Windstar Cruises

Daily Itinerary

1. Day 1

   San Juan, Puerto Rico

   Depart 19:00

   Puerto Rico

   

   San Juan, Puerto Rico's radiant colonial capital, is one of the Americas' most compellingly layered cities — a place where the sixteenth-century fortresses of El Morro and San Cristóbal stand sentinel over streets of painted townhouses and flowering balconies. The cobblestoned lanes of Old San Juan pulse with world-class rum bars, ceviche stands, and rooftop restaurants serving the island's vibrant cocina criolla. La Fortaleza, the oldest executive mansion in the Western Hemisphere still in use, anchors the historic district. Florecer, the district's famed bioluminescent bay, glows emerald after dark. January through April offers the most idyllic conditions.

2. Day 2

   At Sea

   

3. Day 3

   St. Georges, Grenada

   Arrive 09:00Depart 22:00

   Grenada

   

   St. George's, Grenada, is a vibrant port known for its rich history, stunning architecture, and fragrant markets brimming with local spices. Must-do experiences include savoring the local delicacies at the Market Square and exploring nearby Carriacou Island for its tranquil beaches. The best season to visit is from December to April, when the weather is pleasantly warm and dry.

4. Day 4

   Port Elizabeth, Bequia

   Arrive 08:00Depart 22:00

   Saint Vincent and the Grenadines

   

   Port Elizabeth is the beguiling waterfront capital of Bequia, a former whaling island in Saint Vincent and the Grenadines where Caribbean authenticity endures in gingerbread cottages, hand-built schooners, and charcoal-grilled lobster on the sand. Stroll the Belmont Walkway for the island's finest harbour views, then sail to the Tobago Cays for world-class snorkelling among sea turtles. The dry season from December through May offers the most reliable sunshine and the peak of luxury cruise calls into sheltered Admiralty Bay.

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

   Deshaies

   Arrive 08:00Depart 17:00

   Guadeloupe

   

   Deshaies is a charming Creole fishing village on Guadeloupe's lush Basse-Terre coast, beloved for its unspoiled bay, golden Grande Anse beach, and outstanding botanical garden. Visitors should savour accras de morue and colombo de poulet, explore the Route de la Traversée through the volcanic national park, and take a boat trip to the Îles des Saintes. December through May is the ideal season for reliably sunny skies and calm seas.

7. Day 7

   Marigot, Saint Martin

   Arrive 08:00Depart 15:00

   Saint Martin

   

   Marigot, Saint Martin, delivers the Caribbean at its most authentic—stunning waters, vibrant culture, and cuisine that blends African, European, and indigenous traditions into something boldly distinctive. Don't miss the local food scene and the exceptional snorkeling. Best experienced December through April, during the dry season when skies are clearest and seas are calmest. Cruise lines including Ponant feature this port on their most compelling itineraries. Whether you have a few hours or a full day, the port rewards exploration at every pace and in every direction.

8. Day 8

   San Juan, Puerto Rico

   Arrive 07:00Depart 19:00

   Puerto Rico

   

   San Juan, Puerto Rico's radiant colonial capital, is one of the Americas' most compellingly layered cities — a place where the sixteenth-century fortresses of El Morro and San Cristóbal stand sentinel over streets of painted townhouses and flowering balconies. The cobblestoned lanes of Old San Juan pulse with world-class rum bars, ceviche stands, and rooftop restaurants serving the island's vibrant cocina criolla. La Fortaleza, the oldest executive mansion in the Western Hemisphere still in use, anchors the historic district. Florecer, the district's famed bioluminescent bay, glows emerald after dark. January through April offers the most idyllic conditions.

9. Day 9

   Cruz Bay, St John, US Virgin Islands

   Arrive 08:00Depart 18:00

   U.S. Virgin Islands

   

   Cruz Bay, St John, US Virgin Islands, U.S. Virgin Islands, delivers the Caribbean at its most authentic—stunning waters, vibrant culture, and cuisine that blends African, European, and indigenous traditions into something boldly distinctive. Don't miss the local food scene and the exceptional snorkeling. Best experienced December through April, during the dry season when skies are clearest and seas are calmest. Cruise lines including Windstar Cruises feature this port on their most compelling itineraries. Whether you have a few hours or a full day, the port rewards exploration at every pace and in every direction.

10. Day 10

    Basseterre

    Arrive 08:00Depart 17:00

    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.

11. Day 11

    Gustavia

    Arrive 07:00Depart 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.

12. Day 12

    Philipsburg, St. Maarten

    Arrive 08:00Depart 22:00

    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.

13. Day 13

    Jost Van Dyke, British Virgin Islands

    Arrive 09:00Depart 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 14

    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 15

    San Juan, Puerto Rico

    Arrive 07:00

    Puerto Rico

    

    San Juan, Puerto Rico's radiant colonial capital, is one of the Americas' most compellingly layered cities — a place where the sixteenth-century fortresses of El Morro and San Cristóbal stand sentinel over streets of painted townhouses and flowering balconies. The cobblestoned lanes of Old San Juan pulse with world-class rum bars, ceviche stands, and rooftop restaurants serving the island's vibrant cocina criolla. La Fortaleza, the oldest executive mansion in the Western Hemisphere still in use, anchors the historic district. Florecer, the district's famed bioluminescent bay, glows emerald after dark. January through April offers the most idyllic conditions.

Cabin Categories

Balcony Suite

Balcony

277 sq ftMax 2BS

Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.

Queen or Twin ConfigurationShowerToiletries ProvidedRoom Service AvailableSuite BenefitsTV+7

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Balcony Suite

Balcony

277 sq ftMax 2BS1

Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.

Queen or Twin ConfigurationShowerToiletries ProvidedRoom Service AvailableSuite BenefitsTV+7

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Star Balcony Suite

balcony

SBS

As soon as you walk through the door, you’re greeted with an open living area for a more welcoming entrance. Drift off to sleep by the window in your queen bed as you watch the same stars that sailors used to navigate the seas hundreds of years ago.

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Star Balcony Suite

Suite

277 sq ftMax 2SBS1

As soon as you walk through the door, you’re greeted with an open living area for a more welcoming entrance. Drift off to sleep by the window in your queen bed as you watch the same stars that sailors used to navigate the seas hundreds of years ago.

Queen or Twin ConfigurationLounge AreaShowerToiletries ProvidedRoom Service AvailableMini Bar (Additional Cost)+6

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Ocean View Suite

Suite

277 sq ftMax 2S2

Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.

Vanity AreaToiletries ProvidedTVWi-Fi (Additional Cost)SafeMini Bar (Additional Cost)+1

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Ocean View Suite

Suite

277 sq ftMax 2S

Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.

Vanity AreaToiletries ProvidedTVWi-Fi (Additional Cost)SafeMini Bar (Additional Cost)+1

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Ocean View Suite

Suite

277 sq ftMax 2S1

Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.

Vanity AreaToiletries ProvidedTVWi-Fi (Additional Cost)SafeMini Bar (Additional Cost)+1

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Ocean View Suite

Suite

277 sq ftMax 2S3

Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.

Vanity AreaToiletries ProvidedTVWi-Fi (Additional Cost)SafeMini Bar (Additional Cost)+1

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Star Ocean View Suite

Outside

277 sq ftMax 2SS1

As soon as you walk through the door, you’re greeted with an open living area for a more welcoming entrance. Drift off to sleep by the window in your queen bed as you watch the same stars that sailors used to navigate the seas hundreds of years ago.

Queen or Twin ConfigurationLounge AreaShowerToiletries ProvidedRoom Service AvailableMini Bar (Additional Cost)+6

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Star Porthole Suite

Suite

277 sq ftMax 2SP

These rooms represent a nod to the sailing tradition of porthole windows. And while sailors might have had cramped quarters, your 277 square foot stateroom is wonderfully spacious and furnished with all the modern amenities and comforts of home.

Queen or Twin ConfigurationShowerRoom Service AvailableTVSafeHair Dryer+5

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Broadmoor Suite/Sea Island Suite

Suite

400 sq ftMax 2CS

Relax in 400 to 530 spacious square feet. Your living area offers beautiful views from the forward-facing window and French doors onto your private veranda. Two spacious closets give you plenty of room to unpack.

Queen or Twin ConfigurationLounge AreaShowerToiletries ProvidedRoom Service AvailableTV+6

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Deluxe Suite

Suite

468 sq ftMax 2DS

Brand new Deluxe Suites welcome you with 468 square feet of casually elegant living space and an ocean viewing French balcony. All these suites feature 3rd berths, and a sleep-inducing queen bed easily converted to twins.

Queen or Twin ConfigurationLounge AreaShowerToiletries ProvidedRoom Service AvailableSuite Benefits+7

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Owner's Suite

Suite

575 sq ftMax 2OW

With 575 square feet, your Owner’s Suite offers separate living room and dining areas. A veranda, two flat-screen TVs and DVD players, and a full master bath and separate powder room indulge you in spacious comfort.

Queen or Twin ConfigurationLounge AreaShowerRoom Service AvailableTVWi-Fi (Additional Cost)+6

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