14 nights · Netherlands Antilles · Departs Philipsburg St Maarten (Netherlands) · Visiting Gustavia St Barths, Falmouth Antigua, Anguilla Island, Tortola Island BVI, Jost Van Dyke Island BVI, Virgin Gorda Island BVI, Charlestown Nevis, Roseau, Mayreau Island, Iles des Saintes, Basseterre St Kitts · Aboard Windstar Cruises on the Wind Surf
Image courtesy of Windstar Cruises ©
| Cruise line | Windstar Cruises |
|---|---|
| Ship | Wind Surf |
| Duration | 14 nights |
| Port calls | 12 |
| Departures | 24 sailings |
| From fare | $3,872 per person |
| Year built | 1990 |
| Guests | 376 |
| Cabins | 171 |
| Crew | 178 |
| Length | 187 m |
| Beam | 20 m |
| Cruising speed | 15.0 kn |
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.
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.
Falmouth sits on Antigua’s sheltered south coast, where two deep natural harbours draw yachts from around the world. A short journey brings you to Nelson’s Dockyard, the restored Georgian naval base and UNESCO World Heritage site. Walk its stone lanes, browse the marina, then climb to Shirley Heights for a sweeping view over English Harbour. Beyond the historic waterfront, Antigua’s coves and pale-sand beaches invite an easy afternoon by the sea.
Island Harbour is a working fishing village on Anguilla’s quiet eastern shore, where brightly painted boats rest beside the beach. From the waterfront, a short boat ride reaches Scilly Cay, a tiny offshore island known for its beachside dining. Come for fresh seafood, unhurried views and a glimpse of local life beyond the island’s busier resorts. The appeal is simple: salt air, clear water and a village pace.
Tortola gives you a vivid introduction to the British Virgin Islands: green, steep-sided hills rise above a sheltered Caribbean harbour. In Road Town, browse Main Street, visit the J.R. O’Neal Botanic Gardens, or pause at a waterfront café. Beyond town, winding roads lead to Cane Garden Bay and island viewpoints. Ferries make nearby islands accessible, while Tortola itself rewards an unhurried day of beaches, scenery and local rum.
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.
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.
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.
Charlestown is the quiet capital of Nevis, set between the Caribbean Sea and the slopes of Nevis Peak. Georgian-era buildings and a lively market give its compact streets their character. The Museum of Nevis History occupies the house where Alexander Hamilton was born. Beyond town, black-sand coves, the historic Bath Hotel and green mountain trails reward a day spent exploring.
Roseau is Dominica’s compact, characterful capital, where Creole life meets a handsome Caribbean waterfront. Walk its streets to find the Old Market, local shops, and the island’s botanical gardens. For a wider view, climb to Morne Bruce, where the city, coast, and green interior unfold below. Beyond town, rainforest trails lead to waterfalls and hot springs, while volcanic reefs invite exploration. Bring comfortable shoes; Dominica rewards travelers who prefer wild landscapes to polished resort strips.
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.
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.
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.
Published August 21, 2026
Last updated October 3, 2026
Author: J. Richard
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