Early Booking Offer on Windstar's New Itineraries

Windstar Cruises / Specials / Early Booking Offer on Windstar's New Itineraries
Cruise Line Windstar Cruises
Prices From $2,426
Expires 5/31/25

Get $200 shipboard credit, free Wi-Fi, free gratuities and the unlimited beverage package on Windstar's new itineraries!

Experience boutique cruising aboard Windstar's yachts and get pampered, personalized service. Windstar's ships are large enough to pamper, yet small enough to explore charming villages and remote islands.

Reserve select sailings now and take advantage of this early booking offer:

Choose your sailing below or call our experts at 1 (877) 734-6858 to take advantage of this early booking offer now!

Connect With A CruiseInsider Expert About This Special Offer!

Submit the form below or call us at 1 (877) 734-6858

Includes free extras and bonus savings available only from CruiseInsider.

8-night Bermuda Bliss Cruise

Boston to San Juan

Cruise Line
Windstar Cruises
Cruise Ship
Star Pride
Departs
10/20/26
From
$2,426
11-night Gems Of The Leeward Islands Cruise

Roundtrip San Juan

Cruise Line
Windstar Cruises
Cruise Ship
Star Pride
Departs
10/28/26
From
$3,657
10-night Treasures Of Southern Spain & Morocco Cruise

Barcelona to Lisbon

Cruise Line
Windstar Cruises
Cruise Ship
Wind Star
Departs
10/31/26
From
$4,064
14-night Star Collector: Lovely Leewards Cruise

Roundtrip San Juan

Cruise Line
Windstar Cruises
Cruise Ship
Star Pride
Departs
11/8/26
From
$4,093
7-night Windward Islands Surf & Sunsets Cruise

Roundtrip San Juan

Cruise Line
Windstar Cruises
Cruise Ship
Star Pride
Departs
11/8/26
From
$2,530
14-night Ocean Crossings Cruise

Lisbon to Bridgetown (Barbados)

Cruise Line
Windstar Cruises
Cruise Ship
Wind Star
Departs
11/10/26
From
$2,525
14-night Star Collector: Lovely Leewards Cruise

Roundtrip San Juan

Cruise Line
Windstar Cruises
Cruise Ship
Star Pride
Departs
11/15/26
From
$4,093
7-night San Juan & The Virgin Islands Cruise

Roundtrip San Juan

Cruise Line
Windstar Cruises
Cruise Ship
Star Pride
Departs
11/15/26
From
$2,562
14-night Star Collector: Lovely Leewards Cruise

Roundtrip San Juan

Cruise Line
Windstar Cruises
Cruise Ship
Star Pride
Departs
11/22/26
From
$4,093
7-night Windward Islands Surf & Sunsets Cruise

Roundtrip San Juan

Cruise Line
Windstar Cruises
Cruise Ship
Star Pride
Departs
11/22/26
From
$2,530
11-night Colombian & Southern Caribbean Coastlines Cruise

Bridgetown (Barbados) to Colon (Panama)

Cruise Line
Windstar Cruises
Cruise Ship
Wind Star
Departs
11/24/26
From
$3,830
14-night Star Collector: Lovely Leewards Cruise

Roundtrip San Juan

Cruise Line
Windstar Cruises
Cruise Ship
Star Pride
Departs
11/29/26
From
$4,093
7-night San Juan & The Virgin Islands Cruise

Roundtrip San Juan

Cruise Line
Windstar Cruises
Cruise Ship
Star Pride
Departs
11/29/26
From
$2,562
7-night Costa Rica & Panama Canal Cruise

Colon (Panama) to Puerto Caldera (Puntarenas)

Cruise Line
Windstar Cruises
Cruise Ship
Wind Star
Departs
12/5/26
From
$3,669
10-night Monteverde Cloud Forest & Arenal Volcano Cruise/Land Package

Colon (Panama) to San Jose (C.R.)

Cruise Line
Windstar Cruises
Cruise Ship
Wind Star
Departs
12/5/26
From
$6,069
14-night Star Collector: Lovely Leewards Cruise

Roundtrip San Juan

Cruise Line
Windstar Cruises
Cruise Ship
Star Pride
Departs
12/6/26
From
$4,093
7-night Costa Rica & Panama Canal Cruise

Puerto Caldera (Puntarenas) to Colon (Panama)

Cruise Line
Windstar Cruises
Cruise Ship
Wind Star
Departs
12/12/26
From
$3,669
14-night Star Collector: Lovely Leewards Cruise

Roundtrip San Juan

Cruise Line
Windstar Cruises
Cruise Ship
Star Pride
Departs
12/13/26
From
$4,193
11-night Monteverde Cloud Forest & Arenal Volcano Cruise/Land Package

San Jose (C.R.) to Colon (Panama)

Cruise Line
Windstar Cruises
Cruise Ship
Wind Star
Departs
12/8/26
From
$6,069
7-night Windward Islands Surf & Sunsets Cruise

Roundtrip San Juan

Cruise Line
Windstar Cruises
Cruise Ship
Star Pride
Departs
12/6/26
From
$2,530
10-night Monteverde Cloud Forest & Arenal Volcano Cruise/Land Package

Colon (Panama) to San Jose (C.R.)

Cruise Line
Windstar Cruises
Cruise Ship
Wind Star
Departs
12/19/26
From
$6,069
7-night Costa Rica & Panama Canal Cruise

Colon (Panama) to Puerto Caldera (Puntarenas)

Cruise Line
Windstar Cruises
Cruise Ship
Wind Star
Departs
12/19/26
From
$3,669
7-night San Juan & The Virgin Islands Cruise

Roundtrip San Juan

Cruise Line
Windstar Cruises
Cruise Ship
Star Pride
Departs
12/13/26
From
$2,562
14-night Star Collector: Lovely Leewards Cruise

Roundtrip San Juan

Cruise Line
Windstar Cruises
Cruise Ship
Star Pride
Departs
12/20/26
From
$4,393
7-night Costa Rica & Panama Canal Cruise

Puerto Caldera (Puntarenas) to Colon (Panama)

Cruise Line
Windstar Cruises
Cruise Ship
Wind Star
Departs
12/26/26
From
$3,669
14-night Star Collector: Lovely Leewards Cruise

Roundtrip San Juan

Cruise Line
Windstar Cruises
Cruise Ship
Star Pride
Departs
12/27/26
From
$4,193
7-night San Juan & The Virgin Islands Cruise

Roundtrip San Juan

Cruise Line
Windstar Cruises
Cruise Ship
Star Pride
Departs
12/27/26
From
$2,762
7-night Windward Islands Surf & Sunsets Cruise

Roundtrip San Juan

Cruise Line
Windstar Cruises
Cruise Ship
Star Pride
Departs
12/20/26
From
$2,730
11-night Monteverde Cloud Forest & Arenal Volcano Cruise/Land Package

San Jose (C.R.) to Colon (Panama)

Cruise Line
Windstar Cruises
Cruise Ship
Wind Star
Departs
12/22/26
From
$6,069
7-night Costa Rica & Panama Canal Cruise

Colon (Panama) to Puerto Caldera (Puntarenas)

Cruise Line
Windstar Cruises
Cruise Ship
Wind Star
Departs
1/2/27
From
$3,669
10-night Monteverde Cloud Forest & Arenal Volcano Cruise/Land Package

Colon (Panama) to San Jose (C.R.)

Cruise Line
Windstar Cruises
Cruise Ship
Wind Star
Departs
1/2/27
From
$6,069
14-night Star Collector: Lovely Leewards Cruise

Roundtrip San Juan

Cruise Line
Windstar Cruises
Cruise Ship
Star Pride
Departs
1/3/27
From
$4,093
7-night Windward Islands Surf & Sunsets Cruise

Roundtrip San Juan

Cruise Line
Windstar Cruises
Cruise Ship
Star Pride
Departs
1/3/27
From
$2,530
7-night San Juan & The Virgin Islands Cruise

Roundtrip San Juan

Cruise Line
Windstar Cruises
Cruise Ship
Star Pride
Departs
1/10/27
From
$2,562

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.