A flotilla is a group sailing experience where multiple boats follow a planned route, led by an experienced skipper and crew. Whether you’re a seasoned sailor or new to the sport, a flotilla offers the perfect blend of adventure, camaraderie, and exploration.
A lead skipper and crew provide route guidance, assist with navigation, and share local insights about the best destinations, restaurants, and activities. It’s ideal for those new to sailing or exploring unfamiliar waters while still enjoying a hands-on sailing experience.
Flotillas are perfect for meeting other sailing enthusiasts. Group dinners, shared excursions, and evening gatherings create a welcoming community, making every stop a chance to connect.
Depending on your destination, daily sailing includes stops at breathtaking bays, famous beach bars, and top snorkeling spots. You can explore national parks, cultural landmarks, and local hotspots either independently or with the group.
While the flotilla follows a general route, there’s plenty of room for independent exploration. Sail at your own pace and meet up with the group at the designated anchorage each evening.
New sailors can gain confidence knowing an experienced crew is always nearby. A flotilla is a great way to transition into independent chartering while having expert support at hand.
Here’s a 7-day British Virgin Islands (BVI) flotilla itinerary with exciting group activities like a mini regatta, beach parties, and social events to enhance the experience!
Arrive at Beef Island Airport (EIS) or St. Thomas USVI and transfer to the marina.
Flotilla Briefing & Yacht Check-in: Meet your flotilla crew, provision the boat, and review the sailing plan.
Welcome Party at The Dock: Kick off the adventure with a casual meet-and-greet dockside party with island cocktails and live Caribbean music.
Overnight: Moor at The Charter Base or anchor in Soper’s Hole.
Morning Sail to Norman Island, known for its pirate history.
Group Snorkeling at The Caves & The Indians, teeming with tropical fish.
Sunset Drinks & Dinner at Pirate’s Bight, a beachside restaurant with breathtaking views.
Bonfire on the Beach: Gather for a flotilla bonfire, share stories, and enjoy an island-style BBQ.
Optional Late-Night Fun at Willy T, the famous floating bar.
Overnight: Moor at Norman Island.
Morning Swim & Paddleboarding before setting sail.
Short Sail to Cooper Island Beach Club, a tranquil spot with crystal-clear water.
Group Rum Tasting at Cooper Island Rum Bar, featuring over 280 rums from around the world.
Afternoon Beach Games: Friendly competitions like paddleboard races, volleyball, or beach limbo.
Dinner at Cooper Island Beach Club—fresh seafood and a farm-to-table menu.
Overnight: Moor at Cooper Island.
Sail to The Baths, Virgin Gorda, to explore the famous granite boulders and hidden pools.
Mini Regatta at Bitter End Yacht Club: Organize a friendly yacht race around North Sound, with awards and bragging rights at the finish line.
Lunch & Celebratory Drinks at Saba Rock or Bitter End Yacht Club.
Evening Sunset Cocktails & Awards Ceremony for regatta winners.
Overnight: Moor at North Sound.
Early Morning Sail to Anegada, the only coral atoll in the BVI.
Island Exploration: Rent scooters or jeeps to visit Cow Wreck Beach, Loblolly Bay, and Flamingo Pond.
Afternoon Snorkeling at Loblolly Bay, one of the Caribbean’s best spots.
Beach Party at Anegada Beach Club: Enjoy a private flotilla beach BBQ, bonfire, steel drum music, and fresh lobster dinner.
Overnight: Moor at Anegada.
Sail to Jost Van Dyke, the party island of the BVI.
Lunch Stop at Sandy Cay or Little Jost Van Dyke for a swim and beach games.
White Bay Fun Day: Hang out at the world-famous Soggy Dollar Bar (home of the Painkiller cocktail).
Evening Bash at Foxy’s Tamarind Bar in Great Harbour, known for its legendary parties.
Overnight: Moor at Great Harbour or White Bay.
Morning Swim & Farewell Brunch at Foxy’s before sailing.
Option 1: Cane Garden Bay – Enjoy a laid-back day at one of BVI’s most scenic bays, visit the Callwood Rum Distillery, or kayak around the bay.
Option 2: Peter Island – Quiet anchorage for a relaxing last night.
Sunset Cocktail Hour on the beach with a toast to an amazing flotilla week.
Overnight: Moor at Cane Garden Bay or Peter Island.
Early morning sail back to Road Town, Tortola.
Check out & refuel before heading to the airport.
Final Brunch before farewells.
