Sailing in Paradise: Planning Our First Trip to the British Virgin Islands

Since we began seriously considering sailing as a lifestyle, the British Virgin Islands have occupied a near-mythical place in our dreams. And now, this fall, a confluence of events has enabled us to plan our first trip to the BVI. (The “I” in “BVI” stands for “IslandS” and is plural; making “BVIs” redundant–as internet trolls love to point out!)

On the one hand, the BVI is a proxy for “stunning tropical islands.” We watch content from true adventurers who are driven by extreme locales–Cape Horn or the Arctic, for example. That’s not us. In my mind, the sailing lifestyle is synonymous with air temps of 90 and water temps of 80. Beverages containing–and served in–coconuts. Lime and pineapple comprise two of the four food groups. You get the idea. The BVI are certainly that….

But for sailors, the BVI represents something more. It’s not just the beauty and general pleasant-ness of the destination…it’s that the Islands are organized geographically almost perfectly for a week or two of island-hopping sailing. The multiple small islands, short distances, and extremely predictable trade winds really makes it a great place for a sailing vacation. And because of that, there’s an enormous sailboat charter industry and infrastructure.

Thus, when the planets aligned for us to plan a trip this year, we eagerly jumped in. We have a set of defined objectives for this trip: we want to host a trip like this for our entire family some day, but didn’t want that trip to be our first. So this serves as a bit of a recon. Moreover, catamarans are the most popular—and comfortable—boats for charter, and we’ve never sailed a cat. By arranging a day with an expert captain, we will get the hang of catamaran sailing along with a vacation.

We had some constraints: early October was the sweet spot for us. That’s not the busiest season; December through April tends to be more popular. Some of that is school/calendar driven, but we realized that October brings some risk. It’s the tail end of hurricane season, so there’s a chance we could be impacted. Many restaurants and attractions are closed in September, and some might not yet have opened for the season when we go. On the other hand, crowds are likely to be light, which is a huge plus for us.

We found a company (Dream Yacht Charters), and a boat (Fountain Pajot 40 Lucia), on a date (October 5) and at a price we could live with—so we booked it!

Obviously, we also have to get there. Getting to the BVI is challenging. Ordinarily, the advice is to fly to San Juan, Puerto Rico and then a flight on to Tortola (the largest island in the BVI chain). You can either book a roundtrip to SJU and then separately a hop to EIS (airport code for Tortola), or some airlines will codeshare you through. In either case the flight from SJU takes about a half hour total and is on a small plane with about 8 seats. An alternative is to fly to St. Thomas, US Virgin Islands, and then take one of several fast ferries to Tortola.

The other option, and the one we chose, is a relatively new flight on American Airlines from Miami direct to EIS. We will leave from Chicago, layover in MIA for an hour or so, then connect on over.

In a subsequent post I’ll share how we’ve approached planning for our trip—and how I’ve balanced my instinct (to plan to the nth level of detail) with the realities of sailing (you are literally going with the wind and have to be flexible)!

~ Kent

Anyone else a fan of pineapple?