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Bermuda Bliss: 8-Night Windstar Cruise

Oct 20 - 28, 2026

Your Advisor

Ryan Joy

Creating Magic Vacations

ryanjoy@creatingmagicvacations.com

315-212-9775

Email Ryan

Full Itinerary Daily Overview Pricing

Overview

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.

Day 1 · Tue, Oct 20 · Boston, Massachusetts, United States

About Your Cruise Line - Windstar Cruises

Only Windstar brings you close enough so you can truly experience it. Each of Windstar Cruises yachts accommodates between 148 to 342 guests. This intimacy provides you with the luxuries of time, space, and freedom to immerse yourself in both the journey and the destination – in ways you may never have imagined possible. We scour the world for amazing places just this side of unreachable, then seek out the most authentic ways for guests to experience them – in small groups that are easily...

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About Your Ship - Star Pride

Serving just 312 guests, Star Pride is the perfect size — small enough to offer unique experiences that set Windstar apart from other cruise lines (like our complimentary Signature Beach Party), yet large enough for you to make plenty of new connections on board — all without ever feeling crowded.

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Boston, Massachusetts

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...

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Cabins

Starting at $4,370

Oct 20 – Oct 28 · Check in: 1:00PM

10 room options

Windstar cabins offer a luxurious and comfortable experience, with a variety of options to suit different needs and preferences. While specific layouts may vary by ship, common features include spacious accommodations, luxurious amenities, and att...

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Day 4 · Fri, Oct 23 · Hamilton, Bermuda

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...

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Day 5 · Sat, Oct 24 · Saint George, Bermuda

Saint George

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...

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Day 9 · Wed, Oct 28 · San Juan (Puerto Rico), 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. If you associate Puerto Ri...

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