The Complete Guide to Chartering a Catamaran in the US Virgin Islands

If you've decided a Caribbean catamaran charter is on the table, this is the guide I wish every guest had before our first planning call. We'll walk through the decisions that actually shape the trip — crewed vs. bareboat, day vs. term, when to go, what it costs, how to book, what's included, and the questions you'll wish you'd asked. By the end, you'll be able to send a single, well-formed inquiry that gets a real answer back.

Decision 1: crewed vs. bareboat

Bareboat means you skipper the boat yourself. You handle the navigation, the anchoring, the cooking, the cleaning, and the weather calls. It costs less on paper. It also requires real credentials (most owners require ASA 104 or equivalent), a sailing résumé, and a willingness to spend a meaningful chunk of your vacation on logistics. Crewed means the boat comes with a captain and chef. You arrive with a duffel, the captain plans around the weather, the chef plans around your preferences, and you do the part of the vacation that's actually the vacation. For almost everyone we talk to, crewed is the right answer.

Decision 2: day charter vs. term charter

A day charter is six to eight hours on the water with two or three stops — perfect if you're already staying in a villa and want a single great day. A term charter is four to seven nights aboard, with the boat as your home, and is the format that turns a Caribbean trip into the trip you'll talk about for years. The simplest test: if the boat itself is the vacation, book term. If the boat is one good day inside a land-based trip, book a day charter.

Decision 3: when to go

Peak season (mid-December to mid-April) has the most reliable weather, the lowest swell, the steadiest trades, and the highest demand. May–June and November–early December are the shoulder seasons — usually settled weather, meaningfully smaller crowds, better availability, and lower rates. July is busy with family travel. August through October is hurricane season and most of the charter fleet is hauled out. Inside the peak window, the very busiest weeks are Christmas, New Year, Presidents' Week, and spring break — those book first and run highest.

Decision 4: how long

Three nights is the practical minimum to feel like you've actually been on the water — anything shorter and the bookend logistics eat the trip. Four to five nights is the sweet spot for couples. Six to seven is the right answer for a celebration trip, a honeymoon, or a group that wants to see the BVI as well as the USVI. Beyond seven, most charters circle back through the best anchorages — possible, but not always necessary.

What it costs

Day charters in the USVI run roughly $1,500–$3,500 for a private full-day boat, depending on size and crew. Crewed term charters in the USVI typically start around $18,000 per week and run upward of $35,000+, all-inclusive of crew, food, drink, snorkel and water-sports gear, fuel, and the planning. The range reflects boat size, season, and crew. The price feels like a lot until you start subtracting what it replaces: lodging for six, six dinners out, six lunches, snorkel rentals, day charters, paddleboards, beach club fees. By the end of that math, the comparison usually narrows considerably.

What's included — and what isn't

Included on a typical crewed term charter: the yacht, captain and chef, all meals prepared onboard, a stocked bar built around your preferences, snorkel gear, paddleboards and floats, linens and towels, fuel within the standard sailing area, and the day-to-day planning. Not typically included: ashore restaurant meals (a meal at the Soggy Dollar, for example), mooring fees in some parks, BVI customs fees if you cross, scuba diving, and the end-of-week gratuity for the crew. Gratuity is customary at 15–20% of the base charter rate.

How to choose a boat (and a crew)

Three questions to ask any boat you're considering: How many guests does it actually sleep comfortably (not the brochure number)? Is it owner-operated or part of a fleet? And what's the crew résumé — how many seasons, how many charters, and what's the chef's background? The boat matters less than the crew. A great crew on a fine boat outperforms a great boat with a rotating crew, every time. Owner-operated charters (Stella Blue is one) tend to land at the top of this list because the people who care most are the ones aboard.

The booking process, start to finish

Step 1: send a short inquiry with your dates, group size, and any preferences. Step 2: we come back with availability, a sample itinerary, and exact pricing. Step 3: a planning call to walk through it — sailing experience, dietary needs, celebrations, ashore time. Step 4: a deposit (typically 50%) holds the boat; the balance is due before the trip. Step 5: a preference sheet a few weeks out — food, drink, music, dietary needs. Step 6: you arrive at the dock and the rest happens.

Questions you'll wish you'd asked

Is the boat owner-operated? How long has the chef been aboard? Are dietary needs really not a problem, or politely a problem? What happens if the weather changes — do we lose the day or shift the itinerary? Is the crossing to the BVI included or extra? Is gratuity expected and what's customary? What's the cancellation policy? Ask all of them. Any honest charter will answer all of them in plain English.

The one-line summary

Book crewed, book term if the boat is the vacation, book three to six months out for shoulder season and six to twelve months out for peak, choose owner-operated when you can, and send a single inquiry with your dates and group size. The rest is a conversation. We'll have it with you when you're ready.