Anywhere Cruise and Travel

A full service travel agency

55-Night Trip on Wind Surf

STAR COLLECTOR: GRAND CARIBBEAN ADVENTURE

Cruise, Ocean cruise, Small Ship/Yacht

Slideshow offer placeholder
Explore the depth and breadth of the Caribbean on this 35-day odyssey, from tiny yachtsmen’s favorites to glitzy celebrity getaways, historic colonial towns to the incredible jungles of wildlife. Go cave tubing in Belize and diving in Bonaire. Snorkel with friendly sea turtles and rays in waters as clear as glass. Climb the battlements of colonial forts and the arrowhead peak of Gros Piton in St. Lucia. It’s the ultimate cruise, circling the Caribbean discovering the brilliant colors, textures and fascinating history found here.
55 Nights Starting At
Per Person + $1,417.00 taxes/fees
January 04, 2026 through February 28, 2026
Book by:
December 29, 2025 7:00 PM
Category b
Inside Outside Balcony Suite
N/A $15,599.00
Cat: B
$283.62 per night
N/A N/A
More Pricing Information
Inside Outside
N/A $15,599.00
Cat: B
$283.62 per night
Balcony Suite
N/A N/A
More Pricing Information
Itinerary Overview
Day 1
Depart: 7:00 PM
Day 2
Falmouth Harbour
Arrive: 8:00 AM
Depart: 6:00 PM
Day 3
Road Bay
Arrive: 8:00 AM
Depart: 6:00 PM
Day 4
Day 4
Soper's Hole
Arrive: 8:00 AM
Depart: 6:00 PM
Day 5
Depart: 10:00 PM
Day 6
Virgin Gorda / Prickly Pear
Arrive: 8:00 AM
Depart: 5:00 PM
Day 7
Arrive: 8:00 AM
Depart: 10:00 PM
Day 8
Arrive: 6:00 AM
Depart: 7:00 PM
Day 9
Arrive: 7:00 AM
Depart: 10:00 PM
Day 10
Arrive: 8:00 AM
Depart: 6:00 PM
Day 11
Arrive: 8:00 AM
Depart: 11:00 PM
Day 12
Deshaies
Arrive: 12:30 AM
Depart: 10:00 PM
Day 13
Arrive: 8:00 AM
Depart: 5:00 PM
Day 14
Pigeon Island
Arrive: 7:00 AM
Depart: 4:00 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
Man-O-War Bay
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
Isla San Andres
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
Virgin Gorda / Prickly Pear
Arrive: 8:00 AM
Depart: 5:00 PM
Day 56
Arrive: 6:00 AM
Loading Itinerary Content...

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 recently underwent a significant renovation in November 2019 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 $21,899.00 USD
AX Stateroom $19,499.00 USD
A Stateroom $17,699.00 USD
BX Stateroom $16,999.00 USD
B Stateroom $15,599.00 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. Our attentive staff will take care of everything you need and anticipate anything you dream.

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.

Life on Windstar

World Class Dining Experience
We've upped the onboard dining game with our culinary program, featuring an array of fresh, seasonal ingredients sourced from each port along the journey. Each nightly menu is crafted to highlight the spectacular flavors of the regional cuisine.

Activities
Other cruise lines have bingo and trivia nights. Windstsar has a Watersports Platform that opens directly from the back of our ships and includes complimentary kayaks, paddleboards, water trampolines, and water skis. Spend time in the Lounge regaling your fellow guests about the bears you saw catching fish from the river or simply relax in the Library with an intriguing book. Take some "you" time in the tranquil World Spa by Windstar...enjoy a dip in the pool...work off that decadent dessert in the Fitness Center...and, of course, you are always welcome to visit the Bridge to examine navigation charts with the Captain.

Entertainment
A day on board your Windstar ship is a day of choices, all of them good. Perhaps you’ll begin with a relaxing massage in World Spa by Windstar. Or maybe an invigorating workout in the Fitness Center. Even better, why not both? After a sumptuous lunch in Veranda, make a splash from the Watersports Platform off the ship’s stern. Everything you can think of for fun in the water is there — swimming, kayaking, sail-boarding, even water skiing. And it’s all complimentary, of course. Sun yourself on deck, take a dip in the whirlpool, then catch up on email ororder a cheese plate for your stateroom or suite. After dinner, dance to live music in the Lounge. This is your yacht, so of course you’re welcome on the Bridge, where the Captain and officers are delighted to share charts, routes, and vistas with you.

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 recently underwent a significant renovation in November 2019 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 $21,899.00 USD
AX Stateroom $19,499.00 USD
A Stateroom $17,699.00 USD
BX Stateroom $16,999.00 USD
B Stateroom $15,599.00 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. Our attentive staff will take care of everything you need and anticipate anything you dream.

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.

World Class Dining Experience
We've upped the onboard dining game with our culinary program, featuring an array of fresh, seasonal ingredients sourced from each port along the journey. Each nightly menu is crafted to highlight the spectacular flavors of the regional cuisine.

Activities
Other cruise lines have bingo and trivia nights. Windstsar has a Watersports Platform that opens directly from the back of our ships and includes complimentary kayaks, paddleboards, water trampolines, and water skis. Spend time in the Lounge regaling your fellow guests about the bears you saw catching fish from the river or simply relax in the Library with an intriguing book. Take some "you" time in the tranquil World Spa by Windstar...enjoy a dip in the pool...work off that decadent dessert in the Fitness Center...and, of course, you are always welcome to visit the Bridge to examine navigation charts with the Captain.

Entertainment
A day on board your Windstar ship is a day of choices, all of them good. Perhaps you’ll begin with a relaxing massage in World Spa by Windstar. Or maybe an invigorating workout in the Fitness Center. Even better, why not both? After a sumptuous lunch in Veranda, make a splash from the Watersports Platform off the ship’s stern. Everything you can think of for fun in the water is there — swimming, kayaking, sail-boarding, even water skiing. And it’s all complimentary, of course. Sun yourself on deck, take a dip in the whirlpool, then catch up on email ororder a cheese plate for your stateroom or suite. After dinner, dance to live music in the Lounge. This is your yacht, so of course you’re welcome on the Bridge, where the Captain and officers are delighted to share charts, routes, and vistas with you.

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.