Ocean Crossings
Ocean Cruise Memorii Pick
Windstar Cruises  ·  Wind Surf

Ocean Crossings

From Lisbon to Philipsburg  ·  Mediterranean  ·  15 nights

Departure 5 Nov 2027
Return 20 Nov 2027
Duration 15 nights
Ports of call 4 ports
Ship Wind Surf
Journey type Ocean Cruise
From
$2,835
per person
Request a Proposal
Voyage overview

What this voyage is

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.

Day By Day

Itinerary

1
5 Nov 2027
Lisbon

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.

Memory Tip: Don't miss Belem Tower, dating from the 1500s, was both a fortress and the explorers’ departure point. On the façade you will find a stone rhinoceros sculpted into the tower – Europe’s first sight of this extraordinary beast!
2
6 Nov 2027
At Sea
3
7 Nov 2027
At Sea
4
8 Nov 2027
Funchal

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.

5
9 Nov 2027
At Sea
6
10 Nov 2027
At Sea
7
11 Nov 2027
At Sea
8
12 Nov 2027
At Sea
9
13 Nov 2027
At Sea
10
14 Nov 2027
At Sea
11
15 Nov 2027
At Sea
12
16 Nov 2027
At Sea
13
17 Nov 2027
At Sea
14
18 Nov 2027
At Sea
15
19 Nov 2027
Jost Van Dyke

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.

16
20 Nov 2027
Philipsburg

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.

Memory Tip: Our tip For a change of pace, go to Loterie Farm at the foot of Pic Paradis, the highest point on Saint Martin, where you can cool off, see the wildlife and rent a cabana for a day of swimming in the cascades.
What is included

Fare inclusions

Alcohol included
Daytime activities
Meals included
Soft drinks, tea and coffee included
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