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Ocean Crossing
Mar 27, 2027 — Apr 11, 2027
Starting from
PHILIPSBURG, ST. MAARTEN → LISBON
15 Nights on Wind Surf
Indulge yourself in leisurely, unscheduled days where time suspends in the magic of the sea. Sleep late. Dine early. Establish your own rhythm in sync with the waves and the arc of the sun and moon overhead. Watch the constellations drift and let your mind shake off all the cobwebs of shore. Feast on the impossible beauty of liquid sunsets, and let your soul dance with the dolphins in the spray off the bow.






Popular Highlights
Drop by the Bridge for an impromptu navigation lesson.
Extraordinary cuisine – and great fitness equipment to work it off.
Make new friendships with like-minded travelers.
Time for your favorite indulgences – from a relaxing massage to breakfast in bed.
More stars overhead than you ever imagined.
Sweeping ocean vistas from your stateroom or suite.
Private yacht lifestyle with no interruptions.

Pastel-colored buildings and shops filled with tempting souvenirs herald your arrival to bustling Philipsburg. Situated near the harbor on the Dutch side of St. Maarten, Philipsburg owes its discovery to Christopher Columbus in 1493. Today, celebrated Front Street is home to a number of local Creole restaurants as well as jewelry stores, stylish boutiques, and lively casinos for visitors seeking an upbeat island experience.
St. Maarten, Post Island Tour with Transfer to Hotel
St. Maarten, Post Island Tour with Transfer to Hotel
The best way to experience 80 different cultures in one day is to take the "Saint-Martin/Saint-Maarten Island Tour." You will depart from Philipsburg and head to Oyster Pond, a charming little locale with a picturesque marina on the French side of the island. From there, following Coralita Road, along the coast, you will stop at a l ookout point from where you can see St. Barth and Tintamare Island . You will continue past famous Orient Beach, well known for its clothing optional beach, past Grand Case, the Culinary Capital of the Caribbean, on your way to Marigot, capitol of the French side. Marigot is best known for its seaside, open-air market, where you can find truly charming souvenirs of your Caribbean vacation. If you are "shopped out", try one of the French cafés right next door, for a café au lait with a croissant. Upon leaving Marigot, you will make one more photo stop on Cay Hill, from where you have a wonderful view over Simpson Bay Lagoon . Our last stop will be Philipsburg, capital of the Dutch side, best known for its jewelry-, electronics-, and high end clothing stores. On the Boardwalk you will find quaint restaurants for a quick bite to eat before your flight and an excellent photo opportunity of your yacht lying in Philipsburg Harbor. From there, you will be taken straight to your Windstar Hotel Please note : Wear comfortable walking shoes.
St. Maarten, Post Island Tour with Transfer to Airport
St. Maarten, Post Island Tour with Transfer to Airport
The best way to experience 80 different cultures in one day is to take the "Saint-Martin/Saint-Maarten Island Tour. " You will depart from Philipsburg and head to Oyster Pond, a charming little locale with a picturesque marina on the French side of the island. From there, following Coralita Road, along the coast, you will stop at a lookout point from where you can see St. Barth and Tintamare Island. You will continue past famous Orient Beach, well known for its clothing optional beach, past Grand Case, the Culinary Capital of the Caribbean, on your way to Marigot, capitol of the French side. Marigot is best known for its seaside, open-air market , where you can find truly charming souvenirs of your Caribbean vacation. If you are "shopped out", try one of the French cafés right next door, for a café au lait with a croissant. Upon leaving Marigot, you will make one more photo stop on Cay Hill, from where you have a wonderful view over Simpson Bay Lagoon. Our last stop will be Philipsburg, capital of the Dutch side, best known for its jewelry-, electronics-, and high end clothing stores. On the Boardwalk you will find quaint restaurants for a quick bite to eat before your flight and an excellent photo opportunity of your yacht lying in Philipsburg Harbor. From there, you will be taken straight to the airport. Please note : Wear comfortable walking shoes.
St. Maarten: Americas Cup Sailboat Racing with Transfer to Windstar Hotel
St. Maarten: Americas Cup Sailboat Racing with Transfer to Windstar Hotel
Experience the thrill of racing multi-million dollar America's Cup Race sailboat s in the warm blue waters and brisk trade winds of St. Maarten. Previous sailing experience is not necessary for this excursion, which is one of the highest rated in the Caribbean. You will depart directly from your yacht in Marigot to Philipsburg, where after a briefing you will take a 10-minute tender ride out to your allocated sailboat. Either Dennis Conner's America's Cup winning Stars & Stripes, Canada II, or True North are yours for this once-in-a-lifetime adventure . The expert crew will show you exactly what to do if you want to take a "crew member's" position. Then it's off to the racecourse - grind a winch - trim a sail - punch a stopwatch, or just sit back, relax and enjoy the included refreshments. After the race enjoy a victory rum punch party and browse through the museum souvenir boutique before your transfer to your Windstar hotel. Please note : Wear suitable footwear for the sailboat. This event is weather/wind dependent. Every effort is made to accommodate guests with special needs. Guests with special needs may need be accompanied by a companion who has the capability of assisting the guest on and off the boats. Please not that this is a physically demanding tour and may not be suitable for all guests. This tour requires all participants to actively follow the safety briefing, navigate the vessel independently, and participate in the experience without the need for continuous assistance.
St. Maarten: Americas Cup Sailboat Racing with Transfer to Airport
St. Maarten: Americas Cup Sailboat Racing with Transfer to Airport
Experience the thrill of racing multi-million dollar America's Cup Race sailboats in the warm blue waters and brisk trade winds of St. Maarten. Previous sailing experience is not necessary for this excursion, which is one of the highest rated in the Caribbean. You will be tendered out from the 12 Metre Clubhouse dock at Dock Maarten, where after a briefing you will take a 10-minute tender ride out to your allocated sailboat. Either Dennis Conner's America's Cup winning Stars & Stripes , Canada II, or True North IV are yours for this once-in-a-lifetime adventure. The expert crew will show you exactly what to do if you want to take a "crew member's" position. Then it's off to the racecourse - grind a winch - trim a sail - punch a stopwatch, or just sit back, relax and enjoy the included refreshments. After the race enjoy a victory rum punch party at the 12 Metre Clubhouse before your transfer to the airport. Please note : Wear soft-soled suitable footwear for the sailboat. This event is weather/wind dependent. Your flight must depart at 2:30pm or later to book this tour. Every effort is made to accommodate guests with special needs. Guests with special needs may need be accompanied by a companion who has the capability of assisting the guest on and off the boats. Please not that this is a physically demanding tour and may not be suitable for all guests. This tour requires all participants to actively follow the safety briefing, navigate the vessel independently, and participate in the experience without the need for continuous assistance.

Considered one of Portugal's main tourist attractions and home of world-famous footballer Cristiano Ronaldo, Funchal is known for its style and beauty. Visit Cabo Girao, the highest sea cliff in Europe or take a trip to the Pica da Torre for an incredible view of Camara de Lobos, a delightful fishing village. With a long history of Madeira winemaking, there'll be time here for a little wine tasting, a meal at one of the many 5-star restaurants, sightseeing to 15th century Cathedral of Our Lady of the Assumption, shopping the bargains to be found here, or experiencing the vibrant night life.

PORTO SANTO, MADEIRA
Porto Santo, Hike Pico do Castelo
Porto Santo, Hike Pico do Castelo
Begin with a short transfer from the pier to the starting point of your hike at Pico do Castelo, one of Porto Santo’s most iconic peaks. The trail winds through reforested areas of pine and native vegetation, a striking contrast to the island’s naturally dry landscape. As you climb toward the 437-meter summit, enjoy sweeping views over the island’s coastline and inland valleys, with several scenic points perfect for photography along the way. Upon reaching the top, take in panoramic vistas of the Atlantic Ocean and surrounding terrain before descending along the same path. Following your hike, a short transfer will take you to Campo de Cima for a brief refreshment stop before returning to the pier. Tour itinerary may vary depending on local conditions.
Porto Santo, Island Horseback Riding
Porto Santo, Island Horseback Riding
Experience the natural beauty of Porto Santo from a new perspective on a guided horseback adventure through scenic island trails. After a short transfer to the Porto Santo Equestrian Center, you’ll be greeted by professional guides and matched with a well-trained horse suited to your experience level. Following a safety briefing, set out on a relaxing ride across volcanic landscapes, sandy paths, and open countryside, taking in peaceful views of the island’s hills and coastline. This slow-paced excursion offers an enjoyable and accessible way to connect with nature, ideal for both beginners and experienced riders alike. Please note: The tour includes horses and riding gear, a safety briefing, and an escort from the Equestrian Center; no prior riding experience is required.

The rhythm of Lisbon invites you to join its captivating dance. This splendid capital city on the banks of the Rio Teja offers a warm welcome and an unparalleled blend of architectural styles. Elegant outdoor cafés line the cobbled sidewalks. Turn-of-the-century funiculars climb the scenic hills. Find the UNESCO sites of the Tower of Belem and the Monastery of the Hieronymites. And, everywhere, the city engages you with its easy style and remarkable charm.
Staterooms
Starting from
Amenities
- STE Queen Size Bed with Luxurious Linens
- Fully-Stocked Mini-Bar/Refrigerator
- Fully Upgraded Bath Amenity Line Including Pure Pampering L'Occitane
- Fruit Basket with Berries
- Hair Dryers and 110/220 Outlets
- Upgraded High End Quality Bath Robes
- Safe
- Fresh Flowers
- Granite Vanity with Magnifying Mirror
- Bathroom with Granite Countertop and Shower
- Free Internet Service (1 Voucher per Suite)
- Preferred on Board Check In
- Invitation to Captain or Senior Officer Table
- Personalized Wake-Up Call Service with Preferred Beverage Coffee/Tea/Juice
- Preferred Specialty Restaurant Dining
- Preferred Canapes Service
- Maschio Prosecco
- Illy Espresso Machine
- Binoculars
- TV with DVD Player
Suite
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.
Starting from
Amenities
- Queen Size Bed with Luxurious Linens
- Fully-Stocked Mini-Bar/Refrigerator
- L'Occitane Bath Amenities
- Fresh Fruit
- Hair Dryers and 110/220 Outlets
- Waffle Weave Robe and Slippers
- Safe
- Granite Vanity with Magnifying Mirror
- Bathroom with Granite Countertop and Shower
- Wi-Fi (Internet cards can be purchased at reception)
- TV with DVD Player
Category TX Deluxe
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.
Starting from
Amenities
- Queen Size Bed with Luxurious Linens
- Fully-Stocked Mini-Bar/Refrigerator
- L'Occitane Bath Amenities
- Fresh Fruit
- Hair Dryers and 110/220 Outlets
- Waffle Weave Robe and Slippers
- Safe
- Granite Vanity with Magnifying Mirror
- Bathroom with Granite Countertop and Shower
- Wi-Fi (Internet cards can be purchased at reception)
- TV with DVD Player
Category AX Deluxe
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.
Starting from
Amenities
- Queen Size Bed with Luxurious Linens
- Fully-Stocked Mini-Bar/Refrigerator
- L'Occitane Bath Amenities
- Fresh Fruit
- Hair Dryers and 110/220 Outlets
- Waffle Weave Robe and Slippers
- Safe
- Granite Vanity with Magnifying Mirror
- Bathroom with Granite Countertop and Shower
- Wi-Fi (Internet cards can be purchased at reception)
- TV with DVD Player
Category 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 products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers.
Starting from
Amenities
- Queen Size Bed with Luxurious Linens
- Fully-Stocked Mini-Bar/Refrigerator
- L'Occitane Bath Amenities
- Fresh Fruit
- Hair Dryers and 110/220 Outlets
- Waffle Weave Robe and Slippers
- Safe
- Granite Vanity with Magnifying Mirror
- Bathroom with Granite Countertop and Shower
- Wi-Fi (Internet cards can be purchased at reception)
- TV with DVD Player
Category BX Deluxe
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.
Starting from
Amenities
- Queen Size Bed with Luxurious Linens
- Fully-Stocked Mini-Bar/Refrigerator
- L'Occitane Bath Amenities
- Fresh Fruit
- Hair Dryers and 110/220 Outlets
- Waffle Weave Robe and Slippers
- Safe
- Granite Vanity with Magnifying Mirror
- Bathroom with Granite Countertop and Shower
- Wi-Fi (Internet cards can be purchased at reception)
- TV with DVD Player
Category B
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.
Amenities
- Queen Size Bed with Luxurious Linens
- Fully-Stocked Mini-Bar/Refrigerator
- Fully Upgraded Bath Amenity Line Including Pure Pampering L'Occitane
- Fruit Basket with Berries
- Walk-in Closet and Ample Drawer Space
- Hair Dryers and 110/220 Outlets
- Upgraded High End Quality Bath Robes
- Safe
- Fresh Flowers
- Granite Vanity with Magnifying Mirror
- Bathroom with Granite Countertop, Full-Size Tub, and Shower
- Free Internet Service (1 Voucher per Suite)
- Preferred on Board Check In
- Invitation to Captain or Senior Officer Table
- Personalized Wake-Up Call Service with Preferred Beverage Coffee/Tea/Juice
- Preferred Specialty Restaurant Dining
- Preferred Canapes Service
- Maschio Prosecco
- Illy Espresso Machine
- Binoculars
- TV with DVD Player
Broadmoor Suite/Sea Island Suite
For Broadmoor Suite/Sea Island Suite: Enjoy 495 square feet of elevated comfort and refined style. Within this category, each suite embodies a unique design perspective inspired by two renowned Xanterra properties. Suite 503 draws inspiration from Sea Island, reflecting the relaxed coastal elegance and warm Southern hospitality for which the celebrated Xanterra property is known. Suite 502 channels the spirit of The Broadmoor, embracing the grandeur, mountain-resort heritage, and timeless sophistication that define this iconic destination. A separate bedroom and living room, complete with an in-suite dining area, create an inviting setting for relaxation or entertaining. The expansive bathroom further enhances the experience, featuring both a whirlpool spa tub and a rejuvenating massage shower.
Amenities
- Queen Size Bed with Luxurious Linens
- Fully-Stocked Mini-Bar/Refrigerator
- Fully Upgraded Bath Amenity Line Including Pure Pampering L'Occitane
- Fruit Basket with Berries
- Hair Dryers and 110/220 Outlets
- Upgraded High End Quality Bath Robes
- Safe
- Fresh Flowers
- Granite Vanity with Magnifying Mirror
- Bathroom with Granite Countertop, Full-Size Tub, and Shower
- Free Internet Service (1 Voucher per Suite)
- Preferred on Board Check In
- Invitation to Captain or Senior Officer Table
- Personalized Wake-Up Call Service with Preferred Beverage Coffee/Tea/Juice
- Preferred Specialty Restaurant Dining
- Preferred Canapes Service
- Maschio Prosecco
- Illy Espresso Machine
- Binoculars
- TV with DVD Player
Owner’s suite
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.
Amenities
- Y Queen Size Bed with Luxurious Linens
- Fully-Stocked Mini-Bar/Refrigerator
- L'Occitane Bath Amenities
- Fresh Fruit
- Hair Dryers and 110/220 Outlets
- Waffle Weave Robe and Slippers
- Safe
- Granite Vanity with Magnifying Mirror
- Bathroom with Granite Countertop and Shower
- Wi-Fi (Internet cards can be purchased at reception)
- TV with DVD Player
Guaranteed Cabin** (chosen by Windstar) 90
Y Guaranteed Cabin** (chosen by Windstar)
Available Dates
| Date | Yacht | Starting from | Actions |
|---|---|---|---|
| Mar 19 (Sun) – Apr 3 (Mon), 2028March 19 (Sun) – April 3 (Mon), 2028 | Wind Surf |