Puerto Rico to the British Virgin Islands by Catamaran

Splitting the trip into a land stretch and a sea stretch

This trip worked because we treated it as two distinct halves rather than one continuous itinerary. The first half was a “land” stretch through Puerto Rico and Anguilla, staying at Hilton properties in both, which gave us the reliability of a familiar hotel brand, real beds, full bathrooms, and a predictable breakfast while we adjusted into vacation mode. The second half was a “sea” stretch — a multi-day catamaran trip through the British Virgin Islands, based out of Tortola — which is a completely different kind of travel: smaller space, constant movement, and a much more physical, hands-on relationship with the weather and the water.

Doing the hotel stretch first and the boat stretch second made sense to us, since it’s easier to go from structured comfort into the looser rhythm of a boat than the other way around, and it gave us a chance to settle any jet lag before living out of a cabin.

Why Puerto Rico and Anguilla as the land stops

Puerto Rico works well as an entry point into this part of the Caribbean because it’s a US territory, which simplifies things considerably for US-based travelers — no passport stamps, no currency conversion, and a well-developed airport with strong connectivity back to the mainland. San Juan gives you a genuine city stay with historic old-town streets, beaches within the city itself, and enough restaurants and nightlife to fill a few days comfortably before the pace of the trip changes.

Anguilla is a different register entirely — a small, quiet British Overseas Territory known for a handful of genuinely excellent beaches and a slower, more low-key atmosphere than some of its more built-up Caribbean neighbors. Stopping there between Puerto Rico and the BVI stretch gave us a few days of pure beach relaxation before trading solid ground for a boat deck, and it sits close enough to the BVI region that the onward connection isn’t an ordeal.

What a BVI catamaran trip actually involves

The first decision is crewed versus bareboat. A crewed charter comes with a captain and often a cook, so you’re a passenger with input on the itinerary rather than the one navigating and provisioning — this is the lower-effort, more relaxing option and the one most people our age gravitate toward. A bareboat charter means you or someone in your party is qualified to skipper the boat yourselves, which gives you more control over the pace but is a meaningfully bigger undertaking.

A typical multi-night BVI itinerary hops between a handful of islands rather than sailing continuously — Virgin Gorda, with its granite boulder formations at the Baths, Jost Van Dyke, known for its beach bars and laid-back anchorages, and Norman Island, one of the popular spots for snorkeling, are all common stops on a several-night route out of Tortola. Days are generally a mix of sailing between anchorages, swimming and snorkeling stops, and evenings either on board or ashore at a beach bar near where you’ve moored for the night.

Packing and logistics for a hotel-to-boat trip

Packing for two very different environments in one bag takes a bit of planning. The boat stretch calls for soft-sided luggage rather than hard suitcases, since storage on a catamaran is limited and duffel-style bags simply pack away better. Pack noticeably lighter on clothing than you would for a hotel-only trip — swimwear, quick-dry layers, and a light jacket for evenings on the water cover most of it — and bring a dry bag for phones and other electronics, since spray and the occasional splash are part of the experience even on calm days. Anything you don’t need on the boat is worth leaving at the Tortola hotel or with left-luggage rather than hauling it on board.

Inter-island travel takes longer than it looks

The distances between Puerto Rico, Anguilla, and the BVI are short in absolute terms, but getting between them typically means small aircraft and ferries rather than direct commercial flights, and that combination is more schedule-dependent than mainland travel. Small planes in this region run on tighter, less frequent schedules, and ferries can be affected by weather and sea conditions in ways a bus or train wouldn’t be. Building a buffer day — or at least a generous connection window — between the hotel stretch and the boat stretch, and again on the way home, saves you from a missed onward connection turning into a genuinely stressful day.

Good to know: Puerto Rico and Anguilla both have Hilton properties, which made this an easy trip to stretch Hilton Honors points across two very different Caribbean stops before switching over to the boat portion, where points obviously don’t apply. If you’re trying to make points go further on a mixed hotel-and-charter trip like this, front-loading the points redemptions onto the hotel nights and simply budgeting the charter in cash is the straightforward way to think about it.