Multi-day trip plans designed by someone who lives it — not a travel agency on the mainland. Every itinerary is built from real experience in the US & British Virgin Islands.
These aren't cookie-cutter vacation packages. Each itinerary is based on trips Tracy has personally taken, routes he knows by heart, and partnerships he's built over years of living in St. Thomas. Use them as a starting point — we customize everything to fit your group, your budget, and your idea of the perfect trip.
Perfect for honeymooners, anniversaries, or couples who want to unplug and reconnect. This itinerary combines private boat time, hidden beaches only locals know, and the kind of sunset views you can't get from a resort balcony.
Settle into your waterfront accommodation in St. Thomas. In the late afternoon, board a private sunset champagne cruise departing from Yacht Haven Grande. Sail past the harbor lights as the sun drops behind the islands, with a bottle of bubbly and appetizers on deck.
End the evening with dinner at a cliffside restaurant overlooking Charlotte Amalie — we'll make the reservation at a spot most tourists never find.
Full-day private charter to the most secluded spots in the islands. Start at Honeymoon Beach on Water Island — a pristine strip of sand with almost no one on it. Snorkel the coral gardens at Turtle Cove where sea turtles feed in the seagrass.
Your captain anchors at a hidden cay for a private lunch on the water. Afternoon stop at Christmas Cove for some of the best snorkeling in the USVI, then a slow cruise through Pillsbury Sound as the light turns golden.
Morning ferry to St. John for a leisurely breakfast in Cruz Bay. Explore Trunk Bay — consistently rated one of the top 10 beaches in the world — and snorkel the underwater trail. Browse the shops and galleries in town before heading back.
If your flight is later, we can arrange a half-day spa experience or a guided hike through the Virgin Islands National Park.
This is the trip for people who want to see and do it all. Five days of private charters, legendary beach bars, world-class snorkeling, and the kind of island exploration that makes you never want to go home. Built for friends, families, or anyone with a serious appetite for adventure.
Arrive in St. Thomas, check into your accommodation, and get your bearings. Afternoon at Magens Bay — one of the most beautiful beaches in the Caribbean. Evening welcome dinner at a beachfront restaurant on the east end with your toes in the sand.
Private charter to St. John. Morning snorkel at Waterlemon Cay — one of the best reef spots in the park. Beach time at Trunk Bay, then cruise down to the south shore for lunch at a hidden beach bar. Afternoon stop at Caneel Bay for a final swim before heading back as the sun starts to set.
Cross to the British Virgin Islands for a day at the legendary Jost Van Dyke. Morning at White Bay — powdery white sand and crystal-clear water. Walk the beach to the Soggy Dollar Bar for their world-famous Painkiller cocktail. Afternoon at Foxy's for lunch and live music, then a stop at Sandy Spit — a tiny deserted island that looks like a postcard.
Morning guided jet ski tour along the St. Thomas coastline — hit hidden coves and sea turtle spots most people never see. Afternoon private charter to Norman Island for The Caves — snorkel through underwater sea caves lit up by the sun. End the day anchored at the floating bar at Willy T's for drinks and jumping off the upper deck.
Half-day charter to Water Island — the "fourth" Virgin Island that most visitors never see. Honeymoon Beach for a relaxed morning in the sand, snorkel the reef right off shore, and explore the old fort ruins. Afternoon back in St. Thomas for last-minute shopping at Havensight or a farewell rum punch at a rooftop bar.
Whether it's the bachelor party, bachelorette weekend, or a big birthday celebration — this itinerary is built for groups who want to go hard on the water and keep the party rolling on shore. Open bars, beach bars, group boat charters, and enough stories to fill a best man speech.
Everyone arrives and meets at a waterfront bar in Red Hook for welcome drinks and lunch. Afternoon group catamaran cruise with open bar, music, snorkeling stops, and the famous water swing. End up at a beach bar on St. John for sunset cocktails before heading back.
Private charter to the BVI for the ultimate beach bar crawl. Start at Soggy Dollar Bar on Jost Van Dyke for Painkillers, walk the beach to Hendo's Hideout, then hit Ivan's Stress Free Bar. Afternoon at Sandy Spit for photos on the most photogenic island in the Caribbean. Last stop: Foxy's for live music and dancing.
Sleep in. Late brunch at a waterfront restaurant with bottomless mimosas. Optional half-day activity: jet ski tour for the crew that still has energy, or paddleboard and beach time at Sapphire Beach for those in recovery mode. Group photo, farewell drinks, and flights home with a lifetime of stories.
Built for families who want more than a resort pool. Gentle snorkeling with sea turtles, calm beaches perfect for little ones, pirate legends, and boat rides that kids will talk about for years. Every activity is chosen for safety and fun at all ages.
Arrive and head straight to Coki Beach for easy snorkeling right off the sand — colorful fish, sea urchins, and the occasional sea turtle just steps from shore. Perfect for kids getting comfortable with snorkeling gear. Lunch at a beachside grill, then explore the Coral World Ocean Park next door.
Private boat charter with a family-friendly captain. First stop: Turtle Cove, where sea turtles are almost guaranteed — kids will be over the moon. Then cruise to Lovango Cay for lunch at the hilltop restaurant with panoramic views. Afternoon at Maho Bay on St. John, where turtles come right up to the shoreline in the seagrass.
Morning kayak and paddleboard adventure at Mangrove Lagoon — paddle through the mangroves and spot starfish and juvenile sea life. Afternoon trip to Blackbeard's Castle and the 99 Steps for a dose of pirate history and panoramic views of the harbor. Ice cream stop in town before an early sunset dinner.
Take the short ferry to Water Island for a relaxed final morning. Honeymoon Beach is shallow, calm, and perfect for little swimmers. Explore the old military fort ruins — kids love pretending to be explorers. Ferry back, grab lunch in Crown Bay, and head to the airport with sandy toes and big smiles.
This is the big one. A week aboard a crewed luxury catamaran with a private captain and gourmet chef. Wake up in a new anchorage every morning, eat meals prepared just for you, and explore both the USVI and BVI at your own pace. All-inclusive — the only thing you need to bring is yourself.
Board your crewed catamaran at the marina in St. Thomas. Meet your captain and chef, settle into your cabin, and enjoy a welcome cocktail on deck. Short afternoon sail to Christmas Cove for your first snorkel and a gourmet dinner under the stars as the harbor lights twinkle in the distance.
Wake up anchored in calm water. Breakfast on deck, then sail along the north shore of St. John. Morning snorkel at Waterlemon Cay, lunch at anchor in Caneel Bay, and an afternoon hike to a scenic overlook in the National Park. Sundowners on the bow as your chef prepares a Caribbean-inspired dinner.
Sail to Norman Island — the real-life inspiration for Treasure Island. Snorkel through The Caves, then motor over to The Indians, a cluster of rock pinnacles with some of the best diving and snorkeling in the BVI. Afternoon at Pirates Bight for drinks and the pirate vibe. Night at anchor in The Bight.
A longer sail east to Virgin Gorda. Explore The Baths — massive granite boulders forming pools, grottoes, and tunnels leading to a hidden beach. Lunch on board, then hike to the top of Gorda Peak for 360-degree views of the entire BVI chain. Anchor at North Sound for the night near Bitter End.
Sail north to Anegada, a flat coral island unlike anywhere else in the Caribbean. Famous for its lobster, flamingos, and 18 miles of empty white sand beaches. Fresh lobster lunch at a beachside shack, afternoon on Loblolly Bay with world-class snorkeling, and a sunset beach bonfire if conditions allow.
Sail to Jost Van Dyke for the legendary beach bar tour. Soggy Dollar for Painkillers, Hendo's for the view, Ivan's Stress Free for the vibe, and Foxy's for the stories. Your chef prepares a farewell gourmet dinner on deck — lobster, fresh catch, and a special dessert under the Caribbean stars.
Final breakfast on deck as your captain sails back to St. Thomas. Disembark at the marina with a week of memories, a tan, and the strong suspicion that you'll be back. Transfer to the airport — or extend your stay with a resort night on our recommendation.
The ultimate in Caribbean luxury. Exclusive use of Richard Branson's iconic Necker Island — all villas, master suites, and the entire island staff at your command. Private jet transfers, a personal chef, butler, spa therapists, and unlimited watersports. This isn't a vacation — it's a once-in-a-lifetime experience.
Round-trip private jet transfer from your home airport to Beef Island (EIS), Tortola. From there, a private helicopter whisks you over turquoise waters to Necker Island. Arrive to a champagne welcome, island orientation with your dedicated butler, and a sunset dinner on the Great House terrace.
Wake to a gourmet breakfast prepared by your private chef. Morning of unlimited watersports — kitesurfing, wakeboarding, paddleboarding, snorkeling, or diving on pristine reefs. Afternoon spa treatment, then an evening beach barbecue with premium wines and cocktails under the stars.
Three days of pure freedom. Explore hidden trails and wildlife sanctuaries on the island. Take the private yacht to nearby islands for beach picnics and snorkeling. Daily spa treatments, tennis, yoga, and wellness activities. Every meal is a gourmet experience — Caribbean fusion, fresh seafood, and fine wines curated to your preferences.
A day designed around your celebration — whether it's an anniversary, birthday, or simply being alive in paradise. Your personal photographer captures the memories. Evening culminates in a themed gala dinner with live entertainment, fire dancers, and flowing champagne on the beach.
Final breakfast overlooking the Caribbean. Helicopter transfer back to Beef Island and private jet home. You'll leave with memories that money can't buy — and the knowledge that you've experienced one of the most exclusive properties on Earth.
Seven nights in one of the Caribbean's most exclusive villa communities. Oil Nut Bay on Virgin Gorda offers breathtaking natural beauty, world-class amenities, and the kind of secluded luxury that makes you forget the outside world exists. Private chef, yacht charter, couples' spa — everything is arranged for you.
Private charter flight from San Juan (SJU) to Virgin Gorda (VIJ). Private ground transportation delivers you to your luxury villa or estate home at Oil Nut Bay. Your dedicated concierge welcomes you, orients you to the property, and your private chef prepares a welcome dinner on your villa terrace overlooking the sea.
Daily gourmet breakfast and dinner by your private chef. Access Oil Nut Bay's exclusive Beach Club, marina village, state-of-the-art fitness center, and infinity pools. Watersports on demand — kayaking, paddleboarding, snorkeling, or simply soaking in the sun on pristine beaches. Two 90-minute couples' massages at the Oil Nut Bay Spa.
Full-day private yacht charter exploring The Baths — Virgin Gorda's world-famous granite boulder formations with hidden grottoes and pools. Continue to surrounding islands for snorkeling, beach lunch, and exploration. Return to your villa for a sunset champagne toast and gourmet dinner.
Explore Virgin Gorda at your own pace. Hike to Gorda Peak for panoramic views of the entire BVI chain. Visit the charming Spanish Town for shopping and local cuisine. Sunset champagne cruise through North Sound. Your concierge arranges every detail — from restaurant reservations to private beach setups.
Final breakfast by your private chef. Last swim at the Beach Club. Private transfer to the airport and charter flight back to San Juan. You'll leave Oil Nut Bay wondering how the rest of the world gets by without this kind of beauty.
The ultimate BVI sailing adventure. A week aboard a luxurious 60ft+ crewed catamaran with your own captain, private chef, and stewardess. Every meal, every drink, every watersport — included. Your itinerary is fully customizable, from The Baths to Anegada's lobster shacks to Jost Van Dyke's legendary beach bars.
Private transfer from San Juan (SJU) to Beef Island (EIS), Tortola, then to your awaiting yacht. Meet your captain, chef, and stewardess. Settle into your cabin on a stunning crewed catamaran, enjoy welcome cocktails, and cruise to your first anchorage as the chef prepares a gourmet dinner onboard.
Sail to Virgin Gorda and explore The Baths — massive granite boulders forming grottoes, tide pools, and tunnels leading to a hidden beach. Snorkel the crystal-clear waters, then enjoy a fresh seafood lunch onboard. Afternoon at leisure in North Sound near the Bitter End Yacht Club.
Sail north to Anegada, the flat coral island famous for its lobster and 18 miles of pristine white-sand beaches. Lunch at a beachside shack with the freshest Caribbean lobster you'll ever taste. Snorkel at Loblolly Bay, spot flamingos in the salt ponds, and fall asleep at anchor under a blanket of stars.
Sail to Cooper Island for a stop at the eco-friendly Beach Club — craft cocktails, locally brewed beer, and fresh-caught fish. Then over to The Indians, a cluster of rock pinnacles with some of the best snorkeling and diving in the BVI. Evening at anchor with a gourmet chef-prepared dinner.
Two days in the BVI's most beloved island. Hit all the legendary spots — Soggy Dollar Bar for Painkillers, Foxy's for stories and live music, Ivan's Stress Free for the vibe, and Hendo's Hideout for the view. Paddleboard, kayak, snorkel, or simply float. Your chef pulls out all the stops for a farewell dinner under Caribbean stars.
Final breakfast on deck as your captain sails back to Tortola. Disembark with a week of extraordinary memories. Private transfer to the airport for your flight home — or ask us about extending with a villa stay on Virgin Gorda or a resort night on Tortola.