Windstar's Caribbean Cruise Deals

Set sail for paradise with up to a bonus $300 shipboard credit on select voyages.

Windstar is not your typical cruise experience. Leave the crowds behind on an intimate luxury yacht and enjoy the Caribbean, Panama Canal, or Costa Rica like never before. Book early to set sail on your tropical adventure at an unbelievable value.

Plus, when you book with CruiseInsider, we'll treat you to a little pampering onboard with up to a bonus $300 shipboard credit added to your voyage on select sailings!

Contact CruiseInsider at 1 (877) 734-6858 to help you plan, perfect and save on your next journey.
Cruises Top
Cruises marked with are part of our Insider Advantage program which include free extras only available at CruiseInsider.
  Itinerary Cruise Line Ship Departing Extras Price
14-night Ocean Crossing Cruise Windstar Cruises
Wind Surf
Wind Surf 4/9/19
St. Maarten to Lisbon
From $1,399
13-night Stars Over the Azores Cruise Windstar Cruises
Star Pride
Star Pride 3/19/19
San Juan to Lisbon
  From $1,599
14-night Ocean Crossing Cruise Windstar Cruises
Wind Star
Wind Star 11/12/19
Lisbon to St. Maarten
  From $1,399
14-night Ocean Crossing Cruise Windstar Cruises
Wind Surf
Wind Surf 11/30/19
Lisbon to St. Maarten
  From $1,399
15-night Ocean Crossing Cruise Windstar Cruises
Wind Star
Wind Star 3/25/20
St. Maarten to Lisbon
  From $1,499
7-night Classic Caribbean Cruise Windstar Cruises
Wind Surf
Wind Surf 3/2/19
Roundtrip St. Maarten
From $1,499
7-night Yachtsman's Caribbean Cruise Windstar Cruises
Wind Surf
Wind Surf 3/9/19
Roundtrip St. Maarten
  From $1,599
7-night Classic Caribbean Cruise Windstar Cruises
Wind Surf
Wind Surf 3/16/19
Roundtrip St. Maarten
  From $1,599
7-night Caribbean Legends Cruise Windstar Cruises
Star Breeze
Star Breeze 3/16/19
St. Maarten to Bridgetown
  From $1,499
7-night Antilles Island Hopping Cruise Windstar Cruises
Star Pride
Star Pride 2/23/19
Bridgetown to San Juan
 
Call for pricing
11-night Autumn Latitudes of the Eastern Seaboard Cruise Windstar Cruises
Star Pride
Star Pride 10/26/19
New York City to San Juan
  From $1,799
7-night Classic Caribbean Cruise Windstar Cruises
Wind Surf
Wind Surf 2/16/19
Roundtrip St. Maarten
From $1,699
10-night The Caribbean's Perfect Ten Cruise Windstar Cruises
Wind Surf
Wind Surf 3/30/19
Roundtrip St. Maarten
From $1,799
8-night Saints of the Caribbean Cruise Windstar Cruises
Star Breeze
Star Breeze 3/23/19
Bridgetown to St. Maarten
  From $1,699
7-night San Juan and the Virgin Islands Cruise Windstar Cruises
Star Legend
Star Legend 11/16/19
Roundtrip San Juan
  From $1,799
7-night Yachtsman's Caribbean Cruise Windstar Cruises
Wind Surf
Wind Surf 1/4/20
Roundtrip St. Maarten
  From $1,999
7-night Lush and Lovely Islands of the Lesser Antilles Cruise Windstar Cruises
Wind Surf
Wind Surf 1/11/20
St. Maarten (Philipsburg) to Bridgetown
  From $1,999
7-night Windward Ways & Tobago Cays Cruise Windstar Cruises
Wind Surf
Wind Surf 1/25/20
Bridgetown (Barbados) to Oranjestad, Aruba
  From $1,999
7-night Sweet Southern Caribbean Cruise Windstar Cruises
Wind Star
Wind Star 3/23/19
Oranjestad to Bridgetown
From $2,299
7-night Jewels of the Windward Islands Cruise Windstar Cruises
Wind Surf
Wind Surf 1/18/20
Roundtrip Bridgetown
  From $2,199
19-night Star Collector: Caribbean Rhythms, Transatlantic Tides Cruise Windstar Cruises
Star Breeze
Star Breeze 4/7/19
Bridgetown (Barbados) to Lisbon
  From $2,499
8-night Mayan Legacies Cruise Windstar Cruises
Wind Surf
Wind Surf 2/10/20
Colon (Panama) to Cozumel
  From $2,299
11-night Dutch Treats, Steel Drum Beats Cruise Windstar Cruises
Wind Star
Wind Star 3/14/20
Colon to St. Maarten
  From $2,374
24-night Star Collector: Caribbean Carousing & an Atlantic Crossing Cruise Windstar Cruises
Wind Surf
Wind Surf 3/30/19
St. Maarten to Lisbon
From $2,699
7-night Windward Islands Surf and Sunsets Cruise Windstar Cruises
Star Legend
Star Legend 12/21/19
Roundtrip San Juan
  From $2,899
7-night San Juan and the Virgin Islands Cruise Windstar Cruises
Star Legend
Star Legend 12/28/19
Roundtrip San Juan
  From $2,899
14-night Star Collector – Lovely Leewards Cruise Windstar Cruises
Star Legend
Star Legend 11/2/19
Roundtrip San Juan
  From $2,899
14-night Star Collector: Caribbean Explorations Cruise Windstar Cruises
Wind Surf
Wind Surf 2/16/19
Roundtrip St. Maarten
From $3,499
14-night Star Collector: Coffee, Canal, & Callaloo – Central America, Colombia, and the Caribbean Cruise Windstar Cruises
Star Legend
Star Legend 10/19/19
Puerto Caldera to San Juan
  From $3,499
14-night Star Collector: Caribbean Explorations Cruise Windstar Cruises
Wind Surf
Wind Surf 12/14/19
Roundtrip St. Maarten (Philipsburg)
  From $3,799
19-night Star Collector: Caribbean Cultures – Latin America & the Greater Antilles Cruise Windstar Cruises
Wind Surf
Wind Surf 2/10/20
Colon (Panama) to St. Maarten (Philipsburg)
  From $3,899
Looking for assistance? Speak to an expert at  1 (877) 734-6858  and we'll help find the perfect cruise that fits your travel needs.

Terms and Conditions: Fares/rates are per person, based on double occupancy for select sail and travel dates; are capacity controlled and subject to availability at time booking and may be pulled without notice. We reserve the right to correct errors. Information and pricing is subject to change without notice. While we do our very best to ensure that information and pricing appearing in this website is complete and accurate, we cannot be responsible for incomplete and inaccurate representations, which may or may not be under our control. In the event of a pricing error, misrepresentation or omission, we reserve the right to adjust the pricing or make any other corrections. *$300 shipboard credit is per stateroom for select sailings and categories. Single occupancy bookings receive half the listed shipboard credit.

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