
We may take a few land breaks over the next year, but will largely live on Osprey. She has all we need, and to us, there is nothing more thrilling than exploring awesome destinations while bringing our home with us.
What will you eat?
TLDR: the same stuff we always do, plus hopefully some fresh-caught seafood!
Our diet and cooking habits will remain largely unchanged. Our galley has a refrigerator, freezer, stove and oven. They’re all just a bit smaller than home appliances.
While we are on the Instracoastal Waterway, we will have regular access to grocery stores, so provisioning the boat should be relatively easy (if your definition of easy is walking a mile or two to the store, loading groceries into backpacks and walking back to the boat). Accessible is likely a better description than easy…
Once in the Bahamas, fresh groceries will be pricier and more difficult to come by. That means we may rely more on pantry staples that we stock up on in Florida. We’re hoping to do some fishing along the way, so stay tuned to hear how that pans out.
What about the dog? How does she like the boat? Where does she relieve herself?
Our 65lb mixed-breed dog, Maisie is coming with us! She deserves a TON of praise because 3 years ago she wouldn’t even walk on a dock. Now she’s a champ on the boat.
Eventually we will train her to use the bathroom on an astroturf pee pad on the deck of the boat. Until we do that, we will stick close to land to bring her ashore at least twice a day.
Maisie wears a life vest while we are underway, so get ready for some pretty adorable pictures!
Will you work remotely? Or did you quit your jobs?
We are both taking a break from our full-time corporate jobs. It was really important to us to be able to give as much energy to our adventure as possible, and we’re fortunate enough to have savings to support us while we are funemployed.
What happens if there is no wind?
Osprey is equipped with a 35 horsepower engine. We use this when navigating tight spaces, when we need to move the boat in light (or no) wind conditions, or when the wind is from an unfavorable condition. We try our best to move on days when there is favorable wind, but sometimes the motor is needed.
What about hurricanes?
The Atlantic hurricane season is June 1 - November 30, with North Carolina and further south being the most impacted areas. Considering that, we will not begin heading south of Virginia until November. In the spring, we will plan to be back north before the 2026 hurricane season begins.
Tracking the weather is a critical part of living on a boat. We have multiple weather forecasting apps on our phone that we check multiple times a day while on the boat. We also have access to an expert on weather routing, who gives us and other sailboats in our area a heads up when there is the potential for severe weather, and helps us navigate based on large weather patterns. We are also part of many communities of sailors who track the weather and communicate about safe harbor areas through the east coast.
How do you get to shore?
Our 10 foot inflatable dinghy serves as our “car”. We use it to get ashore for Maisie’s breaks, exercising, shopping, recreation etc. We also use it to visit other sailboats and sailors! Additionally, we have two stand-up-paddle boards that we use to get to shore for beach visits etc. Maisie LOVEs the dinghy and the SUPs!
What about alone time? Will you get sick of one another?
Privacy is a luxury on a sailboat. This will likely be one of the more significant changes we’ll face during our adventure. We will keep you posted!
What are you most looking forward to?
From Jen: I’m most looking forward to living life at a slower pace, and with fewer obligations. I’m looking forward to the mental peace this will bring.
From Michael: I’ve spent most of my life thinking and planning years into the future, so I’m most excited about the day to day journey and living more in the present. On a boat, you can have ideas about what you might do in the future, but day to day and week to week is driven heavily by weather and immediate/tangible problems to solve such as where to stock up on groceries, how to get an engine part we need.
If you’ve made it this far, thanks for reading! Let us know in the comments what other questions you have for us.
Thank you for this overview! This is my favorite substack and I look forward to your podcast episode whenever it airs!
Great reading! Thanks for posting this. Looking forward to reading about Osprey adventures!