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

Windstar Cruises to Caribbean - Eastern 2024/2025

Save up to 80% on Windstar cruises

As a large-scale seller of Windstar Cruises to Caribbean - Eastern 2024/2025, 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 80% 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.

Windstar Image

Filter Cruises

Sail Date Cruise Line Ship Destination Departs Length Price You Save Discounts
15 reviews
Itinerary Map/Ship Image
22 night Star Collector Voyages (Fall Leaves & Caribbean Breezes 22D MTR-SJU (Oct 12 2024))WindstarStar PrideCanadaMontrealSan Juan22 NightsBar Harbor | Basseterre | Boston | Cap aux Meules | Gaspe | Gustavia | Halifax | Hamilton | Louisbourg | Lunenburg | Montreal | Portland | Quebec City | San Juan | St. George's | Virgin Gorda$7,929
Up To $1000 Onboard Credit
Suite!
View ItineraryGet FREE Quote
15 reviews
Itinerary Map/Ship Image
13 night Star Collector Voyages (Lovely Leewards 13D SJU-SJU (Nov 3 2024))WindstarStar PrideCaribbean - EasternSan JuanSan Juan13 NightsBequia | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Pigeon Island | San Juan | St. George's | St. Maarten | Virgin Gorda$5,049
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)View ItineraryGet FREE Quote
15 reviews
Itinerary Map/Ship Image
6 night Caribbean (San Juan & the Virgin Islands 6D SJU-SJU (Nov 3 2024))WindstarStar PrideCaribbean - EasternSan JuanSan Juan6 NightsGustavia | Jost Van Dyke, Great Harbour | Little Bay | San Juan | St. Maarten | Virgin Gorda$2,599
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)View ItineraryGet FREE Quote
15 reviews
Itinerary Map/Ship Image
7 night Caribbean (Windward Islands Surf & Sunsets 7D SJU-SJU (Nov 9 2024))WindstarStar PrideCaribbean - EasternSan JuanSan Juan7 NightsBequia | Les Saintes | Pigeon Island | San Juan | St. George's | St. Maarten$2,999
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)View ItineraryGet FREE Quote

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
15 reviews
Itinerary Map/Ship Image
14 night Star Collector Voyages (Lovely Leewards 14D SJU-SJU (Nov 9 2024))WindstarStar PrideCaribbeanSan JuanSan Juan14 NightsBequia | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Pigeon Island | San Juan | St. George's | St. Maarten | St. Thomas | Virgin Gorda / Prickly Pear$4,499
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)View ItineraryGet FREE Quote
15 reviews
Itinerary Map/Ship Image
14 night Star Collector Voyages (Lovely Leewards 14D SJU-SJU (Nov 16 2024))WindstarStar PrideCaribbean - EasternSan JuanSan Juan14 NightsBequia | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Pigeon Island | San Juan | St. George's | St. Maarten | St. Thomas | Virgin Gorda$4,399
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)View ItineraryGet FREE Quote
15 reviews
Itinerary Map/Ship Image
7 night Caribbean (San Juan & the Virgin Islands 7D SJU-SJU (Nov 16 2024))WindstarStar PrideCaribbean - EasternSan JuanSan Juan7 NightsGustavia | Jost Van Dyke, Great Harbour | Little Bay | San Juan | St. Maarten | St. Thomas | Virgin Gorda$2,599
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)View ItineraryGet FREE Quote
15 reviews
Itinerary Map/Ship Image
14 night Star Collector Voyages (Lovely Leewards 14D SJU-SJU (Nov 23 2024))WindstarStar PrideCaribbean - EasternSan JuanSan Juan14 NightsBequia | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Pigeon Island | San Juan | St. George's | St. Maarten | St. Thomas | Virgin Gorda$4,449
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)View ItineraryGet FREE Quote
15 reviews
Itinerary Map/Ship Image
7 night Caribbean (Windward Islands Surf & Sunsets 7D SJU-SJU (Nov 23 2024))WindstarStar PrideCaribbean - EasternSan JuanSan Juan7 NightsBequia | Les Saintes | Pigeon Island | San Juan | St. George's | St. Maarten$2,599
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)View ItineraryGet FREE Quote
15 reviews
Itinerary Map/Ship Image
7 night Caribbean (San Juan & the Virgin Islands 7D SJU-SJU (Nov 30 2024))WindstarStar PrideCaribbean - EasternSan JuanSan Juan7 NightsGustavia | Jost Van Dyke, Great Harbour | Little Bay | San Juan | St. Maarten | St. Thomas | Virgin Gorda$2,999
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)View ItineraryGet FREE Quote
15 reviews
Itinerary Map/Ship Image
7 night Caribbean (Winter Antilles Escape 7C SJU-BGI (Dec 7 2024))WindstarStar PrideCaribbean - EasternSan JuanBridgetown7 NightsBridgetown | Gustavia | Little Bay | Pigeon Island | Roseau | San Juan | St. George's | St. Thomas$2,699
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)View ItineraryGet FREE Quote
15 reviews
Itinerary Map/Ship Image
14 night Star Collector Voyages (White Sands of the Windwards 14D SJU-ORJ (Dec 7 2024))WindstarStar PrideCaribbeanSan JuanOranjestad14 NightsBridgetown | Gustavia | Kralendijk | Little Bay | Man-O-War Bay | Mayreau | Oranjestad | Pigeon Island | Roseau | San Juan | Soufriere | St. George's | St. Thomas | Willemstad$4,299
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)View ItineraryGet FREE Quote
24 reviews
Itinerary Map/Ship Image
14 night Star Collector Voyages (Caribbean Explorations 14D PH1-PH1 (Dec 21 2024))WindstarWind SurfCaribbean - EasternPhilipsburgPhilipsburg14 NightsBasseterre | Charlestown | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. Maarten | Virgin Gorda$5,699
Up To $750 Onboard Credit
 View ItineraryGet FREE Quote
24 reviews
Itinerary Map/Ship Image
7 night Caribbean (Classic Caribbean 7D PH1-PH1 (Dec 21 2024))WindstarWind SurfCaribbean - EasternPhilipsburgPhilipsburg7 NightsBasseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten$2,999
Up To $300 Onboard Credit
Onboard Credit!
View ItineraryGet FREE Quote
24 reviews
Itinerary Map/Ship Image
14 night Star Collector Voyages (Caribbean Explorations 14D PH1-PH1 (Dec 28 2024))WindstarWind SurfCaribbean - EasternPhilipsburgPhilipsburg14 NightsBasseterre | Charlestown | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. Maarten | Virgin Gorda$5,699
Up To $750 Onboard Credit
Onboard Credit!
View ItineraryGet FREE Quote
24 reviews
Itinerary Map/Ship Image
7 night Caribbean (Beach Fun & Sun: A Remote Caribbean Getaway 7D PH1-PH1 (Dec 28 2024))WindstarWind SurfCaribbean - EasternPhilipsburgPhilipsburg7 NightsFalmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Road Bay | Soper's Hole | St. Maarten | Virgin Gorda$3,799
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)View ItineraryGet FREE Quote
24 reviews
Itinerary Map/Ship Image
14 night Star Collector Voyages (Caribbean Explorations 14D PH1-PH1 (Jan 4 2025))WindstarWind SurfCaribbean - EasternPhilipsburgPhilipsburg14 NightsBasseterre | Charlestown | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. Maarten | Virgin Gorda$5,299
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)View ItineraryGet FREE Quote
24 reviews
Itinerary Map/Ship Image
7 night Caribbean (Classic Caribbean 7D PH1-PH1 (Jan 4 2025))WindstarWind SurfCaribbean - EasternPhilipsburgPhilipsburg7 NightsBasseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten$2,999
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)View ItineraryGet FREE Quote
24 reviews
Itinerary Map/Ship Image
14 night Star Collector Voyages (Caribbean Explorations 14D PH1-PH1 (Jan 11 2025))WindstarWind SurfCaribbean - EasternPhilipsburgPhilipsburg14 NightsBasseterre | Charlestown | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. Maarten | Virgin Gorda$5,299
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)View ItineraryGet FREE Quote
24 reviews
Itinerary Map/Ship Image
7 night Caribbean (Beach Fun & Sun: A Remote Caribbean Getaway 7D PH1-PH1 (Jan 11 2025))WindstarWind SurfCaribbean - EasternPhilipsburgPhilipsburg7 NightsFalmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Road Bay | Soper's Hole | St. Maarten | Virgin Gorda$3,299
Up To $500 Onboard Credit
Onboard Credit!
View ItineraryGet FREE Quote

How It Works

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

Freq Quote 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!

Dedicated Travel Consultant 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!

Low Price Guaranteed 3. Low 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!

Stress Free Travel 4. Stress Free Travel

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


AffordableTours.com BBB Business Review

Better Business Bureau

AffordableTours.com is a proud recipient of the Better Business Bureau (BBB) awards 2006-2024 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.

Read More

Get discounts by Email!