14 nights · Puerto Rico · Departs San Juan · Visiting St John Island USVI, Basseterre St Kitts, Gustavia St Barths, Philipsburg St Maarten, Jost Van Dyke Island BVI, Virgin Gorda Island BVI, St Georges Grenada, Bequia Island, Mayreau Island, Iles des Saintes, Marigot · Aboard Windstar Cruises on the Star Legend
Image courtesy of Windstar Cruises ©
| Cruise line | Windstar Cruises |
|---|---|
| Ship | Star Legend |
| Duration | 14 nights |
| Port calls | 12 |
| Departures | 9 sailings |
| From fare | $3,902 per person |
| Year built | 1992 |
| Guests | 343 |
| Cabins | 156 |
| Crew | 190 |
| Length | 159 m |
| Beam | 19 m |
| Cruising speed | 15.0 kn |
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.
St George’s is one of the Caribbean’s most handsome harbour towns, its pastel waterfront curving around a horseshoe-shaped bay. Walk the Carenage, where fishing boats and yachts share the water beneath Fort George. Grand Anse Beach lies a short drive south, with clear water and a long sweep of sand. In town, market stalls sell nutmeg, cocoa and cinnamon, helping earn Grenada its title, the Spice Isle.
Port Elizabeth sits on Bequia’s Admiralty Bay, where fishing boats and yachts share a sheltered anchorage. Step ashore into a compact waterfront of cafés and shops, then follow the Belmont Walkway towards Princess Margaret Beach. Bequia’s boatbuilding tradition remains visible in its working yards and local craft. Come for unhurried island life, swimming in clear water and views across the Grenadines.
Mayreau is one of the Grenadines’ smallest inhabited islands, with a village reached by a steep road from the shore. Its appeal is quiet beaches, clear water and Salt Whistle Bay, a sheltered crescent popular with sailors. Walk uphill to the compact settlement and its Catholic church, then look across the neighboring Grenadines. For a day ashore, Mayreau rewards unhurried exploration rather than a packed itinerary.
The Îles des Saintes reward visitors who prefer a quieter Caribbean. Most calls centre on Terre-de-Haut, where pastel houses, fishing boats and cafés line a compact waterfront. Above town, Fort Napoléon surveys one of the world’s most beautiful bays and houses a small museum and botanical garden. Rent a scooter or walk to Pain de Sucre, a sheltered beach with clear water and good snorkeling. Try the island’s famed tourment d’amour, a coconut-filled pastry, before returning to the harbor.
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.
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 10, 2026
Last updated October 3, 2026
Author: J. Richard
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