Windstar Cruises

Daily Itinerary

1. Day 1

   Philipsburg, St. Maarten

   Depart 19:00

   Sint Maarten

   

   Philipsburg, capital of the Dutch side of Sint Maarten, packs extraordinary energy onto a narrow sand spit between Great Bay and the Great Salt Pond — two parallel streets of duty-free boutiques, creole restaurants, and rum bars backed by a beach where cruise ships anchor so close that their hulls seem to dominate the shoreline. The island's most celebrated spectacle is entirely involuntary: Princess Juliana International Airport, where landing aircraft pass at rooftop height over Maho Beach, drawing crowds of thrill-seekers every day. The 1648 Mount Concordia Treaty, dividing this sliver of land between France and the Netherlands, created the world's smallest territory shared by two nations. The dry season from December to April is optimal.

2. Day 2

   Gustavia

   Arrive 08:00Depart 22:00

   Saint Barthélemy

   

   Gustavia, the capital of Saint Barthélemy, is a charming port known for its luxurious yachts, vibrant boutiques, and rich historical tapestry. Must-do experiences include exploring Fort Karl for stunning views and indulging in local dishes like accras de morue while enjoying the sun at Colombier Beach. The best season to visit is from December to April, when the weather is pleasantly warm and the island is bustling with activity.

3. Day 3

   Charlestown, Nevis

   Arrive 08:00Depart 17:00

   Saint Kitts and Nevis

   

   Charlestown is the two-thousand-person capital of Nevis, birthplace of Alexander Hamilton, where eighteenth-century Georgian architecture and the Caribbean's first hotel line streets untouched by mass tourism. Visit December through April via Windstar or Ponant for Hamilton heritage, volcanic hot springs, Pinney's Beach perfection, and the rare Caribbean experience of being a guest rather than a tourist.

4. Day 4

   Roseau

   Arrive 08:00Depart 16:00

   Dominica

   

   Roseau, the capital of Dominica, is a vibrant port city characterized by its colonial architecture and rich cultural heritage. Must-do experiences include savoring local delicacies like mountain chicken curry and visiting the bustling Roseau Market. The best time to visit is during the dry season from December to April, when the island showcases its natural beauty and festive spirit.

5. Day 5

   Mayreau

   Arrive 08:00Depart 17:00

   Saint Vincent and the Grenadines

   

   Mayreau is the smallest inhabited island in the Grenadines, a car-free Caribbean gem with fewer than three hundred residents, the exquisite Salt Whistle Bay beach, and views across the pristine Tobago Cays Marine Park. Must-do experiences include snorkelling with sea turtles in the Tobago Cays, feasting on fresh grilled lobster, and watching sunset from the hilltop church. January through May's dry season offers the most reliable weather.

6. Day 6

   Guadeloupe

   Arrive 12:01Depart 18:00

   Guadeloupe

   

   Guadeloupe is a butterfly-shaped French Caribbean archipelago where volcanic rainforests, pristine beaches, and refined Creole-French cuisine create one of the region's most distinctive destinations. Must-dos include hiking La Soufrière volcano, tasting rhum agricole, and day-tripping to the Saintes islands. December through May offers the driest, most comfortable conditions for visiting.

7. Day 7

   Basseterre

   Arrive 08:00Depart 22:00

   Saint Kitts and Nevis

   

   Basseterre, capital of Saint Kitts and Nevis — the smallest sovereign nation in the Americas — is the gateway to an island whose volcanic drama and layered colonial history distinguish it from every other Caribbean port. Mount Liamuiga's cloud-capped summit and its rainforest-filled crater lake await hikers, while the UNESCO-listed Brimstone Hill Fortress, one of the finest surviving examples of British colonial military architecture, commands sweeping views across neighboring islands. The surrounding plantation inns — sugar estates converted into intimate boutique hotels — offer the most atmospheric accommodation in the Eastern Caribbean. Visit November through April for the driest, sunniest weather.

8. Day 8

   Philipsburg, St. Maarten

   Arrive 06:00Depart 19:00

   Sint Maarten

   

   Philipsburg, capital of the Dutch side of Sint Maarten, packs extraordinary energy onto a narrow sand spit between Great Bay and the Great Salt Pond — two parallel streets of duty-free boutiques, creole restaurants, and rum bars backed by a beach where cruise ships anchor so close that their hulls seem to dominate the shoreline. The island's most celebrated spectacle is entirely involuntary: Princess Juliana International Airport, where landing aircraft pass at rooftop height over Maho Beach, drawing crowds of thrill-seekers every day. The 1648 Mount Concordia Treaty, dividing this sliver of land between France and the Netherlands, created the world's smallest territory shared by two nations. The dry season from December to April is optimal.

9. Day 9

   Falmouth, Antigua

   Arrive 08:00Depart 18:00

   Antigua and Barbuda

   

   Falmouth Harbour, Antigua, is home to Nelson's Dockyard—the world's only continuously operating Georgian naval dockyard, now a UNESCO World Heritage Site where colonial-era sail lofts and officers' quarters have been beautifully restored. Must-dos include exploring the dockyard, hiking to Shirley Heights for sunset views, and sampling Antigua's black pineapple. December through April is the dry season, with Sailing Week in April the calendar highlight.

10. Day 10

    Road Bay

    Arrive 08:00Depart 18:00

    Anguilla

    

    Road Bay is the anchorage for Anguilla, whose sixteen miles harbor some of the world's finest beaches — including Shoal Bay East's two-mile masterpiece — and a dining scene that defies the island's modest population of fifteen thousand. Visit December through April via Ponant or Windstar for the Caribbean's most convincing synthesis of perfect sand, exceptional cuisine, and the genuine exclusivity that comes from having no deep-water cruise port.

11. Day 11

    British Virgin Islands, Great Britain

    Arrive 08:00Depart 18:00

    British Virgin Islands

    

    The British Virgin Islands are one of the world's premier sailing archipelagos, comprising over sixty islands offering pristine beaches, legendary beach bars like the Soggy Dollar, and the fantastical granite grottoes of The Baths on Virgin Gorda. Visitors should dive the historic RMS Rhone wreck, feast on Anegada's famous grilled lobster, and explore Norman Island's snorkeling caves. The dry season from December to May offers ideal sailing conditions and the most comfortable weather.

12. Day 11

    Jost Van Dyke, British Virgin Islands

    Arrive 19:00

    British Virgin Islands

    

    Jost Van Dyke is a tiny, uncommercialised island in the British Virgin Islands named after a Dutch privateer, celebrated for its pristine white-sand beaches, legendary beach bars, and barefoot Caribbean culture. Visitors should not miss savouring a Painkiller cocktail at the Soggy Dollar Bar on White Bay and exploring the granite grottos of The Baths on nearby Virgin Gorda. The dry season from December through April offers the most radiant sailing conditions and calm turquoise waters, making it the ideal window for a luxury small-ship call at this intimate Caribbean gem.

13. Day 12

    Jost Van Dyke, British Virgin Islands

    Depart 22:00

    British Virgin Islands

    

    Jost Van Dyke is a tiny, uncommercialised island in the British Virgin Islands named after a Dutch privateer, celebrated for its pristine white-sand beaches, legendary beach bars, and barefoot Caribbean culture. Visitors should not miss savouring a Painkiller cocktail at the Soggy Dollar Bar on White Bay and exploring the granite grottos of The Baths on nearby Virgin Gorda. The dry season from December through April offers the most radiant sailing conditions and calm turquoise waters, making it the ideal window for a luxury small-ship call at this intimate Caribbean gem.

14. Day 13

    Virgin Gorda, British Virgin Islands

    Arrive 08:00Depart 17:00

    British Virgin Islands

    

    Virgin Gorda is a stunning port in the British Virgin Islands known for its dramatic landscapes and rich history. Must-do experiences include exploring The Baths' unique rock formations and savoring local dishes like Roti and Fish Escovitch. The best season to visit is from December to April, when the weather is optimal for outdoor adventures.

15. Day 14

    Gustavia

    Arrive 08:00Depart 22:00

    Saint Barthélemy

    

    Gustavia, the capital of Saint Barthélemy, is a charming port known for its luxurious yachts, vibrant boutiques, and rich historical tapestry. Must-do experiences include exploring Fort Karl for stunning views and indulging in local dishes like accras de morue while enjoying the sun at Colombier Beach. The best season to visit is from December to April, when the weather is pleasantly warm and the island is bustling with activity.

16. Day 15

    Philipsburg, St. Maarten

    Arrive 06:00

    Sint Maarten

    

    Philipsburg, capital of the Dutch side of Sint Maarten, packs extraordinary energy onto a narrow sand spit between Great Bay and the Great Salt Pond — two parallel streets of duty-free boutiques, creole restaurants, and rum bars backed by a beach where cruise ships anchor so close that their hulls seem to dominate the shoreline. The island's most celebrated spectacle is entirely involuntary: Princess Juliana International Airport, where landing aircraft pass at rooftop height over Maho Beach, drawing crowds of thrill-seekers every day. The 1648 Mount Concordia Treaty, dividing this sliver of land between France and the Netherlands, created the world's smallest territory shared by two nations. The dry season from December to April is optimal.

Cabin Categories

Category A

Outside

188 sq ftMax 2A

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.

Toiletries ProvidedTVWi-Fi (Additional Cost)SafeHair DryerMini Bar (Additional Cost)+1

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Category AX Deluxe

Outside

188 sq ftMax 2AX

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.

Queen or Twin ConfigurationToiletries ProvidedTVWi-Fi (Additional Cost)SafeHair Dryer+1

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Category B

Outside

188 sq ftMax 2B

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.

Toiletries ProvidedTVWi-Fi (Additional Cost)SafeHair DryerMini Bar (Additional Cost)+1

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Category BX Deluxe

Outside

188 sq ftMax 2BX

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.

Toiletries ProvidedTVWi-Fi (Additional Cost)SafeHair DryerMini Bar (Additional Cost)+1

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Broadmoor Suite/Sea Island Suite

Suite

495 sq ftMax 3BRS

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.

Queen or Twin ConfigurationSofa BedDining AreaShowerWhirlpool BathToiletries Provided+10

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Category TX Deluxe

Outside

188 sq ftMax 2TX

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.

Toiletries ProvidedTVWi-Fi (Additional Cost)SafeHair DryerMini Bar (Additional Cost)+1

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Officers’ Suite

Suite

376 sq ftMax 3OS

For the ultimate in nautical experiences, reserve the new Officer’s Suite located close to the Bridge where our own ship’s officers have their quarters. With its unique “insider” location and 242 square feet of comfort, the nautically appointed Officer’s Suite offers an experience you won’t find on any other cruise line.

Toiletries ProvidedTVFree Wi-FiCoffee MachineSafeHair Dryer+2

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Suite

Suite

376 sq ftMax 3STE

With 376 square feet, you’ll find the perfect space for time together — and plenty of room for time to yourself. You’ll even enjoy two full separate bathrooms. All the amenities of the staterooms await you, plus a beautiful sitting area, and two flat-screen television sets with DVD players.

Toiletries ProvidedTVFree Wi-FiCoffee MachineSafeHair Dryer+2

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Owner's Suite

Outside

242 sq ftMax 2OW

<p>For the ultimate in nautical experiences, reserve the new Owner's Suite located close to the Bridge where our own ship's officers have their quarters. With its unique "insider" location and 242 square feet of comfort, this suite offers an experience you won't find on any other cruise line. Inspired by classic yacht craftsmanship, the suite blends timeless elegance with subtle curves, leather accents, and tailored patterns.</p><p><b>Amenities: Owner’s suite</b><br></p><ul><li>Queen Size Bed with Luxurious Linens</li><li>Buttery soft velour bathrobe and slippers</li><li>Upgraded L'Occitane bath amenities</li><li>Mini Bar offering and fridge</li><li>In-room premium filtered water</li><li>Large upgraded fruit plate</li><li>Macarons &amp; Berries upon arrival</li><li>Daily Canapés service</li><li>Chilled bottle of Champagne upon arrival</li><li>Fresh flower arrangement</li><li>Illy capsule espresso machine</li><li>Magnifying mirror, hairdryer and umbrella</li><li>TV with complimentary on-demand entertainment</li><li>Safe</li><li>110/220-volt outlets</li><li>Ultimate Internet Package (Complimentary)</li><li>Preferred check-in</li><li>Personalized wake-up call with beverage</li><li>Binoculars</li><li>Invitation to Captain or Senior officer table</li><li>Preferred Specialty Restaurant dining</li><li>Laundry Service (various packages available for purchase)</li><li>24 Hour In-Room dining (complimentary)</li></ul><p></p>

Lounge AreaRoom Service AvailableQueen or Twin ConfigurationVanity AreaShowerToiletries Provided+7

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