8-night Bermuda Bliss Cruise From Boston, Massachusetts

Windstar

A turquoise and white ferry boat cruises through the harbor in Hamilton, Bermuda, with a backdrop of pastel-colored buildings and houses along the waterfront.
Windstar's Star Pride cruise ship sailing at sunset.
1 of 2

Sailing Oct 20, 2026

Your 8-night Bermuda Cruise at a Glance

Sailings aboard Star Pride depart from Boston, Massachusetts with 3 stops in ports-of-call including Hamilton, St. George's, Bermuda, and San Juan. The Cruise Web can help you find the best deals and stateroom prices on the next sailing October 20, 2026.

Departure Port

Boston, Massachusetts

Boston is home to great sports, great foods, and loads of history with the Freedom Trail and Harvard. Before you depart Boston, Massachusetts, we can help you plan travel and accommodations for your Bermuda cruise.

Destination

Bermuda

Stops on your Bermuda voyage will include St. George's, Bermuda on day 5 and San Juan on day 9. We can help you with excursions and making the most of any itinerary.

Cruise Ship

Star Pride

Star Pride, built in 1988 and refurbished in 2021, carries 312 passengers with a crew of 190.

Cruise Line

Windstar Cruises

Get away from the crowd and journey to unique destinations aboard Windstar’s intimate small ships. We can help you maximize deals on Bermuda cruises aboard Star Pride or 7 of Windstar’s other ships.