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Caribbean Yacht Charters: An Insider’s Guide to Doing It Right
With a private yacht you can sail wherever you want—like this quiet bay off Virgin Gorda. Photo: WLMS Yacht Charters
The insider advice on this page is from Wendy’s Trusted Travel Expert for Yacht Charters: Mandy Walker of WLMS Charters.
Mandy knows every yacht in the Virgin Islands (where she lives for part of the year) and a vast number elsewhere in the Caribbean and the Bahamas. She can match you to the right location, vessel, and crew for your needs—whether you’re a couple on a romantic getaway, grandparents and grandkids with disparate interests, or a group of friends looking to let loose at sea. She knows which captains and crews have a long and successful history together, which chefs are vegetarian or gluten-free, and which boats have dive instructors onboard (which means you need not be scuba-certified to dive). Some of Mandy’s yachts can carry as few as two travelers, but the sweet spot for pricing is with a group of eight.
A great crew earns Ebb & Flow consistently excellent reviews. Photo: WLMS Yacht Charters
Which Boat to Charter
Best bang-for-your-buck boats
Ebb & Flow is an immaculately-cared-for, 56-foot catamaran that sleeps six guests. One cabin has a king-sized bed (rare among charters), and two others have queens; all have private bathrooms. There’s also a hydraulic swim platform, large covered flybridge, and abundant water toys, including underwater sea scooters. Captain Adam and Chef Rosemary make up Ebb & Flow’s award-winning crew. Rosie’s skills are on par with those of yachts in the $80k+ range, and yet this boat costs $25 to $27k for a six-night charter, inclusive of activities, meals, and drinks.
A spread of delicious snacks onboard Ebb & Flow. Photo: WLMS Yacht Charters
It’s the people in charge who make a charter top-notch. On a Whim is a brand-new, 46-foot catamaran managed by the most reputable company in the Virgin Islands—which usually handles far more expensive boats and holds this one to its same high standards for both finishes and service. Whereas most of their boats are in the $40-80k/week range, this one fits a family of six on a weeklong charter for $20k, all-inclusive.
Best boat for families
The owners of the Olivia Charles have small kids, so they’ve chosen a crew who loves families. This four-cabin, 58-foot catamaran has a large primary suite with a couch—great for small kids who want to sleep with their parents—plus a desk, in case you can’t fully disconnect from the office. Also included: games that you can play onboard and bring to the beach, snorkeling gear, sea scooters, and a variety of floating mats.
An array of water toys—and a large trampoline area—make the Olivia Charles a hit with kids. Photo: WLMS Yacht Charters
Best-value splurge boat
The eight-passenger, 67-foot Colibri consistently wins best yacht at the annual Charter Yacht Show. Its crew of three, who have been running charters for over eight years and are professional without being pretentious, have set the standard for what a crewed sailing charter should look like: Captain Graham keeps the yacht looking brand-new, Kristiann delivers stunning, tailored meals, while Matilda leads guests on scuba dives. They treat travelers like family while also giving them privacy and space. The catamaran has a Jacuzzi, commercial-grade espresso machine, BBQ and smoker, and two Fliteboards; the charter rate also includes three dives per certified diver.
You can soak in style—and with a view—on the deck of Colibri. Photo: WLMS Yacht Charters
Vacation like a magnate
Mandy has relationships with a handful of boats that look and feel like baby superyachts, without the six-figure charter rate. These Horizon Power Catamarans have high-end wood finishes, king beds, large primary suites, air conditioning, and top-notch crews who carefully curate each trip to whoever’s onboard.
A luxurious cabin on a Horizon yacht. Photo: WLMS Yacht Charters
What to See and Do
A beach on Saba Rock, British Virgin Islands. Photo: WLMS Yacht Charters
Cheap Thrill
Visit the conch shell graveyard off Anegada, in the British Virgin Islands. You can navigate this towering maze of shells by paddleboard or dinghy.
Bragging rights
Whether it’s a casino night, setting up a projector screen and a bevy of snacks for the Super Bowl, or keeping a box of costumes so you can dress up as the cast of Gilligan’s Island, the best crews and yachts go out of their way to surprise guests. Which boats are best at this? Mandy can tell you…
Prime Picnic Spot
Guana Island is a small spot in the BVIs that is only accessible by private boat (no ferries), and thus gets very few visitors. Your crew will drop you off on a secluded beach here with umbrellas, blankets, and a basket of goodies, and pick you up whenever you’re ready!
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Best Times to Go
You can charter a yacht somewhere in the Caribbean any month of the year. Overall, February through July and mid-November to early December are the best, but different parts of the region are ideal in different months:
November through April is best for the British Virgin Islands and Belize, which have warmer water and more protection from wind.
The Leeward islands, including St. Martin and St. Barts, see the best weather and least wind from May through July.
The Bahamas are ideal from April through August; at other times, the water can be quite cold.
The Windward Islands, including Grenada and St. Vincent and the Grenadines, are prime from June through September. Yes, this is hurricane season in the Caribbean, but these islands are far enough south to be out of the typical storm paths.
Worst Times to Go
During the height of hurricane season in September and October, many boats relocate or dock for seasonal repairs and maintenance.
Unless you’re headed to the BVIs or Belize, avoid “March Madness,” when trade winds from Africa create very rough sailing conditions in less sheltered spots.
Don't Bother
Chartering a yacht around the Leeward islands of St. Martin or St. Barts over the Christmas/New Year’s holidays. You’ll still be paying peak holiday rates but will likely experience strong “Christmas winds” that limit where you can sail and anchor. Better to opt for a more protected region of the Caribbean, such as the BVIs.
Minimum Stays
Rates are based on a seven-night trip that begins and ends at 12pm. You can always do a longer cruise, and many boats will also accept six-night bookings, or five nights at a higher nightly rate. Four-night charters are only offered for last-minute bookings or outside of popular dates.
Worth Splurging On
The latest water toys are all the rage with the younger set: eFoils, which are essentially electric surfboards that hover over the water, and SeaBobs (pictured above)—like a handheld Jet Ski that you can take underwater.
If anyone in your group has limited mobility, choose a yacht with a hydraulic swim platform, which makes getting into and out of the water much easier.
Scam Alert
There are no Ubers in the Caribbean (except on Puerto Rico). So come prepared: Taxi rates tend to be high, drivers often charge extra for luggage, and you usually need to pay in cash. Mandy has personal relationships with the most reliable drivers on each island.
Must-Have App
WhatsApp is often the only way to communicate with taxi drivers and yacht crew; U.S. phone service will be intermittent, but WhatsApp always works. All yachts also include Wi-Fi onboard.
Airport Intel
Airports in the Caribbean vary from the wonderfully efficient and modern, such as the new airport on St. Martin, to a single airstrip that can’t be used if it’s raining.
St. Thomas’ airport is not known for efficiency. Among other issues, airlines will refuse to check luggage less than 90 minutes prior to departure.
While the airport in St. Thomas is part of the U.S. Virgin Islands, U.S. citizens still need to clear Customs and Border Protection when they leave the island. A passport isn’t required, but give yourself extra time, as the line can be quite long. If you have Global Entry, you must have your physical card in order to bypass the line.
Tipping Tip
Make sure to factor in gratuities when considering your overall budget: It’s typical to tip your crew 15-20% of the charter cost. (Mandy can make arrangements so that you don’t have to carry that much cash.)
Don’t Forget to Pack
Less! On a yacht charter, travelers usually end up needing about half of what they brought. Also make sure to use soft-sided luggage, which is easier to store in a compact cabin.
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