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Classic Caribbean

Classic Caribbean

At a glance

Duration: 8 Days, 7 Nights

Coverage: Roundtrip Philipsburg, St. Maarten

From: $1,999

Season: January - March, December

Activities: Adventure, Culture, History, Wildlife

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

Wind Star Cruises

Discover Windstar’s landmark Caribbean cruise.

From the stunning drama of the Pitons to the captivating charm of Les Saintes. From hidden coves and secret beaches to exotic markets and lively cafés. Discover the best of this region with one single Caribbean cruise. Sandy beaches, turquoise waters, lush mountains, and beautiful waterfalls blend with the music, tastes, and joie de vivre unique to the Caribbean life.

Popular Highlights

  • Anchor alongside the pristine beaches of Pigeon Island’s 40-acre National Park and explore at your leisure
  • Discover St. Lucia’s twin Pitons, rising majestically from the turquoise sea
  • Savor the distinctive French charm of enchanting Les Saintes
  • Embrace the island life on St. Kitt’s one-of-a-kind Shipwreck Beach
  • Let yourself go – at Windstar’s signature beach barbecue, the Caribbean’s best party
  • Enjoy the unspoiled paradise of Barbuda, with its pink beaches and soaring frigate birds

Day-to-Day Itinerary

Day 1 - Philipsburg, St. Maarten

Pastel-colored buildings and shops filled with tempting souvenirs herald your arrival to bustling Philipsburg. Situated near the harbor on the Dutch side of St. Maarten, Philipsburg owes its discovery to Christopher Columbus in 1493. Today, celebrated Front Street is home to a number of local Creole restaurants as well as jewelry stores, stylish boutiques, and lively casinos for visitors seeking an upbeat island experience.

Day 2 - Barbuda, Barbuda

Oh so pretty in pink. Beaches, that is. This is another of those ports reserved for the yachting set, with an appropriately laid-back atmosphere that ranks bird watching and collecting conch shells as an ambitious day.

Day 3 - Roseau, Dominica

Get ready for a full day with plenty to do. Snorkel alongside brilliant parrot fish in the bubbly waters of Champagne Beach. Take a break to enjoy more than 150 species of plants and brilliant red-necked Jaco parrots at the botanical gardens. If you’re up for an optional hike, don’t miss Boiling Lake and the Valley of Desolation at Dominica’s Morne Trios Pitons National Park, a UNESCO World Heritage Site.

Day 4 - Pigeon Island, St. Lucia

The Pitons’ two volcanic peaks rise more than 2,400 feet to welcome you to St. Lucia, an island of lush green valleys, vast banana plantations, and bubbling sulfur springs. With 24 miles of vibrant coral reef, this is a slice of maritime heaven for divers and snorkelers. Nearby Pigeon Island National Park features impressive ruins of English forts, archaeological relics of Arawak Indians, and more splendid beaches.

Day 5 - 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. Thanks to their relative isolation, the islands of Les Saintes have maintained much of their original character. The underwater world here has attracted the likes of Jacques Cousteau, but even novice snorkelers will enjoy exploring these impossibly blue waters.

Day 6 - Basseterre, St. Kitts - Nevis, The Federation of St. Kitts and Nevis

Situated against an irresistible backdrop of emerald green hills, Basseterre is one of the loveliest of the Caribbean’s small capitals. Although the town is populated by elegant Georgian architecture, more than a quarter of St. Kitts has been set aside as a national park.

A nature lover’s delight is found on this tiny Caribbean paradise of secluded black-sand beaches, protected reefs, crystal-clear water, and lush velvety rainforest. Nevis is home to a broad range of animal life including Southern stingrays, hawksbill turtles, tropical birds, and the well-known green vervet monkey.

Day 7 - Gustavia, St. Barthelemy

A favorite destination of yachtsmen, chic St. Barts is a treasure in every way. Put in alongside the mega yachts of the rich and famous and head for the white sands of nearby Shell Beach. A short walk into town leads you to Le Cellier du Gouverneur. Housed in a lovely pale blue building, the shop offers a distinctive selection of fine French wines. As evening comes, you’ll slip away under the gentle power of open sails.

Day 8 - Philipsburg, St. Maarten

Pastel-colored buildings and shops filled with tempting souvenirs herald your arrival to bustling Philipsburg. Situated near the harbor on the Dutch side of St. Maarten, Philipsburg owes its discovery to Christopher Columbus in 1493. Today, celebrated Front Street is home to a number of local Creole restaurants as well as jewelry stores, stylish boutiques, and lively casinos for visitors seeking an upbeat island experience.

Disembark for your travel back home.

Dates & Rates

Dates Ship B BX A AX TX Suite Bridge Suite
Nov 25, 2017 Wind Surf $1,499 $1,599 $1,699 $1,899 $2,099 $2,599 $3,499
Dec 9, 2017 Wind Surf $1,699 $1,799 $1,899 $2,099 $2,299 $2,799 $3,699
Dec 23, 2017 Wind Surf $2,699 $2,899 $3,099 $3,399 $3,699 $4,899 $6,499
Jan 6, 2018 Wind Surf $1,699 $1,799 $1,899 $2,099 $2,299 $2,999 $3,999
Jan 20, 2018 Wind Surf $1,999 $2,199 $2,299 $2,499 $2,799 $3,599 $4,799
Feb 3, 2018 Wind Surf $1,999 $2,199 $2,299 $2,499 $2,799 $3,599 $4,799
Feb 17, 2018 Wind Surf $1,999 $2,199 $2,299 $2,499 $2,799 $3,599 $4,799
Mar 3, 2018 Wind Surf $1,999 $2,199 $2,299 $2,499 $2,799 $3,599 $4,799

Map

Classic Caribbean

Ships

Wind Surf

Wind Surf Hosting only 310 privileged guests, the gleaming decks and sparkling sails of the Wind Surf invite you to discover a world of gracious indulgence. From sumptuous staterooms and suites to the cozy sophistication of the Yacht Club living room and library, every detail is designed for contemporary luxury. Treat your palate to the nouveau French cuisine of Stella Bistro. Work out in the state-of-the-art top deck Fitness Room with a sweeping sea view. Relax in the whirlpools or swimming pool. Or bask like royalty in the beautiful WindSpa. With an international crew of 191, your wish is our command. View ship details...

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