Ocean Crossings
Nov 18, 2025 — Dec 2, 2025
Starting from $5,058 Displayed pricing is based off of double occupancy per person. Pricing subject to change based on occupancy and cabin selection.
See more routes around Ocean CrossingLISBON → PHILIPSBURG, ST. MAARTEN
14 Nights in Wind Surf
Popular Highlights

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.

St. John's is a city of Old World charm and elegance which lingers in the varied architecture of Georgian, Victorian, Vernacular, Romantic and International flavors. The picturesque seafront where tiny, colorful boats are moored, the cheerful wooden buildings carefully refurbished to retain their original features, the vibrant Market Street offering vegetables, fruit and fish and the duty-free Heritage Quay shopping area provide a delightful atmosphere to captivate you. Sites to see include St. John's Cathedral with its white Baroque towers, the Botanical Garden, St. John's Antigua Lighthouse, and Fort James.
St.John's, Concierge Collection: Sail Snorkel and Beach
St.John's, Concierge Collection: Sail Snorkel and Beach
No additional details available for this excursion.
St. Johns, Spectacular Antigua
St. Johns, Spectacular Antigua
Courteous and knowledgeable guides are eager to indulge you in the magnificent colonial history of Antigua. Once the Naval Base for the British in the Caribbean, Antigua's strategic location and excellent natural harbors create an Island haven for both ships and Sun Seekers alike. Only the best Coach buses, fully air-conditioned are waiting to take you on your Island discovery adventure! Your first stop will be at Dow's Hi ll, offering one of the best panoramic views on the island - perfect for taking photos. Take a short guided tour of the area and enjoy a multimedia presentation at the onsite visitors' center. Then it's on to Blockhouse Ruins built in 1787 standing 446 ft. atop a sheer cliff above the mighty Atlantic Ocean, you will overlook Indian Creek where the first Arawak Indians settled and lived. In this modern day, see the prestigious St. James' Club on Mamora Bay. On to Shirley Heights Lookout , the most southerly point in Antigua, named after Sir Thomas Shirley. There is a commanding cliff top view over the Atlantic Ocean and English Harbor 487 ft. above sea level. On a clear day, the volcanic island of Montserrat, 28 miles away, can be seen. Finish your tour at Nelson's Dockyard village, named after Admiral Lord Horatio Nelson, and built in 1725, to provide a base for a squadron of ships patrolling the West Indies maintaining England's sea. Please note : Bring your camera.
St. Johns, Segway Fort Conqueror
St. Johns, Segway Fort Conqueror
You will be met on the pier by a guide before being escorted to an awaiting air-conditioned taxi that will take you to Fort James Beach 40 minutes away from the pier. Travel back to a time in Antigua's history in 1706 when the British built one of its most impressive Forts to protect against French invasion. Conquer the trail leading to this most impressive structure of defense, built with full Masonic honors as your Segway PT moves you securely down the path of history after a complete safety orientation. You'll be amazed at how easy it is to manoeuver this phenomenon of motion as it carries you through the large wooden gates of Fort James where a spectacular sight of the Caribbean Sea awaits. After conquering the fort, embark on an endless adventure cruising by beach picnic parks, scores of fruit trees and miles of beach in minutes on your zero emission Segway as knowledgeable and fun guides fill you in on interesting facts about the area. After the tour enjoy delicious refreshments and cool drinks around a picnic table while indulging in a breathtaking view of one of the islands most popular beach bars and restaurant. With time to relax on the beach you can catch up on that good read or take a dip or just do absolutely nothing. Please note : Segway orientation, safety gear (helmets), bottled water, and soft-drinks are included. Bring sunscreen, your swimsuit, towel and camera.
St Johns, Concierge Collection, Jet Ski Adventure
St Johns, Concierge Collection, Jet Ski Adventure
Captain your own 2-seater jet ski on a guided tour of Antigua's south coast and discover the exciting and amazing Antigua shoreline and some of its 365 beaches! Board your air-conditioned transportation for a 15-minute ride through Antigua's countryside, rich in daily West Indian life, local villages, and old churches, that exemplifies West Indian culture, to Hawksbill Beach in Five Islands. Whether you have driven a jet ski or not, or you own your own, this tour is for you. Our experienced and courteous guides ensure that you are comfortable operating the jet ski and then you will navigate at a pace that matches your comfort and experience level. At the calm waters of Hawksbill Beach you will be met by an experienced Guide, who will give you a safety briefing on how to operate your 2-seater Yamaha jet ski, equipped with all the latest safety features. Then it's time to follow your experienced Guide out of the harbor for a spectacular adventure along Antigua's south coast in and out of bays and around reefs and the south coast white-sand beaches. There will be chance to stop and simply take a swim or relax and soak up the sun in the idyllic beach location. You then will be guided back to Hawksbill Beach along the shoreline seeing dozens of beaches along the crystal-clear Caribbean waters and have another opportunity to soak up the Antiguan sun and see the Antiguan southwest coastline. There will be some time to just chill on the beach, to have a swim and a walk along the beach with a drink from the bar or browse the gift shop. Your air-conditioned transportation will be waiting for the return to the yacht. Please note: Jet skis are sold on the basis there are 2 guests on each jet ski and single guests will be charged double. Guests must be 18 years of age to drive the jet skis and show a valid id. Maximum weight of combined participants is 400 pounds. The tour is not suitable for guests with back problems, guests who are pregnant. Non-swimmers are welcome. Guests should bring sunglasses, sun cream, a towel and wear swim wear. GoPro cameras are available for rent to capture your Antigua tour memories.
St Johns, Chocolate and Rum Making
St Johns, Chocolate and Rum Making
Upon arrival at the pier, you will be greeted by your knowledgeable and friendly guide, who will escort you to your comfortable, air-conditioned transportation. After a short 10-minute drive, you'll arrive in the charming and tropical village of Hodges Bay. Here, you'll meet one of Antigua's most renowned chocolatiers and her expert team. They will welcome you with delicious homemade chocolate samples as they introduce you to your upcoming chocolate-making experience. Using fresh, locally sourced ingredients, you'll have the chance to craft your own gourmet chocolates. In this hands-on workshop, you'll be guided through every step of the chocolate-making process, from dipping and glazing to using molds, with plenty of local stories and insights along the way. You'll gain a deep appreciation for the art of chocolate-making as you create your own sweet creations, which will be packaged for you to take home. Next, we'll embark on a scenic 35-minute drive to the picturesque Galleon Beach in the historic English Harbour area. There, you'll delve into the fascinating history of Caribbean rum, which dates back to the 17th century when enslaved people on sugarcane plantations discovered how to turn molasses into fermented alcohol and eventually distilled rum. In a fun and interactive 90-minute rum masterclass, you'll explore this rich history while creating your own bespoke 750ml bottle of flavored rum. Under the guidance of experts, you'll choose your flavors and design your own label, making for a personalized and unforgettable rum experience.
St. Johns: Presidents Tour
St. Johns: Presidents Tour
This tour has been created especially for Windstar's President and guests. You will be greeted at the pier by your professional Tour Guide for the start of this interesting tour and listen to your Guide through the Whisper Radio System for ease and clarity, so you miss nothing even for those with hearing aids as there are special adaptors! Your first stop will be at Betty's Hope. Built in 1674 by Sir Christopher Codrington, this was the site of one of the first full-scale sugar plantations on Antigua and is located just south of Pares Village. For more than 300 years, this prominent sugar plantation has played a leading role in, and influenced the lives of many generations of Antiguans. This is the only twin sugar mill, standing side by side in the Eastern Caribbean and has several renovated sugar trains used to transport sugar cane across the island which you can view and photograph. Your tour will continue to Devil's Bridge. For hundreds of thousands of years, the Atlantic's waves have crashed into the east coast of Antigua creating a natural arch, or bridge. Numerous geysers and blowholes surround the arch as waves continually break against the coastal rocks. In addition to being a natural phenomenon, Devil's Bridge also holds cultural importance in Antiguan history. A prehistoric, Amerindian site is located within its vicinity and suggests that prehistoric peoples may have used the area for fishing and settlement. Popular belief suggests slaves leapt to their death off of the natural arch during the period of slavery in Antigua. Devil's Bridge gets its name from these myths as the stories contend the devil claimed those who leapt off the bridge. Your tour will continue where you will hug the south coast line and drive past Darkwood Beach, Turner's Beach, Fryes Beach, Jolly Harbour, many secluded beaches, 5* hotels and exclusive homes through Fig Tree Drive, Antigua's lush rainforest area through Antigua's countryside, rich in daily West Indian life, local villages, and old churches, that exemplify West Indian culture. Please note: Wear comfortable clothes and shoes. There is one step in and out of the bus.
St Johns, Swim with the Stingrays
St Johns, Swim with the Stingrays
Here is an outstanding tour and an opportunity to swim with, touch, and feed the stingrays of Antigua in the Caribbean Sea. The stingrays are very friendly and very gentle. You will board your air-conditioned transportation in Falmouth Marina and ride through Antigua's countryside, rich in daily West Indian life, local villages, and old churches. Start your adventure at Stingray City's land base where you can enjoy the company of their monkeys and parrots , and the hospitality of the experienced Stingray City's Guides. Following your safety briefing a short speedboat ride will whisk you to a shallow pool with a white-sand bottom surrounded by a beautiful coral reef in the Caribbean Sea. You will be able to stand up or swim with the stingrays, who will greet you with the familiarity of an old friend. You will be given an opportunity to hand-feed the stingrays and capture the moment with photographs! After feeding, snorkeling, and taking pictures with your new friends, you will return to the land base where you can rinse off the seawater under the bright Caribbean sun, with a shower under a coconut tree, and enjoy a complimentary rum or fruit punch , browse in the gift shop, and share this unique experience with your fellow guests before your return journey to your ship. Please note: Wear your swimsuit under a cover up, bring a towel, and sunscreen.
St. Johns, Open Course Canopy Challenge
St. Johns, Open Course Canopy Challenge
You will be met at your ship by professional guides and taken by air-conditioned taxi to the Antigua rainforest some 30 minutes away. After a safety briefing and equipment distribution your exciting tour will begin. Starting at the Old Pump House, you will walk over a suspension bridge from the side of the building, which spans the gorge to the far bank. Once across the bridge, your remaining thrilling journey through the forest will begin, as you trail to the first aerial zip, and continue onto the others which criss-cross the vast gorge. There are zip lines of 52 feet to 328 feet in length. The geography of the gorge dictates that you will be above the treetops for large parts of the run - entering a corridor in the foliage at either end. There are a series of 12 zip lines, 9 typical challenge elements and 2 suspension bridges giving a bird's eye view of the flora and fauna in the rainforest while listening to the numerous bird species. You will also see a series of large trees (including the silk cotton, one of Antigua's National Symbols), prominent boulders, a rock pool, small waterfall and a shaded area with interesting plants, wild fruits, vines, mosses and lichens. Please note : This tour includes some slight physical exertion and is not recommended for pregnant women, persons with a history of heart conditions, seizures, back, knee or shoulder problems or other pre-existing health problems. Maximum weight is 235 lbs; minimum height is 5 feet. Participants should not wear strapless shoes or strapless sandals and ladies should wear shorts or long pants. A change of shirt is recommended. Guests are also offered complementary water on the course.
St. Johns, Beach Escape
St. Johns, Beach Escape
To start or end the day in the best way possible you should experience a relaxing and carefree morning or afternoon on the half-mile secluded white-sand beach at Valley Church. The beach is beautiful, the water is warm and blue, and your experienced guides are on hand to make your day special. Board your air-conditioned taxi and drive approximately 30 - 35 minutes from St. John's to the famed Nest Beach Bar & Restaurant on Valley Church Beach. The beach here offers half a mile of soft white sand bordered by coconut palms and sea grape trees. You will be greeted on arrival with your complimentary drink, (rum punch or fruit punch) before you relax in a complimentary lounge chair in a specially designated area of the beach and sip on your welcome cocktail. Enjoy approximately 3 hours of relaxation while you soak up the sun, take a gentle stroll along the beach, refresh yourself by swimming in the Caribbean Sea or treat yourself to a snack or an early lunch in the restaurant overlooking the sand and sea. Umbrellas are available for a nominal charge. The Nest Beach Bar & Restaurant features restrooms, freshwater showers as well as a beach bar and restaurant. Please note : Bring a swimsuit, a towel, adequate sun protection, and a camera to record your special memories!

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.

Available Staterooms
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.
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.
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.
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 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.
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
- 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.