Bermuda Bliss
Oct 20, 2026 — Oct 28, 2026
Starting from $4,852 Displayed pricing is based off of double occupancy per person. Pricing subject to change based on occupancy and cabin selection.
See more routes around CaribbeanBOSTON, MA → SAN JUAN
8 Nights in Star Pride
Embark on an ocean crossing from Manhattan to San Juan with an overnight in St. George’s, Bermuda. Commence your 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, a UNESCO World Heritage Site, the brilliant hues of azure water pastel-colored buildings evoke a sense of timeless charm. Immerse yourself in the culture and history, from the imposing silhouette of St. Peter's Church to the architectural marvel of the Town Hall. Discover a serenity that rejuvenates the soul during an overnight in Bermuda 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.
Popular Highlights
Overnight in UNESCO site St. George’s, with its famous pink-sand beaches and 18th century Town Hall.
Drop by the open Bridge for an impromptu navigation lesson from your friendly crew.
Stretch out in your spacious suite and stay in for a private happy hour.
Conveniently depart from iconic Manhattan, and don’t miss our Signature Sail Away event.
Spend time on self-care, whether it’s reading a book or relaxing in the complimentary thermal suite.
Spend relaxing days at sea with time for making new friends, lounging on deck, and attending onboard enrichment programs.
Have your camera ready for the incredible views from El Morro, San Juan’s UNESCO site.
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.
