Your 7-Day BVI Charter Itinerary Aboard Winged Arrow II
- C&P Enterprises
- 3 days ago
- 4 min read
Planning a BVI sailing itinerary? This is the route we run on Winged Arrow II — a Fountaine Pajot Elba 45 — and it hits the best the British Virgin Islands have to offer without feeling rushed. Seven days, seven anchorages, and enough flexibility to linger where you want. Here's how it unfolds.
Day 1: Pick Your Adventure — Norman Island or Peter Island
Both Peter Island and Norman Island are a short sail from the base in Road Town and sit right next to each other. Your first night is a choice between two very different moods.
If you're looking for a party atmosphere → Norman Island. Head southeast on a broad reach and start with snorkeling at The Indians — dramatic rock pinnacles with some of the best visibility in the BVI. From there, swing by Willy T's, the floating bar moored just off Norman. Have a cocktail, jump off the upper deck if you're feeling it, or just watch the other guests. Dinner at The Pirate's Bight — good food, great setting.
If you're looking to ease into the vacation — family trip, relaxed crowd → Peter Island. The resort recently went through a full renovation. Dock at the marina in Sprat Bay and your fee gets you the pool, pickleball courts, basketball, shuffleboard, and laundry. The Drunken Pelican for casual drinks and lunch. For dinner, make a reservation at The Drake — fine dining on the other side of the island, golf cart pickup included. Long pants required, so pack accordingly. The Lobster Pappardelle is the move. Best meal of our last BVI trip.
Check out our full Peter Island post for more: wingedarrow.com/post/visiting-the-new-peter-island-resort
Either way — this is a marathon, not a sprint.
Day 2: Cooper Island & Resort - Coffee, Solar Beer, and Rum
Cooper Island is a short sail from Norman or Peter and a full day done right. Start the morning with a latte at the Coffee Box, browse the SeaGrape Boutique if you're after something to bring home, then settle in at the Rum Bar. The draft beer here is brewed on-island using only solar power — worth trying just for that.(https://cooperislandbeachclub.com/experiences/)
Cap off the day with dinner at The Beach Club. The outdoor setting with the water right there is tough to beat.
Day 3: Virgin Gorda — The Baths in the Morning, North Sound by Afternoon
Get an early start — The Baths are worth it before the day-tripper crowds arrive. These aren't your typical beach boulders; massive granite rocks the size of houses create a maze of grottos, tide pools, and passages. Start at the top and work your way down through to the Cathedral, where light filters through the rocks. It's one of those places that's genuinely hard to describe until you're standing in it.
Back aboard for burgers on the grill — one of those simple pleasures that sailing somehow makes better — then head up to the North Sound and catch a mooring at the Bitter End Yacht Club. Happy hour at The Reef Sampler, sundowners watching the light change over the sound, then dinner at The Buoy Room. Get the Anegada Lobster Pizza. That's not a suggestion.
Day 4: Oil Nut Bay — Slow Down Day
After three full days, Day 4 is deliberately low-key. Take the Highfield Tender over to Oil Nut Bay Marina Village (https://www.oilnutbay.com/marina-village/) before a leisurely lunch by the pool at Nova. If you can score a day pass to the resort, do it — it's worth asking.
In the evening, head over to Saba Rock for dinner (https://sabarock.com/). The harbor of the North Sound at night is mesmerizing — one of those views where you put the phone down and just sit with it.
Day 5: Anegada - Lobster Night
On a beam to broad reach, we make the passage out to Anegada — the only coral island in the BVI, flat and low and unlike anything else in the chain. Rent a Moke when you get there (a classic open-sided vehicle, basically a golf cart with a personality) and drive out to Cow Wreck Beach and the Anegada Beach Club. Long beach, clear water, no agenda.
The night ends with a lobster dinner on the beach. They pull the lobster fresh, grill it simply, and serve it right there in the sand. It's the kind of meal people talk about for years.
Day 6: Jost Van Dyke - The Soggy Dollar & Foxy's
Jost Van Dyke is the social hub of the BVI, and White Bay is the reason. The Soggy Dollar Bar invented the Painkiller — rum, cream of coconut, orange juice, pineapple — and this is the right place to have one (or two). The beach is long and easy, and the whole bay has a laid-back energy that's hard to leave.
Tonight is your last night on the water. Dinner aboard Winged Arrow II if you want something quiet, or dinghy over to Foxy's in Great Harbour if you want to go out with a proper sendoff.
Day 7: Back to Road Town
The last morning. We sail back to the BVI Yacht Charters base in Road Town, fuel up, and hand the boat back. Seven days, seven islands, and enough memories to start planning the next one.
Link to our Itinerary Map-
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