Ocean Crossings + Ponta Delgada, Azores
 
Philipsburg, St. Maarten to Lisbon
Sat Apr 4, 2026 - Sat Apr 18, 2026,
 14 days
 on Wind Surf
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Starting from $2,599 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
Watersports
Platform
Shore
Excursions
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Sat Apr 4
Philipsburg, St. Maarten
Arrive:
Depart:7:00 PM
Watersports Platform: 
5 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.
5 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, 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 Apr 5
AT SEA
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Mon Apr 6
AT SEA
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Tue Apr 7
AT SEA
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Wed Apr 8
AT SEA
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Thu Apr 9
AT SEA
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Fri Apr 10
AT SEA
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Sat Apr 11
AT SEA
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Sun Apr 12
AT SEA
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Mon Apr 13
AT SEA
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Tue Apr 14
Ponta Delgada
Arrive:8:00 AM
Depart:6:00 PM
Watersports Platform: 
7 Available
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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.
7 Shore Excursions Available
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Ponta Delgada, Concierge Collection: Half Day Private Car with English-speaking Driver*Concierge Collection | Sightseeing
Duration4 Hours
Activity LevelEasy
$449
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Ponta Delgada, Concierge Collection: Half Day Private Van w/ English-speaking DriverConcierge Collection | Sightseeing
Duration4 Hours
Activity LevelEasy
$699
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Ponta Delgada, Best of the Azores: Furnas Valley & Hotsprings with Cozido *Dining | Essentials Collection | Sightseeing | Watersports
Duration8 Hours
Activity LevelModerate
$185
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Ponta Delgada, Sete Cidades Crater Lake *Essentials Collection | Sightseeing | Refreshments
Duration3.5 Hours
Activity LevelEasy
$79
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Ponta Delgada, Concierge Collection: Full Day Private Car with Driver & English-speaking Guide*Concierge Collection | Sightseeing
Duration8 Hours
Activity LevelEasy
$949
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Ponta Delgada, Concierge Collection: Full Day Private Van with Driver & English-speaking Guide*Concierge Collection | Sightseeing
Duration8 Hours
Activity LevelEasy
$1,399
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Ponta Delgada, Hike Sete Cidades *Essentials Collection | Hiking | Sightseeing
Duration4 Hours
Activity LevelModerate-Strenuous
$89
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Wed Apr 15
AT SEA
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Thu Apr 16
AT SEA
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Fri Apr 17
AT SEA
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Sat Apr 18
Lisbon
Arrive:7:00 AM
Depart:
Watersports Platform: 
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.