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Star Collector: Bermuda & Caribbean Island Explorer
Oct 22, 2027 — Nov 8, 2027
Starting from
BOSTON, MA → SAN JUAN
17 Nights on Star Pride
Sail from the North Atlantic into the heart of the Caribbean on an extended journey shaped by island character and days unrushed at sea. Take advantage of rare overnights in Bermuda’s historic towns before continuing toward San Juan’s timeless fortresses and colorful shoreline. You’ll also have two full days to experience Gustavia and Virgin Gorda, giving you more time to enjoy their beaches, cafés, and sheltered bays. From there, explore quiet anchorages in the Virgin Islands, snorkel pristine bays, and wander small-ship harbors like Jost Van Dyke and Virgin Gorda.
Popular Highlights
Two calls in St. Bart's allows for full days of beach clubs, coastal hikes, and French-Caribbean cuisine
Visit Basseterre, St. Kitts for island tours up to Brimstone Hill Fortress with sweeping Caribbean panoramas.
Spot sea turtles while snorkeling St. John’s calm coves inside Virgin Islands National Park.
Swim from the beach at Virgin Gorda’s Prickly Pear, a quiet nature reserve unreachable by big ships.
Enjoy Windstar’s Signature Beach Party, where the Caribbean spirit is in full swing.
Enjoy complimentary laundry during your cruise.
Founded in 1630 by Puritan settlers, Boston is one of the oldest cities in the U.S. It was a pivotal place during the American Revolution for the Boston Massacre, the Boston Tea Party, the Battle of Bunker Hill and the Siege of Boston. Tourists to Boston see the Faneuil Hall Marketplace, the JFK Library and Museum, the Museum of Fine Arts, the New England Aquarium, and the USS Constitution.
The capital of Bermuda is the energetic heart of Bermuda. A walk along Front Street on the harbor features interesting pastel-colored colonial buildings and boutiques. Sites to see here include the Cathedral of the Most Holy Trinity, built in 1869 with a tower that displays panoramic views of the city. Find the Bermuda National Gallery and the Bermuda Aquarium, Museum and Zoo.
The capital of Bermuda is the energetic heart of Bermuda. A walk along Front Street on the harbor features interesting pastel-colored colonial buildings and boutiques. Sites to see here include the Cathedral of the Most Holy Trinity, built in 1869 with a tower that displays panoramic views of the city. Find the Bermuda National Gallery and the Bermuda Aquarium, Museum and Zoo.
In 2000 St. George's was named a UNESCO World Heritage Site, founded in 1609 by an English ship that got blown off course, Strolling the streets of St George's will feel like a step back in time. The well-preserved buildings and fortress have made it a haven of British colonial architecture including St. Peter's Church. Natural sites to see here in addition include Tobacco Bay Beach, Tom Moore's Jungle, Cooper's Island Nature Reserve, Ferry Reach National Park, and the Crystal Caves of Bermuda.
In 2000 St. George's was named a UNESCO World Heritage Site, founded in 1609 by an English ship that got blown off course, Strolling the streets of St George's will feel like a step back in time. The well-preserved buildings and fortress have made it a haven of British colonial architecture including St. Peter's Church. Natural sites to see here in addition include Tobacco Bay Beach, Tom Moore's Jungle, Cooper's Island Nature Reserve, Ferry Reach National Park, and the Crystal Caves of Bermuda.
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