55 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipWind Surf

Nights55

DepartsSun, Jan 4th 2026

ReturnsSat, Feb 28th 2026

Departing PortPhilipsburg

Ports of CallPhilipsburg, Falmouth, Road Bay, Anguilla, Tortola, Great Harbour, Jost Van Dyke BVI (2 Days), Leverick Bay, Virgin Gorda, Gustavia, Philipsburg, Basseterre, Little Bay, Gustavia, Pointe a Pitre, Roseau, Pigeon Island, Bridgetown, Grande Anse, Castries, Pigeon Island (2 Days), Admiralty Bay, Bequia, Mayreau, St. George's, Bridgetown, Man-O-War, Tobago, Mayreau, Soufriere Bay, Kralendijk, Bonaire, Willemstad, Oranjestad, Santa Marta, Cartagena, Bocas Del Toro, Colon (2 Days), Bocas Del Toro, San Andres Island, Roatan, Belize City, Puerto Costa Maya, Mexico, Cozumel, Grand Cayman, Cayman Brac, Port Antonio, Santo Domingo, La Romana, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, Philipsburg

Inside Cabin

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Ocean View

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Balcony

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Suite

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Itinerary

Itinerary for 55 Night Caribbean - All Cruise
Decks
Ship Categories
Dining
Entertainment
Health & Fitness

Ship Details

Year Built
1990
Capacity
342
Meeting Rooms
Yes
Elevators
2
Casino
No
Registry
Bahamas
Restaurants
2
Disco
Yes
Tonnage
14,745
Bars
2
Fitness Center
Yes
Cabins
154
Pools
2
Children's Program
No
Wheelchair Accessible Cabins
N/A
Theaters
No
Internet Cafe
No
Shops
Yes
Library
Yes
Spa
Yes

Decks

Select any deck plan to see more details. Once clicked, hover over the image to zoom.
Star Deck

  • Stella Bistro
  • Veranda/Candles
  • Fitness Centre
  • Terrace Bar

Bridge Deck

  • Bridge
  • World Spa by Windstar
  • Compass Rose Bar
  • Owner's Suite
  • Broadmoor Suite
  • Sea Island Suite

Main Deck
  • Amphora Restaurant
  • Amphora Wine Room
  • Lounge
  • Reception
  • Yacht Club Café
  • Cruise Consultant Desk
  • Destination Desk
  • Star Boutique
  • Pool / Pool Bar / Whirlpools
Deck Three

  • Suites
  • TX Staterooms

Deck Two
  • Watersports Platform
  • A Staterooms
  • AX Staterooms
Deck One

  • BX Staterooms
  • B Staterooms
  • Medical Facility

Ship Categories

Officer's Suite
For the ultimate in nautical experiences, reserve the new Officer’s Suite located close to the Bridge where our own ship’s officers have their quarters. With its unique “insider” location and 242 square feet of comfort, the nautically appointed Officer’s Suite offers an experience you won’t find on any other cruise line.
CATEGORY TX DELUXE
CATEGORY TX DELUXE Deck 3 Forward/Aft or Midship CABIN TYPE: STATEROOM 188 sq. feet Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L'Occitane & reg; bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers.
CATEGORY AX DELUXE
CATEGORY AX DELUXE Deck 2 Midship CABIN TYPE: STATEROOM 188 sq. feet Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L’Occitane® bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers.
CATEGORY BX DELUXE
With 188 square feet, you’ll find the perfect space for time together — and plenty of room for time to yourself. You’ll even enjoy two full separate bathrooms. All the amenities of the staterooms await you, plus a beautiful sitting area, and two flat-screen television sets with DVD players.
Opulent Bridge Suite
The ultimate in space and style surrounds you in 495 square feet of pure indulgence. Separate bedroom and living room with an in-suite dining area is an invitation to relaxation. And possibly best of all, your expansive bathroom features both a whirlpool spa tub and a massage shower.
Category B
Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L’Occitane® bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers.
Bridge Suite
BRIDGE SUITE Deck Bridge Midship CABIN TYPE: SUITE 495 SQ FT The ultimate in space and style surrounds you in 495 square feet of pure indulgence. Separate bedroom and living room with an in-suite dining area is an invitation to relaxation. And possibly best of all, your expansive bathroom features both a whirlpool spa tub and a massage shower.
Suite
SUITE Deck 3 Forward/Aft or Midship CABIN TYPE: SUITE 376 sq. feet With 376 square feet, you’ll find the perfect space for time together — and plenty of room for time to yourself. You’ll even enjoy two full separate bathrooms. All the amenities of the staterooms await you, plus a beautiful sitting area, and two flat-screen television sets with DVD players.
CATEGORY A
CATEGORY A Deck 2 Forward/Aft CABIN TYPE: STATEROOM 188 sq. feet Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L’Occitane® bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers.

Dining

24-Hour Room Service

Stay in tonight and even order from the main Amphora dining menu.

Amphora Restaurant

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. 

Stella Bistro

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) 

Veranda Restaurant

It's breakfast alfresco, full service or buffet-style, anytime till 9:30 a.m. No need to hurry. Again, the choices are many in Veranda. Choose the sumptuous, seemingly endless buffet. Or, order from the lunch menu between noon and 2:30 p.m

Entertainment

Bridge

Located on Bridge Deck

Compass Rose Bar

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. 

Lounge

An expanded lounge with new lights and sound for upcoming stage performances.

Onboard Entertainment

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

Pool Deck & 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. 

Reception

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. 

Star Boutique

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

Wine Room

Located on the Main Deck

Yacht Club Café

The Yacht Club Café can be found on the Main Deck.

Health & Fitness

Health and Fitness Facilities

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

Pool Area

Located on the Main Deck

WindSpa

Relax into the destinations you’re visiting at the new World Spa by Windstar, which will offer regional spa treatments, including massage styles like Swedish, Japanese Shiatsu and Hawaiian Lomi Lomi.