1-800-627-3753 Speak to a Cruise Expert

Windstar Cruises to Caribbean - Southern 2023/2024

Home
Windstar
Cruises to Caribbean - Southern 2023/2024

Save up to 75% on Windstar cruises

As a large-scale seller of Windstar Cruises to Caribbean - Southern 2023/2024, we are able to offer you unbeatable prices and unparalleled value. With cruise line volume buys plus our low everyday prices you can save up to 75% versus the brochure price! Once you have found the discounted Windstar cruise of your choice, please call our cruise consultants to book your vacation and save money with our first-rate personalized service! Book your Windstar cruise today with AffordableTours.com, your discounted cruise headquarters.

Cruises

Refine your search

Destination Date Cruise Line Length Departure Port

Round-trip Repositioning Cruisetour Only

Resident

Senior (55+) Military Airline Employee Civil Service Employee

Sort By

Sail Date	Cruise Line	Ship	Destination	Departs	Length	Price	You Save	Discounts
10 reviews	Dec 05, 2023	Windstar	Wind Star	Transatlantic	Lisbon	Bridgetown	14 Nights	Bridgetown \| Lisbon	$2,199 Up To $250 Onboard Credit View Cruise
24 reviews	Dec 09, 2023	Windstar	Wind Surf	Caribbean	Philipsburg	Philipsburg	7 Nights	Basseterre \| Charlestown \| Gustavia \| Les Saintes \| Pigeon Island \| Roseau \| St. Maarten	$2,199 Up To $250 Onboard Credit View Cruise	Onboard Credit!
10 reviews	Nov 05, 2024	Windstar	Wind Star	Transatlantic	Lisbon	Bridgetown	14 Nights	Bridgetown \| Lisbon	$2,199 Shipboard Credit Per Person ($100) View Cruise	Shipboard Credit Per Person ($100)
10 reviews	Mar 27, 2024	Windstar	Wind Star	Transatlantic	Bridgetown	Lisbon	15 Nights	Bridgetown \| Lisbon	$2,299 Up To $250 Onboard Credit View Cruise	Onboard Credit!
Need Help Planning A Cruise? Our cruise experts can help you: Find the best discounts Hold a cabin for 24 hours for free Receive personalized recommendations Book handicap accessible cabins Call 1-800-627-3753
9 reviews	Apr 04, 2024	Windstar	Wind Spirit	Transatlantic	Bridgetown	Lisbon	15 Nights	Bridgetown \| Lisbon	$2,299 Up To $250 Onboard Credit View Cruise
12 reviews	Nov 25, 2023	Windstar	Star Pride	Caribbean - Southern	Bridgetown	Oranjestad	7 Nights	Bridgetown \| Kralendijk \| Man-O-War Bay \| Mayreau \| Oranjestad \| Soufriere \| Willemstad	$2,399 Up To $250 Onboard Credit View Cruise
12 reviews	Dec 16, 2023	Windstar	Star Pride	Caribbean	Oranjestad	Bridgetown	6 Nights	Bridgetown \| Kralendijk \| Mayreau \| Oranjestad \| Soufriere \| Willemstad	$2,399 Up To $250 Onboard Credit View Cruise
12 reviews	Jan 13, 2024	Windstar	Star Pride	Caribbean - Southern	Oranjestad	Bridgetown	7 Nights	Bridgetown \| Kralendijk \| Man-O-War Bay \| Mayreau \| Oranjestad \| Soufriere \| Willemstad	$2,399 Up To $250 Onboard Credit View Cruise
12 reviews	Jan 20, 2024	Windstar	Star Pride	Caribbean - Southern	Bridgetown	Oranjestad	7 Nights	Bridgetown \| Kralendijk \| Man-O-War Bay \| Mayreau \| Oranjestad \| Soufriere \| Willemstad	$2,399 Up To $250 Onboard Credit View Cruise	Suite!
12 reviews	Nov 11, 2023	Windstar	Star Pride	Caribbean	Philipsburg	Bridgetown	7 Nights	Basseterre \| Bridgetown \| Gustavia \| Les Saintes \| Little Bay \| Pigeon Island \| Roseau \| St. Maarten	$2,499 Up To $250 Onboard Credit View Cruise
12 reviews	Nov 18, 2023	Windstar	Star Pride	Caribbean - Southern	Bridgetown	Bridgetown	7 Nights	Anse Mitan \| Bequia \| Bridgetown \| Castries \| Mayreau \| Pigeon Island \| St. George's \| The Pitons	$2,499 Up To $250 Onboard Credit View Cruise
12 reviews	Dec 09, 2023	Windstar	Star Pride	Caribbean - Southern	Balboa	Oranjestad	7 Nights	Balboa / Fuerte Amador \| Bocas del Toro \| Cartagena \| Oranjestad \| San Blas \| Santa Marta	$2,499 Up To $250 Onboard Credit View Cruise
12 reviews	Jan 06, 2024	Windstar	Star Pride	Caribbean - Southern	Balboa	Oranjestad	7 Nights	Balboa / Fuerte Amador \| Bocas del Toro \| Cartagena \| Oranjestad \| San Blas \| Santa Marta	$2,499 Up To $250 Onboard Credit View Cruise
12 reviews	Jan 27, 2024	Windstar	Star Pride	Caribbean - Southern	Oranjestad	Balboa	7 Nights	Balboa / Fuerte Amador \| Bocas del Toro \| Cartagena \| Oranjestad \| San Blas \| Santa Marta	$2,499 Up To $250 Onboard Credit View Cruise
12 reviews	Feb 10, 2024	Windstar	Star Pride	Caribbean - Southern	Oranjestad	Bridgetown	7 Nights	Bridgetown \| Kralendijk \| Man-O-War Bay \| Mayreau \| Oranjestad \| Soufriere \| Willemstad	$2,499 Up To $250 Onboard Credit View Cruise	Suite!
12 reviews	Mar 02, 2024	Windstar	Star Pride	Caribbean - Southern	Balboa	Oranjestad	7 Nights	Balboa / Fuerte Amador \| Bocas del Toro \| Cartagena \| Oranjestad \| San Blas \| Santa Marta	$2,499 Up To $250 Onboard Credit View Cruise	Suite!
12 reviews	Mar 09, 2024	Windstar	Star Pride	Caribbean - Southern	Oranjestad	Bridgetown	7 Nights	Balboa / Fuerte Amador \| Bocas del Toro \| Cartagena \| Oranjestad \| San Blas \| Santa Marta	$2,499 Up To $250 Onboard Credit View Cruise	Suite!
9 reviews	Nov 13, 2024	Windstar	Wind Spirit	Transatlantic	Lisbon	Bridgetown	14 Nights	Bridgetown \| Lisbon	$2,499 Shipboard Credit Per Person ($100) View Cruise	Shipboard Credit Per Person ($100)
12 reviews	Feb 03, 2024	Windstar	Star Pride	Caribbean - Southern	Balboa	Oranjestad	7 Nights	Balboa / Fuerte Amador \| Bocas del Toro \| Cartagena \| Oranjestad \| San Blas \| Santa Marta	$2,599 Up To $300 Onboard Credit View Cruise	Suite!
12 reviews	Dec 02, 2023	Windstar	Star Pride	Caribbean - Southern	Oranjestad	Balboa	7 Nights	Balboa / Fuerte Amador \| Bocas del Toro \| Cartagena \| Oranjestad \| San Blas \| Santa Marta	$2,699 Up To $300 Onboard Credit View Cruise

Sort By

Departure Ports

Destinations

Departure

Lengths

How It Works

Vacationing has never been easier or cheaper with the help of a dedicated travel consultant from AffordableTours.com

1. Free Quote

Find your perfect trip on our website and simply request a free quote. Need to speak to a live person? Call us 7 days a week at 1-800-627-3753. No robots here!

2. Dedicated Travel Consultant

Your personal travel consultant will reach out and be your point of contact for your entire travel experience from start to finish. Did we mention you'll be working with an award winning team? Sweet!

3. Lowest Price Guaranteed

Because we're one of the largest sellers of travel, we're able to give you a discount on your vacation package. No one beats our prices!

4. Stress Free Travel

Knowing you got the best deal, all that's left is for you to pack your bags and enjoy your vacation!

We Are Committed To:

Better Business Bureau

AffordableTours.com is a proud recipient of the Better Business Bureau (BBB) awards 2006-2022 with A+ Rating.

It Pays To Refer! Earn Up To $200!

It's simple: Sign up your friends, family, and anyone to us and when they book you will receive an American Express gift card worth up to $200 in the mail for simply referring.