25-night Caribbean cruise: Lisbon to Colon, Panama on Wind Star
The Lisbon to Bridgetown is a 25-night Caribbean cruise aboard Wind Star, operated by Windstar Cruises. Departing Lisbon on November 10, 2026 and arriving in Colon, Panama on December 5, 2026, the voyage visits 10 ports including Bridgetown, Barbados, Bequia, St Georges, Grenada. Fares start from $10,924 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.
Bridgetown, Barbados
When you arrive in Barbados on an MSC Caribbean and Antilles cruise, begin your exploration with the capital, Bridgetown. There are many attractions in this small Caribbean city, but by all means pause to admire its many colonial buildings, the Parliament Building and the statue of Lord Nelson standing in what is currently called the National Heroes Square.
Barbados has retained somewhat of a British feel, with its place names, cricket, horse-racing and polo, Anglican parish churches and even a hilly district known as Scotland. But the Britishness can be exaggerated, for this is a distinctly West Indian country, covered by a patch-work of sugarcane fields and dotted with tiny rum shops.
The Garrison Historic Area, a UNESCO World Heritage Site with magnificent 18th- and 19th-century buildings, is a must-see stop, featuring one of the world's finest collection of cannons. It also includes the George Washington House, where the American patriot spent six weeks of his life.
The current St. John's Church, in the eastern parish of the same name, is the fifth reconstruction of the oldest local church, in Barbadian Gothic style. Perched on a cliff 800 feet above the sea, it dates back to 1836. Its interior hosts a sculpture by 18th-century British artist Richard Westmacott, while its churchyard contains the tomb of Ferdinando Paleologus, a direct descendant of the brother of Constantine XI, the last Byzantine emperor.
Book an MSC excursion to discover the island’s history at the Barbados Museum and Historical Society in the St. Michael neighbourhood. And tour Sunbury Plantation House, located in the tranquil St. Philip countryside. Dating back to 1650, it’s a living monument to plantation life and a bygone era.
Harrison’s Cave, in St. Thomas district, is a wonder of nature with its stalactites, stalagmites, streams, lakes and waterfalls. In one of the caverns, the play of light on the rocks is so in-tense that it has been nicknamed “The Crystal Room”.
For some fun at the beach, head to Pirates Cove, one of the best beaches on Barbados. Featuring palm trees and chickee huts, white sand and crystal-clear water, it’s the perfect place to relax, just a stone’s throw from Bridgetown.
If you’re brave enough to dive into the deep, set out on an MSC excursion inside a real submarine, the Atlantis, to explore the coral reef and discover the beauty that the depths reveal.
Bequia
An almost mythical utopia of virgin beaches, rustic rum shacks and bays so scenic you feel like you’re intruding - Bequia Island is an island mirage of Caribbean perfection. This is the real, unspoiled experience - and with just 6,000 locals living here, you quickly start to recognise the same smiling faces, welcoming you with outstretched arms. Offering glorious - often deserted - beaches of pure golden sand, and hillside sweeps of forest and almond trees, Bequia Island is an extraordinary feast for the senses.
Unlike some of the flashier Caribbean islands, Bequia - a part of the Grenadines - is a rustic, unassuming and off-the-beaten-path choice. The staggeringly picturesque natural harbour, Admiralty Bay, greets you on arrival, and is peppered with day-tripping yachts bobbing on the gentle waves. The island’s tiny capital, Port Elizabeth, sits behind, with its bustling fruit and vegetable market, turtle sanctuary, and stalls selling hand-crafted model ships. This tiny, pretty island is ridged along the centre, and you can earn your beachside bliss with a gentle hike to the top of Mount Peggy, looking out over views of Grenada and St Vincent. At just seven miles long, you can discover the whole island in a few hours – but that would be to miss the point somewhat. Bequia Island coaxes you in to slow the pace and soothe your soul on blissful beaches, where you can revel in the uncomplicated joys of sitting, reading and swimming in heavenly shallow waters. The royally approved Princess Margaret Beach is one of the finest - an arching band of soft sand and cobalt-blue waters. As evening sets in, you may find you’re beckoned to share with communal barbecues of the day’s fresh catch with the locals, or to indulge in rum-heavy cocktails at beachside bars, lashed together from sea-blanched wooden limbs.
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Wind Star is a sleek, 4-masted sailing ship accommodating 148 guests. With four decks and a gross tonnage of 5,307, Wind Star feels like your own private small ship.
Wind Star features wide open, teak decks—quite unusual for small ships. Guests will find hidden nooks for private moments giving them a feeling of being on their own private veranda.
All staterooms have ocean views, queen beds, flat-screen TV with DVD player, and Bose SoundDock speakers for Apple iPods. The Owner’s Suite includes a sitting area.
Wind Star offers two primary dining venues. Amphora restaurant offers gourmet, course-by-course cuisine in the evenings and Veranda restaurant offers casual buffet and full-service dining for breakfast and lunch. All dining is open seating. And, for dining under the stars, make a reservation for Candles which features steaks and skewers.
Wind Star amenities include: WindSpa, Watersports Platform, Lounge, Library, Pool, and Hot Tub.
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