The Virgin Islands are where Caribbean yacht charter itinerary dream comes alive. Turquoise waters, trade winds whispering across your sails, and anchorages that feel like private sanctuaries — this is island-hopping at its most effortless. Split between the US and British Virgin Islands, the region offers short sailing distances, protected waters, and endless choices for beaches, snorkeling spots, and laid-back island culture.
This week-long Virgin Islands charter itinerary blends the must-see highlights with hidden coves and local flavor. Whether you’re here for water sports, beach bars, or serene sunsets, every day delivers a new discovery.
Day 1: St. Thomas – Gateway to the Virgins
Your journey begins in St. Thomas, the most accessible hub for the Virgin Islands. After a seamless airport transfer, you’ll step aboard your yacht in Charlotte Amalie or Red Hook. The crew greets you with chilled cocktails and a chef-prepared welcome lunch.
Depending on arrival time, you might fit in a short afternoon cruise to a nearby anchorage like Christmas Cove — a calm spot for your first swim or paddleboard session. As night falls, dine alfresco on deck, the city lights of St. Thomas twinkling in the distance, before retreating to the gentle sway of your cabin.
Day 2: St. John – Pristine National Park
Just a short cruise east lies St. John, where two-thirds of the island is protected as a US National Park. Drop anchor in Caneel Bay or Maho Bay, where turtles drift lazily through the shallows.
Spend the morning snorkeling or trying your first paddleboard session in waters as clear as glass. Onshore, hiking trails wind through tropical forest to ruins and panoramic lookouts — a rewarding change of pace for active families. In the evening, your crew might arrange a beach barbecue under the stars, with the smell of grilled lobster mingling with the warm Caribbean breeze.
Day 3: Jost Van Dyke – Beach Bars and Barefoot Vibes
Sail west to Jost Van Dyke, a British Virgin Island that epitomizes Caribbean fun. White Bay is your anchorage, a perfect crescent of sand lined with iconic beach bars. The most famous is the Soggy Dollar Bar, birthplace of the Painkiller cocktail — a blend of rum, pineapple, orange, and nutmeg that tastes like pure island spirit.
Spend the afternoon beach-hopping, swimming in shallow waters, or simply swaying in a hammock with a drink in hand. As the sun sets, Jost Van Dyke turns into a lively social hub, where yacht crews and locals mingle. Back aboard, your yacht becomes the quiet retreat, letting you savor the night your way.
Day 4: Norman Island – Caves and Legends
From Jost, a gentle sail brings you to Norman Island, long rumored to be the inspiration for Robert Louis Stevenson’s Treasure Island. Drop anchor in The Bight, a sheltered bay with calm waters perfect for every water toy — from jet skis to seabobs.
The highlight here is the Norman Island Caves, where you can snorkel into sea-carved grottoes alive with colorful fish. For divers, the nearby Indians rock formation offers dramatic underwater scenery. Evening brings a unique choice: a lively dinner at the floating restaurant Willy T’s, or a quiet, chef-prepared meal aboard your yacht under a canopy of stars.
Day 5: Virgin Gorda – The Baths and Beyond
Virgin Gorda is a crown jewel of the BVI. Arrive mid-morning and tender ashore to The Baths, a geological wonder where massive granite boulders form caves, pools, and grottoes you can explore on foot and by snorkel.
Afterward, cruise to North Sound, home to luxury resorts and calm anchorages. Leverick Bay or Oil Nut Bay are perfect for a leisurely afternoon. The protected waters here are ideal for kiteboarding, paddleboarding, or simply floating on inflatables while the crew serves chilled rosé. Dinner ashore at a local restaurant can cap off the day, or you can opt for private dining on the aft deck with views stretching to the horizon.
Day 6: Anegada – Off the Beaten Path
Unlike the mountainous terrain of other Virgin Islands, Anegada is a low-lying coral atoll. Its remoteness makes it a unique stop on any charter itinerary. Cruise in early and prepare for a day of exploring.
The highlight? Lobster. Anegada is famed for its beachside lobster feasts, often grilled over open flames just steps from the sand. In between, you can rent scooters to circle the island, lounge on endless beaches with barely another soul in sight, or snorkel Horseshoe Reef, one of the largest barrier reefs in the Caribbean.
Day 7: Return to St. Thomas via Tortola
On your final day, set course westward. Pause at Tortola, the largest of the British Virgin Islands, for a last swim or stroll through Road Town’s bustling markets. Pick up artisanal souvenirs, spices, or Caribbean rum to take home.
From here, it’s a short sail back to St. Thomas, where your charter concludes. Bid farewell to your crew, knowing you’ve not only seen the Virgin Islands but experienced them in a way few travelers ever do — with the sea as your highway and the yacht as your sanctuary.
Insider Tips: Making the Most of a Virgin Islands Charter
- Easy Access: St. Thomas is served by direct flights from many US cities, making the region one of the most convenient charter destinations.
- Passports & Customs: You’ll be crossing between the USVI and BVI. The crew handles customs formalities, but bring valid passports for smooth passage.
- Weather & Seasons: The Virgin Islands enjoy year-round warmth, with peak charter season from December to April. Summer offers quieter anchorages but comes with higher humidity and occasional showers.
- Provisioning: Both St. Thomas and Tortola have excellent provisioning services, ensuring your yacht is fully stocked before departure.
Wrapping Up: The Virgin Islands Promise
The Virgin Islands are often called the “Sailor’s Playground,” and with good reason. Distances are short, anchorages are sheltered, and each island offers its own charm — from the barefoot bars of Jost Van Dyke to the hidden coves of Norman Island and the surreal landscapes of Virgin Gorda.
A week here feels like both an escape and an immersion, balancing relaxation with discovery. And when you charter a yacht, the experience goes beyond sightseeing: it’s about connection — to the sea, to each other, and to a rhythm of life that’s impossible to replicate on land.
