10 nights · Massachusetts · Departs Boston (USA) · Visiting Hamilton, St George, Gustavia St Barths, Virgin Gorda Island BVI, San Juan · Aboard Windstar Cruises on the Star Pride
Image courtesy of Windstar Cruises ©
| Cruise line | Windstar Cruises |
|---|---|
| Ship | Star Pride |
| Duration | 10 nights |
| Port calls | 6 |
| Departures | 1 sailings |
| From fare | $4,477 per person |
| Year built | 1988 |
| Guests | 343 |
| Cabins | 156 |
| Crew | 190 |
| Length | 159 m |
| Beam | 19 m |
| Cruising speed | 15.0 kn |
Boston rewards visitors who like their history close at hand and their cities easy to explore. From the waterfront, follow the Freedom Trail to landmarks of the American Revolution, including Faneuil Hall. Beacon Hill’s brick streets, the Public Garden and North End cafés reveal distinct sides of the city. Make time for harbor views and New England seafood; Boston’s pleasures are as tangible as its past. Its museums and universities give the compact city a lively, modern edge.
Hamilton, Bermuda’s compact capital, pairs pastel façades with a sheltered harbor. The island’s daily life unfolds within easy reach of the waterfront. Smaller ships can dock close to Front Street, lined with boutiques, cafés and restaurants. Ferries link Hamilton with Dockyard and other island stops. Allow time for the Bermuda National Gallery or a stroll through leafy side streets before exploring farther afield.
Step ashore in St. George’s, Bermuda’s oldest town and a UNESCO World Heritage site. Its lanes, pastel-fronted houses and historic churches reward an unhurried walk. Once Bermuda’s capital, the town still gathers around King’s Square, where colonial-era buildings frame the waterfront. St. Peter’s Church and nearby Fort St. Catherine deepen a day of walking, with coastal views as your reward.
Gustavia makes a polished first impression, but its appeal is more than designer boutiques and superyachts. Swedish rule left its mark in the town’s name and the ruins of Fort Gustav above the harbor. From the waterfront, cafés, galleries and shops sit within easy walking distance, while Shell Beach lies just beyond the center. Come ashore for French-Caribbean style, with history close at hand.
Virgin Gorda swaps city bustle for clear water, quiet coves and a dramatic coastline. At The Baths, granite boulders form a maze of sea pools and narrow passages beside the beach. Some routes involve ladders and slippery rocks, so wear shoes with grip. Spanish Town is the island’s main settlement; North Sound is known for sheltered anchorages and sailing. Go early to explore The Baths before the busiest hours, then cool off in the Caribbean.
San Juan puts a remarkable piece of Caribbean history within easy reach of your ship. Founded in 1521, Old San Juan is a compact district of blue cobbles, pastel façades and Spanish colonial landmarks. Walk its steep lanes to El Morro, the 16th-century fortress that guards the harbor. From its ramparts, the Atlantic comes into view. Beyond the old walls, cafés, galleries and contemporary restaurants show a city still shaped by its maritime past.
Published August 20, 2026
Last updated October 3, 2026
Author: J. Richard
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