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  • 7 Night
    Charlotte Amalie, St. Thomas To Marigot

    Leaving:
    St. Thomas
    Visiting:
    Virgin Gorda, Jost Van Dyke ... see more
    Cruise Line:
    SeaDream Yacht Club
    View Deal
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    Hide Cruise Info
    • Itinerary
    • Ship Details
    • Reviews
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    Itinerary

    Cruise Itinerary

    7 Night Gay & Lesbian Cruise Route (SeaDream Yacht Club)
    • Day 1
      St. Thomas
    • Day 2
      Virgin Gorda
    • Day 3
      Virgin Gorda
    • Day 3
      Jost Van Dyke
    • Day 4
      Anguilla
    • Day 4
      St. Barts
    • Day 5
      St. Barts
    • Day 6
      Nevis
    • Day 7
      Nevis
    • Day 7
      South Friars Beach
    • Day 8
      St. Martin
    Ship Details

    SeaDream II - SeaDream Yacht Club

    Pros

    All-inclusive, ultra-small ship with amazing food and service

    Cons

    Limited onboard entertainment, especially if you don't like to socialize over drinks

    Bottom Line

    Closest most people will get to a vacation on a private yacht

    Reviews

    SeaDream II Reviews

    Cruise Critic Editor Ratings
    Overall
    5.0/5
    Cabins5.0
    Dining5.0
    Service5.0
    Value4.5

    "It's yachting, not cruising" has been SeaDream's tagline since the company launched in 2001, but ...

    Cruise Critic Member Ratings
    Perhedegaard
    Sail Date Mar 2018
    18 paying passengers - yet poor service and zero flexibility.
    Read More
    HHB fun
    Sail Date Oct 2018
    Fabulous Caribbean Holiday
    Read More
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  • 7 Night
    San Juan To Charlotte Amalie, St. Thomas

    Leaving:
    San Juan
    Visiting:
    Virgin Gorda, Nevis ... see more
    Cruise Line:
    SeaDream Yacht Club
    View Deal
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    Itinerary

    Cruise Itinerary

    7 Night Gay & Lesbian Cruise Route (SeaDream Yacht Club)
    • Day 1
      San Juan
    • Day 2
      Virgin Gorda
    • Day 3
      Nevis
    • Day 4
      South Friars Beach
    • Day 5
      Anguilla
    • Day 5
      St. Barts
    • Day 6
      St. Barts
    • Day 7
      Jost Van Dyke
    • Day 8
      St. Thomas
    Ship Details

    SeaDream II - SeaDream Yacht Club

    Pros

    All-inclusive, ultra-small ship with amazing food and service

    Cons

    Limited onboard entertainment, especially if you don't like to socialize over drinks

    Bottom Line

    Closest most people will get to a vacation on a private yacht

    Reviews

    SeaDream II Reviews

    Cruise Critic Editor Ratings
    Overall
    5.0/5
    Cabins5.0
    Dining5.0
    Service5.0
    Value4.5

    "It's yachting, not cruising" has been SeaDream's tagline since the company launched in 2001, but ...

    Cruise Critic Member Ratings
    gwennw
    Sail Date Jun 2018
    Best cruise we ever took
    Read More
    BDMCruiser
    Sail Date Feb 2018
    5-Star Cruise, but Could Have Been Better
    Read More
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  • 7 Night
    Charlotte Amalie, St. Thomas To Castries

    Leaving:
    St. Thomas
    Visiting:
    Sopers Hole, Norman Island ... see more
    Cruise Line:
    SeaDream Yacht Club
    View Deal
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    • Reviews
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    Itinerary

    Cruise Itinerary

    7 Night Gay & Lesbian Cruise Route (SeaDream Yacht Club)
    • Day 1
      St. Thomas
    • Day 2
      Sopers Hole
    • Day 2
      Norman Island
    • Day 3
      Virgin Gorda
    • Day 3
      Prickly Pear Island
    • Day 4
      Anguilla
    • Day 4
      St. Barts
    • Day 5
      St. Barts
    • Day 6
      Guadeloupe
    • Day 7
      Dominica
    • Day 8
      St. Lucia
    Ship Details

    SeaDream II - SeaDream Yacht Club

    Pros

    All-inclusive, ultra-small ship with amazing food and service

    Cons

    Limited onboard entertainment, especially if you don't like to socialize over drinks

    Bottom Line

    Closest most people will get to a vacation on a private yacht

    Reviews

    SeaDream II Reviews

    Cruise Critic Editor Ratings
    Overall
    5.0/5
    Cabins5.0
    Dining5.0
    Service5.0
    Value4.5

    "It's yachting, not cruising" has been SeaDream's tagline since the company launched in 2001, but ...

    Cruise Critic Member Ratings
    Vicky2
    Sail Date Feb 2018
    A cruise is more than food and excellent service
    Read More
    jam48
    Sail Date Jan 2018
    SeaDream II - Relaxing, small-ship, luxury cruise
    Read More
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  • 14 Night
    Caribbean Explorations 14d Ph1-ph1 (feb 06 2021)

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

    Cruise Itinerary

    14 Night Gay & Lesbian Cruise 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
    • Day 9
      Charlestown
    • Day 10
      Roseau
    • Day 11
      St. Lucia
    • Day 12
      Iles des Saintes
    • Day 13
      St. Kitts (Port Zante)
    • Day 14
      St. Barts
    • Day 15
      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 Mar 2020
    Great Yachtsman’s Caribbean Cruise
    Read More
    Sgjacobson
    Sail Date Nov 2019
    Repairs galore
    Read More
    Cabin Comparison

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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
    Charlotte Amalie, St. Thomas To San Juan

    Leaving:
    St. Thomas
    Visiting:
    South Friars Beach, St. Barts ... see more
    Cruise Line:
    SeaDream Yacht Club
    View Deal
    View Cruise Info
    Hide Cruise Info
    • Itinerary
    • Ship Details
    • Reviews
    • Cabin Comparison
    • View All Prices
    Itinerary

    Cruise Itinerary

    7 Night Gay & Lesbian Cruise Route (SeaDream Yacht Club)
    • Day 1
      St. Thomas
    • Day 2
      South Friars Beach
    • Day 2
      St. Barts
    • Day 3
      St. Barts
    • Day 4
      Anguilla
    • Day 5
      Virgin Gorda
    • Day 6
      Norman Island
    • Day 6
      Beef Island
    • Day 7
      Beef Island
    • Day 7
      Jost Van Dyke
    • Day 8
      San Juan
    Ship Details

    SeaDream II - SeaDream Yacht Club

    Pros

    All-inclusive, ultra-small ship with amazing food and service

    Cons

    Limited onboard entertainment, especially if you don't like to socialize over drinks

    Bottom Line

    Closest most people will get to a vacation on a private yacht

    Reviews

    SeaDream II Reviews

    Cruise Critic Editor Ratings
    Overall
    5.0/5
    Cabins5.0
    Dining5.0
    Service5.0
    Value4.5

    "It's yachting, not cruising" has been SeaDream's tagline since the company launched in 2001, but ...

    Cruise Critic Member Ratings
    Msdenny
    Sail Date Jan 2018
    The most amazing yacht cruise from beginning to end!
    Read More
    LnG4Crusing
    Sail Date Jul 2017
    Amazing ! We are already booked for 2 more trips !
    Read More
    Cabin Comparison

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  • 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
    View Cruise Info
    Hide Cruise Info
    • Itinerary
    • Ship Details
    • Reviews
    • Cabin Comparison
    • View All Prices
    • Fare Includes
    Itinerary

    Cruise Itinerary

    7 Night Gay & Lesbian Cruise 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
    laurieha
    Sail Date Dec 2019
    Poor service & ship needs an overhaul
    Read More
    Kathytharris
    Sail Date Sep 2019
    Perfection
    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 26 2022)

    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

    7 Night Gay & Lesbian Cruise 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
      Anguilla
    • 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
    Brianbluebird
    Sail Date Oct 2019
    Excellent
    Read More
    Jneil
    Sail Date Oct 2019
    Worn ship and disorganized service. Mediocre All Around.
    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
    Bridgetown To Marigot

    Leaving:
    Barbados
    Visiting:
    Bequia, Iles des Saintes ... see more
    Cruise Line:
    SeaDream Yacht Club
    View Deal
    View Cruise Info
    Hide Cruise Info
    • Itinerary
    • Ship Details
    • Reviews
    • Cabin Comparison
    • View All Prices
    Itinerary

    Cruise Itinerary

    7 Night Gay & Lesbian Cruise Route (SeaDream Yacht Club)
    • Day 1
      Barbados
    • Day 2
      Bequia
    • Day 3
      Iles des Saintes
    • Day 4
      Little Bay
    • Day 5
      St. Barts
    • Day 6
      St. Barts
    • Day 6
      Anguilla
    • Day 7
      Prickly Pear Island
    • Day 8
      St. Martin
    Ship Details

    SeaDream II - SeaDream Yacht Club

    Pros

    All-inclusive, ultra-small ship with amazing food and service

    Cons

    Limited onboard entertainment, especially if you don't like to socialize over drinks

    Bottom Line

    Closest most people will get to a vacation on a private yacht

    Reviews

    SeaDream II Reviews

    Cruise Critic Editor Ratings
    Overall
    5.0/5
    Cabins5.0
    Dining5.0
    Service5.0
    Value4.5

    "It's yachting, not cruising" has been SeaDream's tagline since the company launched in 2001, but ...

    Cruise Critic Member Ratings
    GlitteryUnicorn
    Sail Date Jul 2017
    Really wonderful
    Read More
    jpjolo
    Sail Date Apr 2017
    True Luxury
    Read More
    Cabin Comparison

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    Call to plan your cruise 866-501-1694 866-501-1694
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  • 7 Night
    Marigot To Charlotte Amalie, St. Thomas

    Leaving:
    St. Martin
    Visiting:
    Anguilla, St. Barts ... see more
    Cruise Line:
    SeaDream Yacht Club
    View Deal
    View Cruise Info
    Hide Cruise Info
    • Itinerary
    • Ship Details
    • Reviews
    • Cabin Comparison
    • View All Prices
    Itinerary

    Cruise Itinerary

    7 Night Gay & Lesbian Cruise Route (SeaDream Yacht Club)
    • Day 1
      St. Martin
    • Day 1
      Anguilla
    • Day 2
      Anguilla
    • Day 2
      St. Barts
    • Day 3
      St. Barts
    • Day 4
      St. Barts
    • Day 4
      St. Kitts (Port Zante)
    • Day 5
      Jost Van Dyke
    • Day 6
      Virgin Gorda
    • Day 6
      Jost Van Dyke
    • Day 7
      Tortola
    • Day 7
      Norman Island
    • Day 8
      St. Thomas
    Ship Details

    SeaDream II - SeaDream Yacht Club

    Pros

    All-inclusive, ultra-small ship with amazing food and service

    Cons

    Limited onboard entertainment, especially if you don't like to socialize over drinks

    Bottom Line

    Closest most people will get to a vacation on a private yacht

    Reviews

    SeaDream II Reviews

    Cruise Critic Editor Ratings
    Overall
    5.0/5
    Cabins5.0
    Dining5.0
    Service5.0
    Value4.5

    "It's yachting, not cruising" has been SeaDream's tagline since the company launched in 2001, but ...

    Cruise Critic Member Ratings
    PleaseDontSnoNoMo
    Sail Date Mar 2017
    Forget the 1-5 ratings; your SeaDream experience is about personal style
    Read More
    piratelooksat45
    Sail Date Jan 2017
    Yearly Review of SeaDream
    Read More
    Cabin Comparison

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    Call to plan your cruise 866-501-1694 866-501-1694
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  • 14 Night
    Caribbean Explorations 14d 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

    14 Night Gay & Lesbian Cruise 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
    • Day 9
      Anguilla
    • Day 10
      Sopers Hole
    • Day 10
      Jost Van Dyke
    • Day 11
      Jost Van Dyke
    • Day 11
      Virgin Gorda
    • Day 12
      Virgin Gorda
    • Day 13
      St. Barts
    • Day 14
      Antigua
    • Day 15
      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
    End412
    Sail Date Sep 2019
    Old Ship; Failed air conditioning
    Read More
    Snookycat
    Sail Date Aug 2019
    FRENCH RIVIERA - AUGUST 2019
    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