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Cruise itinerary

8 night bermuda bliss

Ask your friends: Should I go?

Ship: Star Pride (details)
Cruise line: Windstar Cruises

Departure date: Tuesday, October 20, 2026
Return date: Wednesday, October 28, 2026
Departure port: Boston
Ports of call: Hamilton, St. George's
Return port: San Juan

Prices:

Suite $2,426

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Cruiseable's travel advisors can often find you additional savings & lower fares than the public prices listed here.

Day Location

1
Boston
2
Boston
3
Hamilton
4
St. George's
5
San Juan
6
San Juan

The Fairmont Hamilton Princess Hotel overlooks picturesque Hamilton Harbor in Pembroke Parish, Bermuda.

Avocado gazpacho at Toro Salao on Calle Tetuan in Old San Juan, Puerto Rico.

Colorful al fresco dining in Old San Juan, Puerto Rico.

Balconies on Calle San Sebastian in Old San Juan, Puerto Rico, a UNESCO World Heritage Site.

The Garita, or sentry lookout at Castillo de San Cristobal in Old San Juan, Puerto Rico.

Historic Front Street in Hamilton, the capital of Bermuda.

The New World's oldest governor's mansion is still in use. Some 150 consecutive governors have served over the past 300 years. It's at the west end of Calle Fortaleza in Old San Juan, Puerto Rico.

West of San Cristóbal along the coastline is the neighborhood of La Perla in Old San Juan, Puerto Rico. It's part of the area's UNESCO World Heritage Site.

Isla Verde Beach, Puerto Rico.

Visitors flock to Isla Verde Beach in Puerto Rico.

Businessmen in Hamilton, Bermuda, wearing — yes — Bermuda shorts. You'll spot the colorful, comfy shorts all around the island.

Fort San Felipe del Morro in Old San Juan, Puerto Rico, a UNESCO World Heritage Site.

This bronze fountain "Raíces" (for "Roots") in Old San Juan celebrates Puerto Rico’s rich cultural diversity and historical heritage.

A swimming cove in the Condado neighborhood of Puerto Rico.

Visitors flock to Isla Verde Beach in Puerto Rico.

Guard bunks at historic Castillo de San Cristóbal in Old San Juan, Puerto Rico. Completed by Spanish forces in 1783, it was the largest fortification built by Spain in the New World.

Catedral Santiago Apóstol in Fajardo, along the northeast coast of Puerto Rico.

Gombey dancers in Par-la-Ville Park, Hamilton, Bermuda.

Historic San Cristobal Fort sits on a promontory. It once guarded San Juan, Puerto Rico.

Hotels line the beachfront of Isla Verde Beach in Puerto Rico.