--- type: cruise schema_type: TouristTrip id: e344ef20-baa7-432d-90ae-85b58acfe9b2 slug: 2285372 voyage_code: SU20270130-14D cruise_line: Windstar Cruises ship: Wind Surf departure_date: return_date: nights: 14 embarkation_port: Philipsburg, St. Martin disembarkation_port: Philipsburg, St. Martin starting_price_usd: 4799.0 bookable: false last_updated: 2026-05-05T05:37:37Z --- # Caribbean Explorations - Philipsburg, St. Maarten to Philipsburg, St. Maarten > Windstar Cruises · Wind Surf · Jan 30 – Feb 13, 2027   (14 nights) ## Quick Facts | Attribute | Value | |-----------|-------| | **Cruise Line** | Windstar Cruises | | **Ship** | Wind Surf | | **Duration** | 14 nights | | **Departure Date** | N/A | | **Return Date** | N/A | | **Embarkation Port** | Philipsburg, St. Martin | | **Disembarkation Port** | Philipsburg, St. Martin | | **Starting Price** | 4,799 USD per person | | **Voyage Code** | SU20270130-14D | ## Itinerary ### Day 1: Philipsburg, St. Martin **Arrives:** 12:00 AM · **Departs:** 07:00 PM Philipsburg is the capital of Sint Maarten, the Dutch side of the Caribbean island Saint Martin. Beachfront bars line the boardwalk along Great Bay. Voorstraat, or Front Street, has duty-free shops and casinos. The St. Maarten Zoo is home to parrots, monkeys and a playground. Sint Maarten Museum displays artifacts from the indigenous Arawak people. The ruins of 17th-century Fort Amsterdam stand on a nearby peninsula. ### Day 2: Road Bay, Anguilla **Arrives:** 08:00 AM · **Departs:** 06:00 PM ### Day 3: Soper'S Hole, Tortola, B.V.I. **Arrives:** 08:00 AM · **Departs:** 06:00 PM Soper's Hole Marina is arguably one of the most picturesque anchorage in the British Virgin Islands. ### Day 3: Jost Van Dyke, B.V.I **Arrives:** 07:00 PM · **Departs:** 12:00 AM Inviting beaches and tiny shops selling local treasures welcome you to this quiet island haven. Don't miss dining with your feet in the sand at Foxy's on the beach-a perfect lunch stop! ### Day 4: Jost Van Dyke, B.V.I **Arrives:** 12:00 AM · **Departs:** 10:00 PM Inviting beaches and tiny shops selling local treasures welcome you to this quiet island haven. Don't miss dining with your feet in the sand at Foxy's on the beach-a perfect lunch stop! ### Day 5: Virgin Gorda, B.V.I **Arrives:** 08:00 AM · **Departs:** 10:00 PM 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. ### Day 6: Gustavia, St. Barthelemy **Arrives:** 08:00 AM · **Departs:** 10:00 PM Gustavia is the main town and capital of the island of Saint Barthélemy. Originally called Le Carénage, it was renamed in honor of King Gustav III of Sweden. ### Day 7: Falmouth, Antigua **Arrives:** 08:00 AM · **Departs:** 05:00 PM Surrounded by many abandoned sugar mills, the small village of Falmouth is protected in a large horseshoe-shaped bay. Falmouth was the first settlement on Antigua set up by the British. Today Falmouth is a quiet village surrounded by old sugar plantations and mills with the main historic building of interest being St Paul's Church. The main center of activity in Falmouth Harbour is on the eastern side of the large horse-shoe bay where the shops, restaurants and marina are located. ### Day 8: Philipsburg, St. Martin **Arrives:** 06:00 AM · **Departs:** 07:00 PM Philipsburg is the capital of Sint Maarten, the Dutch side of the Caribbean island Saint Martin. Beachfront bars line the boardwalk along Great Bay. Voorstraat, or Front Street, has duty-free shops and casinos. The St. Maarten Zoo is home to parrots, monkeys and a playground. Sint Maarten Museum displays artifacts from the indigenous Arawak people. The ruins of 17th-century Fort Amsterdam stand on a nearby peninsula. ### Day 9: Charlestown, Nevis **Arrives:** 08:00 AM · **Departs:** 05:00 PM Charlestown is a historic waterfront neighborhood with Irish-American roots. The Freedom Trail climbs streets lined with brick townhouses and clapboard triple-decker homes to the Bunker Hill Monument, site of a key Revolutionary War battle. The 1797 U.S.S. Constitution warship and its museum are in the Charlestown Navy Yard. Main Street’s traditional pubs and stylish restaurants draw young professionals and families ### Day 10: Roseau, Dominica **Arrives:** 08:00 AM · **Departs:** 04:00 PM Roseau is the capital of the Caribbean island nation of Dominica. It's on the southwest coast and known for its 18th-century Creole architecture. Its cobblestone Old Market, formerly a slave auction site, sells crafts and fruit. It’s next to the Dominica Museum, with exhibits on the country’s natural and cultural history. The Dominica Botanic Gardens showcase tropical flora and native Sisserou parrots. ### Day 11: Mayreau, Grenadines **Arrives:** 08:00 AM · **Departs:** 05:00 PM In the north of Mayreau is Salt Whistle Bay, a perfect half moon beach, separating the Atlantic from the Caribbean side with a sand spit only 50 yards wide, fringed by palm trees. The windward side of Mayreau is one huge deserted beach; you could spend days picnicking, sunbathing and snorkeling in the underwater world of Mayreau Garden. The southwestern, leeward beach is Saline Bay, nearly a mile of white sand with calm, clear water - ideal to bring your family! ### Day 12: Les Saintes, F.W.I. **Arrives:** 12:01 PM · **Departs:** 06:00 PM The Îles des Saintes, or Les Saintes, are dependency islands of Guadeloupe, a French overseas territory in the Caribbean. The main island, Terre-de-Haut, is known for Pain de Sucre Beach’s coral-rich waters and palm-lined Les Saintes Bay. Overlooking the bay is 19th-century Fort Napoléon, with a museum and cactus garden. Trails cross the volcanic landscape of Terre-de-Bas Island, home to tranquil Grand Anse Beach. ### Day 13: Basseterre, St. Kitts **Arrives:** 08:00 AM · **Departs:** 10:00 PM Basseterre, set against the irresistible backdrop of St. Kitts' emerald green hills and punctuated by elegant Georgian architecture, is one of the best of the Caribbean's small capitals. ### Day 14: Gustavia, St. Barthelemy **Arrives:** 08:00 AM · **Departs:** 10:00 PM Gustavia is the main town and capital of the island of Saint Barthélemy. Originally called Le Carénage, it was renamed in honor of King Gustav III of Sweden. ### Day 15: Philipsburg, St. Martin **Arrives:** 06:00 AM · **Departs:** 12:00 AM Philipsburg is the capital of Sint Maarten, the Dutch side of the Caribbean island Saint Martin. Beachfront bars line the boardwalk along Great Bay. Voorstraat, or Front Street, has duty-free shops and casinos. The St. Maarten Zoo is home to parrots, monkeys and a playground. Sint Maarten Museum displays artifacts from the indigenous Arawak people. The ruins of 17th-century Fort Amsterdam stand on a nearby peninsula. ## Pricing Prices shown are per person based on double occupancy in USD. | Cabin Type | Starting Price | |------------|----------------| | Ocean View | $4,799 | | Suite | $6,499 | ## Cabin Options ### Outside Cabins **Deluxe Stateroom** (Code: AX) 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 produ... **Stateroom** (Code: A) 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 produ... ### Suite Cabins **Officers’ Suite** (Code: OS) 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 ... **Bridge Suite** (Code: BRS) 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. **Suite** (Code: STE) 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. **Deluxe Stateroom** (Code: TX) 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 produ... ## Ship Information ### Wind Surf On any day, our 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 – and, appropriately, that’s only the beginning. When you return to your stateroom, the luxury gets personal. Windstar’s signature bowls of flowers and fresh fruit will still be waiting for you, along with rich tufted headboards, soft seascape colors, beautiful new upholstery, and fine count Egyptian cotton linens welcome you to an oasis of relaxing indulgence. Wind Surf recently underwent a significant renovation in November 2019 of public spaces and suites, including an expanded lounge with new lights and sound for upcoming stage performances. Relax into the destinations you’re visiting at the new World Spa by Windstar, which will offer regional spa treatments, including massage styles like Swedish, Japanese Shiatsu and Hawaiian Lomi Lomi. A new Officer’s Suite, which might be the only one of its kind, provides you the chance to stay in the heart of the officer quarters tucked right behind the Bridge. Everything about Wind Surf speaks of welcome. Come aboard and see it for yourself. #### Specifications | Specification | Value | |---------------|-------| | Passenger Capacity | 342 | | Crew | 210 | | Gross Tonnage | 14,745.0 | | Length | 535.0 ft | | Total Cabins | 0 | ## Ports of Call ### Philipsburg, St. Martin *Coordinates: 18.0237, -63.0458* Philipsburg is the capital of Sint Maarten, the Dutch side of the Caribbean island Saint Martin. Beachfront bars line the boardwalk along Great Bay. Voorstraat, or Front Street, has duty-free shops and casinos. The St. Maarten Zoo is home to parrots, monkeys and a playground. Sint Maarten Museum displays artifacts from the indigenous Arawak people. The ruins of 17th-century Fort Amsterdam stand on... ### Road Bay, Anguilla *Coordinates: 18.2207, -63.0653* ### Soper'S Hole, Tortola, B.V.I. *Coordinates: 18.4236, -64.6271* Soper's Hole Marina is arguably one of the most picturesque anchorage in the British Virgin Islands. ### Jost Van Dyke, B.V.I *Coordinates: 18.4463, -64.7429* Inviting beaches and tiny shops selling local treasures welcome you to this quiet island haven. Don't miss dining with your feet in the sand at Foxy's on the beach-a perfect lunch stop! ### Virgin Gorda, B.V.I *Coordinates: 18.4829, -64.4023* 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... ### Gustavia, St. Barthelemy *Coordinates: 17.895, -62.8493* Gustavia is the main town and capital of the island of Saint Barthélemy. Originally called Le Carénage, it was renamed in honor of King Gustav III of Sweden. ### Falmouth, Antigua *Coordinates: 17.0228, -61.7814* Surrounded by many abandoned sugar mills, the small village of Falmouth is protected in a large horseshoe-shaped bay. Falmouth was the first settlement on Antigua set up by the British. Today Falmouth is a quiet village surrounded by old sugar plantations and mills with the main historic building of interest being St Paul's Church. The main center of activity in Falmouth Harbour is on the eastern ... ### Charlestown, Nevis *Coordinates: 17.137, -62.6251* Charlestown is a historic waterfront neighborhood with Irish-American roots. The Freedom Trail climbs streets lined with brick townhouses and clapboard triple-decker homes to the Bunker Hill Monument, site of a key Revolutionary War battle. The 1797 U.S.S. Constitution warship and its museum are in the Charlestown Navy Yard. Main Street’s traditional pubs and stylish restaurants draw young profe... ### Roseau, Dominica *Coordinates: 15.3014, -61.3883* Roseau is the capital of the Caribbean island nation of Dominica. It's on the southwest coast and known for its 18th-century Creole architecture. Its cobblestone Old Market, formerly a slave auction site, sells crafts and fruit. It’s next to the Dominica Museum, with exhibits on the country’s natural and cultural history. The Dominica Botanic Gardens showcase tropical flora and native Sisserou... ### Mayreau, Grenadines *Coordinates: 12.6412, -61.3896* In the north of Mayreau is Salt Whistle Bay, a perfect half moon beach, separating the Atlantic from the Caribbean side with a sand spit only 50 yards wide, fringed by palm trees. The windward side of Mayreau is one huge deserted beach; you could spend days picnicking, sunbathing and snorkeling in the underwater world of Mayreau Garden. The southwestern, leeward beach is Saline Bay, nearly a mile ... ### Les Saintes, F.W.I. *Coordinates: 16.265, -61.551* The Îles des Saintes, or Les Saintes, are dependency islands of Guadeloupe, a French overseas territory in the Caribbean. The main island, Terre-de-Haut, is known for Pain de Sucre Beach’s coral-rich waters and palm-lined Les Saintes Bay. Overlooking the bay is 19th-century Fort Napoléon, with a museum and cactus garden. Trails cross the volcanic landscape of Terre-de-Bas Island, home to tranq... ### Basseterre, St. Kitts Basseterre, set against the irresistible backdrop of St. Kitts' emerald green hills and punctuated by elegant Georgian architecture, is one of the best of the Caribbean's small capitals. ## Booking Information - **Book This Cruise:** https://cruisepirate.ai/cruise/2285372 - **Compare Prices:** CruisePirate compares prices across multiple booking channels - **Price Alerts:** Set up alerts for price drops on this sailing - **Support:** Contact our AI-powered cruise assistant for personalized recommendations ### Why Book with CruisePirate? - Real-time price comparison across booking channels - AI-powered cruise recommendations - Transparent pricing with no hidden fees - Expert cruise search and filtering --- ## Technical Metadata - **Canonical URL:** https://cruisepirate.ai/cruise/2285372 - **Markdown URL:** https://cruisepirate.ai/cruise/2285372.md - **API Endpoint:** https://cruisepirate.ai/api/cruises/2285372/ - **Primary Image:** https://images.cruisepirate.ai/v3/static/cruise-lines/windstar-cruises/wind-surf/other/131918.webp - **Data Source:** CruisePirate Cruise Database - **Last Updated:** 2026-05-05 05:37:37 UTC