Ocean Crossings

Lisbon to San Juan

Mon Dec 6, 2027 - Mon Dec 20, 2027,

14 days

on Star Legend

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Starting from $2,599 USD

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OVERVIEW & ITINERARY

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.

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Date

Port

Arrive

Depart

Marina

Shore
Excursions

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Mon Dec 6

Lisbon

Arrive:

Depart:5:00 PM

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.

Tue Dec 7

AT SEA

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Wed Dec 8

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Thu Dec 9

Funchal

Arrive:8:00 AM

Depart:3:00 PM

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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 15^th century Cathedral of Our Lady of the Assumption, shopping the bargains to be found here, or experiencing the vibrant night life.

Fri Dec 10

AT SEA

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Sat Dec 11

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Sun Dec 12

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Mon Dec 13

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Tue Dec 14

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Wed Dec 15

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Thu Dec 16

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Fri Dec 17

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Sat Dec 18

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Sun Dec 19

Jost Van Dyke, Great Harbour

Arrive:8:00 AM

Depart:6:00 PM

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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.

Mon Dec 20

San Juan

Arrive:7:00 AM

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The imposing façade of El Morro fortress is just one of the many UNESCO World Heritage Sites in San Juan. Admire the colorful colonial buildings from your casually elegant ship, docked right in the heart of Old San Juan.