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Itinerary & Ports

Star Collector: Caribbean Islands to Portuguese Castles: A Crossing

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From $ 2,499* pp, Shipboard Credit Offer

Jan 25 Sat
10:00 PM
Jan 26 Sun
8:00 AM
9:00 PM
Jan 27 Mon
11:00 AM
10:00 PM
Jan 28 Tue
8:00 AM
5:00 PM
Jan 29 Wed
7:00 AM
10:00 PM
Jan 30 Thu
8:00 AM
11:59 PM
Jan 31 Fri
8:00 AM
5:00 PM
Feb 1 Sat
7:00 AM
4:00 PM
Feb 2 Sun
At Sea
Feb 3 Mon
At Sea
Feb 4 Tue
At Sea
Feb 5 Wed
At Sea
Feb 6 Thu
At Sea
Feb 7 Fri
At Sea
Feb 8 Sat
At Sea
Feb 9 Sun
At Sea
Feb 10 Mon
At Sea
Feb 11 Tue
At Sea
Feb 12 Wed
At Sea
Feb 13 Thu
8:00 AM
11:59 PM
Feb 14 Fri
At Sea
Feb 15 Sat
At Sea
Feb 16 Sun
7:00 AM
TO 10:00 PM San Juan

day 1 San Juan, Puerto Rico

San Juan, Puerto Rico
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. 
8:00 AM TO 9:00 PM Vieques

day 2 Vieques, Puerto Rico

Vieques, Puerto Rico
Just six miles east of mainland Puerto Rico lies the island of Vieques --Though it measures just 55 square miles, Vieques brims with natural flora, exotic animals, secluded beaches, and gracious people. It’s allure is that it is rustic and elegant at the same time. Vieques boasts more than 20 breathtaking and diverse beaches, each with its own character and appeal. Horses roam freely across the island, often flanked by elegant white egrets and brightly colored flamboyant trees dot the hillsides. There are no stoplights, fast-food chains, nightclubs, or shopping malls… the attractions are Mother Nature’s creations. You will find a delightful selection of restaurants with a variety of foods, a few stores and the interesting Vieques Conservation & Historical Trust Museum. It is also home to Hacienda Casa del Frances, a sugar plantation house built in 1910 and listed on the U.S. National Register of Historic Places.
11:00 AM TO 10:00 PM St. Maarten

day 3 Philipsburg, St. Maarten

Philipsburg, St. Maarten
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.
8:00 AM TO 5:00 PM Little Bay

day 4 Little Bay, Montserrat, BWI

Little Bay, Montserrat, BWI
Today we visit “Pompeii of the Caribbean”—an island that is half lush and green, half gray and covered in ash by a volcano in 1995. And if a half-buried city isn’t intriguing enough, there are black-sand beaches and a perplexing Irish heritage to explore.
7:00 AM TO 10:00 PM Gustavia

day 5 Gustavia, St. Barthélemy

Gustavia, St. Barthélemy
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. 
8:00 AM TO 11:59 PM Jost Van Dyke, Great Harbour

day 6 Jost Van Dyke, Great Harbour, B.V.I.

Jost Van Dyke, Great Harbour, B.V.I.
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. 
8:00 AM TO 5:00 PM Virgin Gorda

day 7 Virgin Gorda, B.V.I.

Virgin Gorda, B.V.I.
A beautiful coral reef wavers just beneath you as your ship makes the break into exclusive North Sound. You can imagine the reaction of the locals watching from The Bitter End Yacht Club as your ship comes around the corner under full canvas. At the other end of the island lies the curious assembly of house-sized boulders called “The Baths,” which form huge underground pools and caverns that you’re free to explore.
7:00 AM TO 4:00 PM San Juan

day 8 San Juan, Puerto Rico

San Juan, Puerto Rico
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. 
8:00 AM TO 11:59 PM Funchal

day 20 Funchal, Madeira, Portugal

Funchal, Madeira, Portugal
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.
7:00 AM TO Lisbon

day 23 Lisbon, Portugal

Lisbon, Portugal
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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