17 nights · Massachusetts · Departs Boston (USA) · Visiting Hamilton, St George, Gustavia St Barths, Virgin Gorda Island BVI, San Juan, St John Island USVI, Basseterre St Kitts, Philipsburg St Maarten, Jost Van Dyke Island BVI · Aboard Windstar Cruises on the Star Pride
Image courtesy of Windstar Cruises ©
| Cruise line | Windstar Cruises |
|---|---|
| Ship | Star Pride |
| Duration | 17 nights |
| Port calls | 10 |
| Departures | 1 sailings |
| From fare | $5,194 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.
Cruz Bay is St. John’s harbor town, where ferries, cafés and island roads meet. From here, much of the island opens quickly: Virgin Islands National Park protects roughly two-thirds of St. John. Follow North Shore Road to white-sand beaches and clear water, or visit the sugar plantation ruins at Annaberg. Back in town, browse the shops at Mongoose Junction, then choose a waterfront table for dinner.
Begin in Basseterre, St Kitts’s compact capital, where Georgian buildings and busy market streets reveal the island’s layered past. At Independence Square, once a slave market, pause among mature trees before browsing nearby shops and cafés. Then leave town for Mount Liamuiga’s volcanic slopes, former sugar estates and beaches of dark volcanic sand. Brimstone Hill Fortress, a UNESCO World Heritage site, rewards the drive with stone ramparts and wide Caribbean views.
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.
Philipsburg rewards a shore day spent beyond the cruise terminal. It sits on a narrow strip between Great Bay and the Great Salt Pond. The Dutch-side capital is compact and easy to explore on foot. Front Street pairs duty-free shops with the 1793 courthouse, while the Boardwalk follows Great Bay Beach. Cross the open border into French Saint-Martin for French bakeries, lively markets and another stretch of coast.
Cruz Bay is St. John’s harbor town, where ferries, cafés and island roads meet. From here, much of the island opens quickly: Virgin Islands National Park protects roughly two-thirds of St. John. Follow North Shore Road to white-sand beaches and clear water, or visit the sugar plantation ruins at Annaberg. Back in town, browse the shops at Mongoose Junction, then choose a waterfront table for dinner.
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 13, 2026
Last updated October 3, 2026
Author: J. Richard
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