Plan Your Perfect 8-Day BVI Crewed Charter
Eight days and seven nights is the sweet spot for a British Virgin Islands charter. It’s enough time to complete a full loop of the islands, spend a night on Anegada, linger over a Painkiller at the Soggy Dollar, and still have a slow morning swim before your last sail back to Tortola. On a crewed charter, your captain and private chef handle every detail — the route, the provisioning, the anchorages — so your only decision each day is how much you want to do.
Below you’ll find three different 8-day itineraries, each starting and finishing in Tortola. Use them as inspiration — your charter specialist will work with your captain to customize the route around your group’s pace, interests, and the conditions on the water.
Itinerary 1 — The Classic BVI Loop (approx. 90 nautical miles)
The most popular route. Hits all the iconic stops without rushing, with a night on Anegada and the full Jost Van Dyke beach-bar experience.
Day 1
Board your yacht in Tortola in the afternoon — either from Nanny Cay, Road Town, or Trellis Bay near the airport. Meet your captain and chef, settle in over a welcome drink, and make a short first sail to Norman Island. Anchor in The Bight, snorkel the famous Caves before sunset, and dine aboard.
Begin your charter week at the Nanny Cay full-service Marina, close to Road Town, featuring a Hotel, grocery store, Restaurants and Beach Bar. You can also start your charter in Road Town or wherever the bareboat base is located. You’ll leave Nanny Cay about midday or early afternoon. Take a short sail across the Sir Francis Drake Channel to the Cooper Island Beach Club that features an excellent restaurant w/bar, a little souvenir shop and a Dive shop. Anchoring is permitted outside the mooring field. Moorings are offered @ $35/night for vessels 60’ or under. Don’t forget to start your BVI snorkeling or diving experience at Cistern Point, this is highly recommended and only a short dinghy ride away. Spend the night at Cooper Island.
Day 2:
Morning snorkel at The Indians (one of the finest snorkel sites in the BVI), where a cluster of rock pinnacles teems with marine life. Sail north to Cooper Island for lunch at the beach club and a visit to the rum bar, then overnight in Manchioneel Bay.
Day 3:
Sail to Virgin Gorda and spend the morning exploring The Baths — the otherworldly labyrinth of granite boulders and tidal pools that is the BVI’s most iconic landmark. Arrive early to beat the day-trip crowds, then continue north to Leverick Bay Marina in the North Sound. Cocktails on the dock, dinner ashore.
Day 4:
A full day in the North Sound — kayaking, paddleboarding, visiting the floating bar at Saba Rock, and watching the sun go down from the terrace over rum cocktails. This is one of the most beautiful anchorages in the Caribbean; there’s no need to rush.
Day 5:
The open-water passage to Anegada — the flat coral island unlike anything else in the BVI. Rent an open-air Moke to explore the pink-sand beaches and flamingo flats. In the evening, the island’s great tradition: a beach lobster dinner at sunset, grilled fresh from the sea. Overnight on the island.
Day 6:
Day 7:
Cross to Jost Van Dyke and anchor early at White Bay to secure a good spot. Wade ashore to the legendary Soggy Dollar Bar — birthplace of the Painkiller — for the afternoon. In the evening, walk around to Great Harbour for BBQ and live music at Foxy’s.
Day 8: (half-day)
A final slow morning swim — Smuggler’s Cove or a last drift through White Bay — before your captain sails you back to Tortola for disembarkation. Brunch aboard on the way.
Notes:
- Important Note for Crewed Yacht Guests: In practice, the itinerary should always be discussed with the captain as they are customizable. He will be up-to-date on the latest developments around the islands and will also know what weather to expect and he will adjust the route accordingly.
- We have also omitted the infamous floating bar “The Willy T’s” which is currently moored at Peter island. If the Willy T experience is important to you, you can sail across the Francis Drake Channel on Day 1 and head straight to Great Bay on Peter Island where it was last seen.
- On day 4, you can skip North Sound and spend two nights on Anegada instead. We often do that simply because we LOVE Anegada.
- ITINERARY 2 - USVI Pick Up & Drop Off
From St. Thomas to the British Virgin Islands. The best option for guests flying into St. Thomas (STT) — no ferry, no extra transfer day, and your charter includes both the USVI and BVI.
The majority of international and US flights connect through St. Thomas (STT), and for many guests it’s the most convenient gateway to the Virgin Islands. Rather than taking a ferry to Tortola and losing half a travel day, this itinerary boards your crewed yacht directly in St. Thomas, sails across to the BVI where your captain handles customs clearance underway, and returns you to St. Thomas at the end of the week. You get the best of both island groups in one seamless charter — and the extra sailing time counts as part of the experience, not the transfer.
A note on St. Thomas pickups: not every charter yacht is licensed to take on passengers in the USVI, so this itinerary requires careful yacht selection. Our charter specialists confirm this before making any recommendations — it’s one of the details that can catch guests off guard if not handled correctly at booking.
Passports required for all guests. The BVI is British territory, and every passenger needs a valid passport book for customs clearance — passport cards are not accepted.
Day 1: (half-day)
Arrive at St. Thomas (STT) and transfer to your yacht at Yacht Haven Grande or American Yacht Harbor in Red Hook — both are within 10–30 minutes of the airport. Board, meet your captain and chef, and settle in over a welcome drink before setting sail east through Pillsbury Sound to Maho Bay on St. John. One of the most serene anchorages in the USVI, Maho is tucked inside the Virgin Islands National Park with calm, clear water, white sand, and almost no development ashore. It’s famous for the sea turtles that graze the seagrass beds right off the beach — snorkel before sunset and you’ll almost certainly spot one. Dinner aboard as the stars come out over the national park hillside.
Day 2:
A nice relaxing morning at Maho — an early snorkel with the turtles, paddleboards out, breakfast on deck. Then raise anchor and sail east across the Sir Francis Drake Channel toward Jost Van Dyke. Your captain handles BVI customs clearance at Great Harbour, the western port of entry, while you relax aboard — typically 30–45 minutes. Once cleared, sail around to White Bay and anchor for the afternoon. Wade ashore to the legendary Soggy Dollar Bar — birthplace of the Painkiller — and settle in for the afternoon. Evening at Foxy’s in Great Harbour for BBQ and live music.
Day 3:
Sail south through the Sir Francis Drake Channel to Norman Island. Morning snorkel at The Caves — a series of sea caves teeming with fish, lobster, and coral — then anchor in The Bight for the afternoon. Dinner aboard, or a visit to the floating Willy T bar if the group wants a livelier evening.
Day 4:
North to Virgin Gorda and the morning highlight of the whole BVI — The Baths. Arrive early to explore the granite boulder grottos and tidal pools before the day-trip crowds arrive. Continue north into the North Sound for the afternoon and overnight. Sundowners at Saba Rock, dinner ashore or aboard at anchor.
Day 5:
A full, unhurried day in the North Sound — kayaking, paddleboarding through the mangroves, visiting Prickly Pear Island, and watching the sun go down from Saba Rock’s terrace. This is one of the finest anchorages in the Caribbean; there’s no need to rush it.
Day 6:
The open-water sail to Anegada — the flat coral island that rewards the extra passage with miles of pink-sand beach, wild flamingos, and the BVI’s most famous meal: fresh spiny lobster grilled in the sand at sunset. A full day and overnight on the island, with time to rent a Moke and explore Loblolly Bay and Cow Wreck Beach.
Day 7:
Sail back west through the main island chain — a swim stop at Cooper Island or Peter Island, then position the yacht near Great Thatch Island for a last evening at anchor. Final dinner aboard as the lights of St. Thomas glow on the western horizon — a fitting close to the week.
Day 8: (half-day)
Cross back west and clear USVI customs at Cruz Bay, St. John — 30–45 minutes while you have coffee on deck. Short sail to St. Thomas and disembarkation at Yacht Haven Grande or American Yacht Harbor in Red Hook with plenty of time for afternoon flights.
- ITINERARY 2
The tour of the BVI starting in Tortola
Day 1: (half-day)
Board in Tortola, short sail to Deadman’s Bay on Peter Island — one of the most beautiful and peaceful anchorages in the chain. Dinner aboard as the bay empties out.
Day 2:
A slow morning at Peter Island, then across to Norman Island for the Caves and The Bight. Afternoon swim, evening aboard.
Day 3:
Day trip to The Indians for snorkeling, then anchor at Pelican Island or the south side of Norman for a quiet evening away from the busier anchorages.
Day 4:
Sail up through the Sir Francis Drake Channel to Virgin Gorda at an easy pace. Afternoon at The Baths, overnight at Yacht Harbour or one of the mooring fields.
Day 5:
Explore the North Sound at leisure — Saba Rock, Prickly Pear Island, a stand-up paddleboard through the mangroves. Full day in the Sound.
Day 6:
West to Cane Garden Bay, Tortola — the BVI’s most iconic beach. Swim, sunbathe, and enjoy a long lunch at Quito’s or Stanley’s Welcome Bar.
Day 7:
Final day at Jost Van Dyke — White Bay in the morning, Great Harbour and Foxy’s in the evening. A relaxed last night with no early departure tomorrow.
Day 8: (half-day)
Short sail back to Tortola for disembarkation. Coffee, brunch, and a plan for next year.
- ITINERARY 3
Jost Van Dyke First
Day 1:
Board in Tortola and sail northwest, slipping past Great Thatch Island to Great Harbour, Jost Van Dyke — the BVI’s official western port of entry. Clear customs, then dinner at Foxy’s and an early night.
Day 2:
A slow morning at White Bay — hammocks at the Soggy Dollar, lunch at Hendo’s Hideout, and an afternoon drift along the beach. Head around to Little Harbour in the late afternoon for fresh lobster dinner at Harris’ Place or Sidney’s Peace and Love.
Day 3:
Sail south to Norman Island for the Caves snorkel and an afternoon at The Bight. Willy T for sundowners if the group is up for it.
Day 4:
Morning at Peter Island — a private island with some of the BVI’s most secluded anchorages — then across to Cooper Island for the rum bar in the afternoon.
Day 5:
North to Virgin Gorda and The Baths in the morning, then up into the North Sound for the afternoon and evening. Saba Rock sunset is mandatory.
Day 6:
Full day in the North Sound, then sail across open water to Anegada for the overnight beach lobster experience.
Day 7:
Return across the bank and anchor at Marina Cay or Trellis Bay on Beef Island — a lively anchorage with beach bars, local art, and a full moon party if the calendar cooperates.
Day 8: (half-day)
Final swim and sail back to Tortola for disembarkation.
- ITINERARY 4 - St. Thomas to Fajardo
The Spanish Virgin Islands, Vieques and Culebra and the East Coast of Puerto Rico.
An 8-day crewed charter through one of the Caribbean’s best-kept secrets — no passport required, uncrowded anchorages, and some of the most pristine beaches in the region.
The Spanish Virgin Islands — Culebra and Vieques — sit just off the east coast of Puerto Rico, close enough to reach in a morning’s sail yet a world apart from the resort-lined Caribbean mainstream. Protected marine reserves, free public moorings, world-class snorkeling reefs, a bioluminescent bay that glows electric blue at night, and beaches that consistently rank among the finest in the world — all on US territory, no passport required. This is the Caribbean week most guests don’t know still exists, and one of the most rewarding crewed charter itineraries in the region.
One important logistical note: due to US maritime regulations, a foreign-built charter yacht that both picks up and drops off in Puerto Rico on the same voyage may run into Passenger Vessel Services Act (Jones Act) restrictions. The most common solution — and the itinerary most charter specialists recommend — is to structure this as a one-way voyage: St. Thomas to Fajardo, or Fajardo to St. Thomas. This makes the charter legal, adds a natural arc to the week, and since the trade winds blow east-to-northeast, the St. Thomas to Fajardo direction runs mostly downwind — a comfortable, easy sail. Your charter specialist will confirm the correct structure for your specific yacht before booking.
Day 1:
Board your yacht at Yacht Haven Grande or American Yacht Harbor in Red Hook, St. Thomas. Meet your captain and chef, settle in, and make a short first sail west to Maho Bay on St. John — one of the USVI’s most beautiful anchorages, tucked inside the Virgin Islands National Park. The sea turtle population that grazes the seagrass here makes for an unmissable evening snorkel. Dinner aboard as the trade winds settle and the stars appear over the national park hillside.
Day 2:
This is the big open-water day — and with the trades behind you, it’s a beautiful one. Sail west from St. John across the Vieques Passage to Vieques, Puerto Rico’s second-largest island and one of the most unspoiled in the Caribbean. Much of the island is a US Fish & Wildlife Refuge — former US Navy land returned to nature — giving it a wild, undeveloped character unlike almost anywhere else in the region. Anchor at Sun Bay (Sombé) on the south coast, a crescent of white sand framed by palms and virtually always uncrowded. Dinner aboard.
Day 3:
A full day on Vieques. In the morning, explore the island’s wild beaches by dinghy or rent bikes/jeeps ashore to reach Blue Beach, Secret Beach, and Green Beach — remote white-sand bays inside the refuge that can only be reached by boat or 4WD. Keep an eye out for the island’s famous wild horses, which roam freely across the beaches and hillsides. In the evening, the unmissable highlight: a bioluminescent kayak tour of Mosquito Bay — Puerto Mosquito is consistently ranked as the brightest bioluminescent bay in the world, and on a dark, moonless night the water glows an electric blue with every stroke of the paddle. Your captain arranges the kayak tour from the yacht.
Day 4:
Sail north from Vieques across the Vieques Sound to Culebra — a short, easy crossing of roughly 12 nautical miles. Culebra is the jewel of the Spanish Virgin Islands: a small, laid-back island with a wildlife refuge covering most of its land, free-roaming sea turtles in its bays, and Flamenco Beach — regularly named one of the best beaches in the world. Anchor in Ensenada Honda, the large, well-protected harbor on the south side, and spend the afternoon exploring Flamenco Beach and the colorful painted tanks left over from the US military occupation. Dinner ashore in the small town of Dewey — informal, friendly, and genuinely local.
Day 5:
The best snorkeling in the Spanish Virgin Islands — and it’s outstanding. Sail around to Carlos Rosario reef on Culebra’s northwest coast, one of the finest snorkel sites in Puerto Rico, with healthy staghorn coral, sea turtles, and abundant reef fish. Afternoon at Tamarindo Beach for a swim and a slow lunch, then around to the small uninhabited island of Culebrita — Culebra’s little sister — where a natural tidal pools called The Baths of Culebrita and the island’s historic lighthouse make for a perfect late-afternoon explore. Overnight at anchor off Culebrita, with the island entirely to yourself after the day boats leave.
Day 6:
Back to Culebra for a slower day — paddleboarding in the harbor, a walk into Dewey for breakfast at a local café, and a last swim at Flamenco or the quieter Playa Zoni on the island’s eastern tip, which faces toward St. Thomas and offers a beautiful view of the islands you’ve sailed through this week.
Day 7:
Sail west toward the Puerto Rico mainland — a lovely downwind run along the coast. Stop at Cayo Icacos — the most popular of the reef cays just off Fajardo, surrounded by clear turquoise water with excellent snorkeling along the barrier reef of the La Cordillera Nature Reserve. Also worth a stop: Palomino Island and the smaller Cayo Diablo. Arrive at Puerto del Rey Marina in Fajardo — the largest marina in the Caribbean — for a last dinner ashore at one of the waterfront restaurants.
Day 8:
Leisurely breakfast aboard, final swim off the marina or a last kayak through the mangrove lagoons nearby. Disembark at Puerto del Rey Marina — Fajardo is approximately 50 minutes from San Juan Luis Muñoz Marín International Airport (SJU) by car, making connections easy. Many guests add a night in Old San Juan for the Spanish colonial architecture, excellent restaurants, and a proper send-off after a week on the water.
Frequently Asked Questions
How many days do I need for a BVI crewed yacht charter?
Eight days and seven nights is the ideal length for a BVI charter. It gives you enough time to complete a full loop of the islands — Norman Island, The Baths at Virgin Gorda, Anegada, and Jost Van Dyke — without feeling rushed. Shorter charters of five or six days can still hit the highlights, but Anegada typically gets left for next time. Ten days or more allows you to slow the pace, linger at favorite anchorages, and explore quieter corners of the island group.
Is it better to start my BVI charter in Tortola or St. Thomas?
Both work well, and the right choice depends on your flights and priorities. Starting in Tortola gives you the widest selection of crewed yachts and the most time inside the BVI. Starting in St. Thomas is the better logistics choice for most US guests — direct flights into STT are more frequent, there’s no ferry or water taxi transfer, and the itinerary adds St. John and the USVI national park anchorages to your week. The trade-off is that not every yacht is licensed for USVI passenger pickups, so your charter specialist needs to confirm eligibility at booking.
Do I need a passport for a BVI charter?
Yes — the British Virgin Islands is British territory, and a valid passport book is required for customs clearance for all guests regardless of nationality. Passport cards are not accepted by BVI immigration. If your itinerary stays entirely within the USVI or the Spanish Virgin Islands (Puerto Rico, Culebra, Vieques), no passport is needed for US citizens.
Who handles BVI customs clearance on a crewed charter?
Your captain handles all customs and immigration clearance — for guests, it’s simply a matter of having your passport ready and waiting comfortably aboard while the paperwork is processed. BVI entry is typically cleared at Great Harbour on Jost Van Dyke, West End (Soper’s Hole) on Tortola, or Spanish Town on Virgin Gorda. Clearance usually takes 30–45 minutes. Returning to the USVI, you clear US customs at Cruz Bay on St. John.
What is the best time of year for a BVI or USVI charter?
December through April is peak season — steady trade winds, dry weather, warm water, and the most vibrant social atmosphere in the anchorages. February and March are considered the finest months. May, June, and November offer excellent shoulder-season conditions at lower rates with far fewer boats. July through October is the official hurricane season, and while summer charters are possible in the Virgin Islands, they require flexibility and careful weather monitoring. Your charter specialist will guide you on timing for your specific dates.
Can I visit both the BVI and USVI on one charter?
Yes — and many of our itineraries do exactly this. St. John sits naturally on the route between St. Thomas and the BVI, making it easy to combine a day or two in the USVI national park with the full BVI island-hopping circuit. The key logistical detail is that your yacht must be licensed for USVI passenger pickup and drop-off if you plan to board or disembark in US territory. Your captain handles both BVI entry and USVI re-entry customs clearance along the way.
What is Anegada and is it worth the sail?
Anegada is the flat coral island at the northern edge of the BVI — completely different from every other island in the group. While most BVI islands are volcanic and hilly, Anegada barely rises above sea level, ringed by a barrier reef and miles of pink-and-white sand. It’s famous for its wild flamingos, the clear, shallow water of Loblolly Bay and Cow Wreck Beach, and above all for its fresh spiny lobster grilled on the beach at sunset — one of the best meals in the Caribbean. It requires a short open-water passage beyond the protected Sir Francis Drake Channel, which your captain handles, and it’s absolutely worth including in any BVI charter of seven days or more.
What is the Soggy Dollar Bar and why is it famous?
The Soggy Dollar Bar sits on White Bay, Jost Van Dyke and is one of the most iconic beach bars in the Caribbean. Named for the guests who used to swim ashore with wet dollars to buy drinks — there’s no dock, and arrival by dinghy or swim is still part of the experience — it’s the birthplace of the original Painkiller cocktail (rum, cream of coconut, orange juice, pineapple juice, and a grating of fresh nutmeg). It’s been serving cold drinks on this stretch of white sand since the 1970s, and no BVI charter is complete without a long afternoon here.
How does the BVI customs clearance work when sailing from St. Thomas?
When crossing from the USVI into the BVI, your captain clears the yacht and all guests into British territory at a designated port of entry — typically Great Harbour on Jost Van Dyke or West End (Soper’s Hole) on Tortola. Guests remain comfortably aboard while the captain presents the crew manifest and passports to BVI customs and immigration. The process typically takes 30–45 minutes. All guests then have their passports stamped, and the yacht is free to cruise the BVI for the rest of the charter. On return to the USVI, the captain clears back into US territory at Cruz Bay, St. John — a similar process, again handled by the captain.
What are the best anchorages in the BVI for first-time charter guests?
The BVI is ideal for first-timers because its anchorages are protected, closely spaced, and well-marked. The best for a first visit are The Bight at Norman Island (calm, scenic, with the Caves snorkel just offshore), Manchioneel Bay at Cooper Island (quiet and lovely with a great beach club), The North Sound at Virgin Gorda (one of the most beautiful natural harbors in the Caribbean), White Bay at Jost Van Dyke (the Soggy Dollar experience), and Great Harbour at Jost Van Dyke (for Foxy’s and evening atmosphere). Your captain will guide you through every mooring and anchorage — first-timers are in excellent hands on a crewed charter.
Can these itineraries be customized for our group?
Absolutely — and that is exactly what a crewed charter is designed for. Every itinerary on this page is a starting point, not a fixed schedule. Your captain adjusts the route daily based on conditions, your group’s pace, and what you most want to see. If your group wants two nights on Anegada instead of one, slower mornings and fewer stops, more snorkeling and less sailing, or a different combination of islands entirely, the itinerary flexes around you. Before your charter, your captain reviews your preference sheet — covering everything from dietary needs to how adventurous you want to be — and plans the week from there. Talk to our charter specialists and we will match you with the right captain and yacht for the experience you are after.