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Star Collector: Hearty Ports & Rum Punches - A Transatlantic Crossing
 
Lisbon to Philipsburg, St. Maarten
Tue Nov 18, 2025 - Sun Dec 7, 2025,
 19 days
 on Wind Surf
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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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Tue Nov 18
Lisbon
Arrive:
Depart:7:00 PM
Watersports Platform: 
7 Available
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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.
7 Shore Excursions Available
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Lisbon, Concierge Collection: Half Day Private Car & Guide *Concierge Collection | Sightseeing
Duration4 Hours
Activity LevelEasy
$625
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Lisbon, Concierge Collection: Half Day Private Van & Guide *Concierge Collection | Sightseeing
Duration4 Hours
Activity LevelEasy
$725
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Lisbon, Concierge Collection: Full Day Private Car & Guide *Concierge Collection | Sightseeing
Duration8 Hours
Activity LevelEasy
$999
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Lisbon, Concierge Collection: Full Day Private Van & Guide *Concierge Collection | Sightseeing
Duration8 Hours
Activity LevelEasy
$1,099
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Lisbon, Majestic Sintras & Cascais With Transfer to Windstar Hotel *Essentials Collection | Sightseeing
Duration3.5 Hours
Activity LevelModerate
$135
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Lisbon, Highlights with Transfer to Airport *Essentials Collection | Sightseeing
Duration2.5 Hours
Activity LevelEasy
$109
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Lisbon by Tuk Tuk *Essentials Collection | Sightseeing | Refreshments | Wine
Duration3 Hours
Activity LevelEasy-Moderate
$375
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Wed Nov 19
AT SEA
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Thu Nov 20
AT SEA
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Fri Nov 21
AT SEA
Arrive:
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Sat Nov 22
AT SEA
Arrive:
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Sun Nov 23
AT SEA
Arrive:
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Mon Nov 24
AT SEA
Arrive:
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Tue Nov 25
AT SEA
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Wed Nov 26
AT SEA
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Thu Nov 27
AT SEA
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Fri Nov 28
AT SEA
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Sat Nov 29
AT SEA
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Sun Nov 30
AT SEA
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Mon Dec 1
AT SEA
Arrive:
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Tue Dec 2
Philipsburg, St. Maarten
Arrive:6:00 AM
Depart:7:00 PM
Watersports Platform: 
4 Available
+_
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
$79
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St. Maarten, Post Island Tour with Transfer to HotelEssentials Collection | Sightseeing
Duration4 Hours
Activity LevelEasy-Moderate
$79
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St. Maarten: Americas Cup Sailboat Racing with Transfer to AirportBoating | Essentials Collection | Outdoors | Refreshments
Duration2.5 Hours
Activity LevelModerate
$149
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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
$149
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Wed Dec 3
Soper's Hole
Arrive:8:00 AM
Depart:6:00 PM
Watersports Platform: 
4 Available
+_
Arrive at the boardwalk of Pusser’s Landing and mingle with other yachtsmen in the utterly charming marina at Soper’s Hole. Find a deserted stretch of beach to kick back and ponder this tiny port’s rich heritage of romance, pirates, and adventure. An evening departure features a once-in-a-lifetime romantic sunset Sail Away. 
4 Shore Excursions Available
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Tortola, Snorkel Adventure at Peter IslandBoating | Essentials Collection | Sightseeing | Refreshments | Snorkeling
Duration3 Hours
Activity LevelModerate-Strenuous
$109
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Soper's Hole: Cane Garden Bay Beach BreakBeach | Essentials Collection | Refreshments
Duration4 Hours
Activity LevelModerate
$79
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Tortola, Tortola Jeep & Beach TourBeach | Essentials Collection | Sightseeing
Duration4 Hours
Activity LevelModerate
$165
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Tortola, Scenic Drive & Beach Outdoors | Sightseeing | Beach | Essentials Collection
Duration4.5 Hours
Activity LevelEasy
$99
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Wed Dec 3
Jost Van Dyke, Great Harbour
Arrive:7:00 PM
Depart:
Watersports Platform: 
For an island comprised of a mere eight square miles, it’s amazing how much there is to do on Jost Van Dyke. Visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis  Drake Waterway. After all that, you’ll be ready for an evening drink on the beach — where you can admire your Windstar ship aglow in the harbor.
Thu Dec 4
Jost Van Dyke, Great Harbour
Arrive:
Depart:10:00 PM
Watersports Platform: 
2 Available
+_
For an island comprised of a mere eight square miles, it’s amazing how much there is to do on Jost Van Dyke. Visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis  Drake Waterway. After all that, you’ll be ready for an evening drink on the beach — where you can admire your Windstar ship aglow in the harbor.
2 Shore Excursions Available
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Jost Van Dyke, Catamaran Cruise and BeachBeach | Boating | Essentials Collection | Snorkeling
Duration4.5 Hours
Activity LevelModerate-Strenuous
$169
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Jost Van Dyke, Sail and SnorkelBoating | Essentials Collection | Sightseeing | Refreshments | Watersports
Duration4 Hours
Activity LevelModerate-Strenuous
$159
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Fri Dec 5
AT SEA
Arrive:
Depart:
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Sat Dec 6
Gustavia
Arrive:8:00 AM
Depart:10:00 PM
Watersports Platform: 
7 Available
+_
Affectionately known as St. Barts, the Caribbean’s most chic island adds a French flair to Riviera-like beaches and duty-free boutiques. Walk past gingerbread cottages in search of celebrities, shop for designer fashions, or sip the island’s signature ti punch as kite surfers fly by.
7 Shore Excursions Available
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St Barts, Concierge Collection: St. Barthelemy Beach DayBeach | Concierge Collection | Dining
Duration6 Hours
Activity LevelEasy-Moderate
$399
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St. Barts: Sailing Catamaran AdventureBeach | Boating | Essentials Collection | Refreshments | Snorkeling | Wildlife
Duration3 Hours
Activity LevelModerate
$299
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St. Barts: Independent Explorer by CarEssentials Collection | Sightseeing
Duration6 Hours
Activity LevelEasy-Moderate
$279
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St. Barts: Intimate Island TourEssentials Collection | Sightseeing
Duration Hour
Activity LevelEasy
$99
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St. Barts: Sailing the Leeward CoastBoating | Essentials Collection | Refreshments
Duration3 Hours
Activity LevelEasy-Moderate
$199
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St. Barts, Concierge Collection: Sunset CruiseBoating | Concierge Collection | Sightseeing | Refreshments
Duration1.5 Hours
Activity LevelEasy-Moderate
$159
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St. Barts: Yellow Semi-Sub ExplorationBoating | Essentials Collection | Wildlife
Duration Hour
Activity LevelEasy
$119
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Sun Dec 7
Philipsburg, St. Maarten
Arrive:6:00 AM
Depart:
Watersports Platform: 
4 Available
+_
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
$79
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St. Maarten, Post Island Tour with Transfer to HotelEssentials Collection | Sightseeing
Duration4 Hours
Activity LevelEasy-Moderate
$79
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St. Maarten: Americas Cup Sailboat Racing with Transfer to AirportBoating | Essentials Collection | Outdoors | Refreshments
Duration2.5 Hours
Activity LevelModerate
$149
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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
$149
VIEW DETAILS