15-night Caribbean cruise: Lisbon to Philipsburg, Sint Maarten on Wind Surf
The Ocean Crossings is a 15-night Caribbean cruise aboard Wind Surf, operated by Windstar Cruises. Departing Lisbon on November 5, 2027 and arriving in Philipsburg, Sint Maarten on November 20, 2027, the voyage visits 4 ports including Funchal, Jost Van Dyke. Fares start from $2,550 per person.
Fixed editorial images from the places on this itinerary. They stay stable each time you return to this sailing.
Lisbon
Lisbon, the capital of Portugal, is a city open to the sea and carefully planned with 18th-century elegance. Its founder is said to be the legendary Ulysses, but the theory of an original Phoenician settlement is probably more realistic. Known in Portugal as Lisboa, the city was inhabited by the Romans, Visigoths and, beginning in the 8th century, the Moors. Much of the 16th century was a period of great prosperity and overseas expansion for Portugal. Tragedy struck on All Saints' Day in 1755 with a devastating earthquake that killed about 40,000 people. The destruction of Lisbon shocked the continent. As a result, the Baixa (lower city) emerged in a single phase of building, carried out in less than a decade by the royal minister, the Marques de Pombal. His carefully planned layout of a perfect neo-classical grid survived to this day and remains the heart of the city. Evidence of pre-quake Lisbon can still be seen in the Belém suburb and the old Moorish section of the Alfama that sprawls below the Castle of St. George.
Lisbon is a compact city on the banks of the Tagus River. Visitors find it easy to get around as many places of interest are in the vicinity of the central downtown area. There is a convenient bus and tram system and taxis are plentiful. Rossio Square, the heart of Lisbon since medieval times, is an ideal place to start exploring. After a fire destroyed parts of the historic neighborhood behind Rossio in 1988, many of the restored buildings emerged with modern interiors behind the original façades.
The city boasts a good many monuments and museums, such as the Jeronimos Monastery, Tower of Belém, the Royal Coach Museum and the Gulbenkian Museum. High above the Baixa is the Bairro Alto (upper city) with its teeming nightlife. The easiest way to connect between the two areas is via the public elevator designed by Gustave Eiffel.
Cruising up the Tagus River to the ship's berth, you can already spot three of Lisbon's famous landmarks: the Monument to the Discoveries, the Tower of Belém and the Statue of Christ, which welcomes visitors from its hilltop location high above Europe's longest suspension bridge.
Funchal
As you arrive in Funchal on an MSC cruise, your ship will cast anchor in a bay protected by mountains rising straight up behind the port. The name, Funchal, derives from that of the fennel plant, the funcho still used today in the traditional sweets known as rebuçados de funcho, that one can find anywhere on the island of Madeira.
An excursion will take you around the town centre, to visit historic churches, from the A Sé Cathedral, with its inlaid ceiling, to the majestic Church of the Incarnation, to the church of Carmo without a vault.
Another MSC excursion will take you up to the village of Monte, from where one can admire a spectacular view of the Funchal bay. You can visit its 18th century church and the tomb of the last Austrian emperor, Charles I, and stroll around the magnificent botanic gardens. But if you like heights, there’s nothing more impressive than the Cabo Girão and its 589 metre tall cliffs, amongst the highest in the world, at the foot of which lie the cultivated lands known as Fajãs do Cabo Girão.
If you’re looking for an equipped beach during your MSC cruise, another excursion will take you to Machico. Founded in the 15th century, it hosts the oldest religious building on the island, the Capela dos Milagres, and the fortresses of São João Baptista and Nossa Senhora do Amparo built in the beginning of the 16th century.
The more lively tourist attraction is instead in Calheta, on the south-west coast. Splendid yachts cruising across the Atlantic are moored in the port and if you want to go for a swim there are two beautiful beaches of golden sand; in spite of the modern structures Calheta dates back to the mid-15th century. This is where they make the “Aguardente”, the best white rhum, and fundamental ingredient of Madeira’s typical drink, the “Poncha” .
Philipsburg, Sint Maarten
Offering some of the best vistas in all the Caribbean, St. Maarten is the smallest inhabited island in the world shared by two nations - France in the north and the Netherlands in the south. Dubbed the true melting pot of the Caribbean, the 37-square-mile island is home to people of 47 different nationalities and more than 400 restaurants, featuring a hugely diverse variety of cuisine.
The island also has two capitals: Philipsburg on the Dutch side, and Marigot in the French part. Once you arrive on an MSC Caribbean and Antilles cruise in St. Maarten, explore how the two cultures have blended their very distinct characters on one of our MSC excursions.
Your St. Maarten cruise will dock in Philipsburg, founded in 1763 by John Philips, a Scottish captain in the Dutch Navy. Philipsburg, with its pastel-coloured West Indian houses, is known for its duty-free shopping along Front Street, the Great Salt Pond, which once made the island literally “worth its salt,” and attracted the attention of the French, and Fort Willem, built in 1801, with mag-nificent views of the bay and the surrounding islands.
From there, several MSC excursions take you on a hilly drive to the French side of the island to experience Marigot. Originally a fishing village on a swamp for which it was named, Marigot became the capital during the reign of Louis XVI. Fort Louis, which overlooks Marigot Bay and Anguilla, was built in the late 18th century to protect the town’s warehouses of salt, coffee, sugar cane and especially rum from the English. Today, Marigot showcases quaint colourful gingerbread-like houses, tasty sidewalk bistros and a waterfront market selling fruit and vegetables, spices, local meats and fresh fish from Creole huts worth exploring.
For something special, spend the day on the Dutch side of the island at the restored sugar planta-tion at Rockland Estate. Take in a history lesson at the Emilio Wilson Museum or a nature hike and 360-degree views from Sentry Hill. Participate in a hands-on cooking demonstration of authentic local cuisines with lunch at Emilio’s restaurant, in an exclusive Martha Stewart excursion curated for MSC Cruises.
Also at Rockland Estate, thrill seekers can book other MSC excursions on the Flying Dutchman, a fast and furious zip line ride that will have you whizzing down the line at speeds of up to 56 mph (90 km) per hour. Then take the Pirate Sky Ride cable car back up the top to the Crow’s Nest where several platforms encircling the mountain afford panoramic views of the neighbouring islands of Saba, Sint Eustatius, Saint Barthélemy and Anguilla. Then plunge down the mountain on a Schooner Ride inner tube along a specially designed track.
To experience one of the island’s hottest spots and most popular attractions, visit the famous Maho Beach, also called Airplane Beach. Don’t get too comfortable, though. This is because you watch as planes pass only a short distance above your head as they land and take off from Princess Juli-ana Airport’s short runway next door.
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On any day, our 342-guest flagship, Wind Surf, the world’s largest sailing ship, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. During their cruise, you will find the perfect setting for ‘making an entrance’ in the beautiful reception area – and, appropriately, that’s only the beginning.
When you return to your stateroom, the luxury gets personal. Windstar’s signature bowls of flowers and fresh fruit will still be waiting for you, along with rich tufted headboards, soft seascape colors, beautiful new upholstery, and fine count Egyptian cotton linens welcome you to an oasis of relaxing indulgence.
Wind Surf recently underwent a significant renovation in November 2019 of public spaces and suites, including an expanded lounge with new lights and sound for upcoming stage performances. Relax into the destinations you’re visiting at the new World Spa by Windstar, which will offer regional spa treatments, including massage styles like Swedish, Japanese Shiatsu and Hawaiian Lomi Lomi. A new Officer’s Suite, which might be the only one of its kind, provides you the chance to stay in the heart of the officer quarters tucked right behind the Bridge.
Everything about Wind Surf speaks of welcome. Come aboard and see it for yourself.
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