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Windstar Cruises to the Caribbean

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  • 5 Night
    Caribbean Cruise

    Leaving:
    Miami
    Visiting:
    Bimini, Key West ... 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

    5 Night Cruise to Caribbean Route (Windstar Cruises)
    • Day 1
      Miami
    • Day 2
      Bimini
    • Day 3
      Cruising
    • Day 4
      Key West
    • Day 5
      Key West
    • Day 6
      Miami
    Ship Details

    Star Breeze - Windstar Cruises

    Pros

    Small-ship cruising, port-intensive itineraries

    Cons

    Limited entertainment and enrichment activities

    Bottom Line

    Terrific upscale yet casual cruise line for active travelers

    Reviews

    Star Breeze Reviews

    Cruise Critic Editor Ratings
    Overall
    4.0/5
    Cabins5.0
    Dining4.0
    Service4.0
    Value4.0

    The 212-passenger Star Breeze, which joined Windstar's fleet in May 2015, is a yacht-style smal...

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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
    Caribbean Cruise

    Leaving:
    San Juan
    Visiting:
    St. Maarten, Iles des Saintes ... 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 Cruise to Caribbean Route (Windstar Cruises)
    • Day 1
      San Juan
    • Day 2
      St. Maarten
    • Day 3
      Iles des Saintes
    • Day 4
      Bequia
    • Day 5
      Grenada
    • Day 6
      St. Lucia
    • Day 7
      Cruising
    • Day 8
      San Juan
    Ship Details

    Star Legend - Windstar Cruises

    Pros

    Upscale, destination-driven yacht that visits off-the-beaten-path ports of call

    Cons

    Without sails, it lacks some of the panache of Windstar's original iconic ships

    Bottom Line

    Ideal for active couples seeking a romantic, small ship atmosphere

    Reviews

    Star Legend Reviews

    Cruise Critic Editor Ratings
    Overall
    4.5/5
    Cabins4.0
    Dining5.0
    Service4.0
    Value4.0

    For years, Windstar Cruises had been a fleet of three majestic motor-sail yachts: Wind Surf, Wi...

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    Cabin Comparison

    Compare Cabin Prices

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    Compare Prices

    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.

  • 2019 Best for Dining

    7 Night
    Caribbean Cruise

    Leaving:
    San Juan
    Visiting:
    Island of Mozambique, 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 Cruise to Caribbean Route (Windstar Cruises)
    • Day 1
      San Juan
    • Day 2
      Island of Mozambique
    • Day 3
      St. Barts
    • Day 4
      Little Bay
    • Day 5
      St. Maarten
    • Day 6
      Jost Van Dyke
    • Day 7
      Virgin Gorda
    • Day 8
      San Juan
    Ship Details

    Star Pride - Windstar Cruises

    Pros

    Spacious suites and bathrooms, James Beard-influenced cuisine

    Cons

    Ship decor appears dated in cabins and public areas; limited entertainment

    Bottom Line

    Intimate feel and upscale details make Star Pride a nice choice for port-intensive cruises

    Reviews

    Star Pride Reviews

    Cruise Critic Editor Ratings
    Overall
    4.5/5
    Cabins5.0
    Dining4.5
    Service5.0
    Value4.5

    One of three motor yachts in the Windstar Cruises fleet, Star Pride brings the flavor of the la...

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    Cabin Comparison

    Compare Cabin Prices

    No Results Found
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    Compare Prices

    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
    Caribbean Cruise

    Leaving:
    San Juan
    Visiting:
    St. Maarten, Iles des Saintes ... 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 Cruise to Caribbean Route (Windstar Cruises)
    • Day 1
      San Juan
    • Day 2
      St. Maarten
    • Day 3
      Iles des Saintes
    • Day 4
      St. Lucia
    • Day 5
      Grenada
    • Day 6
      Bequia
    • Day 7
      Cruising
    • Day 8
      San Juan
    Ship Details

    Star Legend - Windstar Cruises

    Pros

    Upscale, destination-driven yacht that visits off-the-beaten-path ports of call

    Cons

    Without sails, it lacks some of the panache of Windstar's original iconic ships

    Bottom Line

    Ideal for active couples seeking a romantic, small ship atmosphere

    Reviews

    Star Legend Reviews

    Cruise Critic Editor Ratings
    Overall
    4.5/5
    Cabins4.0
    Dining5.0
    Service4.0
    Value4.0

    For years, Windstar Cruises had been a fleet of three majestic motor-sail yachts: Wind Surf, Wi...

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    Cabin Comparison

    Compare Cabin Prices

    No Results Found
    Loading...
    View All Prices

    Compare Prices

    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
    Caribbean Cruise

    Leaving:
    San Juan
    Visiting:
    Island of Mozambique, St. Maarten ... 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 Cruise to Caribbean Route (Windstar Cruises)
    • Day 1
      San Juan
    • Day 2
      Island of Mozambique
    • Day 3
      St. Maarten
    • Day 4
      Little Bay
    • Day 5
      St. Barts
    • Day 6
      Jost Van Dyke
    • Day 7
      Virgin Gorda
    • Day 8
      San Juan
    Ship Details

    Star Legend - Windstar Cruises

    Pros

    Upscale, destination-driven yacht that visits off-the-beaten-path ports of call

    Cons

    Without sails, it lacks some of the panache of Windstar's original iconic ships

    Bottom Line

    Ideal for active couples seeking a romantic, small ship atmosphere

    Reviews

    Star Legend Reviews

    Cruise Critic Editor Ratings
    Overall
    4.5/5
    Cabins4.0
    Dining5.0
    Service4.0
    Value4.0

    For years, Windstar Cruises had been a fleet of three majestic motor-sail yachts: Wind Surf, Wi...

    Loading...
    Cabin Comparison

    Compare Cabin Prices

    No Results Found
    Loading...
    View All Prices

    Compare Prices

    Call to plan your cruise 866-501-1694 866-501-1694
    Loading...
    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
    Caribbean Cruise

    Leaving:
    San Juan
    Visiting:
    Island of Mozambique, 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 Cruise to Caribbean Route (Windstar Cruises)
    • Day 1
      San Juan
    • Day 2
      Island of Mozambique
    • Day 3
      St. Barts
    • Day 4
      Little Bay
    • Day 5
      St. Maarten
    • Day 6
      Jost Van Dyke
    • Day 7
      Virgin Gorda
    • Day 8
      San Juan
    Ship Details

    Star Legend - Windstar Cruises

    Pros

    Upscale, destination-driven yacht that visits off-the-beaten-path ports of call

    Cons

    Without sails, it lacks some of the panache of Windstar's original iconic ships

    Bottom Line

    Ideal for active couples seeking a romantic, small ship atmosphere

    Reviews

    Star Legend Reviews

    Cruise Critic Editor Ratings
    Overall
    4.5/5
    Cabins4.0
    Dining5.0
    Service4.0
    Value4.0

    For years, Windstar Cruises had been a fleet of three majestic motor-sail yachts: Wind Surf, Wi...

    Loading...
    Cabin Comparison

    Compare Cabin Prices

    No Results Found
    Loading...
    View All Prices

    Compare Prices

    Call to plan your cruise 866-501-1694 866-501-1694
    Loading...
    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
    Caribbean Cruise

    Leaving:
    St. Maarten
    Visiting:
    St. Barts, Virgin Gorda ... 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

    11 Night Cruise to Caribbean Route (Windstar Cruises)
    • Day 1
      St. Maarten
    • Day 2
      St. Barts
    • Day 3
      Virgin Gorda
    • Day 4
      Cruising
    • Day 5
      Cruising
    • Day 6
      Bonaire
    • Day 7
      Curacao
    • Day 8
      Aruba
    • Day 9
      Cruising
    • Day 10
      Cartagena (Spain)
    • Day 11
      Cruising
    • Day 12
      Colon (Cristobal)
    Ship Details

    Wind Star - Windstar Cruises

    Pros

    Romantic four-mast sailing ship with exceptional service.

    Cons

    Lack of daytime activities and nighttime entertainment.

    Bottom Line

    Perfect for adventurous travelers and sailing enthusiasts who prefer to go off the beaten path.

    Reviews

    Wind Star Reviews

    Cruise Critic Editor Ratings
    Overall
    4.5/5
    Cabins4.5
    Dining4.0
    Service5.0
    Value4.5

    Paying tribute to the golden age of tall ships, Wind Star -- a four-mast, motor-sailing yacht -...

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    Cabin Comparison

    Compare Cabin Prices

    No Results Found
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    Compare Prices

    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.

  • 2019 Best for Dining

    7 Night
    Caribbean Cruise

    Leaving:
    Barbados
    Visiting:
    Bequia, Casablanca ... 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 Cruise to Caribbean Route (Windstar Cruises)
    • Day 1
      Barbados
    • Day 2
      Bequia
    • Day 3
      Casablanca
    • Day 4
      Iles des Saintes
    • Day 5
      St. Kitts (Port Zante)
    • Day 6
      St. Maarten
    • Day 7
      Virgin Gorda
    • Day 8
      San Juan
    Ship Details

    Star Pride - Windstar Cruises

    Pros

    Spacious suites and bathrooms, James Beard-influenced cuisine

    Cons

    Ship decor appears dated in cabins and public areas; limited entertainment

    Bottom Line

    Intimate feel and upscale details make Star Pride a nice choice for port-intensive cruises

    Reviews

    Star Pride Reviews

    Cruise Critic Editor Ratings
    Overall
    4.5/5
    Cabins5.0
    Dining4.5
    Service5.0
    Value4.5

    One of three motor yachts in the Windstar Cruises fleet, Star Pride brings the flavor of the la...

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    Cabin Comparison

    Compare Cabin Prices

    No Results Found
    Loading...
    View All Prices

    Compare Prices

    Call to plan your cruise 866-501-1694 866-501-1694
    Loading...
    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.

  • 2019 Best Overall

    7 Night
    Caribbean Cruise

    Leaving:
    Barbados
    Visiting:
    Martinique, Casablanca ... 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 Cruise to Caribbean Route (Windstar Cruises)
    • Day 1
      Barbados
    • Day 2
      Martinique
    • Day 3
      Casablanca
    • Day 3
      St. Lucia
    • Day 4
      St. Lucia
    • Day 5
      Bequia
    • Day 6
      Mayreau
    • Day 7
      Grenada
    • 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 ...

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    Cabin Comparison

    Compare Cabin Prices

    No Results Found
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    Compare Prices

    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.

  • 2019 Best for Dining

    7 Night
    Caribbean Cruise

    Leaving:
    San Juan
    Visiting:
    St. Maarten, Iles des Saintes ... 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 Cruise to Caribbean Route (Windstar Cruises)
    • Day 1
      San Juan
    • Day 2
      St. Maarten
    • Day 3
      Iles des Saintes
    • Day 4
      Bequia
    • Day 5
      Grenada
    • Day 6
      St. Lucia
    • Day 7
      Cruising
    • Day 8
      San Juan
    Ship Details

    Star Pride - Windstar Cruises

    Pros

    Spacious suites and bathrooms, James Beard-influenced cuisine

    Cons

    Ship decor appears dated in cabins and public areas; limited entertainment

    Bottom Line

    Intimate feel and upscale details make Star Pride a nice choice for port-intensive cruises

    Reviews

    Star Pride Reviews

    Cruise Critic Editor Ratings
    Overall
    4.5/5
    Cabins5.0
    Dining4.5
    Service5.0
    Value4.5

    One of three motor yachts in the Windstar Cruises fleet, Star Pride brings the flavor of the la...

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    Cabin Comparison

    Compare Cabin Prices

    No Results Found
    Loading...
    View All Prices

    Compare Prices

    Call to plan your cruise 866-501-1694 866-501-1694
    Loading...
    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.

  • 10 Night
    Caribbean Cruise

    Leaving:
    San Juan
    Visiting:
    Virgin Gorda, St. Barts ... see more
    Cruise Line:
    Windstar Cruises
    View Deal
    View Cruise Info
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    Itinerary

    Cruise Itinerary

    10 Night Cruise to Caribbean Route (Windstar Cruises)
    • Day 1
      San Juan
    • Day 2
      Virgin Gorda
    • Day 3
      St. Barts
    • Day 4
      St. Maarten
    • Day 5
      Sopers Hole
    • Day 6
      Samana and Cayo Levantado
    • Day 7
      Grand Turk
    • Day 8
      Cruising
    • Day 9
      Key West
    • Day 10
      Key West
    • Day 11
      Miami
    Ship Details

    Star Legend - Windstar Cruises

    Pros

    Upscale, destination-driven yacht that visits off-the-beaten-path ports of call

    Cons

    Without sails, it lacks some of the panache of Windstar's original iconic ships

    Bottom Line

    Ideal for active couples seeking a romantic, small ship atmosphere

    Reviews

    Star Legend Reviews

    Cruise Critic Editor Ratings
    Overall
    4.5/5
    Cabins4.0
    Dining5.0
    Service4.0
    Value4.0

    For years, Windstar Cruises had been a fleet of three majestic motor-sail yachts: Wind Surf, Wi...

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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
    Caribbean Cruise

    Leaving:
    San Juan
    Visiting:
    St. Lucia, Grenada ... see more
    Cruise Line:
    Windstar Cruises
    View Deal
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    Itinerary

    Cruise Itinerary

    7 Night Cruise to Caribbean Route (Windstar Cruises)
    • Day 1
      San Juan
    • Day 2
      Cruising
    • Day 3
      St. Lucia
    • Day 4
      Grenada
    • Day 5
      Bequia
    • Day 6
      Iles des Saintes
    • Day 7
      St. Maarten
    • Day 8
      San Juan
    Ship Details

    Star Legend - Windstar Cruises

    Pros

    Upscale, destination-driven yacht that visits off-the-beaten-path ports of call

    Cons

    Without sails, it lacks some of the panache of Windstar's original iconic ships

    Bottom Line

    Ideal for active couples seeking a romantic, small ship atmosphere

    Reviews

    Star Legend Reviews

    Cruise Critic Editor Ratings
    Overall
    4.5/5
    Cabins4.0
    Dining5.0
    Service4.0
    Value4.0

    For years, Windstar Cruises had been a fleet of three majestic motor-sail yachts: Wind Surf, Wi...

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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.

  • 2019 Best for Dining

    7 Night
    Caribbean Cruise

    Leaving:
    San Juan
    Visiting:
    Virgin Gorda, St. Maarten ... see more
    Cruise Line:
    Windstar Cruises
    View Deal
    View Cruise Info
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    Itinerary

    Cruise Itinerary

    7 Night Cruise to Caribbean Route (Windstar Cruises)
    • Day 1
      San Juan
    • Day 2
      Virgin Gorda
    • Day 3
      St. Maarten
    • Day 4
      Little Bay
    • Day 5
      St. Barts
    • Day 7
      St. Barts
    • Day 7
      Jost Van Dyke
    • Day 8
      San Juan
    Ship Details

    Star Pride - Windstar Cruises

    Pros

    Spacious suites and bathrooms, James Beard-influenced cuisine

    Cons

    Ship decor appears dated in cabins and public areas; limited entertainment

    Bottom Line

    Intimate feel and upscale details make Star Pride a nice choice for port-intensive cruises

    Reviews

    Star Pride Reviews

    Cruise Critic Editor Ratings
    Overall
    4.5/5
    Cabins5.0
    Dining4.5
    Service5.0
    Value4.5

    One of three motor yachts in the Windstar Cruises fleet, Star Pride brings the flavor of the la...

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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.

  • 2019 Best for Public Rooms

    7 Night
    Caribbean Cruise

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

    Cruise Itinerary

    7 Night Cruise to Caribbean Route (Windstar Cruises)
    • Day 1
      St. Maarten
    • Day 2
      St. Barts
    • Day 3
      St. Kitts (Port Zante)
    • Day 4
      Little Bay
    • Day 5
      Martinique
    • Day 6
      St. Lucia
    • Day 7
      Iles des Saintes
    • 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 ...

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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
    Caribbean Cruise

    Leaving:
    Colon
    Visiting:
    Cartagena, Aruba ... see more
    Cruise Line:
    Windstar Cruises
    View Deal
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    Itinerary

    Cruise Itinerary

    11 Night Cruise to Caribbean Route (Windstar Cruises)
    • Day 1
      Colon (Cristobal)
    • Day 2
      Cruising
    • Day 3
      Cartagena (Spain)
    • Day 4
      Cruising
    • Day 5
      Cruising
    • Day 6
      Aruba
    • Day 7
      Curacao
    • Day 8
      Cruising
    • Day 9
      Cruising
    • Day 10
      Virgin Gorda
    • Day 11
      St. Barts
    • Day 12
      St. Maarten
    Ship Details

    Wind Star - Windstar Cruises

    Pros

    Romantic four-mast sailing ship with exceptional service.

    Cons

    Lack of daytime activities and nighttime entertainment.

    Bottom Line

    Perfect for adventurous travelers and sailing enthusiasts who prefer to go off the beaten path.

    Reviews

    Wind Star Reviews

    Cruise Critic Editor Ratings
    Overall
    4.5/5
    Cabins4.5
    Dining4.0
    Service5.0
    Value4.5

    Paying tribute to the golden age of tall ships, Wind Star -- a four-mast, motor-sailing yacht -...

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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.

  • 2019 Best for Dining

    7 Night
    Caribbean Cruise

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

    Cruise Itinerary

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

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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
    Costa Rica Cruise

    Leaving:
    Colon
    Visiting:
    Balboa, Balboa ... see more
    Cruise Line:
    Windstar Cruises
    View Deal
    View Cruise Info
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    Itinerary

    Cruise Itinerary

    11 Night Cruise to Eastern Caribbean Route (Windstar Cruises)
    • Day 1
      Colon (Cristobal)
    • Day 2
      Panama Canal (Cruising)
    • Day 2
      Balboa
    • Day 3
      Balboa
    • Day 4
      Cruising
    • Day 5
      Isla Parida
    • Day 6
      Puerto Jimenez
    • Day 7
      Puntarenas (Puerto Caldera)
    • Day 8
      Puntarenas (Puerto Caldera)
    • Day 9
      Puntarenas (Puerto Caldera)
    • Day 10
      Puntarenas (Puerto Caldera)
    • Day 11
      Puntarenas (Puerto Caldera)
    • Day 12
      Puntarenas (Puerto Caldera)
    Ship Details

    Wind Star - Windstar Cruises

    Pros

    Romantic four-mast sailing ship with exceptional service.

    Cons

    Lack of daytime activities and nighttime entertainment.

    Bottom Line

    Perfect for adventurous travelers and sailing enthusiasts who prefer to go off the beaten path.

    Reviews

    Wind Star Reviews

    Cruise Critic Editor Ratings
    Overall
    4.5/5
    Cabins4.5
    Dining4.0
    Service5.0
    Value4.5

    Paying tribute to the golden age of tall ships, Wind Star -- a four-mast, motor-sailing yacht -...

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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.