BVI and USVI Crewed Yacht Charter Itinerary Suggestions

The U.S. and British Virgin Islands are among the most popular yacht charter destinations in the world. The shorter distances between most of the islands plus the easy ability to visit a new island each day is what makes the Virgin Islands so ideal and popular. With unique beach bars like Cow Wreck Beach Bar on Anegada or the Soggy Dollar Bar on Jost Van Dyke, snorkeling venues like the Indians and Caves off Norman Island, world class dives sites like the Wreck of the Rhone off Salt Island, plus stunning beaches like those found around St. John or the must-see Baths on Virgin Gorda, the BVI and USVI offer a wide variety of charter itinerary options for families, couples or special occasions.

The Source For Our Key Itinerary Suggestions?
Having completed over 300 week long charters in the BVI and USVI from 1994 to 2006 on our own crewed yachts, we know the islands first-hand and extremely well (both above and below the water). We also know that the typical BVI and USVI itineraries, the must-see stops, plus the key activities have largely remained unchanged over time. However, and in order to stay on top of the best of the BVI and USVI for our clients, we also rely on a short list of hand-picked and trusted crews and their insight about their personal favorites as they’re out and about on our charters each season.

Port Options for Your Virgin Island Charter

St. Thomas Ports

For yachts that are willing and legally able to provide them, a round-trip itinerary with a pick-up and drop-off in St. Thomas allows for plenty of time for a stop at St. John plus the balance of the week spent out and about in the BVI. Direct flights into St. Thomas (airport code STT) make this an extremely popular choice for our clients when possible. You'll either use Yacht Haven Grande Marina, the premier marina in the Virgin Islands or Red Hook, the closest point to St. John and the BVI for your St. Thomas ports. Your St. Thomas ports will ultimately be based on the yacht of your choice along with that yachts surrounding calendar and St. Thomas port preference.

Tortola Ports

A start and end in Tortola in the BVI, takes away the opportunity to visit the laid back and lovely island of St. John, but also allows for a slightly more relaxed pace on a charter within the BVI only. In addition, a large majority of the BVI legal yachts currently require BVI ports on both ends of their charters. Clients with Tortola ports can fly into Beef Island/Tortola (airport code EIS) via a puddle jumper or charter flight from San Juan Puerto Rico (airport code SJU). Or, clients can opt to fly in and out of St. Thomas and then take either a commercial ferry, commercial or charter flight, or preferably a private water taxi to and from Tortola. As an added layer of service we are more than happy to assist our clients with any necessary charter flights as well as their private water taxi reservations. Learn more about getting to the BVI.

US Virgin Islands

St. Thomas Champagne Welcome
Carefree Clients, at noon on Day 1, St. Thomas, USVI pick-up


A bustling island and known as the #1 shopping destination in the world, visitors will discover plenty of shops, restaurants, historic downtown alleyways or beaches to explore. A St. Thomas start is ideal for those in the search of some jewelry or for getting on “island time” prior to their charter pick-up. A direct flight into St. Thomas either the day the charter starts or better yet, the day prior to the charter, is a safe bet in our opinion, extremely convenient for our clients, plus by far the most popular choice for our clients over time whether they have St. Thomas or Tortola ports for their charter.
Carefree Clients on final morning with St. John, USVI in background
Carefree Clients on final morning with St. John, USVI in background

St. John

With approximately 60% of the island protected by the National Park, St. John has remained as a pristine gem within the Caribbean. The charming town of Cruz Bay offers some excellent restaurants and interesting shopping. In fact, a visit to Mongoose Junction is one of the most popular last-minute stops for guests, with its variety of high-end shops set among lovely, stone walls. In addition, the beaches and bays along the northwest coast are some of the finest in the Virgin Islands and home to Trunk Bay, having been previously rated as one of the top 10 beaches in the world. If starting and ending in St. Thomas, you'll likely spend one and possibly two nights off St. John.

British Virgin Islands

Carefree clients jumping off the new Willy T, Norman Island, BVI
Carefree clients jumping off the new Willy T, Norman Island, BVI

Norman Island

Captains have various anchorage choices at Norman Island including the Bight, Privateer Bay, Kelly's Cove, Soldier Bay or Benures Bay. A snorkel at the Caves is a very popular activity as you discover the inspiration for Robert Louis Stevenson's "Treasure Island". More adventurous groups can then visit the "The Willy T" bar and restaurant, a floating pirate-like ship moored in the main anchorage and reachable only by dinghy. The Willy T was lost in 2017 during Hurricane Irma, but a new Willy T has once again now returned to its original spot in the Bight. Another restaurant/beach bar in the Bight, "Pirates Bight", further adds to the fun and pirate-theme of Norman Island. The Indians lie a short distance from Norman Island and are a must do for keen snorkelers in the group. This rock formation is teeming with coral and fish plus offers one of the best snorkels in the BVI with depths from 1 to 30 feet.
Our Carefree clients daily itinerary plan, with Peter Island, BVI on the agenda
Our Carefree clients daily itinerary plan, with Peter Island, BVI on the agenda

Peter Island

Several anchorages including White Bay, Little Harbour, Great Harbour and Dead Man's Bay offer Captains a nice selection along with a wonderful opportunity for guests to indulge in quiet relaxation, water sports or snorkeling and diving. Guests can check out some on-island hikes with rewarding views, enjoy a snorkel at Dead-mans Bay and therefore the opportunity to seek out some rays or turtles on a mid-day snorkel in this seagrass bottomed bay, or spend the night stern tied at Little Harbor, a popular favorite among the crews.
Carefree clients sunset view, as seen from Cooper Island, BVI
Carefree clients sunset view, as seen from Cooper Island, BVI

Cooper & Salt Island

Cooper Island is surrounded by some of the best diving and snorkeling in the area. Charter guests can enjoy the restaurant, bar, ice cream shop, some rum tasting and more at the laid-back Cooper Island Beach Club in Manchioneel Bay, the only designated anchorage on the island. This small and welcoming resort was completely remodeled in 2018 and is now better than ever. Guests can enjoy a rewarding snorkel around Cistern point or between the anchorage itself and Cistern Point, where rays, turtles and conch can typically be seen among the seagrass. Surrounding dives include the Wreck of the Rhone on nearby Salt Island, Wreck Alley, Markoe Point, plus Alice in Wonderland and the Steps off nearby Ginger Island. This tranquil anchorage is also an ideal place to simply relax aboard your yacht as you take in one of the breathtaking sunsets before dinner.

Salt Island is the resting place of the RMS Rhone, a state-of-the art steamship that went aground in an 1867 hurricane. One of the best wreck dives in the Caribbean, the Rhone was featured in the movie "The Deep" with Nick Nolte and Jacqueline Bisset. The Rhone features a shallow section which lies in 15' to 50' of water plus a deeper section with depths from 50' to 83' along with a possible penetration of the bow section based on diver's experience. Crews may do the entire Rhone in one dive, tailor the actual dive to the groups experience level, or even opt for a dusk or night dive on the Rhone, a personal favorite for Carefree's team! This island can also be used as an off the beaten path anchorage and one that is more frequently used by some of our larger yachts, those that are simply too large for the moorings at neighboring Cooper Island.
Carefree Clients at Devils Bay, The Baths, Virgin Gorda, BVI
Carefree Clients at Devils Bay, The Baths, Virgin Gorda, BVI

Virgin Gorda

A must-see on any charter is the Baths on Virgin Gorda. Huge granite boulders set among beautiful white sand beaches and crystal-clear water allow guests to hike up, over, through and around these massive boulders as they make their way along the Devil's Bay Trail from one beautiful beach to the next. Additionally, the North Sound is quite famous and popular for yachts as a protected anchorage and jumping off spot for a trip to Anegada. The North Sound is home to the Bitter End Yacht Club as well as the remodeled Saba Rock Resort, a more recent favorite among guests and crew. Virgin Gorda is also home to Little Dix Bay, known as one of the most exclusive resorts in the BVI. Oil Nut Bay is also a more recent and popular favorite with crews for a higher-end lunch ashore for interested guests. With plenty of anchorages as well as lots of things to do and see ashore, Virgin Gorda offers an abundance of land and sea options that crews can specifically tailor to the group that's aboard each week. Notable on-island restaurants include "Coco Maya", a crew favorite which fuses elegance and a white sand beach; "Hog Heaven", a great spot for drinks with an amazing view; plus, "The Restaurant at Leverick Bay", which features Micheal Beans and his pirate themed "Happy Arrr" in peak season.
Carefree Clients view of Cow Wreck Beach Bar, Anegada, BVI
Carefree Clients view of Cow Wreck Beach Bar, Anegada, BVI


Guests will discover endless sand beaches, the chance to spot pink flamingos, plus unique snorkeling on this coral island whose maximum height is 28' above sea level. An Anegada day includes an amazing sail (or possibly power depending on your yacht style choice), an extraordinary beach day, then typically a lobster dinner on the beach. That combination is what Anegada has become known for. Notable beach bars on the island include Big Bamboo and Cow Wreck Beach Bar. For that lobster dinner ashore, a current crew-favorite is undoubtedly "The Wonky Dog", situated in the main anchorage and featuring fresh lobster and a "wacky fun staff". Do bear in mind that a trip to Anegada is weather-dependent and only possible if the weather is cooperating. For divers in the group, a trip to Anegada also means a day off from diving but rewarding snorkeling instead.
Carefree Clients view of Brewer's Bay, Tortola, BVI
Carefree Clients view of Brewer's Bay, Tortola, BVI

Tortola and her nearby islands

Tortola is the largest island in the BVI, but for the most part, simply makes a lovely backdrop as you island hop your way around the smaller, out-lying islands on a typical one-week charter. Tortola can of course prove to be the starting and ending point of your charter. Or, if starting in St. Thomas, West End, Tortola is where you'll likely clear into the BVI and a typical pick-up or drop-off port for commercial ferries and private water taxis. There are however some popular islands and anchorages along Tortola's north and northeast coasts, depending on the weather at hand and your group's overall activity preferences. Guana Island is a bird sanctuary and offers some fabulous snorkeling at Monkey Point. Lee Bay on Great Caminoe is also a favorite if the weather is right and the guests are up for some privacy and a little cliff jumping. On Tortola itself, Cane Garden Bay, as mentioned in a Jimmy Buffet song, is home to a lovely beach, a handful of beach bars, and is a popular stop for crews with charter guests that want to party a bit. Or, Brewers Bay, also on Tortola's north coast, is another crew favorite for quieter groups in search of a more off the beaten path anchorage.
Carefree clients swimming back from Soggy Dollar Beach Bar, Jost Van Dyke, BVI
Carefree clients swimming back from Soggy Dollar Beach Bar, Jost Van Dyke, BVI

Jost Van Dyke

This often proves to be a fun last day and final evening aboard on a typical BVI & USVI charter. Jost Van Dyke is quite famous for her beach bars and in particular, The Soggy Dollar Bar, which offers a fabulous beach, a swim to shore resulting in "soggy dollars", and an opportunity to try a Painkiller or two, the bars renowned rum drink. A trip to the also famous "Foxy's Tamarind Bar" is a nice way to end your day to check out the local scene, visit the boutique, and see if Foxy is playing by chance. The bubbly pools and a dive at the Playground are other favorites for those that aren't necessarily up for the beach bar scene.

A now repeat client and 2 family group that we booked aboard Kelea in March,2019 said:

The booking through Carefree Charters could not have been a better experience. Lynne was beyond knowledgeable about the different boating options, which islands were better than others and how best to plan for our trip. She and her team did an amazing job to help make this once in a lifetime trip that much more memorable. This trip is a must do, we are already talking about booking it again next year, as the whole experience was that great. Thanks again, Lynne, Dan & Alli!
Aaron E., Colorado

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