From Philipsburg to Lisbon · Caribbean · 22 nights
Windstar’s flagship sailing yacht is a stunning sail assisted cruise ship, which combines the refinement of a modern vessel with the romance of a tall ship.
Gracious staterooms provide a compact yet comfortable retreat.
Facilities include several dining options and a variety of bars and
lounges, a small swimming pool with two whirlpools and even a
watersports platform. The décor is fresh and modern and the ship
emerged from the first phase of a multi-year refresh in 2024,
boasting upgrades to several public areas including Amphora and the
pool deck. The second phase of the refresh which includes stateroom
redesigns will occur in 2026.
Philipsburg is the gateway to an intriguing little Caribbean island with a dual personality: the Dutch side, St. Maarten, is the livelier of the two, with shopping malls, casinos and more of a nightlife scene, while French-speaking St. Martin is a more refined (and more expensive) affair, with a laid-back, continental air and a host of exclusive resorts and restaurants. Travelling between the two halves of the island is hassle-free, and both sides boast beautiful beaches, friendly locals and pleasant little towns and villages.
Tiny Anguilla is home to no less than 33 beaches, blessed with some of the most gloriously white sands in the Caribbean. A clutch of high end hotels and gourmet restaurants attract a well-to-do crowd, but the island has a more low key, laid back vibe than its glitzy neighbours, St Martin and St Barths.
The idyllic island of Jost Van Dyke, named after an early Dutch settler, is known for its laid back vibe and friendly beach bars, including the famous Foxy’s, which counts Keith Richards amongst its past customers. It’s a place to kick back and relax, and the clear blue waters are also perfect for snorkelling.
Gustavia is the chic and petite capital of Saint Barths, a tiny French Caribbean island that’s renowned as a haunt of the rich and the famous. You can certainly live well here if you’ve got the means, with an array of gourmet restaurants and luxury boutiques aimed squarely at the A-list. The beautiful beaches, on the other hand, are free and open to all.
Philipsburg is the gateway to an intriguing little Caribbean island with a dual personality: the Dutch side, St. Maarten, is the livelier of the two, with shopping malls, casinos and more of a nightlife scene, while French-speaking St. Martin is a more refined (and more expensive) affair, with a laid-back, continental air and a host of exclusive resorts and restaurants.
Horta is the capital of the island of Faial, in the centre of the Azores archipelago. The harbour is a popular stop-off point for yachts crossing the Atlantic, and it’s also the base for whale watching trips and excursions to the spectacular Caldeira Cabeço Gordo volcanic crater.
Ponta Delgada is the capital of São Miguel, the largest and most populous island of the Azores. Founded in the 15th century, the city is home to elegant architecture and some excellent restaurants, though the main attraction is the tranquility and natural beauty of the surrounding countryside.
Spread across steep hillsides that overlook the Rio Tejo, Lisbon’s colourful cityscape includes Gothic cathedrals, majestic monasteries and quaint museums. But for many the best times will be had wandering the narrow lanes of Lisbon’s lovely backstreets, with their great local food, wine and music.
