White Bay on Jost Van Dyke is the kind of beach that makes you reconsider your life choices — in the best way. With soft sand, clear water, and the Soggy Dollar Bar serving its famous Painkiller cocktail just steps from the surf, it’s easy to see why this tiny island draws day-trippers from across the Caribbean. But Jost Van Dyke is just one stop on a longer arc through the British Virgin Islands, one that takes you from the granite boulders of Virgin Gorda to the flamingo-dotted flats of Anegada.
This 7-day sailing itinerary is built for travelers who want the full BVI range — beach bars, excellent snorkeling, quiet anchorages, and the kind of lobster dinner that becomes a trip highlight. Whether you’re chartering a boat or joining a guided sailing trip, the route connects the islands in a logical arc that maximizes time on the water and on land. For a closer look at where you’ll be snorkeling, check out this guide to the best underwater spots in the BVI.
A 7-day sailing itinerary lets you experience the BVI’s full range — from Jost Van Dyke’s beach-bar energy to Virgin Gorda’s granite boulders and Anegada’s flamingos — but the real trick is pacing. You’ll want to balance sailing time with enough hours on land at each stop, and the weather windows between December and April make the difference between a smooth trip and a rushed one.
Sailing enthusiasts
Beach lovers
Snorkelers
| Day | Destination | Highlight | Dining | Activity |
|---|---|---|---|---|
| 1 | Scrub Island → Spanish Town, Virgin Gorda | The Baths | CocoMaya | Snorkeling at Devil’s Bay |
| 2 | Spanish Town → Anegada | Loblolly Bay and Flamingo Point | Setting Point lobster dinner | Snorkeling Horseshoe Reef |
| 3 | Anegada → Trellis Bay, Tortola | Dog Islands | Jeremy’s Kitchen or Loose Mongoose Café | Aragorn’s Studio arts centre |
| 4 | Trellis Bay → White Bay, Jost Van Dyke | Monkey Point snorkeling | Soggy Dollar Bar | Sundowners on White Bay |
| 5 | Jost Van Dyke → Norman Island | The Bight anchorage | Willie T floating bar | Snorkeling at The Bight |
| 6 | The Bight → Brandywine Bay | Little Harbour, Peter Island | Brandywine Estate Restaurant | Abandoned cigar factory and mansions |
| 7 | Brandywine Bay → Scrub Island | East End Bay yacht spotting | Scrub Island Resort and Spa | Celebratory dinner with rum cocktails |
The 7-Day Island-Hopping Route
The itinerary starts at Scrub Island and loops through the major islands, with each day bringing a new anchorage and a new flavor of BVI life.
Sail from West South Bay through East South Bay to Spanish Town. Spend the afternoon at the Baths, where granite boulders form natural swimming pools and grottos at Virgin Gorda’s southern tip. Moor at Devil’s Bay for a swim before lunch at CocoMaya near the Yacht Harbour. The Baths are one of the most photographed spots in the BVI, and the snorkeling along the west coast of Virgin Gorda rewards anyone who brings a mask.
Sail past the Dog Islands, with an optional stop at Saba Rock — a private resort with a restaurant and sunset bar. Continue to Anegada, a flat coral atoll that looks nothing like the volcanic islands you’ve been sailing through. Visit Loblolly Bay for flamingos and Flamingo Point Lookout for rare ground iguanas. Snorkel Horseshoe Reef, known for its shipwrecks and coral. Dinner is Anegada lobster at Setting Point, a local specialty worth the crossing.
Depart Anegada and stop at the Dog Islands for lunch and snorkeling before arriving at Trellis Bay on Tortola’s northeast coast. The bay gives you access to beaches, Jeremy’s Kitchen, and the Loose Mongoose Café. Visit Aragorn’s Studio arts centre. If you’re visiting during a full moon, the Trellis Bay full moon party is a local institution.
Sail west past Little Camanoe and Monkey Point, an ecological preserve where anchoring is prohibited — use the National Park mooring buoys. Snorkel at Monkey Point, where yellowtail snappers, grunts, and crevalle jacks gather close to the surface. Moor at White Bay and spend the evening at the Soggy Dollar Bar for a Painkiller cocktail. White Bay’s gentle surf works well for families looking for easy swimming conditions and a relaxed beach day.
Sail south from White Bay and stop at Smuggler’s Cove on Tortola’s south end for a break — Nigel’s Boom Boom Beach Bar and Grill is worth a stop. Continue around Tortola’s West End past Frenchman’s Cay and anchor at The Bight on Norman Island. Snorkel the reef at The Bight, then visit Willie T, the legendary floating bar.
Island-hop to Little Harbour on Peter Island, where you’ll find an abandoned cigar factory and 1920s mansions — a quieter, historical detour. Sail north across the Sir Francis Drake Channel to Brandywine Bay on Tortola. Dinner at Brandywine Estate Restaurant, known for lobster thermidor and moules marinière, with sundowners on the terrace.
Sail along Tortola’s southern coast and stop at East End Bay near Parham Town for yacht spotting. Round the Bluff back to Scrub Island for a celebratory dinner at Scrub Island Resort and Spa with rum cocktails on the terrace. The loop is complete.
Planning Your BVI Sailing Trip
The logistics of a 7-day island-hopping trip come down to a few key decisions — when to go, how to book, and what to budget.
Best Time to Go
The prime window is December through April, when temperatures sit in the 70–90°F range and the trade winds are reliable. Summer brings higher heat and humidity, and hurricane season runs June through November. Even in good weather, wind and swell can affect tender operations and small-boat plans, so check marine conditions before each sailing day.
Booking and Costs
Chartering a vessel or joining a guided sailing trip are the two main options. Mooring balls are required at many sites — Devil’s Bay, the Baths, Dog Islands, White Bay, and the Bight — and anchoring is prohibited at Monkey Point, which is a National Park. Costs include boat rental, fuel, customs fees, and captain’s fees. Customs fees run $75–$100 per person. For day-trippers arriving from St. John’s, charter boats to Jost Van Dyke run roughly $145 per person with $30 in customs fees, and lunch around $20. For more on the protected areas you’ll visit, see this overview of BVI marine sanctuaries.
What to Pack
Light clothes, sunscreen, a hat, sunglasses, swimsuit, and towel are the basics. Reef-safe sun protection is requested at snorkeling sites. Water shoes help at the Baths and on rocky landings. A dry bag protects gear during tender transfers. Cash in small bills is useful at beach bars and smaller restaurants, where card acceptance is uneven. The U.S. dollar is the official currency throughout the BVI.
Weather windows close faster than you’d expect. Wind can interrupt tender service, rain slows roads and trails, and heat turns a short walk across an exposed pier into the hardest part of the day. Always protect the final hour before all-aboard time, and photograph the ship’s local contact information before heading ashore.
Before You Go — BVI Island-Hopping
Do I need a passport for the BVI?
Yes. A valid passport or passport card is required for entry to the British Virgin Islands. Carry it with you when clearing customs between islands.
Can I do this itinerary without sailing experience?
Yes — you can join a guided sailing trip or charter with a captain. The route works best with someone who knows the mooring fields and weather patterns.
Which island is better for a shorter trip?
Jost Van Dyke for relaxed beach-bar energy and nightlife (White Bay, Soggy Dollar Bar). Virgin Gorda for natural beauty and exploration (the Baths, Spanish Town). Both work as day trips from Tortola or St. John’s.
What’s the biggest downside of this itinerary?
The sailing days between Anegada and Jost Van Dyke are the longest, and trying to squeeze two islands into one day can turn paradise into a stopwatch exercise. Give yourself buffer time at the anchorages you care about most.
One Arc, Seven Islands
The beauty of this route is that it doesn’t force you to choose between Jost Van Dyke’s beach bars and Virgin Gorda’s boulders — you get both, plus the flamingos of Anegada and the quiet anchorages in between. The BVI reward a slow pace and a willingness to adjust when the wind shifts. For a deeper look at what makes each island distinct, check out this guide to the BVI’s local culture beyond the rum punch.
References
Cruise Ports. “British Virgin Islands Cruise Ports.” Cruise Ports, 2025. ↗
The Culture Trip. “How to Spend 7 Days Island Hopping Around the British Virgin Islands.” The Culture Trip, 2024. ↗
TripJive. “Day Trips from St. John’s: Jost Van Dyke or Virgin Gorda?” TripJive, 2025. ↗
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