23 nights · Portugal · Departs Lisbon (Portugal) · Visiting Funchal, Jost Van Dyke Island BVI, Philipsburg St Maarten, Gustavia St Barths, St Johns Antigua, Deshaies, Anguilla Island, Tortola Island BVI, Virgin Gorda Island BVI · Aboard Windstar Cruises on the Wind Surf
Image courtesy of Windstar Cruises ©
| Cruise line | Windstar Cruises |
|---|---|
| Ship | Wind Surf |
| Duration | 23 nights |
| Port calls | 10 |
| Departures | 1 sailings |
| From fare | $4,890 per person |
| Year built | 1990 |
| Guests | 376 |
| Cabins | 171 |
| Crew | 178 |
| Length | 187 m |
| Beam | 20 m |
| Cruising speed | 15.0 kn |
Lisbon is a city best approached with time and comfortable shoes. Its seven hills rise above the Tagus, linking tiled lanes, grand squares and viewpoints with wide river views. In Alfama, narrow streets preserve the feel of old Lisbon. In Belém, the Jerónimos Monastery and Tower recall Portugal’s age of discovery. Pause for coffee and a warm pastel de nata between sights.
Funchal sits in a broad, sunlit amphitheatre above Madeira’s deep Atlantic harbour. Its compact centre rewards exploration, from the Old Town’s painted doors to the cathedral’s carved cedar ceiling. Ride the cable car uphill to Monte for sweeping views, then descend through gardens or by traditional wicker toboggan. Madeira’s wines and market produce offer a taste of the island before your ship sails.
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.
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.
Antigua rewards a day ashore with more than its celebrated beaches. St John’s, the compact capital, makes an easy starting point. Drive east to Nelson’s Dockyard, a remarkably preserved Georgian naval base and UNESCO World Heritage site. English Harbour’s sheltered waters and restored stone buildings reveal the island’s maritime past. Or trade history for a swim at one of the island’s many coves, from resort beaches to quieter shores.
Deshaies brings you to Guadeloupe’s quieter Caribbean coast, where a fishing village curves around a small harbor. Colorful homes, waterfront cafés and fishing boats give the center an easygoing feel, best explored on foot. Just beyond town, Deshaies Botanical Garden displays tropical plants, waterfalls and birds across a hillside estate. Nearby Grande Anse offers golden sand and a broad sweep of sea; swimming conditions can vary. Spend the day among gardens, beach and village life, at an easy pace.
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.
Published August 2, 2026
Last updated October 3, 2026
Author: J. Richard
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