Up to $300 Shipboard Credit

Windstar's Caribbean Cruise Deals

Windstar Cruises / Specials / Windstar's Caribbean Cruise Deals
Cruise Line Windstar Cruises
Prices From $1,399
Expires 7/31/19

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!

Includes free extras and bonus savings available only from CruiseInsider.

14-night Ocean Crossing Cruise

Lisbon to St. Maarten

Cruise Line
Windstar Cruises
Cruise Ship
Wind Star
Departs
11/12/19
From
$1,399
14-night Ocean Crossing Cruise

Lisbon to St. Maarten

Cruise Line
Windstar Cruises
Cruise Ship
Wind Surf
Departs
11/30/19
From
$1,399
15-night Ocean Crossing Cruise

St. Maarten to Lisbon

Cruise Line
Windstar Cruises
Cruise Ship
Wind Star
Departs
3/25/20
From
$1,499
11-night Autumn Latitudes of the Eastern Seaboard Cruise

New York City to San Juan

Cruise Line
Windstar Cruises
Cruise Ship
Star Pride
Departs
10/26/19
From
$1,399
7-night San Juan and the Virgin Islands Cruise

Roundtrip San Juan

Cruise Line
Windstar Cruises
Cruise Ship
Star Legend
Departs
11/16/19
From
$1,699
7-night Yachtsman's Caribbean Cruise

Roundtrip St. Maarten

Cruise Line
Windstar Cruises
Cruise Ship
Wind Surf
Departs
1/4/20
From
$1,999
7-night Lush and Lovely Islands of the Lesser Antilles Cruise

St. Maarten (Philipsburg) to Bridgetown

Cruise Line
Windstar Cruises
Cruise Ship
Wind Surf
Departs
1/11/20
From
$1,999
7-night Windward Ways & Tobago Cays Cruise

Bridgetown (Barbados) to Oranjestad, Aruba

Cruise Line
Windstar Cruises
Cruise Ship
Wind Surf
Departs
1/25/20
From
$2,399
7-night Jewels of the Windward Islands Cruise

Roundtrip Bridgetown

Cruise Line
Windstar Cruises
Cruise Ship
Wind Surf
Departs
1/18/20
From
$1,999
8-night Mayan Legacies Cruise

Colon (Panama) to Cozumel

Cruise Line
Windstar Cruises
Cruise Ship
Wind Surf
Departs
2/10/20
From
$2,299
11-night Dutch Treats, Steel Drum Beats Cruise

Colon to St. Maarten

Cruise Line
Windstar Cruises
Cruise Ship
Wind Star
Departs
3/14/20
From
$2,374
7-night Windward Islands Surf and Sunsets Cruise

Roundtrip San Juan

Cruise Line
Windstar Cruises
Cruise Ship
Star Legend
Departs
12/21/19
From
$2,699
7-night San Juan and the Virgin Islands Cruise

Roundtrip San Juan

Cruise Line
Windstar Cruises
Cruise Ship
Star Legend
Departs
12/28/19
From
$2,699
14-night Star Collector – Lovely Leewards Cruise

Roundtrip San Juan

Cruise Line
Windstar Cruises
Cruise Ship
Star Legend
Departs
11/2/19
From
$2,999
14-night Star Collector: Coffee, Canal, & Callaloo – Central America, Colombia, and the Caribbean Cruise

Puerto Caldera to San Juan

Cruise Line
Windstar Cruises
Cruise Ship
Star Legend
Departs
10/19/19
From
$2,999
14-night Star Collector: Caribbean Explorations Cruise

Roundtrip St. Maarten (Philipsburg)

Cruise Line
Windstar Cruises
Cruise Ship
Wind Surf
Departs
12/14/19
From
$3,299
19-night Star Collector: Caribbean Cultures – Latin America & the Greater Antilles Cruise

Colon (Panama) to St. Maarten (Philipsburg)

Cruise Line
Windstar Cruises
Cruise Ship
Wind Surf
Departs
2/10/20
From
$4,299

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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