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Wind Surf, The Best of the Windward & Leeward Isles ex St Maarten to Oranjestad

28 Night Cruise sailing from St Maarten to Oranjestad onboard Wind Surf.

Departs
Sunday, 4th January 2026
Ship
Wind Surf
Windstar Cruises
Pricing is From and Per Person
Cabin Twin Triple Quad Single
N/A N/A N/A N/A

Please note, while prices and inclusions are accurate at time of loading they are subject to change due to changes in cruise line policies and pricing and due to currency fluctuations. Currency surcharges may apply. Please check details of price and inclusions at time of booking.

28 Night Cruise sailing from St Maarten to Oranjestad onboard Wind Surf.

Highlights of this cruise:

St. Maarten is one of the most rewarding stops for a cruise-ship passenger. The island is divided between French St. Martin in the north and Dutch St. Maarten in the south. Each side manages to retain its own distinct flavor.

The French side (St. Martin), is certainly more relaxed and sophisticated. There are first-class resorts and secluded white sand beaches. Its capital, Marigot, is Mediterranean resort-like, with yachts in the harbor, and open-air markets and shops lining the waterfront. A bit to the north, Grand Case is known for the island's best restaurants.

The Dutch side (Sint Maarten) is a lively destination of white sand beaches, casinos, historical sites, shopping venues and lot of nightlife. Most ships dock in Philipsburg, the capital of Dutch St. Maarten. Its two main streets, Frontstreet and Backstreet, are bustling thoroughfares lined with shops and restaurants.

Jost Van Dyke
The British Virgin Islands, about 60 (mostly uninhabited) islands and cays, are one of the Caribbean's most popular destinations. Jost Van Dyke is a casual island with protected anchorages, fine beaches and beachfront restaurants and bars. It is said to have been named after an early Dutch settler, a former pirate.

At Great Harbour, Little Harbour, and White Bay there are safe, protected anchorages and unspoilt beaches shaded with coconut palms and seagrape trees. Discover inviting restaurants, bars, and small shops selling local treasures.

Parties here are legendary, especially at Foxy's. This bar and its owner are known to travellers from around the world for the New Year's Eve and Halloween parties, when Great Harbour fills up with yachts.

Basseterre
St. Kitts is located in the Eastern Caribbean. The island is 69 square miles with a population of 31,880. Basseterre is the capital city of St Kitts, a paradise of beaches, ponds and plantations. Basseterre's Historic District, towards the centre of the town exhibits excellent examples of Creole and West Indian architecture. Original structures are restored into museums and cultural centers. The Brimstone Fortress offers spectacular views of neighboring islands and visitors and locals enjoy the waters at Friar's Bay.

The many ship wrecks around Basseterre, make it a magnet for divers and the 15-feet deep waters off Banana Bay are great for snorkeling. Only twelve of 350 known wrecks have been identified. Basseterre Harbor claimed one hundred ships in one hurricane alone.

Bridgetown
Barbados is an ideal Caribbean destination, whether you want to bake in the sun or spend your time discovering island life and culture.

The beaches along the West and South coasts are lovely. Because they're open to the public, though, they lack the privacy some visitors may seek. Elsewhere on the island, linked by almost 900 miles of good roads, are small villages, historic plantation houses, stalactite-studded caves, a wildlife preserve, and the Andromeda Gardens, one of the most attractive small tropical gardens in the world. Culturally, Barbados has retained a very British atmosphere: Afternoon tea is a ritual, cricket is the national passion, and a few luxury hotels request a jacket and tie at dinner.

But Barbados is true blue Caribbean as well, with classic sand beaches, and wild monkeys in the jungle.

Mayreau
Mayreau is part of St. Vincent and the Grenadines, and lies in the middle of the Grenadines, close to the famous Tobago Cays. It is the smallest island of the Grenadines, all inhabitants live in the village on the south-west side of the island. There is a trail from Saltwhistle Bay to the village that is currently being improved. The village boasts four bars and restaurants and colorful local rum shops with domino tournaments and pool tables.

Two beautiful anchorages will satisfy those cruising the islands. Salt Whistle Bay has a sweeping half moon beach, and the Salt Whistle Bay Club is tucked away behind it. A sailboat and motor boat is available to charter to the nearby Tobago cays for some of the best diving and snorkeling in the Caribbean. Snorkeling equipment is available for rent. Hiking trails abound throughout the island with spectacular views of the neighboring Grenadines from Captains Hill.

Willemstad
Curaçao, the largest island in the Netherlands Antilles, is part of the Dutch Leeward Islands, also known as the Dutch Antilles. Willemstad, the capital, is noted for its brightly colored, Dutch-style houses and Cunucu dwellings (based on African-style mud and wattle huts). It is one of the best shopping destinations in the Caribbean. The harbor has a floating market where colorful barges full of agricultural produce are moored. Nearby is the new market building, the design of which is very unusual.

Popular places to visit in Willemstad include Fort Amsterdam, now the seat of government of the Netherlands Antilles, the Queen Emma Pontoon bridge and the Queen Juliana Bridge. The latter spans the harbor at a height of 490m (1600ft). The architecture of the Scharloo area, reached by crossing the Wilhelmina Drawbridge, is fascinating, dating from as early as 1700. The Mikvé Israel Synagogue is the oldest in the Americas and, like the Jewish Beth Heim Cemetery, is worth a visit. Its courtyard museum has a fine collection of historical artifacts.

Oranjestad
Aruba is the smallest island in the Leeward group of the Dutch Caribbean islands. Its Dutch heritage can be seen in its pastel-colored gabled buildings and a windmill brought piece by piece from Holland found in the capital of Oranjestad. Oranjestad has a daily market in the Paardenbaai (Schooner Harbour), and offers numerous shops, boutiques and malls that are all within easy walking distance of the ship. In the main street you will find many stores, shops, boutiques, restaurants and street vendors to investigate.

Oranjestad is a popular tourist destination boasting sunshine, silky sand, aquamarine waters, cooling trade winds, natural scenic wonders, friendly and courteous service, modern and efficient amenities, golf and tennis clubs, duty-free shopping, an array of nightly entertainment and some of the best cuisine in the Caribbean. Most of its 29 hotels sit side by side down one major strip along the southwestern shore, with restaurants, exotic boutiques, fiery floor shows, and glitzy casinos right on their premises.

Aruba’s principal attraction is its beaches and the Natural Bridge, an arch carved from coral cliffs by the surf. The bridge is the biggest and highest in the Caribbean and is Aruba’s most famous natural wonder. On the northern tip of the island is the California Lighthouse, and off this coast is the wreck of a German freighter from World War II, which is now very popular spot for scuba divers. The Chapel of Alto Vista at Alto Vista is another popular site on the north coast. It is bright yellow and hard to miss.

Cruise Itinerary
Date Activity Arrive Depart
04/01/26 St Maarten 7:00 PM
05/01/26 Falmouth, Antigua & Barbuda 8:00 AM 6:00 PM
06/01/26 Road Bay, Anguilla 8:00 PM 6:00 PM
07/01/26 Sopers Hole, British Virgin Islands 8:00 AM 6:00 PM
07/01/26 Jost Van Dyke, British Virgin Islands 7:00 PM overnight
08/01/26 Jost Van Dyke, British Virgin Islands 10:00 PM
09/01/26 Virgin Gorda, British Virgin Islands 8:00 AM 5:00 PM
10/01/26 Gustavia, St Barts 8:00 AM 10:00 PM
11/01/26 St Maarten 6:00 AM
12/01/26 Basseterre, St Kitts & Nevis 7:00 AM 10:00 PM
13/01/26 Montserrat 8:00 AM 6:00 PM
14/01/26 Gustavia, St Barts 8:00 AM 11:00 PM
15/01/26 Deshaies, Guadeloupe 12:30 PM 10:00 PM
16/01/26 Roseau, Dominica 8:00 AM 5:00 PM
17/01/26 Pigeon Island, St Lucia 7:00 AM 4:00 PM
18/01/26 Bridgetown, Barbados 5:00 AM
19/01/26 Anse Mitan, Martinique 9:00 AM 11:00 PM
20/01/26 Castries, St Lucia 8:00 AM 4:00 PM
20/01/26 Pigeon Island, St Lucia 6:00 PM
21/01/26 Pigeon Island, St Lucia 6:00 PM
22/01/26 Bequia, St Vincent & The Grenadines 8:00 AM 10:00 PM
23/01/26 Mayreau, St Vincent & The Grenadines 8:00 AM 6:00 PM
24/01/26 St Georges, Grenada 7:00 AM 2:00 PM
25/01/26 Bridgetown, Barbados 6:00 AM
26/01/26 Man o'War Bay, Tobago 8:00 AM 5:00 PM
27/01/26 Mayreau, St Vincent & The Grenadines 8:00 AM 6:00 PM
28/01/26 Soufriere, St Lucia 8:00 AM 4:00 PM
29/01/26 At sea - -
30/01/26 Kralendijk, Bonair 1:00 PM 10:00 PM
31/01/26 Willemstad, Curacao 8:00 AM 6:00 PM
01/02/26 Oranjestad, Aruba 6:00 AM
Itinerary may vary by sailing date and itineraries may be changed at the cruise lines discretion. Please check itinerary details at time of booking and before booking other travel services such as airline tickets.

Available Sailing Dates