Sailing the Caribbean for a year

Adventure 3 min read

In 2015, my husband and I purchased a sailboat in the Virgin Islands sight unseen, quit our jobs in San Francisco and spent a year sailing the Caribbean and Bahamas, spending time in nearly every island between Venezuela and Florida. The trip was the culmination of years spent dreaming and scheming and it lived up to everything we anticipated as we were planning our adventure. We sailed thousands of miles in rowdy tradewinds, spent hundreds of nights at anchor in pristine bays, started nearly every day by diving on coral reefs and landed mahi-mahi and marlin on deck.

If you’ve got similar aspirations to sail off into the sunset, keep reading. We’re going to lay out the steps that we took to go from land-locked dreamers to stepping foot on to our very own sailboat in the Caribbean.

The dream: Sailing the Caribbean

It all started here, with daydreams of crystal clear water and palm trees dancing in the warm breeze. A sailboat is an escape pod to a world in which time is measured by the height of the sun over the horizon and destinations are determined by the direction that the wind is blowing.

Simultaneously the easiest and most important step in the whole process, building paradise in our minds, is what kept us jumping through all the hoops in the two years it took us to prepare to leave.

Scrimping and saving

There’s no way around it – cruising takes money. Before we even knew when, where or how long we were going to go sailing, we started shaping our lives around the idea. That primarily meant working hard, living in a tiny studio apartment, and not trying to keep up with our peers. We socked away money as aggressively as we could and continually revised our savings goals as we learned more about what we were trying to accomplish our dream journey.


While we were subsisting on plain pasta with boxed wine and diligently saving, we were also researching the trip obsessively. Where did we want to sail? What kind of boat did we need? What kind expenses were we realistically going to have over the course of our trip? Luckil,y the internet has brought all of this information to the tips of our fingers, making it very easy to research and plan. Sailboat listing services like shows thousands of boats for sale all over the world. Discussion forums like are chock-full of practical information for novice sailers. And, let’s not forget the countless blogs and vlogs that helped bring the dream to life.

Finding the boat

We knew that we wanted to spend about a year sailing in the Caribbean. We also knew that we wanted to buy a boat already located there to avoid months smashing into wind and waves trying to get there from the east coast. Our boat budget was set (at less than $40,000) and we knew what kind of features we required for our adventure. Finally, we found a reputable broker to serve as our ears and eyes in the Virgin Islands.

Before we knew it, we had weeded out the junk boats and had a strong contender in the running, Paradox. She was a 1989 CS 36’ sloop that was on budget, in good condition and had all the equipment we needed for our trip. Our broker crawled all over her and took a hundred pictures and answered the questions we peppered him with morning, noon and night for the weeks we spent deliberating about Paradox.

Buying the boat

We were ready – Paradox was the boat. We put in an offer at 30 percent under the asking price. The seller countered, back and forth, back and forth we went before we reached an agreement at 20 percent under asking.

We hired a professional surveyor, went through another round of negotiations, signed a few pieces of paper, and that was it! We handed over a significant portion of our life savings and suddenly became the proud owners of a boat we had never even seen with our own eyes. What could go wrong with that plan?

Wrapping up land life

 With a boat waiting patiently for us in the Virgin Islands, it was time to tie up loose ends. We announced to our friends and family that yes, we really were doing this trip. We gave notice to our employers that we were leaving. Then we packed up our apartment, sold everything that we couldn’t fit in our small car and took off. We were excited. We were a bit terrified (did we mention that we still hadn’t even seen this boat?). But we were confident that in a few days the sunsets would be more than worth it.

And for the most part, they were.



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