--- type: cruise schema_type: TouristTrip id: 6b4c171b-9556-43c2-aa14-6ce06559b4a9 slug: 2317144 voyage_code: SU20271105-23D cruise_line: Windstar Cruises ship: Wind Surf departure_date: return_date: nights: 23 embarkation_port: Lisbon, Portugal disembarkation_port: Philipsburg, St. Martin starting_price_usd: 4792.0 bookable: false last_updated: 2026-07-15T23:48:50Z --- # Star Collector: Hearty Ports & Rum Punches - A Transatlantic Crossing > Windstar Cruises · Wind Surf · Nov 5 – 28, 2027   (23 nights) ## Quick Facts | Attribute | Value | |-----------|-------| | **Cruise Line** | Windstar Cruises | | **Ship** | Wind Surf | | **Duration** | 23 nights | | **Departure Date** | N/A | | **Return Date** | N/A | | **Embarkation Port** | Lisbon, Portugal | | **Disembarkation Port** | Philipsburg, St. Martin | | **Starting Price** | 4,792 USD per person | | **Voyage Code** | SU20271105-23D | ## Itinerary ### Day 1: Lisbon, Portugal **Arrives:** 12:00 AM · **Departs:** 05:00 PM One of Europe's smallest capital cities, Lisbon is for many, one of it most beguiling – an easily accessible mix of new and old worlds. Elegant outdoor cafés line Lisbon's mosaic cobblestone sidewalks along grand 18th-century boulevards. Turn-of-the-century funiculars dot its steep hills. Two-thirds of the city was leveled in a 1755 earthquake, but in its churches, peeling buildings, tiny alleyways, hidden squares, you can still feel the glorious past. ### Day 2: At Sea Enjoy a relaxing day at sea exploring the ship's amenities. ### Day 3: At Sea Enjoy a relaxing day at sea exploring the ship's amenities. ### Day 4: Funchal **Arrives:** 08:00 AM · **Departs:** 03:00 PM Funchal is the capital city of Portugal's Madeira archipelago. It's backed by hills, and known for its harbor, gardens and Madeira wine cellars. The centuries-old Funchal Cathedral, which mixes Gothic and Romanesque styles, is notable for its carved wooden ceiling. Fronting the harbor is the São Tiago Fortress, built in the 1600s. It now houses the Contemporary Art Museum, with a large collection of Portuguese works. ### Day 5: At Sea Enjoy a relaxing day at sea exploring the ship's amenities. ### Day 6: At Sea Enjoy a relaxing day at sea exploring the ship's amenities. ### Day 7: At Sea Enjoy a relaxing day at sea exploring the ship's amenities. ### Day 8: At Sea Enjoy a relaxing day at sea exploring the ship's amenities. ### Day 9: At Sea Enjoy a relaxing day at sea exploring the ship's amenities. ### Day 10: At Sea Enjoy a relaxing day at sea exploring the ship's amenities. ### Day 11: At Sea Enjoy a relaxing day at sea exploring the ship's amenities. ### Day 12: At Sea Enjoy a relaxing day at sea exploring the ship's amenities. ### Day 13: At Sea Enjoy a relaxing day at sea exploring the ship's amenities. ### Day 14: At Sea Enjoy a relaxing day at sea exploring the ship's amenities. ### Day 15: Jost Van Dyke, Great Harbour **Arrives:** 08:00 AM · **Departs:** 06:00 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 16: 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 17: 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 18: St. John's, Antigua **Arrives:** 08:00 AM · **Departs:** 10:00 PM St. John’s is the capital and key port of the Caribbean island nation of Antigua and Barbuda. The city is home to the Museum of Antigua and Barbuda, with exhibits on indigenous tribes and plantation life. St. John’s Cathedral, a 19th-century Anglican church, is on a hill near the 17th-century Government House. A monument to the nation’s founder, V.C. Bird, is next to the Public Market, which sells crafts and produce. ### Day 19: Deshaies, Guadeloupe **Arrives:** 07:00 AM · **Departs:** 05:00 PM Deshaies is a commune in the French overseas region and department of Guadeloupe, in the Lesser Antilles. It is on the northwest coast of Basse-Terre Island. The inhabitants are called Deshaisiens. ### Day 20: Road Bay, Anguilla **Arrives:** 08:00 AM · **Departs:** 06:00 PM ### Day 21: 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 21: Jost Van Dyke, Great Harbour **Arrives:** 07:00 PM · **Departs:** 11:59 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 22: Jost Van Dyke, Great Harbour **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 23: Virgin Gorda / Prickly Pear, British Virgin Island **Arrives:** 08:00 AM · **Departs:** 05:00 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 24: Philipsburg, St. Martin **Arrives:** 06:00 AM · **Departs:** 07:00 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 | $4,792 | | Suite | $7,000 | ## 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 ### Lisbon, Portugal *Coordinates: 38.7223, -9.13934* One of Europe's smallest capital cities, Lisbon is for many, one of it most beguiling – an easily accessible mix of new and old worlds. Elegant outdoor cafés line Lisbon's mosaic cobblestone sidewalks along grand 18th-century boulevards. Turn-of-the-century funiculars dot its steep hills. Two-thirds of the city was leveled in a 1755 earthquake, but in its churches, peeling buildings, tiny alleyway... ### Funchal *Coordinates: 32.6448, -16.9097* Funchal is the capital city of Portugal's Madeira archipelago. It's backed by hills, and known for its harbor, gardens and Madeira wine cellars. The centuries-old Funchal Cathedral, which mixes Gothic and Romanesque styles, is notable for its carved wooden ceiling. Fronting the harbor is the São Tiago Fortress, built in the 1600s. It now houses the Contemporary Art Museum, with a large collection ... ### Jost Van Dyke, Great Harbour *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! ### 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... ### 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. ### St. John's, Antigua *Coordinates: 17.1167, -61.85* St. John’s is the capital and key port of the Caribbean island nation of Antigua and Barbuda. The city is home to the Museum of Antigua and Barbuda, with exhibits on indigenous tribes and plantation life. St. John’s Cathedral, a 19th-century Anglican church, is on a hill near the 17th-century Government House. A monument to the nation’s founder, V.C. Bird, is next to the Public Market, which sells... ### Deshaies, Guadeloupe *Coordinates: 16.3108, -61.7897* Deshaies is a commune in the French overseas region and department of Guadeloupe, in the Lesser Antilles. It is on the northwest coast of Basse-Terre Island. The inhabitants are called Deshaisiens. ### 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. ### Virgin Gorda / Prickly Pear, British Virgin Island *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 for s... ## Booking Information - **Book This Cruise:** https://cruisepirate.ai/cruise/2317144 - **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/2317144 - **Markdown URL:** https://cruisepirate.ai/cruise/2317144.md - **API Endpoint:** https://cruisepirate.ai/api/cruises/2317144/ - **Primary Image:** https://images.cruisepirate.ai/v3/static/cruise-lines/windstar-cruises/wind-surf/other/131918.webp - **Data Source:** CruisePirate Cruise Database - **Last Updated:** 2026-07-15 23:48:50 UTC