Bermuda Bliss

From $2,426 per person

9 days

Ship: Star Pride

A vibrant cityscape featuring historic buildings, modern skyscrapers, and autumn trees against a colorful sunset sky.
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Embark on a voyage from the East Coast to San Juan with an overnight in St. George’s, Bermuda. Indulge in the luxury of multiple sea days, where you’ll have uninterrupted relaxation. Explore the UNESCO World Heritage Site of St. George’s, Bermuda.  Take in the charming streets lined with colonial buildings, visit the iconic St. Peter's Church, one of the oldest Anglican churches in the Western Hemisphere, and discover the fascinating history at the Bermuda National Trust Museum. For nature enthusiasts, St. George's offers stunning coastal views, and Tobacco Bay provides an opportunity for snorkeling in crystal-clear waters teeming with marine life. Arrive in the historic and vibrant city of San Juan, Puerto Rico. Traverse the cobblestone streets of Old San Juan, visit ancient forts, and immerse yourself in the rich local culture. From colonial charm to lively markets, San Juan welcomes 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. - St. George's
  • Day 8 - Oct. 27, 2026, Tue. -
  • Day 9 - Oct. 28, 2026, Wed. -

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

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 8 - October 27, 2026

Day 9 - October 28, 2026

Dates and Prices

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Oct 20, 2026

Ship

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The Star Pride ship sails serenely on calm waters under a clear blue sky, showcasing its elegant design.
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