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Knot Your Average Crossing
Apr 4, 2026 — Apr 18, 2026
Starting from
PHILIPSBURG, ST. MAARTEN → LISBON
14 Nights on Wind Surf
Set sail on an unforgettable ocean crossing aboard one of our majestic sailing ships, where you’ll immerse yourself in the timeless art of seafaring. This voyage features a guest speaker offering fascinating talks on navigation history, legendary explorers, and even swashbuckling pirates. You’ll learn to read charts, tie sailor’s knots, and even navigate the vessel on the Flying Bridge alongside our Officers. Enjoy stargazing and star mapping sessions, and hear navigational insights directly from the Captain himself. Throughout the journey, hands-on workshops and immersive activities will deepen your connection to the sea — and for a final splash of fun, join our lively "Pirates of the Atlantic” themed party, so don’t forget to pack your nautical outfits!.





Popular Highlights
Learn how to read a navigational chart and participate in a knot tying workshop
Private yacht lifestyle with no interruptions
Star gaze and map the constellations with one of the ships Officers.
Learn how to navigate the vessel on the Flying Bridge.
Time for your favorite indulgences – from a relaxing massage to breakfast in bed.
Indulge in gourmet dining options with dishes created by James Beard Foundation award winning chefs.

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 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, 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: 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.
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, 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.

Ponta Delgada is the capital of São Miguel Island, gateway to the crater lakes and volcano of Sete Cidades and to the Azores Archipelago of Portugal. There is much to do here including horseback riding, golfing, and inviting beaches with volcanic sand, tidal pools and inviting surfing or body boarding. Sites to see include the impressive, 3-arched city gates and the Gothic-style Church of St. Sebastian near the harbor, the Hermitage of Our Lady of Peace Temple, the quirky street art and the Carlos Machado Museum with a variety of artifacts of the Azorean culture.
Ponta Delgada, Best of the Azores: Furnas Valley & Hotsprings with Cozido *


Ponta Delgada, Best of the Azores: Furnas Valley & Hotsprings with Cozido *
Traveling by coach, you'll follow the road that heads north over the island, stopping at the Sta Iria viewpoint to look over the north coast. You'll visit the local tea plantation and factory, and sample some of the better-known Azorean blends. Then, continue to the Pico do Ferro viewpoint with a magnificent outlook over the Furnas Valley. You'll head up to the lake in time to see your lunch being taken out of an earthen oven in the ground , where it has been cooked using natural geo-thermal power. Return to the village to dine on your special lunch: "Cozido das Caldeiras." Afterwards you will see the Terra Nostra Garden -among the most beautiful gardens in the Azores. This park features a natural hot-water swimming pool. You'll have time for a quick swim if you wish. Visit some hot springs in the village to learn about the different mineral water sources; then return to Ponta Delgada via the south coast,passing by at Vila Franca, which was the island's first capital. Please note : Wear comfortable clothes and walking shoes and bring a camera, hat, ,sunscreen, and local currency if you wish to purchase any goods. Bring your swim suit, towel and flip flops if you wish to swim at Terra Nostra's pool. The swiming pool's ferrous water fades bright colors. A swim suit with dark colors is recommended. The facilities include a few changing rooms and two cold water showers. Terra Nostra Garden is currently under renovation, including the changing rooms available for those who wish to swim at the thermal pool. During the renovation works there are temporary changing rooms/facilities available.
Ponta Delgada, Concierge Collection: Full Day Private Van with Driver & English-speaking Guide*


Ponta Delgada, Concierge Collection: Full Day Private Van with Driver & English-speaking Guide*
Explore at your leisure with a private vehicle, driver and English-speaking guide. This exclusive tour will allow you to customize your time ashore and explore the most interesting sites in the comfort and privacy of your own van. With your private vehicle, and the personalized attention of your driver and English-speaking guide, you will have the flexibility and independence to design your itinerary ashore. See the iconic sites, or create your own personal stops to make the experience your own. Please note : Capacity: 3 - 6 guests. Private vans are ordered per vehicle (not per person). This tour includes transport in a private van, driver and English Speaking Guide. Itinerary can be adjusted with tour guide as long as it's in the area and does not exceed the duration of 8 hours. Recommended for physically challenged guests.
Ponta Delgada, Hike Sete Cidades *


Ponta Delgada, Hike Sete Cidades *
Lace up your boots and grab your sense of adventure, you'll be heading out on a spectacular journey on foot through the Azores' stunning natural landscapes. After a 30-minute drive across São Miguel island , you'll arrive at Vista do Rei , a breathtaking viewpoint considered one of the seven wonders of Portugal, famous for its magnificent views of the Sete Cidades caldera. Also called the King's View, from here you'll not only be awed by panoramic views of two dazzling alpine lakes, but also begin a 2-hour moderate-level hike at the nearby trailhead. Set out with an expert guide across steep pathways, passing the 3-mile-wide crater and verdant forest environs dappling the island's western coast. Along the way, hear the fascinating geothermal and geographical history of the region while identifying native flora and fauna. The trek will conclude at the quaint village of Sete Cidades on the western edge of the lake, where you'll enjoy some time to cool down before being transported back to the port. Please note : Wear comfortable outdoor clothes and hiking footwear ( dress in layers and bring a rain protection), a hat and sunscreen, water and energy bar, camera, and local currency if you wish to purchase any goods.
Ponta Delgada, Concierge Collection: Half Day Private Car with English-speaking Driver*
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Ponta Delgada, Concierge Collection: Half Day Private Car with English-speaking Driver*
Explore at your leisure with a private vehicle, driver, and English-speaking guide. This exclusive tour will allow you to customize your time ashore and explore the most interesting sites in the comfort and privacy of your own car. With your private vehicle, and the personalized attention of your driver and English-speaking guide, you will have the flexibility and independence to design your itinerary ashore. See the iconic sites, or create your own personal stops to make the experience your own. Please note : Capacity: 1-2 guests. Private cars are ordered per vehicle (not per person). This tour includes transport in a private car, driver and English Speaking Guide. Itinerary can be adjusted with tour guide as long as it's in the area and does not exceed the duration of 4 hours. Recommended for physically challenged guests.
Ponta Delgada, Sete Cidades Crater Lake *


Ponta Delgada, Sete Cidades Crater Lake *
Discover one of the seven natural wonders of Portugal. From Ponta Delgada you will head to Fajã de Baixo to visit a pineapple plantation where the fruit grows in hothouses. See the different phases of the pineapple's growing cycle and taste a sample of pineapple liqueur, juice or fruit (subject to the supplier's availability), with time for souvenir shopping afterwards. Continue along the mountain road, descending into the village of Sete Cidades, named for the volcano towering above. You'll have free time for a quick coffee (not included) or to stretch your legs before you continue to the Santiago Lake and Vista do Rei viewpoints . You will reach the main crater of this extinct volcano at an elevation of 1,900 feet above sea level. From the edge of the crater, eight miles in circumference, take in the magnificent view of the "twin" lakes at the bottom. Return to Ponta Delgada upon completion of your tour. Please note : Wear comfortable clothes and walking shoes and bring a camera, hat, sunscreen, and local currency if you wish to purchase any goods.
Ponta Delgada, Concierge Collection: Full Day Private Car with Driver & English-speaking Guide*
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Ponta Delgada, Concierge Collection: Full Day Private Car with Driver & English-speaking Guide*
Explore at your leisure with a private vehicle, driver, and English-speaking guide. This exclusive tour will allow you to customize your time ashore and explore the most interesting sites in the comfort and privacy of your own car. With your private vehicle, and the personalized attention of your driver and English-speaking guide, you will have the flexibility and independence to design your itinerary ashore. See the iconic sites, or create your own personal stops to make the experience your own. Please note : Capacity: 1-2 guests. Private cars are ordered per vehicle (not per person). This tour includes transport in a private car, driver and English Speaking Guide. Itinerary can be adjusted with tour guide as long as it's in the area and does not exceed the duration of 8 hours. Recommended for physically challenged guests.
Ponta Delgada, Concierge Collection: Half Day Private Van w/ English-speaking Driver


Ponta Delgada, Concierge Collection: Half Day Private Van w/ English-speaking Driver
Explore at your leisure with a private vehicle, driver, and English-speaking guide. This exclusive tour will allow you to customize your time ashore and explore the most interesting sites in the comfort and privacy of your own van. With your private vehicle, and the personalized attention of your driver and English-speaking guide, you will have the flexibility and independence to design your itinerary ashore. See the iconic sites, or create your own personal stops to make the experience your own. Please note : Capacity: 3 - 6 guests. Private vans are ordered per vehicle (not per person). This tour includes transport in a private van, driver and English Speaking Guide. Itinerary can be adjusted with tour guide as long as it's in the area and does not exceed the duration of 4 hours. Recommended for physically challenged guests.

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
- 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.
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
- 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
No other dates are available.