Note: Lee & Rachel Cumberland quit their jobs, sold their house and cars and moved aboard Satori, their Tayana 37. Mia and I spent nearly a month rafted up with them in Back Creek, Annapolis, as we both finished the refits to our respective boats. They've just made landfall in Marsh Harbor as part of the ARC Bahamas fleet, and are embarking on an indefinite cruise to wherever the wind may take them. They are the youngest couple in the rally fleet this year by far - in their late 20's, Lee & Rachel just got married this fall. Here they answer some common questions from friends and family back home about their plans. This is a guest post by my good friends Lee & Rachel Cumberland, re-published from their website beautifulcrazyhappiness.com.


I know I know, a list? I thought I would answer some common questions and provide some context for anyone who doesn’t know that crossing oceans in a tiny boat is in fact a thing.

1.) Are you rich? How can you afford to do this? I thought sailboats were only for rich people?

Above all I hope that through sharing our story on this site we inspire other people to go out and live their own adventure. For that reason we’re going to be very frank about the money issue and talk dollars and cents with you as the months progress.

There’s a quote I read somewhere that I’ve been repeating as of late “Any true adventure must lie on a solid foundation of financial insecurity” I feel like that pretty much sums up the current financial situation. Fortunately we’re in the home stretch of the refit and monthly living costs should be well within our budget. I hope.

So back to how we’re paying for this. Since I’ve graduated college I’ve been rehabbing and flipping houses on the side. I’ve done this on nights and weekends for the last 5 years. It was a ton of lonely, messy and frustrating work. At this point we’ve got a few rentals and that makes some passive income each month. The other key component is we have no debt. We also had the luxury of our parents paying for our college and we’re grateful for that. While our parents guide and support us emotionally, this is not a parent funded expedition. We’ve paid all the bills to get where we are.

Still think cruising is out of reach? This might change your mind. 

2.) How big is the boat? A boat that small can cross an ocean?!

Our Tayana 37 cutter is 37 ft on deck, 42ft overall including the bowsprit and 31 ft at the waterline. Shocking as it might seem, boats this size and smaller cross oceans routinely without incident. It’s much more about the preparation and decisions you make than what boat you’re sailing on.

3.) Are you crazy? What about pirates?

Probably. As for the pirate issue I’m not even sure why we get asked this. It’s like worrying about sharks, aliens or hitting the lottery. There is a pirate problem in some isolated parts of the world. We do not plan on going near these areas. Places where people give cruising boats a hard time tend to circulate quickly by word of mouth. Any additional risks can be mitigated by using the same common sense you would if you were to park your car on a city street at night.

4.) How long are you leaving for?

The basic plan is to take three years. We reserve the right to pack it in at 10 weeks or stay out 10 years.

5.) Where are you going? When will you be in a certain place? What’s you plan?

The only concrete destination so far is the northern Bahamas. The nice thing about long term traveling is you don’t need a real plan. Our only real time constraint is getting out of the Caribbean before the next hurricane season starts. The ironic part is how much planning we’ve had to do to have the luxury of not having a plan.

6.) Lee are you dragging Rachel into this?

I’m not. She’s taken to boat life like…like a fish/duck/other pretty waterfowl to water.

7.) How do you live on a boat? Is it like camping?

Its actually pretty rad. We’ve got all your modern comforts. Running water, hot showers, refrigeration, an oven, stove and a super comfortable bed. It costs nothing to anchor out and we can move the entire house as fast as we can pull up the anchor. All you tiny house hipster types should check out boats.

8.) When are you leaving?

We’re leaving Annapolis on the 1st of November and the mainland on the 8th of November. Note: Satori just made landfall in Marsh Harbor following their first successful offshore passage!

9.) Is cruising safe?

Cruising is very safe. It comes down to the decisions you make. Just like life ashore you must sleep in the proverbial bed you make. By being conservative about the way we sail the boat and the weather we choose to sail in, we will try and minimize any risks we encounter. That sounded like something I would have written for work.

10.) Where can I follow the trip?

Follow the trip from this site! We also have an instagram account we will be sharing on.

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