
Cruise LineWindstar Cruises
ShipWind Surf
Nights21
DepartsSat, Mar 28th 2026
ReturnsSat, Apr 18th 2026
Departing PortPhilipsburg
Ports of CallPhilipsburg, St. John Island, Road Bay, Anguilla, Tortola, Great Harbour, Jost Van Dyke BVI (2 Days), Leverick Bay, Virgin Gorda, Gustavia, Philipsburg, Ponta Delgada, Lisbon
Inside Cabin
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Ocean View
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Balcony
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Suite
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Itinerary
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Day
Port
Arrive
Depart
-
Day 1
Arrival --
Departure 7:00pm
-
Day 2
Port St. John Island, U.S. Virgin Islands
Arrival 8:00am
Departure 5:00pm
-
Day 3
Port Road Bay, Anguilla
Arrival 8:00am
Departure 6:00pm
-
Day 4
Port Tortola, British Virgin Islands
Arrival 8:00am
Departure 6:00pm
-
Day 4
Port Great Harbour, Jost Van Dyke BVI
Arrival 7:00pm
Departure --
-
Day 5
Port Great Harbour, Jost Van Dyke BVI
Arrival --
Departure 10:00pm
-
Day 6
Port Leverick Bay, Virgin Gorda, British Virgin Islands
Arrival 8:00am
Departure 5:00pm
-
Day 7
Port Gustavia
Arrival 8:00am
Departure 10:00pm
-
Day 8
Arrival 6:00am
Departure 7:00pm
-
Day 9
Port At Sea
Arrival --
Departure --
-
Day 10
Port At Sea
Arrival --
Departure --
-
Day 11
Port At Sea
Arrival --
Departure --
-
Day 12
Port At Sea
Arrival --
Departure --
-
Day 13
Port At Sea
Arrival --
Departure --
-
Day 14
Port At Sea
Arrival --
Departure --
-
Day 15
Port At Sea
Arrival --
Departure --
-
Day 16
Port At Sea
Arrival --
Departure --
-
Day 17
Port At Sea
Arrival --
Departure --
-
Day 18
Arrival 8:00am
Departure 6:00pm
-
Day 19
Port At Sea
Arrival --
Departure --
-
Day 20
Port At Sea
Arrival --
Departure --
-
Day 21
Port At Sea
Arrival --
Departure --
-
Day 22
Port Lisbon, Portugal
Arrival 7:00am
Departure --
Ship Details
Decks
Select any deck plan to see more details. Once clicked, hover over the image to zoom.- Amphora Restaurant
- Amphora Wine Room
- Lounge
- Reception
- Yacht Club Café
- Cruise Consultant Desk
- Destination Desk
- Star Boutique
- Pool / Pool Bar / Whirlpools

Ship Categories









Dining
Wind Surf’s main dining room has been entirely refreshed setting the scene for a timeless dining experience. Amphora’s new design concept draws from elements of the sea, such as pearls, smooth stones, and sea glass, which guests will see integrated into the new architecture and furniture details. The complementing colour tones were inspired by the horizon at sunset. New seating arrangements include curved booths to seat 2-8 people, new larger dining chairs for comfort.

Treat your palate to the French-inspired café cuisine of Stella Bistro, Wind Surf's alternative restaurant. You'll find delightfully indulgent desserts and a wonderful array of wines specifically paired to the meal. (Wind Surf only)

Entertainment
The ship’s Compass Rose features comfortable, modern décor with pops of blue and orange, a chic bar, and a new multi-purpose stage area ideal for live music and local performances.

Onboard entertainment facilities include: a casino, a watersports platform, the Compass Rose Cocktail Bar, The Lounge, and The Terrace Bar.

This space will now maximise Wind Surf’s ocean views and create a more convivial vibe for poolside lounging and top-shelf mixology. Tropical scenes and greenery at the bar pull in a natural, outdoor atmosphere. Soothing natural colours convey a beach scene and new arty tiling on the two whirlpools take the form of ocean waves. Look for a variety of new outdoor furniture as well.

A new, more welcoming location that’s better able to serve guests with additional seating options, plus an updated and fresh (yet still nautical) vibe akin to a boutique hotel.

A larger retail area with upscale details, reminiscent of a luxury brand store’s shopping experience.

Health & Fitness
Health & Fitness facilities include a Fitness Centre, whirlpool, and swimming pool.

Prices are per person, double occupancy, cruise only and on select sailings. Prices shown are for stateroom categories as noted and are shown in US Dollars. Pricing listed includes taxes and fees. Airfare is not included. Prices and itineraries are based on availability and are subject to change without notice.