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Windstar Star Legend Cruises to the Caribbean

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  • 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 Star Legend 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...

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    Cabin Comparison

    Compare Cabin Prices

    No Results Found
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    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:
    Colon
    Visiting:
    San Blas Islands, Cartagena ... 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 Star Legend Cruise to Caribbean Route (Windstar Cruises)
    • Day 1
      Colon (Cristobal)
    • Day 2
      San Blas Islands
    • Day 3
      Cartagena (Spain)
    • Day 4
      Santa Marta
    • Day 5
      Cruising
    • Day 6
      Santo Domingo
    • Day 7
      Catalina Island (Dominican Republic)
    • 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:
    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 Star Legend 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...

    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. 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 Star Legend 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:
    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 Star Legend 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...

    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:
    St. Lucia, Grenada ... 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 Star Legend 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...

    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:
    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 Star Legend Cruise to Caribbean Route (Windstar Cruises)
    • Day 1
      San Juan
    • Day 2
      St. Maarten
    • Day 3
      Iles des Saintes
    • Day 4
      Bequia
    • Day 5
      St. Lucia
    • Day 6
      Grenada
    • 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...

    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.

  • 10 Night
    Caribbean Cruise

    Leaving:
    San Juan
    Visiting:
    Virgin Gorda, 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

    10 Night Star Legend 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...

    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.

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  • Cruise Critic is not a booking agent and does not charge any service fees to users of our site. Our partners who list cruise pricing on Cruise Critic are required to provide prices for cruise only, per person, double occupancy, and are based on specific cabin types and sailing dates, and may not be available for all cabin types/sailings. Taxes, fees and port expenses not included. Rates are in USD and valid for US and Canadian residents only. Fuel supplement may apply. When you book with one of our partners, please be sure to check their site for a full disclosure of all applicable fees as required by the U.S. Department of Transportation.

    For any cruises listed, Cruise Critic does not guarantee any specific rates or prices. In addition, average cruise prices are updated nightly.

    Furthermore, Cruise Critic makes no guarantees for availability of prices advertised on our site. Listed prices may have blackout dates, qualifications or restrictions.

    Cruise Critic is not responsible for content on external web sites.

  • Lowest pricing is based on our 3rd party pricing supplier and valid as of October 21st, 2019.