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55-Night Trip on Wind Surf

STAR COLLECTOR: GRAND CARIBBEAN ADVENTURE

Cruise, Ocean cruise, Small Ship/Yacht

Slideshow offer placeholder
See all the flavors of the Caribbean as you visit 28 islands and 39 ports from the lush jungles of Dominica to arid Aruba, trendy French enclaves to quiet ports known only to yachtsmen. Then go beyond, to the shores of the conquistadors in Colombia, to the Mayan legacy in Belize, and to Mexico’s golden Yucatán. On Day 36, part-way through your 55-day voyage, explore one of mankind’s greatest achievements as you make a partial transit of the Panama Canal, passing through three sets of locks and sailing into Lake Gatun before returning to the Caribbean. There’s a little bit of everything on this voyage: cultures, cuisine, beaches, nature, history, and shopping. With this epic tour of the Caribbean, you’re sure to come home with unforgettable memories, new friends, and new perspectives.
55 Nights Starting At

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January 04, 2026 through February 28, 2026
Book by:
December 29, 2025 7:00 PM
Category b
Inside Outside Balcony Suite
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Cat: B
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More Pricing Information
Inside Outside
CALL CALL
Cat: B
Balcony Suite
CALL CALL
More Pricing Information
Itinerary Overview
Day 1
Day 2
Falmouth Harbour
Arrive: 8:00 AM
Depart: 6:00 PM
Day 3
Arrive: 8:00 AM
Depart: 6:00 PM
Day 4
Day 4
Arrive: 8:00 AM
Depart: 6:00 PM
Day 5
Day 6
Day 7
Arrive: 8:00 AM
Depart: 10:00 PM
Day 8
Arrive: 6:00 AM
Depart: 7:00 PM
Day 9
Arrive: 8:00 AM
Depart: 9:00 PM
Day 10
Arrive: 8:00 AM
Depart: 10:00 PM
Day 11
Arrive: 8:00 AM
Depart: 10:00 PM
Day 12
Arrive: 8:00 AM
Depart: 9:00 PM
Day 13
Pigeon Island
Arrive: 8:00 AM
Depart: 5:00 PM
Day 14
Arrive: 7:00 AM
Depart: 2:00 PM
Day 15
Arrive: 5:00 AM
Depart: 6:00 PM
Day 16
Anse Mitan
Arrive: 9:00 AM
Depart: 11:00 PM
Day 17
Pigeon Island
Arrive: 6:00 PM
Day 17
Arrive: 8:00 AM
Depart: 4:00 PM
Day 18
Pigeon Island
Depart: 6:00 PM
Day 19
Arrive: 8:00 AM
Depart: 10:00 PM
Day 20
Arrive: 8:00 AM
Depart: 6:00 PM
Day 21
Arrive: 7:00 AM
Depart: 2:00 PM
Day 22
Arrive: 6:00 AM
Depart: 6:00 PM
Day 23
Arrive: 8:00 AM
Depart: 5:00 PM
Day 24
Arrive: 8:00 AM
Depart: 6:00 PM
Day 25
Arrive: 8:00 AM
Depart: 4:00 PM
Day 26
Day 27
Arrive: 1:00 PM
Depart: 10:00 PM
Day 28
Arrive: 8:00 AM
Depart: 6:00 PM
Day 29
Arrive: 6:00 AM
Depart: 6:00 PM
Day 30
Day 31
Santa Marta
Arrive: 7:00 AM
Depart: 6:00 PM
Day 32
Arrive: 8:00 AM
Depart: 3:30 PM
Day 33
Day 34
Depart: 5:30 PM
Day 35
Day 36
Arrive: 7:00 AM
Day 37
Depart: 4:00 PM
Day 38
Arrive: 10:00 AM
Depart: 4:00 PM
Day 39
Arrive: 1:00 PM
Depart: 7:00 PM
Day 40
Day 41
Day 42
Arrive: 9:00 AM
Depart: 5:00 PM
Day 43
Arrive: 9:00 AM
Depart: 7:00 PM
Day 44
Arrive: 8:00 AM
Depart: 5:00 PM
Day 45
Arrive: 8:00 AM
Depart: 6:00 PM
Day 46
Day 47
Arrive: 8:00 AM
Depart: 6:00 PM
Day 48
Arrive: 7:00 AM
Depart: 1:00 PM
Day 49
Port Antonio
Depart: 6:00 PM
Day 50
Day 51
Arrive: 1:00 PM
Depart: 10:00 PM
Day 52
Arrive: 7:00 AM
Depart: 5:00 PM
Day 53
Day 54
Day 55
Day 56
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About Wind Surf

Ship Overview
Wind Surf

Windstar's Flagship Sailing Yacht
On any day, our 342-guest flagship, Wind Surf, the world’s largest sailing ship, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. During their cruise, you will find the perfect setting for ‘making an entrance’ in the beautiful reception area – and, appropriately, that’s only the beginning.

When you return to your stateroom, the luxury gets personal. Windstar’s signature bowls of flowers and fresh fruit will still be waiting for you, along with rich tufted headboards, soft seascape colors, beautiful new upholstery, and fine count Egyptian cotton linens welcome you to an oasis of relaxing indulgence.

Wind Surf underwent a significant renovation of public spaces and suites, including an expanded lounge with new lights and sound for upcoming stage performances. 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. A new Officer’s Suite, which might be the only one of its kind, provides you the chance to stay in the heart of the officer quarters tucked right behind the Bridge.

Everything about Wind Surf speaks of welcome. Come aboard and see it for yourself.

Ship Details
Ship Class
Windstar
Ship's Registry
Bahamas
Ship Length
617 ft
Ship Beam
66 ft
Cruising Speed
10-12 knots
Gross Tonnage
14,745
Total Capacity
342
Crew Size
210
Crew-to-Passenger Ratio
1 to 1.75
Suites
21
Oceanview Rooms
150
Hot Tubs
2
Pools
1
Laundromats
Number of Decks
6
Deck Plan Details
Ship small image
Cabin Categories
TX Stateroom $24,199.00 USD
AX Stateroom $22,129.00 USD
A Stateroom $20,349.00 USD
BX Stateroom $19,299.00 USD
B Stateroom $17,899.00 USD
Symbol Legend
Legend Image for Public Space Public Space
Legend Image for Stairs-Elevator Stairs-Elevator
Deck plans are not yet available
Wind Surf Amenities

ONBOARD SPACES

  • Reception
  • Amphora Restaurant
  • Stella Bistro
  • Candles
  • Veranda
  • Yacht Club Sandwich & Espresso Bar
  • Compass Rose
  • The Lounge
  • Terrace Bar
  • Pool Bar
  • Watersports Platform
  • Pool
  • Two Whirlpools
  • Fitness Center
  • Nautilus Room
  • Signature Shop
  • WindSpa
  • Photo Gallery
  • The Bridge (with Windstar's Open Bridge Policy)
What's Included on Windstar

We strive to provide you the best experience at sea. We believe in taking care of our guests and making them feel welcome, and so we've included all the things you'd want on your cruise.

All Meals
All meals in all venues at all times, including room service menu available 24 hours.

Non-Alcoholic Beverages
All non-alcoholic beverages, including cappucino, espresso, and other specialty non-alcoholic drinks.

Welcome Cocktail
Welcome cocktails at reception.

Water Sports Equipment
Unlimited use of all water sports equipment.

Entertainment
All onboard entertainment.

Fitness Center & Classes
Unlimited use of Fitness Center and Exercise Classes.

Destination Briefings
Informative nightly port talks and destination briefings.

Ship Overview
Ship Overview
Wind Surf

Windstar's Flagship Sailing Yacht
On any day, our 342-guest flagship, Wind Surf, the world’s largest sailing ship, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. During their cruise, you will find the perfect setting for ‘making an entrance’ in the beautiful reception area – and, appropriately, that’s only the beginning.

When you return to your stateroom, the luxury gets personal. Windstar’s signature bowls of flowers and fresh fruit will still be waiting for you, along with rich tufted headboards, soft seascape colors, beautiful new upholstery, and fine count Egyptian cotton linens welcome you to an oasis of relaxing indulgence.

Wind Surf underwent a significant renovation of public spaces and suites, including an expanded lounge with new lights and sound for upcoming stage performances. 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. A new Officer’s Suite, which might be the only one of its kind, provides you the chance to stay in the heart of the officer quarters tucked right behind the Bridge.

Everything about Wind Surf speaks of welcome. Come aboard and see it for yourself.

Ship Details
Ship Class
Windstar
Ship's Registry
Bahamas
Ship Length
617 ft
Ship Beam
66 ft
Cruising Speed
10-12 knots
Gross Tonnage
14,745
Total Capacity
342
Crew Size
210
Crew-to-Passenger Ratio
1 to 1.75
Suites
21
Oceanview Rooms
150
Hot Tubs
2
Pools
1
Laundromats
Number of Decks
6
Deck Plan Details
Ship small image
Cabin Categories
TX Stateroom $24,199.00 USD
AX Stateroom $22,129.00 USD
A Stateroom $20,349.00 USD
BX Stateroom $19,299.00 USD
B Stateroom $17,899.00 USD
Symbol Legend
Legend Image for Public Space Public Space
Legend Image for Stairs-Elevator Stairs-Elevator
Deck plans are not yet available

ONBOARD SPACES

  • Reception
  • Amphora Restaurant
  • Stella Bistro
  • Candles
  • Veranda
  • Yacht Club Sandwich & Espresso Bar
  • Compass Rose
  • The Lounge
  • Terrace Bar
  • Pool Bar
  • Watersports Platform
  • Pool
  • Two Whirlpools
  • Fitness Center
  • Nautilus Room
  • Signature Shop
  • WindSpa
  • Photo Gallery
  • The Bridge (with Windstar's Open Bridge Policy)

We strive to provide you the best experience at sea. We believe in taking care of our guests and making them feel welcome, and so we've included all the things you'd want on your cruise.

All Meals
All meals in all venues at all times, including room service menu available 24 hours.

Non-Alcoholic Beverages
All non-alcoholic beverages, including cappucino, espresso, and other specialty non-alcoholic drinks.

Welcome Cocktail
Welcome cocktails at reception.

Water Sports Equipment
Unlimited use of all water sports equipment.

Entertainment
All onboard entertainment.

Fitness Center & Classes
Unlimited use of Fitness Center and Exercise Classes.

Destination Briefings
Informative nightly port talks and destination briefings.

About Windstar Cruises
Windstar Cruises logo

THE WORLD'S BEST SMALL SHIP CRUISE LINE

NO ONE ELSE GOES SO FAR TO GET TRAVELERS SO CLOSE …
You’re closer to secluded coves, tiny villages, misty fjords. To ancient ruins, medieval alleyways, quaint marinas. To unspoiled beaches, unfamiliar cultures, undiscovered atolls. To enlivening your curiosity and awakening your sense of wonder. You’re closer than ever to the kind of authentic and unforgettable experiences that you travel to find in the first place. You’re about to board Windstar. And you’re closer to all the places that larger ships can’t reach.

SEE A WORLD FEW WILL EVER SEE …
Welcome to a world of understated elegance and uncommon beauty. A world that leaves crowds and commonplace behind to find unique ports of call, and local, exotic cultures that are at once fascinating and wondrous. A world that’s equal parts intimate, indulgent and inspiring. Where the allure and beauty and magic of the places you sail to is equaled only by the ship that takes you there.
 

Read More

About Windstar Cruises

THE WORLD'S BEST SMALL SHIP CRUISE LINE

NO ONE ELSE GOES SO FAR TO GET TRAVELERS SO CLOSE …
You’re closer to secluded coves, tiny villages, misty fjords. To ancient ruins, medieval alleyways, quaint marinas. To unspoiled beaches, unfamiliar cultures, undiscovered atolls. To enlivening your curiosity and awakening your sense of wonder. You’re closer than ever to the kind of authentic and unforgettable experiences that you travel to find in the first place. You’re about to board Windstar. And you’re closer to all the places that larger ships can’t reach.

SEE A WORLD FEW WILL EVER SEE …
Welcome to a world of understated elegance and uncommon beauty. A world that leaves crowds and commonplace behind to find unique ports of call, and local, exotic cultures that are at once fascinating and wondrous. A world that’s equal parts intimate, indulgent and inspiring. Where the allure and beauty and magic of the places you sail to is equaled only by the ship that takes you there.
 

Read More

Prices are per-person based on double occupancy, unless otherwise noted.