Icon image 5 Days Island hopping in the Virgin Islands

Inspiring Itinerary

5 Days Island hopping in the Virgin Islands

5 Days4 NightsSt Croix to Anegada
73 nautical miles
SeasonIdeal for Winter and Early Spring Season

Itinerary summary


Day 1St Croix

Day 2St John

Day 3Cooper Island

Day 4Trellis Bay

Day 5Anegada

About

This curated itinerary takes you from the cultural richness of St. Croix, with its Danish colonial architecture and vibrant local spirit, to the untouched natural beauty of St. John, where two-thirds of the island is protected national parkland. As you cruise into the British Virgin Islands, enjoy the tranquil charm of Cooper Island, known for its eco-friendly beach club and excellent snorkeling just off the mooring field. At Trellis Bay, immerse yourself in a creative community famous for its full moon parties and art installations—don’t miss the fire balls lit over the water. Your journey concludes in Anegada, the only coral atoll in the Virgin Islands, boasting powdery white beaches, flamingo-filled salt ponds, and fresh grilled lobster that’s practically a rite of passage.

Destination image
Destination image
Destination image
Day 1 - St Croix
Day 1

St Croix

Home to the only underwater U.S. national monument

LocationStarting point

Set sail for St. Croix, the largest of the US Virgin Islands. For an unforgettable snorkelling experience, head to the Pier, where you'll encounter a vibrant array of tropical reef fish. If you're seeking seclusion, make your way south to Sandy Point, the longest beach in the US Virgin Islands! Another popular spot is Christiansted, the island's largest town, with a picturesque harbor and charming colonial architecture. Here, you can explore the historic buildings, visit the Fort Christiansvaern museum, and sample the local cuisine at the many restaurants and cafes. If you're a history buff, a visit to the Estate Whim Plantation Museum is a must, where you'll learn about the island's colonial past and the history of the sugar industry. Also explore the coral reefs, underwater caves, and shipwrecks all teeming with exotic marine life. Avid divers can experience the thrill of diving in one of the world's most stunning underwater landscapes.

Day 2 - St John
Day 2

St John

Two-thirds of the island is protected national park

Distance36nm

The island is the least populated in the U.S. Virgin Islands (USVI), but what this tiny beauty lacks in size, it makes up for in magnificence and natural charm. Once you set anchor, you will reconnect with unspoiled nature. Saint John is widely known for having some of the whitest beaches in the world, as evident with a visit to Maho Bay, particularly Maho Beach, a 3-mile stretch of fine sand for your late afternoon walking enjoyment. Take advantage of a visit to Cruz Bay or Caneel Bay for a spot of shopping.  

Where to eat: Any place operating since the 1980s must be doing something right, which is most definitely the case at Morgan’s Mango. The restaurant is a melting pot of cultures and flavors of the Caribbean. Influences from French, Spanish, Indian, Chinese, and many more are melded into Morgan's menu.

Day 3 - Cooper Island
Day 3

Cooper Island

An eco-friendly island known for its solar-powered beach club

Distance13nm

Cooper Island, one of the most beautiful British Virgin Islands, has a fascinating history.  It was once known as Bergen Island when it was administered by Sweden and Norway until 1905. Today it is home to the magnificent  Cooper Island Beach Club, a relaxing eco-resort that is a perfect stop for yachts seeking shelter in the bay, or for lunch and happy hour. The area's variety of fish, turtles and rays makes it ideal for snorkeling. The Cooper Island Beach Club Rum Bar has over 280 rums and is a great place to relax and enjoy the views. Cooper Island offers natural beauty, history, and a laid-back atmosphere, perfect for yachting.

Day 4 - Trellis Bay
Day 4

Trellis Bay

Famous for its Full Moon Parties

Distance4nm

The Trellis Bay area with its rich history and vibrant present is a superb destination to experience pristine island life. As you set sail from mainland Tortola, cross over the iconic Queen Elizabeth Bridge to Beef Island, where you'll experience the quintessential beauty of the unspoiled British Virgin Islands. The vibrant Trellis Bay is a hub of activity year-round, offering an array of popular restaurants, bars, and shops, perfect for stocking up on unique local artworks, souvenirs, and delicious local cuisine. Drop anchor at Bellamy Cay, a picturesque islet nestled in the heart of the bay. Take a plunge into the crystal-clear waters and explore the magnificent waters around the bay. Trellis Bay is the epitome of pristine island life that will offer you unparalleled opportunities to explore the unspoiled British Virgin Islands.

Day 5 - Anegada
Day 5

Anegada

The only coral island in the Virgin Islands

Distance20nm

An island surrounded by just as many shipwrecks as fish, Anegada is best explored below the surface. Horseshoe Reef is a particularly good spot to snorkel or dive with centuries-old wrecks, such as the Astraea shipwreck. Sea turtles are aplenty, while above the surface you'll likely see more pink flamingos than people. Learn to kitesurf at Keel Point, cruise lazily alongside the resident turtles on a paddleboard at Loblolly Bay. Take a midday break dining on fresh seafood at Lobster Trap Restaurant or swaying in a hammock with a novel and a drink at Anegada Beach Club.