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Day 1: Lisbon
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.
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Day 4: Funchal
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.
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Day 6: San Sebastian
Though you won’t find canaries here you will find people who can whistle like them. Whistled speech helped shepherds communicate across the steep ravines and in the lush cloud forest of Garajonay National Park, a UNESCO World Heritage Site. Columbus paused here on all three voyages so you’re in good company as you explore historic San Sebastián, but with all the natural beauty around, you’ll find your gaze drawn inexorably up the terraced hillsides and across to views of Mount Teide.
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Day 7: Santa Cruz de Palma
Santa Cruz de Palma has a distinct Caribbean feel with its colorful houses and relaxed, casual feel. Walk along the cobblestone streets of this charming port that once was a connecting port on the route to the Americas. Learn about the town’s history at the Island Museum of La Palma located in a 16th century monastery and the Naval Museum housed in a full-sized reproduction of the Santa Maria. And see some of the 15 large telescopes along the ridge of Caldera del Taburieint National Park.
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Day 8: Las Palmas
Magnificent scenery surrounds you in the capital of Gran Canaria. Two lovely bays and their beautiful beaches frame the city. The Vegueta District, the older quarter of the town, is a UNESCO World Heritage Site. Explore its historical and cultural treasures, dating back to the city’s founding in 1478. 
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Day 9: Santa Cruz de Tenerife
Here in this privileged setting you’ll discover two UNESCO World Heritage Site beaches of tantalizing beauty; San Cristóbal de La Laguna; and the island’s symbol, Teide National Park. Wide avenues, exotic landscapes, and striking examples of modernist architecture complete one of the world’s most popular destinations.
Itinerary at a Glance
Date
Port
Arrive
Depart
MarinaWatersports Platform: 
Wed Nov 12
Lisbon
Arrive:  
Depart:  3:00 PM
Watersports Platform: 
Thu Nov 13
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Fri Nov 14
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Sat Nov 15
Funchal
Arrive:  8:00 AM
Depart:  11:00 PM
Watersports Platform: 
Sun Nov 16
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Mon Nov 17
San Sebastian
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Tue Nov 18
Santa Cruz de Palma
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Wed Nov 19
Las Palmas
Arrive:  1:00 PM
Depart:  10:00 PM
Watersports Platform: 
Thu Nov 20
Santa Cruz de Tenerife
Arrive:  7:00 AM
Depart:  
Watersports Platform: 
Wind Star
Wind Star is a sleek, 4-masted sailing ship accommodating 148 guests. With four decks and a gross tonnage of 5,307, Wind Star feels like your own private yacht.
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Accommodations & Pricing
Boutique cruising with fewer than 350 guests. Our expertly designed itineraries and unexpected shore excursions bring you closer to each destination.
The Windstar Life
The Windstar staff-to-guest ratio is 1:1.5, and it shows.The moment you board you’ll feel it: an ever-attentive crew at your service, providing you with what you want and need, when you want and need it.
Friendly and Relaxed Atmosphere
Signature Onboard Barbecue
Cooking Demonstrations
Genuine and Thoughtful Crew
Crew Talent Show
Open Bridge
Local and Live Performances
Relax at the Pool or Hot Tub
Complimentary 24 Hour Room Service
Signature Sail Away
Shopping With The Chef
Take In The Sun
Marina
Enjoy regionally inspired treatments at World Spa by Windstar
Relax With A Morning Yoga Session