Bermuda Bliss

From $2,399 per person

Ship: Star Pride

Bermuda Bliss
Windstar Cruises

Embark on a 7-day ocean crossing from Manhattan to San Juan with an overnight in St. George’s, Bermuda. Commence your cruise adventure amid the iconic skyline of Manhattan, absorbing the grandeur of the Statue of Liberty and the Brooklyn Bridge. Indulge in the bliss of multiple sea days, where you’ll have uninterrupted relaxation. As you traverse the cobblestone streets of St. George, Bermuda, a UNESCO World Heritage Site, the vibrant hues of pastel-colored buildings evoke a sense of timeless charm. Immerse yourself in the rich tapestry of culture and history, from the imposing silhouette of St. Peter's Church to the architectural marvel of the Town Hall. Gaze upon the crystal-clear waters surrounding Bermuda, and you'll discover a serenity that rejuvenates the soul during an overnight before a few more tranquil days at sea. Arrive in the historic and vibrant city of San Juan, Puerto Rico, a city welcoming  you with a blend of history and Caribbean flair.

Journey Summary

  • Day 1 - Oct. 20, 2026, Tue. - Boston
  • Day 2 - Oct. 21, 2026, Wed. -
  • Day 3 - Oct. 22, 2026, Thu. -
  • Day 4 - Oct. 23, 2026, Fri. - Hamilton
  • Day 5 - Oct. 24, 2026, Sat. - Hamilton
  • Day 6 - Oct. 25, 2026, Sun. - St. George's
  • Day 7 - Oct. 26, 2026, Mon. -
  • Day 8 - Oct. 27, 2026, Tue. -
  • Day 9 - Oct. 28, 2026, Wed. - San Juan

Itinerary Highlights

Dropping by the Bridge for an impromptu navigation lesson.

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Detailed Itinerary

Day-by-day description of your cruise and cruise activities.

Day 1 - October 20, 2026

Boston

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 <em>USS</em> <em>Constitution.</em>

Day 2 - October 21, 2026

Day 3 - October 22, 2026

Day 4 - October 23, 2026

Hamilton

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.

Day 5 - October 24, 2026

Hamilton

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.

Day 6 - October 25, 2026

St. George's

In 2000 St. George&rsquo;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&rsquo;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&rsquo;s Church. Natural sites to see here in addition include Tobacco Bay Beach, Tom Moore&rsquo;s Jungle, Cooper&rsquo;s Island Nature Reserve, Ferry Reach National Park, and the Crystal Caves of Bermuda.

Day 7 - October 26, 2026

Day 8 - October 27, 2026

Day 9 - October 28, 2026

San Juan

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.

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Oct 20, 2026

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