From Lisbon to Philipsburg · Caribbean · 23 nights
From Lisbon to Philipsburg
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.
The roots of historic Lisbon's fame lie in its strategic position on the edge of the Atlantic and the fact it offers one of the world's greatest natural harbours. No surprise therefore that it became the home of the world's most famous explorers such as Vasco da Gama, Magellan and Prince Henry the Navigator. Built on seven hills, we always find Lisbon to be soulful, captivating and picturesque, with architecture which reflects its status as a great port.
Funchal, Madeira’s bustling capital, tumbles down a dramatic hillside towards a beautiful sweeping bay. Highlights include colourful markets, wine lodges and the spectacular cable car ride up to the village of Monte, home of the famous toboggan run.
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.
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.
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.
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.
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.
