CLASSIC CARIBBEAN

Trip Details

7-Night Trip on Wind Surf

CLASSIC CARIBBEAN

Cruise, Ocean cruise, Small Ship/Yacht

Exterior view of Wind Surf sailing near Capri, Italy

Photo Credit: Roger Paperno

Exterior view of Wind Surf

Photo Credit: Jeff Zaruba

Close-up exterior view of Wind Surf bow

Photo Credit: Roger Paperno

Exterior view of Wind Surf

Photo Credit: Roger Paperno

From the stunning drama of the Pitons to the captivating charm of Les Saintes. From hidden coves and secret beaches to exotic markets and lively cafés. Discover the best of this region with one single Caribbean cruise. Sandy beaches, turquoise waters, lush mountains, and beautiful waterfalls blend with the music, tastes, and joie de vivre unique to the Caribbean life.

7 Nights Starting At

CALL

December 07, 2025 through December 14, 2025

Book by:

December 01, 2025 7:00 PM

Category b

Inside	Outside	Balcony	Suite
CALL	CALL Cat: B	CALL	CALL Cat: OS
More Pricing Information

Inside	Outside
CALL	CALL Cat: B
Balcony	Suite
CALL	CALL Cat: OS
More Pricing Information

Amenity Departure Dates

(See details)

Terms & Disclaimers

ID: 8493349

Itinerary Overview

Day 1

Philipsburg, St. Maarten

Depart: 7:00 PM

Day 2

Charlestown

Arrive: 8:00 AM

Depart: 5:00 PM

Day 3

Roseau

Arrive: 8:00 AM

Depart: 4:00 PM

Day 4

Mayreau

Arrive: 8:00 AM

Depart: 5:00 PM

Day 5

Les Saintes

Depart: 6:00 PM

Day 6

Basseterre

Arrive: 8:00 AM

Depart: 10:00 PM

Day 7

Gustavia

Arrive: 8:00 AM

Depart: 10:00 PM

Day 8

Philipsburg, St. Maarten

Arrive: 6:00 AM

Loading Itinerary Content...

Dates & prices

Additional Offers	Inside	Outside	Balcony	Suite
December 07, 2025 to December 14, 2025 7 Nights from CALL (View Additional Details) Category b Book by: December 01, 2025 7:00 PM Category b Amenity Departure Dates (See details) Terms & Disclaimers ID: 8493349 Terms and Disclaimers Charges not included in the price may include but are not limited to: airfare to and from the start of your trip; airline baggage fees including checked and/or excess baggage fees; Federal inspection fees for the Federal U.S. Customs and Immigrations; agricultural tax; other per person taxes imposed by government entities; applicable cruise taxes, fees, fares and port charges; passports; visas and vaccinations; transfers; tips to your Tour or Cruise Director, Local Host, driver, Local Guides, and/or ships' crew; gratuities on ferries, trains, and cruise ships; laundry; telephone; minibar; alcohol, beverages, and food outside of the contracted menu as presented at a hotel or restaurant (these extra items will be billed to you before leaving the hotel, ship, or restaurant); additional excursions and activities not listed as 'included' in the itinerary; porterage at airports or train stations; Travel Protection premiums; and all other items of a personal nature. If you are interested in an offer, please click on Contact Us . This will open a "Trip Request" that will allow you to send your request to us. We will be able to confirm availability and make further recommendations. Ship's registry: Bahamas	CALL	CALL	CALL	CALL	Contact Us	Terms & Disclaimers ID: 8493349 Terms and Disclaimers Charges not included in the price may include but are not limited to: airfare to and from the start of your trip; airline baggage fees including checked and/or excess baggage fees; Federal inspection fees for the Federal U.S. Customs and Immigrations; agricultural tax; other per person taxes imposed by government entities; applicable cruise taxes, fees, fares and port charges; passports; visas and vaccinations; transfers; tips to your Tour or Cruise Director, Local Host, driver, Local Guides, and/or ships' crew; gratuities on ferries, trains, and cruise ships; laundry; telephone; minibar; alcohol, beverages, and food outside of the contracted menu as presented at a hotel or restaurant (these extra items will be billed to you before leaving the hotel, ship, or restaurant); additional excursions and activities not listed as 'included' in the itinerary; porterage at airports or train stations; Travel Protection premiums; and all other items of a personal nature. If you are interested in an offer, please click on Contact Us . This will open a "Trip Request" that will allow you to send your request to us. We will be able to confirm availability and make further recommendations. Ship's registry: Bahamas
December 21, 2025 to December 28, 2025 7 Nights from CALL (View Additional Details) Category b Book by: December 15, 2025 7:00 PM Category b Amenity Departure Dates (See details) Terms & Disclaimers ID: 8533875 Terms and Disclaimers Charges not included in the price may include but are not limited to: airfare to and from the start of your trip; airline baggage fees including checked and/or excess baggage fees; Federal inspection fees for the Federal U.S. Customs and Immigrations; agricultural tax; other per person taxes imposed by government entities; applicable cruise taxes, fees, fares and port charges; passports; visas and vaccinations; transfers; tips to your Tour or Cruise Director, Local Host, driver, Local Guides, and/or ships' crew; gratuities on ferries, trains, and cruise ships; laundry; telephone; minibar; alcohol, beverages, and food outside of the contracted menu as presented at a hotel or restaurant (these extra items will be billed to you before leaving the hotel, ship, or restaurant); additional excursions and activities not listed as 'included' in the itinerary; porterage at airports or train stations; Travel Protection premiums; and all other items of a personal nature. If you are interested in an offer, please click on Contact Us . This will open a "Trip Request" that will allow you to send your request to us. We will be able to confirm availability and make further recommendations. Ship's registry: Bahamas	CALL	CALL	CALL	CALL	Contact Us	Terms & Disclaimers ID: 8533875 Terms and Disclaimers Charges not included in the price may include but are not limited to: airfare to and from the start of your trip; airline baggage fees including checked and/or excess baggage fees; Federal inspection fees for the Federal U.S. Customs and Immigrations; agricultural tax; other per person taxes imposed by government entities; applicable cruise taxes, fees, fares and port charges; passports; visas and vaccinations; transfers; tips to your Tour or Cruise Director, Local Host, driver, Local Guides, and/or ships' crew; gratuities on ferries, trains, and cruise ships; laundry; telephone; minibar; alcohol, beverages, and food outside of the contracted menu as presented at a hotel or restaurant (these extra items will be billed to you before leaving the hotel, ship, or restaurant); additional excursions and activities not listed as 'included' in the itinerary; porterage at airports or train stations; Travel Protection premiums; and all other items of a personal nature. If you are interested in an offer, please click on Contact Us . This will open a "Trip Request" that will allow you to send your request to us. We will be able to confirm availability and make further recommendations. Ship's registry: Bahamas
March 21, 2026 to March 28, 2026 7 Nights from CALL (View Additional Details) Category b Book by: March 15, 2026 7:00 PM Category b Amenity Departure Dates (See details) Terms & Disclaimers ID: 8494147 Terms and Disclaimers Charges not included in the price may include but are not limited to: airfare to and from the start of your trip; airline baggage fees including checked and/or excess baggage fees; Federal inspection fees for the Federal U.S. Customs and Immigrations; agricultural tax; other per person taxes imposed by government entities; applicable cruise taxes, fees, fares and port charges; passports; visas and vaccinations; transfers; tips to your Tour or Cruise Director, Local Host, driver, Local Guides, and/or ships' crew; gratuities on ferries, trains, and cruise ships; laundry; telephone; minibar; alcohol, beverages, and food outside of the contracted menu as presented at a hotel or restaurant (these extra items will be billed to you before leaving the hotel, ship, or restaurant); additional excursions and activities not listed as 'included' in the itinerary; porterage at airports or train stations; Travel Protection premiums; and all other items of a personal nature. If you are interested in an offer, please click on Contact Us . This will open a "Trip Request" that will allow you to send your request to us. We will be able to confirm availability and make further recommendations. Ship's registry: Bahamas	CALL	CALL	CALL	CALL	Contact Us	Terms & Disclaimers ID: 8494147 Terms and Disclaimers Charges not included in the price may include but are not limited to: airfare to and from the start of your trip; airline baggage fees including checked and/or excess baggage fees; Federal inspection fees for the Federal U.S. Customs and Immigrations; agricultural tax; other per person taxes imposed by government entities; applicable cruise taxes, fees, fares and port charges; passports; visas and vaccinations; transfers; tips to your Tour or Cruise Director, Local Host, driver, Local Guides, and/or ships' crew; gratuities on ferries, trains, and cruise ships; laundry; telephone; minibar; alcohol, beverages, and food outside of the contracted menu as presented at a hotel or restaurant (these extra items will be billed to you before leaving the hotel, ship, or restaurant); additional excursions and activities not listed as 'included' in the itinerary; porterage at airports or train stations; Travel Protection premiums; and all other items of a personal nature. If you are interested in an offer, please click on Contact Us . This will open a "Trip Request" that will allow you to send your request to us. We will be able to confirm availability and make further recommendations. Ship's registry: Bahamas

Additional Offers	December 07, 2025 December 14, 2025 Price Details 7 Nights from CALL (USD) Per Person (View Additional Details) Category b Book by: December 01, 2025 7:00 PM Amenity Departure Dates (See details) Terms & Disclaimers ID: 8493349 Terms and Disclaimers Charges not included in the price may include but are not limited to: airfare to and from the start of your trip; airline baggage fees including checked and/or excess baggage fees; Federal inspection fees for the Federal U.S. Customs and Immigrations; agricultural tax; other per person taxes imposed by government entities; applicable cruise taxes, fees, fares and port charges; passports; visas and vaccinations; transfers; tips to your Tour or Cruise Director, Local Host, driver, Local Guides, and/or ships' crew; gratuities on ferries, trains, and cruise ships; laundry; telephone; minibar; alcohol, beverages, and food outside of the contracted menu as presented at a hotel or restaurant (these extra items will be billed to you before leaving the hotel, ship, or restaurant); additional excursions and activities not listed as 'included' in the itinerary; porterage at airports or train stations; Travel Protection premiums; and all other items of a personal nature. If you are interested in an offer, please click on Contact Us . This will open a "Trip Request" that will allow you to send your request to us. We will be able to confirm availability and make further recommendations. Ship's registry: Bahamas	December 21, 2025 December 28, 2025 Price Details 7 Nights from CALL (USD) Per Person (View Additional Details) Category b Book by: December 15, 2025 7:00 PM Amenity Departure Dates (See details) Terms & Disclaimers ID: 8533875 Terms and Disclaimers Charges not included in the price may include but are not limited to: airfare to and from the start of your trip; airline baggage fees including checked and/or excess baggage fees; Federal inspection fees for the Federal U.S. Customs and Immigrations; agricultural tax; other per person taxes imposed by government entities; applicable cruise taxes, fees, fares and port charges; passports; visas and vaccinations; transfers; tips to your Tour or Cruise Director, Local Host, driver, Local Guides, and/or ships' crew; gratuities on ferries, trains, and cruise ships; laundry; telephone; minibar; alcohol, beverages, and food outside of the contracted menu as presented at a hotel or restaurant (these extra items will be billed to you before leaving the hotel, ship, or restaurant); additional excursions and activities not listed as 'included' in the itinerary; porterage at airports or train stations; Travel Protection premiums; and all other items of a personal nature. If you are interested in an offer, please click on Contact Us . This will open a "Trip Request" that will allow you to send your request to us. We will be able to confirm availability and make further recommendations. Ship's registry: Bahamas	March 21, 2026 March 28, 2026 Price Details 7 Nights from CALL (USD) Per Person (View Additional Details) Category b Book by: March 15, 2026 7:00 PM Amenity Departure Dates (See details) Terms & Disclaimers ID: 8494147 Terms and Disclaimers Charges not included in the price may include but are not limited to: airfare to and from the start of your trip; airline baggage fees including checked and/or excess baggage fees; Federal inspection fees for the Federal U.S. Customs and Immigrations; agricultural tax; other per person taxes imposed by government entities; applicable cruise taxes, fees, fares and port charges; passports; visas and vaccinations; transfers; tips to your Tour or Cruise Director, Local Host, driver, Local Guides, and/or ships' crew; gratuities on ferries, trains, and cruise ships; laundry; telephone; minibar; alcohol, beverages, and food outside of the contracted menu as presented at a hotel or restaurant (these extra items will be billed to you before leaving the hotel, ship, or restaurant); additional excursions and activities not listed as 'included' in the itinerary; porterage at airports or train stations; Travel Protection premiums; and all other items of a personal nature. If you are interested in an offer, please click on Contact Us . This will open a "Trip Request" that will allow you to send your request to us. We will be able to confirm availability and make further recommendations. Ship's registry: Bahamas
Inside	CALL	CALL	CALL
Outside	CALL	CALL	CALL
Balcony	CALL	CALL	CALL
Suite	CALL	CALL	CALL
	Contact Us	Contact Us	Contact Us
	Terms & Disclaimers ID: 8493349 Terms and Disclaimers Charges not included in the price may include but are not limited to: airfare to and from the start of your trip; airline baggage fees including checked and/or excess baggage fees; Federal inspection fees for the Federal U.S. Customs and Immigrations; agricultural tax; other per person taxes imposed by government entities; applicable cruise taxes, fees, fares and port charges; passports; visas and vaccinations; transfers; tips to your Tour or Cruise Director, Local Host, driver, Local Guides, and/or ships' crew; gratuities on ferries, trains, and cruise ships; laundry; telephone; minibar; alcohol, beverages, and food outside of the contracted menu as presented at a hotel or restaurant (these extra items will be billed to you before leaving the hotel, ship, or restaurant); additional excursions and activities not listed as 'included' in the itinerary; porterage at airports or train stations; Travel Protection premiums; and all other items of a personal nature. If you are interested in an offer, please click on Contact Us . This will open a "Trip Request" that will allow you to send your request to us. We will be able to confirm availability and make further recommendations. Ship's registry: Bahamas	Terms & Disclaimers ID: 8533875 Terms and Disclaimers Charges not included in the price may include but are not limited to: airfare to and from the start of your trip; airline baggage fees including checked and/or excess baggage fees; Federal inspection fees for the Federal U.S. Customs and Immigrations; agricultural tax; other per person taxes imposed by government entities; applicable cruise taxes, fees, fares and port charges; passports; visas and vaccinations; transfers; tips to your Tour or Cruise Director, Local Host, driver, Local Guides, and/or ships' crew; gratuities on ferries, trains, and cruise ships; laundry; telephone; minibar; alcohol, beverages, and food outside of the contracted menu as presented at a hotel or restaurant (these extra items will be billed to you before leaving the hotel, ship, or restaurant); additional excursions and activities not listed as 'included' in the itinerary; porterage at airports or train stations; Travel Protection premiums; and all other items of a personal nature. If you are interested in an offer, please click on Contact Us . This will open a "Trip Request" that will allow you to send your request to us. We will be able to confirm availability and make further recommendations. Ship's registry: Bahamas	Terms & Disclaimers ID: 8494147 Terms and Disclaimers Charges not included in the price may include but are not limited to: airfare to and from the start of your trip; airline baggage fees including checked and/or excess baggage fees; Federal inspection fees for the Federal U.S. Customs and Immigrations; agricultural tax; other per person taxes imposed by government entities; applicable cruise taxes, fees, fares and port charges; passports; visas and vaccinations; transfers; tips to your Tour or Cruise Director, Local Host, driver, Local Guides, and/or ships' crew; gratuities on ferries, trains, and cruise ships; laundry; telephone; minibar; alcohol, beverages, and food outside of the contracted menu as presented at a hotel or restaurant (these extra items will be billed to you before leaving the hotel, ship, or restaurant); additional excursions and activities not listed as 'included' in the itinerary; porterage at airports or train stations; Travel Protection premiums; and all other items of a personal nature. If you are interested in an offer, please click on Contact Us . This will open a "Trip Request" that will allow you to send your request to us. We will be able to confirm availability and make further recommendations. Ship's registry: Bahamas

About Wind Surf

Ship Overview Deck Plans Wind Surf Amenities What's Included on Windstar

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

Oceanview Rooms

150

Hot Tubs

Pools

Laundromats

Number of Decks

Deck Plan Details

Cabin Categories

OS	Officer's Suite	$5,399.00 USD
TX	Stateroom	$3,199.00 USD
AX	Stateroom	$2,799.00 USD
A	Stateroom	$2,599.00 USD
BX	Stateroom	$2,499.00 USD
B	Stateroom	$2,299.00 USD

Symbol Legend

	Public Space
	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

Wind Surf

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

Oceanview Rooms

150

Hot Tubs

Pools

Laundromats

Number of Decks

Deck Plan Details

Cabin Categories

OS	Officer's Suite	$5,399.00 USD
TX	Stateroom	$3,199.00 USD
AX	Stateroom	$2,799.00 USD
A	Stateroom	$2,599.00 USD
BX	Stateroom	$2,499.00 USD
B	Stateroom	$2,299.00 USD

Symbol Legend

	Public Space
	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.

About Windstar Cruises

More trips from Windstar Cruises Health and Safety Overview

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.

More trips from Windstar Cruises Health and Safety Overview

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

Trip Details