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

   Cruz Bay, St. John

   Arrive 08:00Depart 18:00

   

3. Day 3

   Gustavia

   Arrive 08:00Depart 17:00

   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.

4. Day 4

   Basseterre

   Arrive 07:00Depart 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.

5. Day 5

   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.

6. Day 6

   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.

7. Day 7

   Virgin Gorda, B.V.I

   Arrive 08:00Depart 17:00

   

   The most chic resorts of the British Virgin Isles are located on Virgin Gorda, an eight-square-mile island divided nearly in two, with settlements at each end. The south of the island is best known for the curious assembly of house- sized rocks called “the Baths,” which are jumbled together to form huge underground pools and caverns. The beach at the Baths is large, wide, and sandy – perfect for sunning and swimming.

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.

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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