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Antilles Island Hopping

Antilles Island Hopping

At a glance

Duration: 8 Days, 7 Nights

Coverage: Barbados to San Juan, Puerto Rico

From: $1,899

Season: January - February

Activities: Adventure, Culture, History, Wildlife

Book this Trip › or call us toll-free 1-888-815-5428

Wind Star Cruises

Trade your down-filled comforter for a bright beach towel during this weeklong cruise up the Windward and Leeward Islands from Bridgetown, Barbados to San Juan, Puerto Rico. Whether you’re eager for new adventures or simply want a relaxing beach and a rum punch, this journey melts winter doldrums.

Ride an electric tram deep into underground chambers near Bridgetown and discover waterfalls, bubbling streams, towering stalagmites and daunting stalactites. Observe endangered Hawksbill sea turtles as they are rehabilitated at the Old Hegg Turtle Sanctuary in Bequia. Sample sweet green figs or fried plantains in a St. Lucia open market, or savor pork hocks among the small cafés in the port capital of Castries. Paddle a glass-bottom, two-person kayak through the turquoise shallows surrounding the remote archipelago of Les Saintes in Guadeloupe. Discover the convenience and visual clarity of Snuba snorkeling among vibrant gobies, squirrelfishes and surgeonfishes off South Friars Beach in Basseterre. Shop for unique handcrafted rings, bracelets and necklaces, summer-ready beachwear, or simply sip an iced coffee in Gustavia on St. Barts.

Before your week wraps up, you’ll land at Virgin Gorda, where you can relax at nearby bays and beaches, or elevate your heartrate with an invigorating hike up to the scenic summit of Virgin Gorda Peak. At the end of your week you’ll land at San Juan, the capital of Puerto Rico. Shop Old San Juan, explore the elegant and historic La Fortaleza governor’s house or take in the local artistic works and historic artifacts at several museums.

Popular Highlights

  • Discover the magic of Harrison’s Cave and the UNESCO sites of Bridgetown
  • Stand on deck for scenic cruising past the UNESCO World Heritage Site Pitons (volcanic spires) on St. Lucia
  • Take a walk up Mount Pleasant and see the amazing view from Fort Hamilton on Bequia
  • Make time for a visit to Brimstone Hill Fortress National Park, a UNESCO site in lovely Basseterre
  • Savor the beauty of scenic cruising around St. Vincent & the Grenadines
  • Save your appetite for Windstar's Signature Beach Party with plenty of Caribbean flavors and spirit

Day-to-Day Itinerary

Day 1 - Bridgetown, Barbados

Jolly old England comes to life in the city and its garrison, both UNESCO World Heritage Sites. Further afield, you’ll find historic sugar plantations and the fairyland magic of Harrison’s Cave.

Day 2 - Bequia, St. Vincent & the Grenadines

The only ships in port are those small enough to anchor alongside the yachts and fishing boats in Admiralty Bay. Bequia’s whaling heritage is on display in the museum in pretty Port Elizabeth, or watch the island’s famed model boat builders at work on their miniature masterpieces.

Day 3 - Castries, St. Lucia

The capital and largest city of St. Lucia is a bustling port where shoppers flock. Most of the city’s historic buildings were destroyed in major fires between 1785 and 1948 but you’ll see the beautiful, scenic backdrop of Morne Fortune (elev. 2,795 ft.) and the bustling harbor. Visit the Castries Market for handicrafts, fruits and vegetables, see the murals painted by a local artist and housed in the Cathedral of the Immaculate Conception, and check out one of the many restaurants or Derek Walcott Square.

Day 4 - Les Saintes, Guadeloupe

This is the Caribbean as you’ve always imagined it, with yacht-filled harbors set against volcanic mountains and endless stretches of palm-fringed beach. The underwater world here attracted the likes of Jacques Cousteau, but even novice snorkelers will enjoy exploring these impossibly blue waters.

Day 5 - Basseterre, St. Kitts

With Georgian architecture situated against an irresistible backdrop of emerald green hills, Basseterre is one of the loveliest of the Caribbean’s small capitals. Beyond town, more than a quarter of St. Kitts has been set aside as Brimstone Hill Fortress national Park, a UNESCO World Heritage Site.

Day 6 - Gustavia, St. Barthélemy

Affectionately known as St. Barts, the Caribbean’s most chic island adds a French flair to Riviera-like beaches and duty-free boutiques. Walk past gingerbread cottages in search of celebrities, shop for designer fashions, or sip the island’s signature ti punch as kite surfers fly by.

Day 7 - Virgin Gorda, Prickly Pear Beach, B.V.I

A beautiful coral reef wavers just beneath you as your ship makes the break into exclusive North Sound. You can imagine the reaction of the locals watching from The Bitter End Yacht Club as your ship comes around the corner under full canvas. At the other end of the island lies the curious assembly of house-sized boulders called “The Baths,” which form huge underground pools and caverns that you’re free to explore.

Day 8 - San Juan, Puerto Rico

The imposing façade of El Morro fortress is just one of the many UNESCO World Heritage Sites in San Juan. Admire the colorful colonial buildings from your casually elegant ship, docked right in the heart of Old San Juan.

Antilles Island Hopping

Dates & Rates

Dates Ocean View Suite Ocean View Suite 1 Ocean View Suite 2 Ocean View Suite 3 Balcony Suite Balcony Suite 1 Classic Suite Owner's Suite
1/12/2019 $1,999 $2,099 $2,299 $2,499 $2,899 $3,099 $4,499 $5,799
1/26/2019 $1,899 $1,999 $2,199 $2,399 $2,799 $2,999 $4,399
2/9/2019 $2,199 $2,299 $2,499 $2,699 $3,099 $3,299 $4,699 $5,699
2/23/2019 $2,199 $2,299 $2,499 $2,699 $3,099 $3,299 $4,699 $5,699


Star Pride

Star Pride The graceful, suite-only Star Pride is the first of Windstar's three new power yachts. With only 212 guests, you begin to feel like it's your own private yacht almost as soon as you step aboard. View ship details...