Island Hopping in Paradise: The Ultimate Charter Itinerary for the British Virgin Islands
For many travelers, the idea of island hopping in the British Virgin Islands sounds like a dream come true. Turquoise waters, sandy beaches, and a new adventure waiting at every stop.
But for those who have never done it before, the logistics can feel a little overwhelming. Which islands should you visit first? How much time should you spend at each one? And how do you make sure you don’t miss those hidden gems that only the locals know about?
Without a clear plan, it’s easy to spend more time making decisions than actually soaking in the experience. That’s exactly why we created a specially curated island-hopping itinerary for first-time guests.
Designed to take the guesswork out of planning, this blog highlights the best routes, top spots to explore, and insider tips for making the most of each destination. With this itinerary in hand, you can relax knowing your trip is thoughtfully mapped out, leaving you free to focus on enjoying the sail, the sunsets, and the unforgettable moments along the way.
Your 7-Day Caribbean Island-Hopping Itinerary
Day 1: St. Thomas to St. John
Step aboard Barefoot Cowboy in St. Thomas, meet your crew, and settle in with a welcome cocktail. As you leave St. Thomas behind, choose your first stop in St. John: Waterlemon Cay for incredible snorkeling, Maho Bay to swim alongside sea turtles, or a forest hike along Reef Bay Trail. Spend your first evening soaking in the sunset and enjoying those warm island breezes.
Day 2: Soper’s Hole, Tortola to Norman Island
After a short sail, clear customs at Soper’s Hole on Tortola, a charming harbor with pastel buildings and local shops. Make your way to Smuggler’s Cove for snorkeling in the turquoise waters and lunch at one of the two beach bars.
Then head to Norman Island, legendary for its pirate history. Explore the sea caves, swim in The Bight, and end the day with a floating boat party at the Willy T.
Day 3: Cooper Island
Sail to Cooper Island Beach Club, a boutique eco-resort perfect for relaxing on the sand, enjoying a rum tasting, or snorkeling the nearby reefs. This is a great place to slow the pace and soak in island serenity.
Shop for souvenirs, and after a lunch at the Cooper Island Beach Club, spend the afternoon jet-skiing or lounging in pool floaties. After sunset, head back to the boat for dinner aboard the Barefoot Cowboy and a dance party with the crew.
Day 4: Virgin Gorda – The Baths, Saba Rock & Bitter End
Make your way to Virgin Gorda for one of the Caribbean’s most iconic adventures. You’ll need plenty of time to enjoy The Baths, a natural wonder complete with massive granite boulders, hidden pools, and winding trails. Devil’s Bay National Park is just around the corner, along with sandwiches at Mad Dog Cafe.
Hike at Gorda Peak Trail for unbelievable views. Then end the day at with lobster on a private island at Saba Rock, or upscale dining at Bitter End Yacht Club.
Day 5: Anegada
Venture off the beaten path to Anegada, the BVI’s only coral island. Here, you’ll find endless white sand beaches, flamingos in the salt ponds, and some of the best Caribbean lobster you’ll ever taste.
Snorkel at Cow Wreck Beach or explore Conch Island, a natural wonder unlike anything else in the BVIs. Check off a must on your bucket list with kite surfing or horseback riding along the beach. Then enjoy the sunset with cool drinks and fresh fish at Tipsy by Ann Beach Bar.
Day 6: Jost Van Dyke – Foxy’s & Soggy Dollar
The next morning, head to Jost Van Dyke, home of legendary beach bars and even more legendary beaches. Spend the day sipping a Painkiller at the Soggy Dollar Bar, floating in the turquoise shallows of Great Harbour, exploring the national beauty of the Bubbly Pool, and snorkeling at White Bay.
End the day dancing to live music at Foxy’s, home to some of the finest rum and burgers you’ll find in the Caribbean.
Day 7: St. Thomas – Farewell for Now
Begin your journey home with a sail back to St. Thomas. Enjoy one last breakfast onboard, take a final dip in the Caribbean, and wave goodbye to the islands, knowing you’ll be back for more.
Why Choose Barefoot Cowboy?
If you love this itinerary, we’ll follow it to a T. But if you want to tweak the destinations, activities, meals, or excursions, we’d love to get creative.
Unlike cookie-cutter cruises, Barefoot Cowboy doesn’t tell you where to go or what to eat. You call the shots. Whether you're a snorkeling fanatic, a beach bum, or a foodie with a love for local flavor, we tailor every detail just for you.
What’s included in your adventure:
Owner-operated crew with over a decade of local experience
Personal itinerary planning with safety-first navigation
Chef-prepared meals and cocktails (customized to your tastes)
Plenty of space for everyone, from couples to 10-person groups
You deserve a vacation that doesn’t come with stress, crowds, or compromises. Let’s create the vacation of a lifetime and a Caribbean experience you’ll never forget.
