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Windstar Wind Surf Cruises to the Caribbean

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  • 7 Night
    Yachtsmans Caribbean 7d Ph1-ph1 (mar 07 2020)

    Leaving:
    St. Maarten
    Visiting:
    Road Town, Jost Van Dyke ... see more
    Cruise Line:
    Windstar Cruises
    View Deal
    View Cruise Info
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    • Itinerary
    • Ship Details
    • Reviews
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    • View All Prices
    • Fare Includes
    Itinerary

    Cruise Itinerary

    7 Night Wind Surf Cruise to Caribbean Route (Windstar Cruises)
    • Day 1
      St. Maarten
    • Day 2
      Road Town
    • Day 2
      Jost Van Dyke
    • Day 3
      Jost Van Dyke
    • Day 3
      Virgin Gorda
    • Day 4
      Virgin Gorda
    • Day 5
      Anguilla
    • Day 6
      St. Barts
    • Day 7
      Antigua
    • Day 8
      St. Maarten
    Ship Details

    Wind Surf - Windstar Cruises

    Pros

    Laid-back yacht feel; unique watersports platform; fantastic deck barbecue; friendly crew

    Cons

    No balcony cabins; food and service hit and miss; stairwells and passageways feel tired

    Bottom Line

    Intimate seven-sail ship with low-key entertainment; needs improvements to dining options

    Reviews

    Wind Surf Reviews

    Cruise Critic Editor Ratings
    Overall
    4.0/5
    Cabins4.0
    Dining4.0
    Service3.5
    Value4.0

    The stunning five-mast, seven-sail Wind Surf takes the prize of largest vessel in the Windstar ...

    Cruise Critic Member Ratings
    laurieha
    Sail Date Dec 2019
    Poor service & ship needs an overhaul
    Read More
    SonnyDelight
    Sail Date Feb 2019
    Special Needs
    Read More
    Cabin Comparison

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    Call to plan your cruise 866-501-1694 866-501-1694
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    Fare Includes

    What’s included in My Cruise Fare?

    • Cabin
      Room with bed and private bathroom
    • Port Taxes & Fees
    • Service Gratuities
    • Most Onboard Entertainment
    • Kids Club
    • Shore Excursions
    • Wi-Fi
    • Spa Services
    • Select Dining
      Main dining room and/or buffet
    • Specialty Alternative Dining
    • Room Service
    • Butler Service
    • Basic Drinks
      Still water, coffee, and tea
    • Soft Drinks
      Soda and Juice
    • Alcohol
      Beer, wine, and spirits
    • Specialty Coffee Drinks
      Including smoothies and blended drinks
    • Specialty Fitness Classes

    ** inclusions in your cruise fare are based on Cruise Critic’s editorial expertise and not provided by the individual cruise lines. When you book with one of our cruise partners, please be sure to check their site for a full disclosure of all applicable fees. Cruise Critic does not guarantee any specific rates, prices, or amenities included in the fare. Inclusion items in the fare may change at any time and fees may apply for additional items.

  • 7 Night
    Classic Caribbean 7d Ph1-ph1 (mar 28 2020)

    Leaving:
    St. Maarten
    Visiting:
    Charlestown, Roseau ... see more
    Cruise Line:
    Windstar Cruises
    View Deal
    View Cruise Info
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    • Itinerary
    • Ship Details
    • Reviews
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    • View All Prices
    • Fare Includes
    Itinerary

    Cruise Itinerary

    7 Night Wind Surf Cruise to Caribbean Route (Windstar Cruises)
    • Day 1
      St. Maarten
    • Day 2
      Charlestown
    • Day 3
      Roseau
    • Day 4
      St. Lucia
    • Day 5
      Iles des Saintes
    • Day 6
      St. Kitts (Port Zante)
    • Day 7
      St. Barts
    • Day 8
      St. Maarten
    Ship Details

    Wind Surf - Windstar Cruises

    Pros

    Laid-back yacht feel; unique watersports platform; fantastic deck barbecue; friendly crew

    Cons

    No balcony cabins; food and service hit and miss; stairwells and passageways feel tired

    Bottom Line

    Intimate seven-sail ship with low-key entertainment; needs improvements to dining options

    Reviews

    Wind Surf Reviews

    Cruise Critic Editor Ratings
    Overall
    4.0/5
    Cabins4.0
    Dining4.0
    Service3.5
    Value4.0

    The stunning five-mast, seven-sail Wind Surf takes the prize of largest vessel in the Windstar ...

    Cruise Critic Member Ratings
    Misty Morning
    Sail Date Feb 2019
    Wind Surf Delivers Again
    Read More
    Strenz
    Sail Date Jan 2019
    The Best Way to Experience the Caribbean
    Read More
    Cabin Comparison

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    Call to plan your cruise 866-501-1694 866-501-1694
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    Fare Includes

    What’s included in My Cruise Fare?

    • Cabin
      Room with bed and private bathroom
    • Port Taxes & Fees
    • Service Gratuities
    • Most Onboard Entertainment
    • Kids Club
    • Shore Excursions
    • Wi-Fi
    • Spa Services
    • Select Dining
      Main dining room and/or buffet
    • Specialty Alternative Dining
    • Room Service
    • Butler Service
    • Basic Drinks
      Still water, coffee, and tea
    • Soft Drinks
      Soda and Juice
    • Alcohol
      Beer, wine, and spirits
    • Specialty Coffee Drinks
      Including smoothies and blended drinks
    • Specialty Fitness Classes

    ** inclusions in your cruise fare are based on Cruise Critic’s editorial expertise and not provided by the individual cruise lines. When you book with one of our cruise partners, please be sure to check their site for a full disclosure of all applicable fees. Cruise Critic does not guarantee any specific rates, prices, or amenities included in the fare. Inclusion items in the fare may change at any time and fees may apply for additional items.

  • 7 Night
    Classic Caribbean 7d Ph1-ph1 (mar 14 2020)

    Leaving:
    St. Maarten
    Visiting:
    Charlestown, Roseau ... see more
    Cruise Line:
    Windstar Cruises
    View Deal
    View Cruise Info
    Hide Cruise Info
    • Itinerary
    • Ship Details
    • Reviews
    • Cabin Comparison
    • View All Prices
    • Fare Includes
    Itinerary

    Cruise Itinerary

    7 Night Wind Surf Cruise to Caribbean Route (Windstar Cruises)
    • Day 1
      St. Maarten
    • Day 2
      Charlestown
    • Day 3
      Roseau
    • Day 4
      St. Lucia
    • Day 5
      Iles des Saintes
    • Day 6
      St. Kitts (Port Zante)
    • Day 7
      St. Barts
    • Day 8
      St. Maarten
    Ship Details

    Wind Surf - Windstar Cruises

    Pros

    Laid-back yacht feel; unique watersports platform; fantastic deck barbecue; friendly crew

    Cons

    No balcony cabins; food and service hit and miss; stairwells and passageways feel tired

    Bottom Line

    Intimate seven-sail ship with low-key entertainment; needs improvements to dining options

    Reviews

    Wind Surf Reviews

    Cruise Critic Editor Ratings
    Overall
    4.0/5
    Cabins4.0
    Dining4.0
    Service3.5
    Value4.0

    The stunning five-mast, seven-sail Wind Surf takes the prize of largest vessel in the Windstar ...

    Cruise Critic Member Ratings
    LuvDCaribbean
    Sail Date Jan 2019
    A bit disappointed, something has changed with Windstar
    Read More
    ColoradoTraveler1120
    Sail Date Mar 2018
    Two Thumbs Way Up - A Wonderful Experience
    Read More
    Cabin Comparison

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    Call to plan your cruise 866-501-1694 866-501-1694
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    Fare Includes

    What’s included in My Cruise Fare?

    • Cabin
      Room with bed and private bathroom
    • Port Taxes & Fees
    • Service Gratuities
    • Most Onboard Entertainment
    • Kids Club
    • Shore Excursions
    • Wi-Fi
    • Spa Services
    • Select Dining
      Main dining room and/or buffet
    • Specialty Alternative Dining
    • Room Service
    • Butler Service
    • Basic Drinks
      Still water, coffee, and tea
    • Soft Drinks
      Soda and Juice
    • Alcohol
      Beer, wine, and spirits
    • Specialty Coffee Drinks
      Including smoothies and blended drinks
    • Specialty Fitness Classes

    ** inclusions in your cruise fare are based on Cruise Critic’s editorial expertise and not provided by the individual cruise lines. When you book with one of our cruise partners, please be sure to check their site for a full disclosure of all applicable fees. Cruise Critic does not guarantee any specific rates, prices, or amenities included in the fare. Inclusion items in the fare may change at any time and fees may apply for additional items.

  • 7 Night
    Yachtsmans Caribbean 7d Ph1-ph1 (dec 12 2020)

    Leaving:
    St. Maarten
    Visiting:
    Anguilla, Sopers Hole ... see more
    Cruise Line:
    Windstar Cruises
    View Deal
    View Cruise Info
    Hide Cruise Info
    • Itinerary
    • Ship Details
    • Reviews
    • Cabin Comparison
    • View All Prices
    • Fare Includes
    Itinerary

    Cruise Itinerary

    7 Night Wind Surf Cruise to Caribbean Route (Windstar Cruises)
    • Day 1
      St. Maarten
    • Day 2
      Anguilla
    • Day 3
      Sopers Hole
    • Day 3
      Jost Van Dyke
    • Day 4
      Jost Van Dyke
    • Day 4
      Virgin Gorda
    • Day 5
      Virgin Gorda
    • Day 6
      St. Barts
    • Day 7
      Antigua
    • Day 8
      St. Maarten
    Ship Details

    Wind Surf - Windstar Cruises

    Pros

    Laid-back yacht feel; unique watersports platform; fantastic deck barbecue; friendly crew

    Cons

    No balcony cabins; food and service hit and miss; stairwells and passageways feel tired

    Bottom Line

    Intimate seven-sail ship with low-key entertainment; needs improvements to dining options

    Reviews

    Wind Surf Reviews

    Cruise Critic Editor Ratings
    Overall
    4.0/5
    Cabins4.0
    Dining4.0
    Service3.5
    Value4.0

    The stunning five-mast, seven-sail Wind Surf takes the prize of largest vessel in the Windstar ...

    Cruise Critic Member Ratings
    h20Sprite
    Sail Date Mar 2018
    Almost as good as we had expected
    Read More
    grada289
    Sail Date Feb 2018
    Windsurf 100% AWESOME !
    Read More
    Cabin Comparison

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    Call to plan your cruise 866-501-1694 866-501-1694
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    Fare Includes

    What’s included in My Cruise Fare?

    • Cabin
      Room with bed and private bathroom
    • Port Taxes & Fees
    • Service Gratuities
    • Most Onboard Entertainment
    • Kids Club
    • Shore Excursions
    • Wi-Fi
    • Spa Services
    • Select Dining
      Main dining room and/or buffet
    • Specialty Alternative Dining
    • Room Service
    • Butler Service
    • Basic Drinks
      Still water, coffee, and tea
    • Soft Drinks
      Soda and Juice
    • Alcohol
      Beer, wine, and spirits
    • Specialty Coffee Drinks
      Including smoothies and blended drinks
    • Specialty Fitness Classes

    ** inclusions in your cruise fare are based on Cruise Critic’s editorial expertise and not provided by the individual cruise lines. When you book with one of our cruise partners, please be sure to check their site for a full disclosure of all applicable fees. Cruise Critic does not guarantee any specific rates, prices, or amenities included in the fare. Inclusion items in the fare may change at any time and fees may apply for additional items.

  • 7 Night
    Classic Caribbean 7d Ph1-ph1 (feb 29 2020)

    Leaving:
    St. Maarten
    Visiting:
    Charlestown, Roseau ... see more
    Cruise Line:
    Windstar Cruises
    View Deal
    View Cruise Info
    Hide Cruise Info
    • Itinerary
    • Ship Details
    • Reviews
    • Cabin Comparison
    • View All Prices
    • Fare Includes
    Itinerary

    Cruise Itinerary

    7 Night Wind Surf Cruise to Caribbean Route (Windstar Cruises)
    • Day 1
      St. Maarten
    • Day 2
      Charlestown
    • Day 3
      Roseau
    • Day 4
      St. Lucia
    • Day 5
      Iles des Saintes
    • Day 6
      St. Kitts (Port Zante)
    • Day 7
      St. Barts
    • Day 8
      St. Maarten
    Ship Details

    Wind Surf - Windstar Cruises

    Pros

    Laid-back yacht feel; unique watersports platform; fantastic deck barbecue; friendly crew

    Cons

    No balcony cabins; food and service hit and miss; stairwells and passageways feel tired

    Bottom Line

    Intimate seven-sail ship with low-key entertainment; needs improvements to dining options

    Reviews

    Wind Surf Reviews

    Cruise Critic Editor Ratings
    Overall
    4.0/5
    Cabins4.0
    Dining4.0
    Service3.5
    Value4.0

    The stunning five-mast, seven-sail Wind Surf takes the prize of largest vessel in the Windstar ...

    Cruise Critic Member Ratings
    golfdale2
    Sail Date Mar 2018
    Improvements in all areas
    Read More
    KnottyCanadian
    Sail Date Feb 2018
    Great ship & crew - not for unsociable people
    Read More
    Cabin Comparison

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    Call to plan your cruise 866-501-1694 866-501-1694
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    Fare Includes

    What’s included in My Cruise Fare?

    • Cabin
      Room with bed and private bathroom
    • Port Taxes & Fees
    • Service Gratuities
    • Most Onboard Entertainment
    • Kids Club
    • Shore Excursions
    • Wi-Fi
    • Spa Services
    • Select Dining
      Main dining room and/or buffet
    • Specialty Alternative Dining
    • Room Service
    • Butler Service
    • Basic Drinks
      Still water, coffee, and tea
    • Soft Drinks
      Soda and Juice
    • Alcohol
      Beer, wine, and spirits
    • Specialty Coffee Drinks
      Including smoothies and blended drinks
    • Specialty Fitness Classes

    ** inclusions in your cruise fare are based on Cruise Critic’s editorial expertise and not provided by the individual cruise lines. When you book with one of our cruise partners, please be sure to check their site for a full disclosure of all applicable fees. Cruise Critic does not guarantee any specific rates, prices, or amenities included in the fare. Inclusion items in the fare may change at any time and fees may apply for additional items.

  • 6 Night
    Yachtsmans Caribbean 6d Ph1-ph1 (nov 29 2020)

    Leaving:
    St. Maarten
    Visiting:
    Sopers Hole, Jost Van Dyke ... see more
    Cruise Line:
    Windstar Cruises
    View Deal
    View Cruise Info
    Hide Cruise Info
    • Itinerary
    • Ship Details
    • Reviews
    • Cabin Comparison
    • View All Prices
    • Fare Includes
    Itinerary

    Cruise Itinerary

    6 Night Wind Surf Cruise to Caribbean Route (Windstar Cruises)
    • Day 1
      St. Maarten
    • Day 2
      Sopers Hole
    • Day 2
      Jost Van Dyke
    • Day 3
      Jost Van Dyke
    • Day 3
      Virgin Gorda
    • Day 4
      Virgin Gorda
    • Day 5
      St. Barts
    • Day 6
      Antigua
    • Day 7
      St. Maarten
    Ship Details

    Wind Surf - Windstar Cruises

    Pros

    Laid-back yacht feel; unique watersports platform; fantastic deck barbecue; friendly crew

    Cons

    No balcony cabins; food and service hit and miss; stairwells and passageways feel tired

    Bottom Line

    Intimate seven-sail ship with low-key entertainment; needs improvements to dining options

    Reviews

    Wind Surf Reviews

    Cruise Critic Editor Ratings
    Overall
    4.0/5
    Cabins4.0
    Dining4.0
    Service3.5
    Value4.0

    The stunning five-mast, seven-sail Wind Surf takes the prize of largest vessel in the Windstar ...

    Cruise Critic Member Ratings
    BostonTia
    Sail Date Jan 2018
    Windstar Wins!
    Read More
    Redtravel
    Sail Date Jan 2018
    Relaxing in style
    Read More
    Cabin Comparison

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    Call to plan your cruise 866-501-1694 866-501-1694
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    Fare Includes

    What’s included in My Cruise Fare?

    • Cabin
      Room with bed and private bathroom
    • Port Taxes & Fees
    • Service Gratuities
    • Most Onboard Entertainment
    • Kids Club
    • Shore Excursions
    • Wi-Fi
    • Spa Services
    • Select Dining
      Main dining room and/or buffet
    • Specialty Alternative Dining
    • Room Service
    • Butler Service
    • Basic Drinks
      Still water, coffee, and tea
    • Soft Drinks
      Soda and Juice
    • Alcohol
      Beer, wine, and spirits
    • Specialty Coffee Drinks
      Including smoothies and blended drinks
    • Specialty Fitness Classes

    ** inclusions in your cruise fare are based on Cruise Critic’s editorial expertise and not provided by the individual cruise lines. When you book with one of our cruise partners, please be sure to check their site for a full disclosure of all applicable fees. Cruise Critic does not guarantee any specific rates, prices, or amenities included in the fare. Inclusion items in the fare may change at any time and fees may apply for additional items.

  • 7 Night
    Yachtsmans Caribbean 7d Ph1-ph1 (mar 21 2020)

    Leaving:
    St. Maarten
    Visiting:
    Antigua, Road Town ... see more
    Cruise Line:
    Windstar Cruises
    View Deal
    View Cruise Info
    Hide Cruise Info
    • Itinerary
    • Ship Details
    • Reviews
    • Cabin Comparison
    • View All Prices
    • Fare Includes
    Itinerary

    Cruise Itinerary

    7 Night Wind Surf Cruise to Caribbean Route (Windstar Cruises)
    • Day 1
      St. Maarten
    • Day 2
      Antigua
    • Day 3
      Cruising
    • Day 4
      Road Town
    • Day 4
      Jost Van Dyke
    • Day 5
      Jost Van Dyke
    • Day 5
      Virgin Gorda
    • Day 6
      Virgin Gorda
    • Day 7
      St. Barts
    • Day 8
      St. Maarten
    Ship Details

    Wind Surf - Windstar Cruises

    Pros

    Laid-back yacht feel; unique watersports platform; fantastic deck barbecue; friendly crew

    Cons

    No balcony cabins; food and service hit and miss; stairwells and passageways feel tired

    Bottom Line

    Intimate seven-sail ship with low-key entertainment; needs improvements to dining options

    Reviews

    Wind Surf Reviews

    Cruise Critic Editor Ratings
    Overall
    4.0/5
    Cabins4.0
    Dining4.0
    Service3.5
    Value4.0

    The stunning five-mast, seven-sail Wind Surf takes the prize of largest vessel in the Windstar ...

    Cruise Critic Member Ratings
    Strenz
    Sail Date Jan 2018
    We love the Caribbean on the Wind Surf!
    Read More
    labadee70
    Sail Date Dec 2017
    Super cruise. Great way to bring in new year
    Read More
    Cabin Comparison

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    Call to plan your cruise 866-501-1694 866-501-1694
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    Fare Includes

    What’s included in My Cruise Fare?

    • Cabin
      Room with bed and private bathroom
    • Port Taxes & Fees
    • Service Gratuities
    • Most Onboard Entertainment
    • Kids Club
    • Shore Excursions
    • Wi-Fi
    • Spa Services
    • Select Dining
      Main dining room and/or buffet
    • Specialty Alternative Dining
    • Room Service
    • Butler Service
    • Basic Drinks
      Still water, coffee, and tea
    • Soft Drinks
      Soda and Juice
    • Alcohol
      Beer, wine, and spirits
    • Specialty Coffee Drinks
      Including smoothies and blended drinks
    • Specialty Fitness Classes

    ** inclusions in your cruise fare are based on Cruise Critic’s editorial expertise and not provided by the individual cruise lines. When you book with one of our cruise partners, please be sure to check their site for a full disclosure of all applicable fees. Cruise Critic does not guarantee any specific rates, prices, or amenities included in the fare. Inclusion items in the fare may change at any time and fees may apply for additional items.

  • 7 Night
    Classic Caribbean 7d Ph1-ph1 (dec 05 2020)

    Leaving:
    St. Maarten
    Visiting:
    Charlestown, Roseau ... see more
    Cruise Line:
    Windstar Cruises
    View Deal
    View Cruise Info
    Hide Cruise Info
    • Itinerary
    • Ship Details
    • Reviews
    • Cabin Comparison
    • View All Prices
    • Fare Includes
    Itinerary

    Cruise Itinerary

    7 Night Wind Surf Cruise to Caribbean Route (Windstar Cruises)
    • Day 1
      St. Maarten
    • Day 2
      Charlestown
    • Day 3
      Roseau
    • Day 4
      St. Lucia
    • Day 5
      Iles des Saintes
    • Day 6
      St. Kitts (Port Zante)
    • Day 7
      St. Barts
    • Day 8
      St. Maarten
    Ship Details

    Wind Surf - Windstar Cruises

    Pros

    Laid-back yacht feel; unique watersports platform; fantastic deck barbecue; friendly crew

    Cons

    No balcony cabins; food and service hit and miss; stairwells and passageways feel tired

    Bottom Line

    Intimate seven-sail ship with low-key entertainment; needs improvements to dining options

    Reviews

    Wind Surf Reviews

    Cruise Critic Editor Ratings
    Overall
    4.0/5
    Cabins4.0
    Dining4.0
    Service3.5
    Value4.0

    The stunning five-mast, seven-sail Wind Surf takes the prize of largest vessel in the Windstar ...

    Cruise Critic Member Ratings
    Hos1985
    Sail Date Dec 2017
    The good, the bad and the ugly. An Honest Review.
    Read More
    elklemi
    Sail Date Dec 2017
    My First Wind Star Cruise
    Read More
    Cabin Comparison

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    Call to plan your cruise 866-501-1694 866-501-1694
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    Fare Includes

    What’s included in My Cruise Fare?

    • Cabin
      Room with bed and private bathroom
    • Port Taxes & Fees
    • Service Gratuities
    • Most Onboard Entertainment
    • Kids Club
    • Shore Excursions
    • Wi-Fi
    • Spa Services
    • Select Dining
      Main dining room and/or buffet
    • Specialty Alternative Dining
    • Room Service
    • Butler Service
    • Basic Drinks
      Still water, coffee, and tea
    • Soft Drinks
      Soda and Juice
    • Alcohol
      Beer, wine, and spirits
    • Specialty Coffee Drinks
      Including smoothies and blended drinks
    • Specialty Fitness Classes

    ** inclusions in your cruise fare are based on Cruise Critic’s editorial expertise and not provided by the individual cruise lines. When you book with one of our cruise partners, please be sure to check their site for a full disclosure of all applicable fees. Cruise Critic does not guarantee any specific rates, prices, or amenities included in the fare. Inclusion items in the fare may change at any time and fees may apply for additional items.

  • 7 Night
    Classic Caribbean 7d Ph1-ph1 (dec 11 2021)

    Leaving:
    St. Maarten
    Visiting:
    Charlestown, Roseau ... see more
    Cruise Line:
    Windstar Cruises
    View Deal
    View Cruise Info
    Hide Cruise Info
    • Itinerary
    • Ship Details
    • Reviews
    • Cabin Comparison
    • View All Prices
    • Fare Includes
    Itinerary

    Cruise Itinerary

    7 Night Wind Surf Cruise to Caribbean Route (Windstar Cruises)
    • Day 1
      St. Maarten
    • Day 2
      Charlestown
    • Day 3
      Roseau
    • Day 4
      St. Lucia
    • Day 5
      Iles des Saintes
    • Day 6
      St. Kitts (Port Zante)
    • Day 7
      St. Barts
    • Day 8
      St. Maarten
    Ship Details

    Wind Surf - Windstar Cruises

    Pros

    Laid-back yacht feel; unique watersports platform; fantastic deck barbecue; friendly crew

    Cons

    No balcony cabins; food and service hit and miss; stairwells and passageways feel tired

    Bottom Line

    Intimate seven-sail ship with low-key entertainment; needs improvements to dining options

    Reviews

    Wind Surf Reviews

    Cruise Critic Editor Ratings
    Overall
    4.0/5
    Cabins4.0
    Dining4.0
    Service3.5
    Value4.0

    The stunning five-mast, seven-sail Wind Surf takes the prize of largest vessel in the Windstar ...

    Cruise Critic Member Ratings
    schlichtjames@gmail.com
    Sail Date Nov 2017
    Fabulous Staff, Food, Facilities and value for your money
    Read More
    Orangeman68
    Sail Date Jan 2017
    Outstanding Cruise; One of Our Best!
    Read More
    Cabin Comparison

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    Call to plan your cruise 866-501-1694 866-501-1694
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    Fare Includes

    What’s included in My Cruise Fare?

    • Cabin
      Room with bed and private bathroom
    • Port Taxes & Fees
    • Service Gratuities
    • Most Onboard Entertainment
    • Kids Club
    • Shore Excursions
    • Wi-Fi
    • Spa Services
    • Select Dining
      Main dining room and/or buffet
    • Specialty Alternative Dining
    • Room Service
    • Butler Service
    • Basic Drinks
      Still water, coffee, and tea
    • Soft Drinks
      Soda and Juice
    • Alcohol
      Beer, wine, and spirits
    • Specialty Coffee Drinks
      Including smoothies and blended drinks
    • Specialty Fitness Classes

    ** inclusions in your cruise fare are based on Cruise Critic’s editorial expertise and not provided by the individual cruise lines. When you book with one of our cruise partners, please be sure to check their site for a full disclosure of all applicable fees. Cruise Critic does not guarantee any specific rates, prices, or amenities included in the fare. Inclusion items in the fare may change at any time and fees may apply for additional items.

  • 7 Night
    Yachtsmans Caribbean 7d Ph1-ph1 (feb 06 2021)

    Leaving:
    St. Maarten
    Visiting:
    Anguilla, Sopers Hole ... see more
    Cruise Line:
    Windstar Cruises
    View Deal
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    Itinerary

    Cruise Itinerary

    7 Night Wind Surf Cruise to Caribbean Route (Windstar Cruises)
    • Day 1
      St. Maarten
    • Day 2
      Anguilla
    • Day 3
      Sopers Hole
    • Day 3
      Jost Van Dyke
    • Day 4
      Jost Van Dyke
    • Day 4
      Virgin Gorda
    • Day 5
      Virgin Gorda
    • Day 6
      St. Barts
    • Day 7
      Antigua
    • Day 8
      St. Maarten
    Ship Details

    Wind Surf - Windstar Cruises

    Pros

    Laid-back yacht feel; unique watersports platform; fantastic deck barbecue; friendly crew

    Cons

    No balcony cabins; food and service hit and miss; stairwells and passageways feel tired

    Bottom Line

    Intimate seven-sail ship with low-key entertainment; needs improvements to dining options

    Reviews

    Wind Surf Reviews

    Cruise Critic Editor Ratings
    Overall
    4.0/5
    Cabins4.0
    Dining4.0
    Service3.5
    Value4.0

    The stunning five-mast, seven-sail Wind Surf takes the prize of largest vessel in the Windstar ...

    Cruise Critic Member Ratings
    pintmere
    Sail Date Feb 2017
    Windstar vs star clippers
    Read More
    K11TEXAS
    Sail Date Mar 2017
    Excellent Service and Great Itinerary
    Read More
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    Fare Includes

    What’s included in My Cruise Fare?

    • Cabin
      Room with bed and private bathroom
    • Port Taxes & Fees
    • Service Gratuities
    • Most Onboard Entertainment
    • Kids Club
    • Shore Excursions
    • Wi-Fi
    • Spa Services
    • Select Dining
      Main dining room and/or buffet
    • Specialty Alternative Dining
    • Room Service
    • Butler Service
    • Basic Drinks
      Still water, coffee, and tea
    • Soft Drinks
      Soda and Juice
    • Alcohol
      Beer, wine, and spirits
    • Specialty Coffee Drinks
      Including smoothies and blended drinks
    • Specialty Fitness Classes

    ** inclusions in your cruise fare are based on Cruise Critic’s editorial expertise and not provided by the individual cruise lines. When you book with one of our cruise partners, please be sure to check their site for a full disclosure of all applicable fees. Cruise Critic does not guarantee any specific rates, prices, or amenities included in the fare. Inclusion items in the fare may change at any time and fees may apply for additional items.

  • 7 Night
    Jewels Of Windward Islands 7d Bgi-bgi (feb 27 2021)

    Leaving:
    Barbados
    Visiting:
    St. Lucia, Casablanca ... see more
    Cruise Line:
    Windstar Cruises
    View Deal
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    Itinerary

    Cruise Itinerary

    7 Night Wind Surf Cruise to Caribbean Route (Windstar Cruises)
    • Day 1
      Barbados
    • Day 2
      St. Lucia
    • Day 3
      St. Lucia
    • Day 3
      Casablanca
    • Day 3
      Cruising
    • Day 4
      Martinique
    • Day 5
      Mayreau
    • Day 6
      Grenada
    • Day 7
      Bequia
    • Day 8
      Barbados
    Ship Details

    Wind Surf - Windstar Cruises

    Pros

    Laid-back yacht feel; unique watersports platform; fantastic deck barbecue; friendly crew

    Cons

    No balcony cabins; food and service hit and miss; stairwells and passageways feel tired

    Bottom Line

    Intimate seven-sail ship with low-key entertainment; needs improvements to dining options

    Reviews

    Wind Surf Reviews

    Cruise Critic Editor Ratings
    Overall
    4.0/5
    Cabins4.0
    Dining4.0
    Service3.5
    Value4.0

    The stunning five-mast, seven-sail Wind Surf takes the prize of largest vessel in the Windstar ...

    Cruise Critic Member Ratings
    AztecCraig
    Sail Date Mar 2017
    Good but probably not worth the premium price
    Read More
    Waterloo traveller
    Sail Date Mar 2017
    Rocky seas made trip a disappointment
    Read More
    Cabin Comparison

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    Call to plan your cruise 866-501-1694 866-501-1694
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    Fare Includes

    What’s included in My Cruise Fare?

    • Cabin
      Room with bed and private bathroom
    • Port Taxes & Fees
    • Service Gratuities
    • Most Onboard Entertainment
    • Kids Club
    • Shore Excursions
    • Wi-Fi
    • Spa Services
    • Select Dining
      Main dining room and/or buffet
    • Specialty Alternative Dining
    • Room Service
    • Butler Service
    • Basic Drinks
      Still water, coffee, and tea
    • Soft Drinks
      Soda and Juice
    • Alcohol
      Beer, wine, and spirits
    • Specialty Coffee Drinks
      Including smoothies and blended drinks
    • Specialty Fitness Classes

    ** inclusions in your cruise fare are based on Cruise Critic’s editorial expertise and not provided by the individual cruise lines. When you book with one of our cruise partners, please be sure to check their site for a full disclosure of all applicable fees. Cruise Critic does not guarantee any specific rates, prices, or amenities included in the fare. Inclusion items in the fare may change at any time and fees may apply for additional items.

  • 11 Night
    Stars Of The Greater Antilles 11d Czm-ph1 (feb 22 2022)

    Leaving:
    Cozumel
    Visiting:
    Grand Cayman, Cayman Brac ... see more
    Cruise Line:
    Windstar Cruises
    View Deal
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    Itinerary

    Cruise Itinerary

    11 Night Wind Surf Cruise to Caribbean Route (Windstar Cruises)
    • Day 1
      Cozumel
    • Day 2
      Cruising
    • Day 3
      Grand Cayman (Georgetown)
    • Day 4
      Cayman Brac
    • Day 5
      Port Antonio
    • Day 6
      Cruising
    • Day 7
      Santo Domingo
    • Day 8
      La Romana (Casa de Campo)
    • Day 9
      Cruising
    • Day 10
      Jost Van Dyke
    • Day 11
      Jost Van Dyke
    • Day 11
      Virgin Gorda
    • Day 12
      St. Maarten
    Ship Details

    Wind Surf - Windstar Cruises

    Pros

    Laid-back yacht feel; unique watersports platform; fantastic deck barbecue; friendly crew

    Cons

    No balcony cabins; food and service hit and miss; stairwells and passageways feel tired

    Bottom Line

    Intimate seven-sail ship with low-key entertainment; needs improvements to dining options

    Reviews

    Wind Surf Reviews

    Cruise Critic Editor Ratings
    Overall
    4.0/5
    Cabins4.0
    Dining4.0
    Service3.5
    Value4.0

    The stunning five-mast, seven-sail Wind Surf takes the prize of largest vessel in the Windstar ...

    Cruise Critic Member Ratings
    romeo801
    Sail Date Feb 2017
    Sorry to say, disappointed!!
    Read More
    labadee70
    Sail Date Jan 2017
    This wind surf cruise can't be beat!
    Read More
    Cabin Comparison

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    Call to plan your cruise 866-501-1694 866-501-1694
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    Fare Includes

    What’s included in My Cruise Fare?

    • Cabin
      Room with bed and private bathroom
    • Port Taxes & Fees
    • Service Gratuities
    • Most Onboard Entertainment
    • Kids Club
    • Shore Excursions
    • Wi-Fi
    • Spa Services
    • Select Dining
      Main dining room and/or buffet
    • Specialty Alternative Dining
    • Room Service
    • Butler Service
    • Basic Drinks
      Still water, coffee, and tea
    • Soft Drinks
      Soda and Juice
    • Alcohol
      Beer, wine, and spirits
    • Specialty Coffee Drinks
      Including smoothies and blended drinks
    • Specialty Fitness Classes

    ** inclusions in your cruise fare are based on Cruise Critic’s editorial expertise and not provided by the individual cruise lines. When you book with one of our cruise partners, please be sure to check their site for a full disclosure of all applicable fees. Cruise Critic does not guarantee any specific rates, prices, or amenities included in the fare. Inclusion items in the fare may change at any time and fees may apply for additional items.

  • 7 Night
    Lush & Lovely Islands Of The Lesser Antilles 7d Ph1-bgi (jan 02 2021)

    Leaving:
    St. Maarten
    Visiting:
    St. Kitts, St. Barts ... see more
    Cruise Line:
    Windstar Cruises
    View Deal
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    Itinerary

    Cruise Itinerary

    7 Night Wind Surf Cruise to Caribbean Route (Windstar Cruises)
    • Day 1
      St. Maarten
    • Day 2
      St. Kitts (Port Zante)
    • Day 3
      St. Barts
    • Day 4
      Little Bay
    • Day 5
      Iles des Saintes
    • Day 6
      Roseau
    • Day 7
      St. Lucia
    • Day 8
      Barbados
    Ship Details

    Wind Surf - Windstar Cruises

    Pros

    Laid-back yacht feel; unique watersports platform; fantastic deck barbecue; friendly crew

    Cons

    No balcony cabins; food and service hit and miss; stairwells and passageways feel tired

    Bottom Line

    Intimate seven-sail ship with low-key entertainment; needs improvements to dining options

    Reviews

    Wind Surf Reviews

    Cruise Critic Editor Ratings
    Overall
    4.0/5
    Cabins4.0
    Dining4.0
    Service3.5
    Value4.0

    The stunning five-mast, seven-sail Wind Surf takes the prize of largest vessel in the Windstar ...

    Cruise Critic Member Ratings
    labgirl
    Sail Date Jan 2017
    Top Notch Staff
    Read More
    newdec
    Sail Date Jan 2017
    Classy, well-organized, fun
    Read More
    Cabin Comparison

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    Call to plan your cruise 866-501-1694 866-501-1694
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    Fare Includes

    What’s included in My Cruise Fare?

    • Cabin
      Room with bed and private bathroom
    • Port Taxes & Fees
    • Service Gratuities
    • Most Onboard Entertainment
    • Kids Club
    • Shore Excursions
    • Wi-Fi
    • Spa Services
    • Select Dining
      Main dining room and/or buffet
    • Specialty Alternative Dining
    • Room Service
    • Butler Service
    • Basic Drinks
      Still water, coffee, and tea
    • Soft Drinks
      Soda and Juice
    • Alcohol
      Beer, wine, and spirits
    • Specialty Coffee Drinks
      Including smoothies and blended drinks
    • Specialty Fitness Classes

    ** inclusions in your cruise fare are based on Cruise Critic’s editorial expertise and not provided by the individual cruise lines. When you book with one of our cruise partners, please be sure to check their site for a full disclosure of all applicable fees. Cruise Critic does not guarantee any specific rates, prices, or amenities included in the fare. Inclusion items in the fare may change at any time and fees may apply for additional items.

  • 7 Night
    Classic Caribbean 7d Ph1-ph1 (apr 03 2021)

    Leaving:
    St. Maarten
    Visiting:
    Charlestown, Roseau ... see more
    Cruise Line:
    Windstar Cruises
    View Deal
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    Itinerary

    Cruise Itinerary

    7 Night Wind Surf Cruise to Caribbean Route (Windstar Cruises)
    • Day 1
      St. Maarten
    • Day 2
      Charlestown
    • Day 3
      Roseau
    • Day 4
      St. Lucia
    • Day 5
      Iles des Saintes
    • Day 6
      St. Kitts (Port Zante)
    • Day 7
      St. Barts
    • Day 8
      St. Maarten
    Ship Details

    Wind Surf - Windstar Cruises

    Pros

    Laid-back yacht feel; unique watersports platform; fantastic deck barbecue; friendly crew

    Cons

    No balcony cabins; food and service hit and miss; stairwells and passageways feel tired

    Bottom Line

    Intimate seven-sail ship with low-key entertainment; needs improvements to dining options

    Reviews

    Wind Surf Reviews

    Cruise Critic Editor Ratings
    Overall
    4.0/5
    Cabins4.0
    Dining4.0
    Service3.5
    Value4.0

    The stunning five-mast, seven-sail Wind Surf takes the prize of largest vessel in the Windstar ...

    Cruise Critic Member Ratings
    roccocaiazza
    Sail Date Jan 2017
    Wind Star fail to deliver
    Read More
    ael123
    Sail Date Dec 2016
    Wind Surf is not a luxury experience but is good.
    Read More
    Cabin Comparison

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    Call to plan your cruise 866-501-1694 866-501-1694
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    Fare Includes

    What’s included in My Cruise Fare?

    • Cabin
      Room with bed and private bathroom
    • Port Taxes & Fees
    • Service Gratuities
    • Most Onboard Entertainment
    • Kids Club
    • Shore Excursions
    • Wi-Fi
    • Spa Services
    • Select Dining
      Main dining room and/or buffet
    • Specialty Alternative Dining
    • Room Service
    • Butler Service
    • Basic Drinks
      Still water, coffee, and tea
    • Soft Drinks
      Soda and Juice
    • Alcohol
      Beer, wine, and spirits
    • Specialty Coffee Drinks
      Including smoothies and blended drinks
    • Specialty Fitness Classes

    ** inclusions in your cruise fare are based on Cruise Critic’s editorial expertise and not provided by the individual cruise lines. When you book with one of our cruise partners, please be sure to check their site for a full disclosure of all applicable fees. Cruise Critic does not guarantee any specific rates, prices, or amenities included in the fare. Inclusion items in the fare may change at any time and fees may apply for additional items.

  • 7 Night
    Lush & Lovely Islands Of The Lesser Antilles 7d Ph1-bgi (feb 20 2021)

    Leaving:
    St. Maarten
    Visiting:
    St. Kitts, St. Barts ... see more
    Cruise Line:
    Windstar Cruises
    View Deal
    View Cruise Info
    Hide Cruise Info
    • Itinerary
    • Ship Details
    • Reviews
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    • View All Prices
    • Fare Includes
    Itinerary

    Cruise Itinerary

    7 Night Wind Surf Cruise to Caribbean Route (Windstar Cruises)
    • Day 1
      St. Maarten
    • Day 2
      St. Kitts (Port Zante)
    • Day 3
      St. Barts
    • Day 4
      Little Bay
    • Day 5
      Iles des Saintes
    • Day 6
      Roseau
    • Day 7
      St. Lucia
    • Day 8
      Barbados
    Ship Details

    Wind Surf - Windstar Cruises

    Pros

    Laid-back yacht feel; unique watersports platform; fantastic deck barbecue; friendly crew

    Cons

    No balcony cabins; food and service hit and miss; stairwells and passageways feel tired

    Bottom Line

    Intimate seven-sail ship with low-key entertainment; needs improvements to dining options

    Reviews

    Wind Surf Reviews

    Cruise Critic Editor Ratings
    Overall
    4.0/5
    Cabins4.0
    Dining4.0
    Service3.5
    Value4.0

    The stunning five-mast, seven-sail Wind Surf takes the prize of largest vessel in the Windstar ...

    Cruise Critic Member Ratings
    So Cal Cruise Mom
    Sail Date Dec 2016
    15 Things I Loved About the Wind Surf
    Read More
    Sailor dogs
    Sail Date Nov 2016
    Absolutely wonderful experience!
    Read More
    Cabin Comparison

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    Call to plan your cruise 866-501-1694 866-501-1694
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    Fare Includes

    What’s included in My Cruise Fare?

    • Cabin
      Room with bed and private bathroom
    • Port Taxes & Fees
    • Service Gratuities
    • Most Onboard Entertainment
    • Kids Club
    • Shore Excursions
    • Wi-Fi
    • Spa Services
    • Select Dining
      Main dining room and/or buffet
    • Specialty Alternative Dining
    • Room Service
    • Butler Service
    • Basic Drinks
      Still water, coffee, and tea
    • Soft Drinks
      Soda and Juice
    • Alcohol
      Beer, wine, and spirits
    • Specialty Coffee Drinks
      Including smoothies and blended drinks
    • Specialty Fitness Classes

    ** inclusions in your cruise fare are based on Cruise Critic’s editorial expertise and not provided by the individual cruise lines. When you book with one of our cruise partners, please be sure to check their site for a full disclosure of all applicable fees. Cruise Critic does not guarantee any specific rates, prices, or amenities included in the fare. Inclusion items in the fare may change at any time and fees may apply for additional items.

  • 7 Night
    Yachtsmans Caribbean - Holiday 7d Ph1-ph1 (dec 26 2020)

    Leaving:
    St. Maarten
    Visiting:
    Antigua, St. Barts ... see more
    Cruise Line:
    Windstar Cruises
    View Deal
    View Cruise Info
    Hide Cruise Info
    • Itinerary
    • Ship Details
    • Reviews
    • Cabin Comparison
    • View All Prices
    • Fare Includes
    Itinerary

    Cruise Itinerary

    7 Night Wind Surf Cruise to Caribbean Route (Windstar Cruises)
    • Day 1
      St. Maarten
    • Day 2
      Antigua
    • Day 3
      St. Barts
    • Day 4
      Cruising
    • Day 5
      Sopers Hole
    • Day 5
      Jost Van Dyke
    • Day 7
      Jost Van Dyke
    • Day 7
      Virgin Gorda
    • Day 8
      St. Maarten
    Ship Details

    Wind Surf - Windstar Cruises

    Pros

    Laid-back yacht feel; unique watersports platform; fantastic deck barbecue; friendly crew

    Cons

    No balcony cabins; food and service hit and miss; stairwells and passageways feel tired

    Bottom Line

    Intimate seven-sail ship with low-key entertainment; needs improvements to dining options

    Reviews

    Wind Surf Reviews

    Cruise Critic Editor Ratings
    Overall
    4.0/5
    Cabins4.0
    Dining4.0
    Service3.5
    Value4.0

    The stunning five-mast, seven-sail Wind Surf takes the prize of largest vessel in the Windstar ...

    Cruise Critic Member Ratings
    rondavis
    Sail Date Dec 2016
    Windsurf 12-30-16
    Read More
    ROBNBOBBI
    Sail Date Dec 2016
    Just amazing
    Read More
    Cabin Comparison

    Compare Cabin Prices

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    Call to plan your cruise 866-501-1694 866-501-1694
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    Fare Includes

    What’s included in My Cruise Fare?

    • Cabin
      Room with bed and private bathroom
    • Port Taxes & Fees
    • Service Gratuities
    • Most Onboard Entertainment
    • Kids Club
    • Shore Excursions
    • Wi-Fi
    • Spa Services
    • Select Dining
      Main dining room and/or buffet
    • Specialty Alternative Dining
    • Room Service
    • Butler Service
    • Basic Drinks
      Still water, coffee, and tea
    • Soft Drinks
      Soda and Juice
    • Alcohol
      Beer, wine, and spirits
    • Specialty Coffee Drinks
      Including smoothies and blended drinks
    • Specialty Fitness Classes

    ** inclusions in your cruise fare are based on Cruise Critic’s editorial expertise and not provided by the individual cruise lines. When you book with one of our cruise partners, please be sure to check their site for a full disclosure of all applicable fees. Cruise Critic does not guarantee any specific rates, prices, or amenities included in the fare. Inclusion items in the fare may change at any time and fees may apply for additional items.