Sublime Southern Caribbean

Detailed Itinerary

Day-by-day description of your cruise and cruise activities.

Day 1 - January 04, 2026

Bridgetown

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 - January 05, 2026

Mayreau

With fewer than 300 inhabitants and miles of secluded beaches, it's easy to feel as if you're on your own private island. Saline Bay is a delightful anchorage that separates the Caribbean from the Atlantic - and a perfect place to play with some of the toys from the Watersports Platform.

Day 3 - January 06, 2026

Roseau

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 Trois Pitons National Park, a UNESCO World Heritage Site.

Day 4 - January 07, 2026

Anse Mitan

Martinique offers a delightful and distinctive blend of French and Caribbean influences, with a bounty of historical sites, museums and a wide array of excellent shopping. Be sure to take a tour of the beautiful Jardin de Balata Botanical Gardens with exotic plants from around the world and a treetop walkway affording mountain views.

Day 5 - January 08, 2026

Charlestown

This capital of Nevis with its narrow streets and brightly painted Victorian and Georgian stone buildings is full of colonial history. Alexander Hamilton lived here as a child and you can see the ruins of the Hamilton Estate. Lovely Pinney’s Beach is nearby and a group of volunteers work at night tagging sea turtles here and on the other beautiful beaches. Walk the main street and check out the Museum of Nevis History, St. Thomas Lowland Church and the Nevisian Heritage Village to name a few of the historic sites here.

Day 6 - January 09, 2026

Basseterre

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 7 - January 10, 2026

St. John's

St. John’s is a city of Old World charm and elegance which lingers in the varied architecture of Georgian, Victorian, Vernacular, Romantic and International flavors. The picturesque seafront where tiny, colorful boats are moored, the cheerful wooden buildings carefully refurbished to retain their original features, the vibrant Market Street offering vegetables, fruit and fish and the duty-free Heritage Quay shopping area provide a delightful atmosphere to captivate you. Sites to see include St. John’s Cathedral with its white Baroque towers, the Botanical Garden, St. John’s Antigua Lighthouse, and Fort James.

Day 8 - January 11, 2026

Falmouth Harbour

It’s said that Antigua has 365 beaches – one for every day of the year. See how many you can discover as our stay in port stretches into the evening to accommodate them all. Watch the stars come out as darkness falls and imagine how residents of Andromeda must envy you.

Day 9 - January 12, 2026

Gustavia

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 10 - January 13, 2026

Road Bay

With its protected shoreline, calm surf, spectacular coral reefs and sugar-soft beaches, Road Bay has become a destination for boaters, with its delightful restaurants, bars, and shops. Anguilla has some of the most beautiful sunsets and delicious rum punch to be found in the Caribbean. It is also home to Cuban tree frogs, red-footed tortoise, green iguanas and five species of bats. Worth checking out is Wallblake House, a heritage plantation house and museum said to be the oldest building on the island and located nearby.

Day 11 - January 14, 2026

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.

Ship

Your cruise ship

The Wind Spirit sails through tranquil waters, flanked by lush green mountains under a clear sky.

About this ship

Wind Spirit

Wind Spirit is a graceful four-masted sailing yacht that reflects Windstar Cruises’ dedication to authentic, small-ship exploration. Designed for just 148 guests, this intimate vessel offers an elegant blend of traditional seafaring charm and contemporary comfort, creating a uniquely personal and immersive cruise experience.

Launched in 1988 and meticulously updated over the years, Wind Spirit sails primarily under wind power, with computer-assisted sails that unfurl silently above its teak decks. Its sleek design and shallow draft allow it to glide into quiet harbors, secluded coves, and hidden ports that are beyond the reach of larger cruise ships. Whether anchored off a pristine island or docked in a bustling coastal town, the ship brings guests closer to each destination—both physically and culturally.

The yacht features 74 well-appointed oceanview staterooms, including one spacious Owner’s Suite. Each stateroom is designed for comfort and relaxation, with a soothing coastal color palette, soft lighting, and thoughtful details. Guests enjoy queen-size beds with fine linens, marble-accented bathrooms stocked with L’Occitane amenities, flat-screen TVs, and fully stocked minibars. The Owner’s Suite provides additional space with a sitting area and a refined, residential feel.

Dining on Wind Spirit is relaxed yet sophisticated. Amphora, the main dining room, serves a rotating menu of regionally inspired cuisine crafted with fresh, local ingredients. Veranda offers a bright, airy setting for breakfast and lunch with both buffet and à la carte options. In the evenings, Candles transforms an open deck into a romantic al fresco restaurant featuring expertly grilled entrees under the stars. Room service is available around the clock for those who prefer the privacy of in-suite dining.

Onboard amenities support both leisure and adventure. A small plunge pool and whirlpool provide refreshing spots to unwind with ocean views. The World Spa offers rejuvenating treatments, while the fitness center is equipped with modern cardio and strength-training machines. A standout feature of the ship is the aft watersports platform, which lowers directly into the sea and offers complimentary kayaks, paddle boards, snorkel gear, and more when the ship is at anchor.

Wind Spirit sails to some of the world’s most naturally stunning and culturally rich destinations, including the Greek Isles, Tahiti, the Caribbean, and coastal Central America. Every itinerary is carefully curated to showcase the character and charm of each region, with immersive shore excursions and Windstar’s signature small-port access.

Offering the romance of true sailing, the comfort of a luxury yacht, and the warmth of personalized service, Wind Spirit is a perfect choice for travelers who want to slow down, savor the journey, and experience the world from the water’s edge.

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