Destination	Arrival	Departure
St. Maarten (Philipsburg) St. Maarten (Philipsburg) 01/04/2026 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.	01/04/2026	01/04/2026
Falmouth Harbour, Antigua Falmouth Harbour, Antigua 01/05/2026 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.	01/05/2026	01/05/2026
Road Bay Road Bay 01/06/2026 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.	01/06/2026	01/06/2026
Sopers Hole, Tortola Sopers Hole, Tortola 01/07/2026 Arrive at the boardwalk of Pusser’s Landing and mingle with other yachtsmen in the utterly charming marina at Soper’s Hole. Find a deserted stretch of beach to kick back and ponder this tiny port’s rich heritage of romance, pirates, and adventure. An evening departure features a once-in-a-lifetime romantic sunset Sail Away.	01/07/2026	01/07/2026
Jost Van Dyke Jost Van Dyke 01/07/2026 For an island comprised of a mere eight square miles, it’s amazing how much there is to do on Jost Van Dyke. Visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis Drake Waterway. After all that, you’ll be ready for an evening drink on the beach — where you can admire your Windstar ship aglow in the harbor.	01/07/2026	01/07/2026
Jost Van Dyke Jost Van Dyke 01/08/2026 For an island comprised of a mere eight square miles, it’s amazing how much there is to do on Jost Van Dyke. Visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis Drake Waterway. After all that, you’ll be ready for an evening drink on the beach — where you can admire your Windstar ship aglow in the harbor.	01/08/2026	01/08/2026
Virgin Gorda Virgin Gorda 01/09/2026 The beautiful Bank Barrier coral reef wavers just beneath you as your ship makes the break to the bird sanctuary of Prickly Pear Island, so named because it is dotted with prickly pear cacti. Althought uninhabited, it does have a beach bar and water sports facilities. Not far away lies the curious assembly of house-sized boulders called “The Baths,” which form huge underground pools and caverns	01/09/2026	01/09/2026
Gustavia Gustavia 01/10/2026 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.	01/10/2026	01/10/2026
St. Maarten (Philipsburg) St. Maarten (Philipsburg) 01/11/2026 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.	01/11/2026	01/11/2026
Basseterre, St. Kitts Basseterre, St. Kitts 01/12/2026 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.	01/12/2026	01/12/2026
Little Bay Little Bay 01/13/2026 Today we visit “Pompeii of the Caribbean”—an island that is half lush and green, half gray and covered in ash by a volcano in 1995. And if a half-buried city isn’t intriguing enough, there are black-sand beaches and a perplexing Irish heritage to explore.	01/13/2026	01/13/2026
Gustavia Gustavia 01/14/2026 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.	01/14/2026	01/14/2026
Deshaies, Guadeloupe Deshaies, Guadeloupe 01/15/2026 Situated near the Grand Anse beach, Deshaies has the deepest bay of all the Caribbean coasts with the best natural protection which made it a shelter for pirates of days gone by and is said to still be housing treasures on the Island. Grand Anse beach is one of the most beautiful of the islands with its over half a mile of fine golden sand and coconut palms.	01/15/2026	01/15/2026
Roseau, Dominica Roseau, Dominica 01/16/2026 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.	01/16/2026	01/16/2026
Pigeon Island, St. Lucia Pigeon Island, St. Lucia 01/17/2026 The UNESCO site Pitons’ with their two majestic volcanic peaks and 24 miles of vibrant coral reef welcome you to St. Lucia. Nearby Pigeon Island National Park features impressive ruins of English forts, archaeological relics of Arawak Indians, and splendid beaches.	01/17/2026	01/17/2026
Bridgetown (Barbados) Bridgetown (Barbados) 01/18/2026 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.	01/18/2026	01/18/2026
Anse Mitan Anse Mitan 01/19/2026 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.	01/19/2026	01/19/2026
Castries Castries 01/20/2026 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. Optional Private Excursions Avoid the crowds and hustle and bustle associated with a group activity. For a memorable trip ashore, we invite you to consider a private shore excursion. Enjoy the undivided attention of your own driver/guide and the flexibility of experiencing the aspects of the local culture that most interest you. Below are just some samples of the private shore excursions we can arrange for you. Let us personalize your experience! Essence of St. Lucia Enjoy an authentic St. Lucian experience blending the past and present as you See, Taste and Smell the flavors of the island while discovering, exploring and learning about life here in days gone by. Depart your hotel/or Cruise Ship for Greenwood Terrace where you stroll through the gardens amidst tropical fruit trees and flowering plants growing in profusion. See a Traditional Medicinal herb Garden and learn how our forefathers and local folklore used those herbs. Travel back in time as you view the ancient “Platene” used in the making of Sugar and Farine (a by -product of Cassava – an Amerindian dish). See an “Old Styled Fowl Coop” (Chicken House), the outdoor cooking fireplace, and Clay Oven used for baking bread. Discover the secrets of local Coconut Oil and of Bay Rum, a by- product of the Bay Leaf Learn intriguing facts about our Traditional Creole Headwear and Dress. View a brilliant and interesting display of Historic artifacts depicting the Amerindian, European and African influences on our history. Taste a variety of tropical fruits, island delicacies, local rums and much more. An interactive experience which showcases the island and offers you a deep insight into the “Essence of St. Lucia.” HIGHLIGHTS: . Guided tour through herbal tropical garden . Tour of the onsite museum . Tasting of local fruits juices and delicacies Tour Duration: 2.5 hours Further Information Resort and Cruise passengers will be met and escorted by a Barefoot Holidays Representative. Flavors of St. Lucia Enhance your visit to St. Lucia as you explore the island’s creole cuisine through a specially designed “Culinary Experience” and learn how over the years, St. Lucian folk lore combined and blended a fascinating number of herbs, vegetables and fruits into an array of cooked foods that must be tasted to be believed. Participate in the preparation of the various dishes ……get involved in the process ….. Try your hand (if you wish) under the guidance of our expert island chef. See the transformation take place right before your very eyes. Enjoy the tasty dishes. Take home not only fond memories of this authentic “Island Culinary Experience” but also those of a relaxing walk through the beautiful garden , replete with an array of tropical fruits, flowering plants, a local medicinal garden. Visit to the onsite museum, and much more. A Hands On, Informative, Relaxing and Educational experience for all. HIGHLIGHTS · An authentic culinary experience · Discover the secrets of authentic St. Lucian cooking . Learn from a renowned island Chef . Become a certified St. Lucian cook . Enjoy a delicious meal · Admire our onsite museum · Visit a traditional herb garden and a walk amidst beautiful tropical flora and fruit trees Duration – 3 hours	01/20/2026	01/20/2026
Pigeon Island, St. Lucia Pigeon Island, St. Lucia 01/20/2026 The UNESCO site Pitons’ with their two majestic volcanic peaks and 24 miles of vibrant coral reef welcome you to St. Lucia. Nearby Pigeon Island National Park features impressive ruins of English forts, archaeological relics of Arawak Indians, and splendid beaches.	01/20/2026	01/20/2026
Pigeon Island, St. Lucia Pigeon Island, St. Lucia 01/21/2026 The UNESCO site Pitons’ with their two majestic volcanic peaks and 24 miles of vibrant coral reef welcome you to St. Lucia. Nearby Pigeon Island National Park features impressive ruins of English forts, archaeological relics of Arawak Indians, and splendid beaches.	01/21/2026	01/21/2026
Bequia, Grenadines Bequia, Grenadines 01/22/2026 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.	01/22/2026	01/22/2026
Mayreau, Grenadines Mayreau, Grenadines 01/23/2026 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.	01/23/2026	01/23/2026
St. George's, Grenada St. George's, Grenada 01/24/2026 Inhale the intoxicating aroma of the “Isle of Spice” as your eyes feast on what is widely claimed to be the most beautiful city in the Caribbean. Spend the day on 2-mile-long Grand Anse beach, and before you go, a taste of nutmeg ice cream is a must.	01/24/2026	01/24/2026
Bridgetown (Barbados) Bridgetown (Barbados) 01/25/2026 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.	01/25/2026	01/25/2026
Man O'War Bay, Tobago Man O'War Bay, Tobago 01/26/2026 Listen for the sound of a conch announcing the return of the fishing boats. Bobbing next to us are flotillas of pelicans – hinting at the excellent snorkeling waiting for you here and in neighboring Pirate’s Bay.	01/26/2026	01/26/2026
Mayreau, Grenadines Mayreau, Grenadines 01/27/2026 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.	01/27/2026	01/27/2026
Soufriere Soufriere 01/28/2026 Nestled in the shadows of the UNESCO Pitons, Soufriere represents the heart and soul of St. Lucia. The tiny town center is full of street vendors and stores and some of the best resorts on the island can be found here. Nearby are secluded waterfalls and the waters here boast some of the best diving around. Sights to see include the Edmund Rainforest Trail, fond Doux Holiday plantation, Robot Estate and the Gros Piton Nature Trail. Optional Private Excursions Avoid the crowds and hustle and bustle associated with a group activity. For a memorable trip ashore, we invite you to consider a private shore excursion. Enjoy the undivided attention of your own driver/guide and the flexibility of experiencing the aspects of the local culture that most interest you. Below are just some samples of the private shore excursions we can arrange for you. Let us personalize your experience! St. Lucia - Gros Piton Climb Life has its rewards, you will find many of them on the Gros Piton Nature Trail. Travel by coach along the scenic West Coast of the island through lush tropical vegetation onto the Fond Gens Libre, "village of the free people" community, to the welcome center. From this point, you are joined by a knowledgeable guide, who would guide you along the trail which winds around the mountain at a gradual gradient. Enjoy panoramic vistas in every direction and see Petit Piton in the distance. The first half of the trail is moderate and can be enjoyed by everyone, while the second half involves a steep accent to the summit suitable to the more adventurous hiker. After a strenuous but exhilarating climb, return to the bus for a scenic ride back to your resort or Cruise pier. Inclusions: Knowledgeable Guide ? Duration: 8 hours Tip off: This is a very strenuous hike suitable for the physically fir. Not for those with heart, back, neck problems or may be pregnant. Cameras are a must. Wear comfortable hiking shoes (no heels or flip flops allowed)	01/28/2026	01/28/2026
At Sea	01/29/2026	01/29/2026
Kralendijk Kralendijk 01/30/2026 The ice cream colors of the stucco houses will draw your lens, as will the pink flamingos on the salt pans. But you’ll need a waterproof camera to complete the portrait since more than 400 fish species and 50 types of coral wait beneath the surface	01/30/2026	01/30/2026
Willemstad, Curacao Willemstad, Curacao 01/31/2026 Savor the pastel colors of the historic UNESCO site Old Town and the way the elaborate Dutch gables cut baroque curlicues from the sky. It’s the perfect appetizer for a day of watersports or an adventure below ground at the magical Hato Caves—filled with eerie limestone formations and ancient petroglyphs.	01/31/2026	01/31/2026
Oranjestad, Aruba Oranjestad, Aruba 02/01/2026 Known for having some of the best beaches in the Caribbean, this Dutch port makes it easy to just … take it easy. Walk through town to choose your favorite carved wooden door, or spend the day like the Arubans do playing dominos at a beachside table.	02/01/2026	02/01/2026

On any day, the 342-guest flagship, Wind Surf, the world’s largest sailing ship, draws admiring glances as she glides majestically into port with her tall sails billowing and her beauty is far more than skin deep. During their cruise, you will find the perfect setting for ‘making an entrance’ in the beautiful reception area.

Ship Statistics

Maiden Voyage: 1990
Last Refurbished: 2019
Registry: Bahamas
Gross Tonnage: 14,745
Beam: 66 ft (20.1 m)
Maximum Speed: 12 knots
Ship Length: 535 ft (163.1 m)
Passenger Capacity: 342
Number of Crew: 210
Crew Nationality: International

Number of Staterooms: 150
Number of Suites: 21
Dining / Restaurants: 5
Pool: Yes
Number of Decks: 6
Spa: Yes
Bars / Lounges: 4
Fitness Center: Yes
Wheelchair Accessible: Yes

Dining

Veranda

It's breakfast alfresco, full service or buffet-style, anytime till 9:30 a.m. No need to hurry. Again, the choices are many in Veranda. Choose the sumptuous, seemingly endless buffet. Or, order from the lunch menu between noon and 2:30 p.m. / Here’s the perfect place for a romantic tete-a-tete under the stars in Candles, Windstar’s signature outdoor restaurant transformed by night into a dreamlike paradise. Delectable cuisine, memorable surroundings, inspired wine pairings.

Bars & Lounges

Onboard Activities

Outdoor Activities

Wellness

Oceanview

Ocean View Stateroom (B) $8,495

Category: B
Deck One

Size: 188 square feet (18 square meters). Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L’Occitane® bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers. Note: Staterooms with 3rd Berths: 117–139; all suites (excluding 501). Staterooms with One Queen Size Bed Only (no twin option): 101, 102, 157, 301-304.

Deluxe Ocean View Stateroom (BX) $9,195

Category: BX
Deck One

Deluxe Ocean View Stateroom (TX) $11,995

Category: TX
Deck Three

Guarantee Stateroom (Y) Call for pricing

Category: Y

With this selection, you are guaranteed to receive a stateroom within a selected category, anywhere on the ship. However, the actual room assignment and location on the ship may be determined at any time after your reservation has been completed and paid in full up to the day of sailing.

Suite

Bridge Suite (BRS) $24,995

Category: BRS

Size: 495 square feet (46 square meters). The ultimate in space and style surrounds you in 495 square feet of pure indulgence. Separate bedroom and living room with an in-suite dining area is an invitation to relaxation. And possibly best of all, your expansive bathroom features both a whirlpool spa tub and a massage shower.

Bridge Suite (BS) Call for pricing

Category: BS
Bridge

Rates are cruise only, per person, based on double occupancy and include government fees/taxes of $96. Optional transfers and airfare (unless otherwise stated) additional for all guests.

Prices are per person, based on double occupancy and include government fees and taxes. Optional airfare and transfers additional.

All fares are quoted in US Dollars.

Star

Stateroom Key

Officer's Suite (OS)
Suite (STE)
Bridge Suite (BRS)
Suite (Owner)
Bridge Suite (BS)
Deluxe Ocean View Stateroom (TX)
(AX)
Deluxe Ocean View Stateroom (BX)
(A)
Ocean View Stateroom (B)
Guarantee Stateroom (Y)

Bridge

Stateroom Key

Officer's Suite (OS)
Suite (STE)
Bridge Suite (BRS)
Suite (Owner)
Bridge Suite (BS)
Deluxe Ocean View Stateroom (TX)
(AX)
Deluxe Ocean View Stateroom (BX)
(A)
Ocean View Stateroom (B)
Guarantee Stateroom (Y)

Main

Stateroom Key

Officer's Suite (OS)
Suite (STE)
Bridge Suite (BRS)
Suite (Owner)
Bridge Suite (BS)
Deluxe Ocean View Stateroom (TX)
(AX)
Deluxe Ocean View Stateroom (BX)
(A)
Ocean View Stateroom (B)
Guarantee Stateroom (Y)

Deck Three

Stateroom Key

Officer's Suite (OS)
Suite (STE)
Bridge Suite (BRS)
Suite (Owner)
Bridge Suite (BS)
Deluxe Ocean View Stateroom (TX)
(AX)
Deluxe Ocean View Stateroom (BX)
(A)
Ocean View Stateroom (B)
Guarantee Stateroom (Y)

Deck Two

Stateroom Key

Officer's Suite (OS)
Suite (STE)
Bridge Suite (BRS)
Suite (Owner)
Bridge Suite (BS)
Deluxe Ocean View Stateroom (TX)
(AX)
Deluxe Ocean View Stateroom (BX)
(A)
Ocean View Stateroom (B)
Guarantee Stateroom (Y)

Deck One

Stateroom Key

Officer's Suite (OS)
Suite (STE)
Bridge Suite (BRS)
Suite (Owner)
Bridge Suite (BS)
Deluxe Ocean View Stateroom (TX)
(AX)
Deluxe Ocean View Stateroom (BX)
(A)
Ocean View Stateroom (B)
Guarantee Stateroom (Y)

28-night Star Collector: The Best Of The Windward & Leeward Isles Cruise

Cruise Inclusions

Available Add-Ons

St. Maarten (Philipsburg) 01/04/2026

Falmouth Harbour, Antigua 01/05/2026

Road Bay 01/06/2026

Sopers Hole, Tortola 01/07/2026

Jost Van Dyke 01/07/2026

Jost Van Dyke 01/08/2026

Virgin Gorda 01/09/2026

Gustavia 01/10/2026

St. Maarten (Philipsburg) 01/11/2026

Basseterre, St. Kitts 01/12/2026

Little Bay 01/13/2026

Gustavia 01/14/2026

Deshaies, Guadeloupe 01/15/2026

Roseau, Dominica 01/16/2026

Pigeon Island, St. Lucia 01/17/2026

Bridgetown (Barbados) 01/18/2026

Anse Mitan 01/19/2026

Castries 01/20/2026

Optional Private Excursions

Pigeon Island, St. Lucia 01/20/2026

Pigeon Island, St. Lucia 01/21/2026

Bequia, Grenadines 01/22/2026

Mayreau, Grenadines 01/23/2026

St. George's, Grenada 01/24/2026

Bridgetown (Barbados) 01/25/2026

Man O'War Bay, Tobago 01/26/2026

Mayreau, Grenadines 01/27/2026

Soufriere 01/28/2026

Optional Private Excursions

Kralendijk 01/30/2026

Willemstad, Curacao 01/31/2026

Oranjestad, Aruba 02/01/2026

Dining

Bars & Lounges

Onboard Activities

Outdoor Activities

Wellness

Oceanview

Suite

Stateroom Key

Stateroom Key

Stateroom Key

Stateroom Key

Stateroom Key

Stateroom Key