Trade winds push steady across the Sir Francis Drake Channel at around 15 knots, making the British Virgin Islands one of the world’s most forgiving sailing destinations. With over 60 islands and cays connected by line-of-sight navigation, you can cover a new anchorage every day without ever pushing a passage past three hours. This 7-day itinerary follows a classic loop from Tortola through The Baths, Anegada, and Jost Van Dyke, built around realistic sailing times, mooring-ball logistics, and the beach bars that make this corner of the Caribbean genuinely distinct. It suits first-time charterers and anyone who wants a relaxed pace with reliable winds.
Over 60 islands and cays connected by line-of-sight navigation; most passages take 2–4 hours at 7–15 nautical miles per leg.
This is the easiest multi-island sailing itinerary in the Caribbean for a family or first-time charter crew — short hops, protected waters, and English-speaking ports. The trade-off is that classic stops like The Baths and the Soggy Dollar Bar get crowded by late morning, so your timing matters more than your sailing skill.
First-time charterers
Families with kids
Beach-bar hoppers
| Day | Where | What | Time Needed | Key Tip |
|---|---|---|---|---|
| 1 | Tortola → Cooper Island | Settle in, snorkel, dinner at Cooper Island Beach Club | 2 hr sail | Pick up provisions at Rite Way or Bobby’s Marketplace in Road Town before departing |
| 2 | Cooper Island → The Baths | Explore granite boulders, caves, tidal pools | 3 hr sail + 2 hr shore | Moor on National Parks buoys; arrive before 9 a.m. to beat the day-tripper crowds |
| 3 | The Baths → Spanish Town → North Sound | Provision, then head to Leverick Bay for water sports | 0.5 hr + 2 hr sail | Leverick Bay has a fuel dock and a well-stocked grocery for restocking |
| 4 | North Sound → Anegada | Coral island, lobster shacks, world-class snorkeling | 3–4 hr sail | Anchor off Loblolly Bay; book a lobster dinner at Anegada Reef Hotel in advance |
| 5 | Anegada → Marina Cay | Snorkel the reef, relax at the Pusser’s bar | 2–3 hr sail | Pusser’s Marina Cay serves a solid painkiller; grab a mooring early as space is limited |
| 6 | Marina Cay → Jost Van Dyke | White Bay, Soggy Dollar Bar, Foxy’s | 2 hr sail | Soggy Dollar’s mooring field fills by 11 a.m.; anchor further east and dinghy in |
| 7 | Jost Van Dyke → Tortola | Stop at Cane Garden Bay or Great Harbour, return to Road Town | 2–3 hr sail | Clear customs in Road Town before your charter ends; fuel and water at Village Cay Marina |
Day 1: Tortola to Cooper Island — Settling into the Rhythm
Your charter typically starts in Road Town on Tortola, where you’ll clear customs, meet the boat, and do a final provision run. Bobby’s Marketplace and Rite Way both allow online ordering with boat delivery, which saves an hour of cart-pushing in the heat. Once you’re loaded, motor east across the channel toward Cooper Island — a 2-hour sail that lets the crew get comfortable with the boat’s systems.
Clear customs at the Road Town office (open 8 a.m.–4 p.m. weekdays). Order provisions from Rite Way or Bobby’s Marketplace for delivery to the marina — saves carrying bags through town. Stock plenty of drinking water; island tap water is typically desalinated and not everyone loves the taste.
Head east-northeast toward Cooper Island’s Manchioneel Bay. The passage is straight across the Sir Francis Drake Channel with steady trade winds. Average sailing time is about 2 hours. Pick up a National Parks mooring ball — anchoring is restricted here to protect seagrass beds.
Cooper Island Beach Club has a restaurant, rum bar, and small shop. They serve dinner from 6 p.m.; the conch fritters are a local staple. If you have energy, snorkel along the reef on the island’s south side at slack tide — visibility often reaches 60 feet.
Day 2: Cooper Island to The Baths — The BVI’s Most Photogenic Hike
The Baths on Virgin Gorda are the single most-visited natural attraction in the BVI, and for good reason. The 11-nautical-mile sail takes about 3.5 hours, but the real trick is timing your arrival. Mooring buoys at The Baths are managed by National Parks Trust and fill fast — by 9 a.m. on peak-season mornings, they’re often gone.
Set out by 7 a.m. to reach The Baths by 10 a.m. The sail is southwest toward Virgin Gorda’s southwestern tip. Keep an eye out for the National Parks mooring field off the beach — you’ll see the white buoys from half a mile out.
The Baths are a maze of giant granite boulders forming sea pools, tunnels, and shaded grottoes. The trail from the beach to the “cathedral” cave takes about 20 minutes and involves some scrambling over wet rock — wear water shoes with grip. The reward is a deep, cool pool that catches the morning light.
By noon the day-tripper ferries arrive. Head back to the boat and motor 2 nautical miles to Spanish Town for lunch and provisions. The Spanish Town market has fresh produce and baked goods, and the Yacht Harbour offers fuel and water.
The Baths get packed with cruise-ship excursions between 11 a.m. and 2 p.m. If you’re not moored by 9 a.m., skip the visit and instead snorkel at The Caves on Norman Island — similar rock formations, far fewer people.
Day 3: Spanish Town to North Sound — Leverick Bay’s Water Sports Hub
North Sound on Virgin Gorda’s eastern side is a sheltered lagoon with two marinas, multiple restaurants, and the best water-sports rental on the island. The 8-nautical-mile sail from Spanish Town takes about 2 hours, skirting the island’s rocky eastern shore. Leverick Bay has a fuel dock, a grocery store, and a beachfront restaurant that does a solid Sunday barbecue.
Head east out of Spanish Town, then north around the point into North Sound. The channel is well-marked with red and green buoys — stay mid-channel to avoid the shallow flats on either side. Moor at Leverick Bay’s guest moorings or at the Bitter End Yacht Club if you prefer a quieter anchorage.
Leverick Bay rents kayaks, stand-up paddleboards, and small dinghies. The water is flat and clear — ideal for kids learning to snorkel. Ethan spent a good hour chasing needlefish along the dock pilings. If you want a proper dive, the reef at The Dogs is a 15-minute motor north.
The restaurant at Leverick Bay serves Caribbean-style seafood and has a kids’ menu that covers the basics. Reservations aren’t usually needed on weeknights, but call ahead if you’re there on a Friday — that’s when they fire up the barbecue and the place fills with charter crews.
North Sound gets a wind funnel effect in the afternoon — gusts can hit 20 knots. If you’re docking at Leverick Bay, come in bow-first and have a spring line ready. The marina staff are helpful but it’s a tight squeeze when the wind is up.
Day 4: North Sound to Anegada — The Lobster Run
Anegada is the outlier of the BVI — a flat coral island ringed by 10 miles of white-sand beaches and the only place in the territory with serious lobster shacks. The 15-nautical-mile passage from North Sound is the longest of the trip, taking 3–4 hours in typical trade-wind conditions. Anegada’s lobster season runs year-round, and the island’s Anegada Reef Hotel is famous for its grilled spiny lobster dinners.
Depart North Sound early — aim for 8 a.m. to catch the best wind. The passage crosses the deeper Anegada Passage, where the sea can get choppy in afternoon gusts. Keep a lookout for the reef that surrounds Anegada; the approach is marked by red and green buoys at the entrance to the anchorage off Loblolly Bay.
Anegada’s Horseshoe Reef is one of the largest fringing reefs in the Caribbean, stretching for miles. The best snorkeling is off Loblolly Bay — swim out to the drop-off where you’ll see parrotfish, sergeant majors, and occasional turtles. The water is shallow enough for beginners, but current can pick up on the outer edge.
Book a table at the Anegada Reef Hotel for dinner — they serve grilled lobster with rice and peas, and the portions are generous. The hotel also runs a small bar with live music on weekends. If you want a change of pace, the Wonky Dog at Loblolly Bay does fish tacos and cold beers in a barefoot setting.
Anegada has no natural harbor — you anchor off the beach in open water. The holding is good in sand, but overnight winds can shift. Set a stern anchor or use a Bahamian moor if you’re staying the night. Dinghy landings are straightforward on Loblolly Bay’s gentle shore break.
Day 5: Anegada to Marina Cay — A Quiet Reset
Marina Cay is a private island with a single resort and a Pusser’s bar that feels like a throwback to 1970s chartering. The sail from Anegada is around 12 nautical miles, taking 2–3 hours depending on wind angle. Marina Cay’s mooring field is small — maybe 15 balls — so arriving by early afternoon is key.
Head southwest from Anegada toward the small island of Marina Cay, just east of Tortola’s Beef Island. The passage is a beam reach in typical conditions. The mooring field sits off the island’s west side, protected from the prevailing easterly swell.
Marina Cay has a healthy coral head off the southern point, accessible by a short swim from the beach. The reef is home to schools of blue tang and sergeant majors. Current is mild — good for children who are comfortable with fins and a mask.
Pusser’s Marina Cay bar is a classic BVI watering hole. Their painkiller — a blend of rum, pineapple, coconut, and nutmeg — is the house specialty. The bar also serves a decent burger menu if you’re tired of seafood. It’s a low-key evening compared to Jost Van Dyke, which makes it a good recovery day.
Day 6: Marina Cay to Jost Van Dyke — Beach Bars and White Sand
Jost Van Dyke is the social hub of the BVI, home to the Soggy Dollar Bar, Foxy’s, and a string of beach bars along White Bay. The 8-nautical-mile sail from Marina Cay takes about 2 hours. White Bay’s mooring field is often full by 11 a.m., so an early start pays off.
Depart Marina Cay by 8 a.m. The route takes you south of Tortola’s Beef Island, then west across the channel to Jost Van Dyke. White Bay is on the island’s south side — look for the cluster of mooring balls off the beach. If the field is full, anchor further east toward the rocky point and dinghy in.
The Soggy Dollar Bar is the origin of the painkiller cocktail and draws a lively crowd. The beach is shallow and gentle — good for wading. Foxy’s, a short walk east, is more of a restaurant with a gift shop and a small museum of BVI sailing history. Both get packed by midday.
If you prefer a quieter evening, motor around to Great Harbour on Jost’s north side. It’s more protected from the easterly swell, and the beach has fewer bars. The local conch fritters at the little shack near the ferry dock are worth the walk.
The Soggy Dollar Bar doesn’t take reservations, and the mooring field is first-come, first-served. If you can’t get a ball by 10:30 a.m., skip White Bay entirely and head to Cane Garden Bay on Tortola — it has a similar beach-bar vibe with more mooring options.
Day 7: Jost Van Dyke to Tortola — The Return
The final leg brings you back to Road Town, with a recommended stop at Cane Garden Bay or Great Harbour for a last swim. The 10-nautical-mile return takes 2–3 hours. Clearing customs and immigration is required before returning your charter boat; the office in Road Town is open until 4 p.m.
Cane Garden Bay on Tortola’s north coast is a wide, protected bay with a beach bar called the Elm — they serve breakfast until 11 a.m. The snorkeling is decent off the western point. It’s a good spot to let the kids burn off last energy before the flight home.
Motor south around Tortola’s western tip into Road Harbour. Fuel and water at Village Cay Marina before returning the boat. Leave time to clean the boat and do a final inventory — most charter companies charge for missing items.
The customs and immigration office at Road Town is near the ferry dock. You’ll need your boat’s registration, crew list, and cruising permit. The process takes about 20 minutes. If you’re flying out of Tortola’s Beef Island Airport, allow 30 minutes for the drive from Road Town.
Practical Tips for Your BVI Sailing Charter
Charter logistics in the BVI are straightforward, but a few decisions can make or break your trip. Here’s what to sort before you step aboard.
When to Go
The peak season runs from mid-November through February, with stable trade winds and daytime temperatures in the low 80s. Shoulder months of May and June offer similar weather with fewer boats and lower charter rates. Hurricane season officially runs June through November — September is the statistically most active month, but many charters still operate with flexible cancellation policies.
Chartering Options
Bareboat charters are available for experienced sailors with a skipper’s resume. If you’re not confident, a skippered charter adds roughly $200–300 per day but removes all navigation stress. Fully crewed options include a cook, which is worth considering if you want to focus entirely on relaxation. Most charter companies require a refundable security deposit of $1,500–$3,000.
Provisioning and Costs
Stock up in Tortola before heading out. Supermarket prices are about 20–30% higher than mainland US, especially for imported goods. A typical week’s provisions for a family of four runs around $400–$600. If you’re weighing which side of the island to sleep on, this interactive map of the island’s hotels and rentals makes it easier to compare against the beach or the trailhead. Mooring fees are $20–$40 per night at National Parks sites; marinas charge $50–$80 per night including water and electricity.
Gear to Bring
A good pair of water shoes with grip is essential for The Baths and rocky shore landings. A beginner-friendly drone under 249g doesn’t require FAA registration and can capture the coastline from angles you can’t get from the deck. Snorkel gear is usually provided on charter boats, but many travelers prefer their own mask for fit. If you’re planning to film underwater, an 8K 360° camera lets you shoot first and frame later — useful when you’re bobbing in current and don’t have time to compose a shot.
Most charter boats come with a basic first-aid kit, but you’ll want to bring seasickness medication (Dramamine or Bonine) if anyone in your crew is prone to motion sickness. The Anegada crossing can be choppy, and the trade winds pick up in the afternoon.
- This 7-day loop works best with a 9 a.m. departure each day — any later and you risk missing mooring balls at popular stops.
- The Baths and Soggy Dollar Bar are the two most crowded spots; arriving before 10 a.m. is non-negotiable if you want a peaceful experience.
- Anegada is the longest passage (3–4 hours) and the most exposed — plan it for a day with calm wind forecasts under 15 knots.
- Provision in Tortola before departing; island grocery stores are limited and expensive.
- Book your charter at least 3 months ahead for peak season (December–February); shoulder season bookings can be made 4–6 weeks out.
Before You Go: BVI Sailing Questions Answered
Do I need a sailing license to charter a boat in the BVI?
No formal license is required, but charter companies will ask for a sailing resume showing you’ve handled a similar-sized boat. If you can’t provide one, you’ll need to hire a skipper. Most companies offer a free “checkout sail” with a captain who evaluates your skills before handing over the keys.
What happens if the weather turns bad?
Hurricane season runs June through November, but even in good months, afternoon squalls can roll through. The BVI has a network of safe hurricane holes — places like Gorda Sound and Trellis Bay offer protected anchoring. Monitor channel 16 on VHF for weather updates, and your charter company will have a 24/7 support number.
Can I anchor anywhere in the BVI?
No. National Parks areas — including The Baths, Cooper Island, and parts of Norman Island — require you to use mooring balls to protect the seafloor. Anchoring is allowed in sand patches outside these zones, but always check for seagrass or coral before dropping the hook. The fine for anchoring in a protected area can exceed $500.
Is the BVI safe for families with kids?
Yes, with the usual precautions. The water is warm and calm in most anchorages, and the short sailing days mean kids don’t get bored on passage. Lily and Ethan wore life jackets whenever they were on deck, and we kept a close eye on currents during snorkeling. The BVI is English-speaking and has good medical facilities on Tortola and Virgin Gorda.
What’s the real cost of a week-long charter?
A bareboat charter for a 40-foot catamaran runs $4,000–$7,000 per week in peak season. Add $400–$600 for provisions, $200–$300 in mooring fees, and $150 for fuel. Skippered charters add $200–$300 per day. The total for a family of four typically lands between $6,000 and $9,000 all-in, not including flights.
Trade Winds and Tides
The BVI’s real magic isn’t any single beach or bar — it’s the way the islands sit close enough that every morning brings a new anchorage without the stress of a long passage. The steady trade wind that pushes you west one day will bring you back east the next, and the tidal range of just 12 inches means you barely think about depth. That predictability is what makes this itinerary work for first-time charterers and families. If you want to extend the loop, a deeper exploration of the BVI’s lesser-known anchorages is worth reading before you plan your next trip.
References
SailChecker. “BVI Sailing Itinerary.” SailChecker.com, 2024. ↗
Yacht Journeys. “Your Ultimate Guide to Sailing British Virgin Islands: From Itineraries to Island Hopping.” YachtJourneys.com. ↗
SEARADAR. “BVI Sailing Itinerary.” SEARADAR.com. ↗
If you’re still planning your trip, the guide to the best snorkeling hotspots in the BVI pairs well with this itinerary, as does the deep dive into abandoned military forts on the islands for days when you want to trade the beach for a bit of history. And for anyone dreaming of Anegada’s spiny lobster, our guide to Anegada’s hidden beaches and lobster legends covers everything from the best shacks to the reef conditions.
Explore Places to Stay in BVI
Feel free to zoom in and out of the map to explore the area and find the best place to stay for your trip.