Ocean Crossings

 
Philipsburg, St. Maarten to Lisbon
Sat Mar 27, 2027 - Sun Apr 11, 2027,
 15 days
 on Wind Surf
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Starting from $2,799 USD
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ITINERARY AND SHORE EXCURSIONS

The best on land brought to you by the best at sea. Get to the heart of local cultures with Windstar shore excursions. You don't want to just dip a toe in local culture, you want to dive into the deep end, and that's exactly what Windstar shore excursions are designed to do. All of our excursion are created to provide authentic local experience - the kind travelers like you are looking for. And with more than 2,500 excursions to choose from, you can experience your destination in whatever way is most meaningful to you. Whether you're an outdoor enthusiast, a foodie, a history buff, or someone who loves to get to know the faces behind the many places we travel.

Date
Port
Arrive
Depart
Marina
Shore
Excursions
Expand
Sat Mar 27
Philipsburg, St. Maarten
Arrive:
Depart:5:00 PM
Watersports Platform: 
4 Available
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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.
4 Shore Excursions Available
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St. Maarten, Post Island Tour with Transfer to AirportEssentials Collection | Sightseeing
Duration4 Hours
Activity LevelEasy
$99
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St. Maarten, Post Island Tour with Transfer to HotelEssentials Collection | Sightseeing
Duration4 Hours
Activity LevelEasy-Moderate
$99
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St. Maarten: Americas Cup Sailboat Racing with Transfer to AirportBoating | Essentials Collection | Outdoors | Refreshments
Duration2.5 Hours
Activity LevelModerate
$179
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St. Maarten: Americas Cup Sailboat Racing with Transfer to Windstar Hotel Outdoors | Refreshments | Boating | Essentials Collection
Duration2.5 Hours
Activity LevelModerate
$179
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Sun Mar 28
AT SEA
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Mon Mar 29
AT SEA
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Tue Mar 30
AT SEA
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Wed Mar 31
AT SEA
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Thu Apr 1
AT SEA
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Fri Apr 2
AT SEA
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Sat Apr 3
AT SEA
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Sun Apr 4
AT SEA
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Mon Apr 5
AT SEA
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Tue Apr 6
AT SEA
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Wed Apr 7
Funchal
Arrive:8:00 AM
Depart:11:59 PM
Watersports Platform: 
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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.
Thu Apr 8
PORTO SANTO, MADEIRA
Arrive:8:00 AM
Depart:1:00 PM
Watersports Platform: 
3 Available
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PORTO SANTO, MADEIRA
3 Shore Excursions Available
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Porto Santo, Hike Pico do CasteloHiking | Sightseeing
Duration3 Hours
Activity LevelStrenuous
$79
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Porto Santo, Island Horseback RidingHorseback | Outdoors | Sightseeing
Duration1.5 Hours
Activity LevelModerate
$145
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Porto Santo, Porto Santo Island TourOutdoors | Sightseeing
Duration5 Hours
Activity LevelModerate
$105
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Fri Apr 9
AT SEA
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Sat Apr 10
AT SEA
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Sun Apr 11
Lisbon
Arrive:8:00 AM
Depart:
Watersports Platform: 
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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.