Windstar Cruises to Caribbean - All 2023/2024
Save up to 75% on Windstar cruises
As a large-scale seller of Windstar Cruises to Caribbean - All 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.

Sail Date | Cruise Line | Ship | Destination | Departs | Length | Price | You Save | Discounts | |
---|---|---|---|---|---|---|---|---|---|
10 reviews ![]() | Feb 11, 2023 | Windstar | Star Pride | San Juan | San Juan | 14 Nights | Bequia | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Pigeon Island | San Juan | St. George's | St. Maarten | St. Thomas | Virgin Gorda | $2,899 Up To $300 Onboard Credit | Suite! |
10 reviews ![]() | Feb 11, 2023 | Windstar | Star Pride | San Juan | San Juan | 7 Nights | Gustavia | Jost Van Dyke, Great Harbour | Little Bay | San Juan | St. Maarten | St. Thomas | Virgin Gorda | $1,799 Up To $200 Onboard Credit | Suite! |
24 reviews ![]() | Feb 11, 2023 | Windstar | Wind Surf | Bridgetown | Philipsburg | 7 Nights | Basseterre | Bridgetown | Gustavia | Les Saintes | Little Bay | Pigeon Island | Roseau | St. Maarten | $1,499 Up To $150 Onboard Credit | Onboard Credit! |
24 reviews ![]() | Feb 11, 2023 | Windstar | Wind Surf | Bridgetown | Philipsburg | 14 Nights | Basseterre | Bridgetown | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Pigeon Island | Roseau | Soper's Hole | St. Maarten | Virgin Gorda | $2,599 Up To $300 Onboard Credit | Onboard Credit! |
9 reviews ![]() | Feb 11, 2023 | Windstar | Wind Star | Puerto Caldera | Colon | 7 Nights | Balboa / Fuerte Amador | Colón | Golfo Dulce | Isla Parida | Panama Canal | Puerto Caldera | Quepos | $1,699 Up To $200 Onboard Credit | Onboard Credit! |
3 reviews ![]() | Feb 11, 2023 | Windstar | Star Legend | Oranjestad | Bridgetown | 7 Nights | Bridgetown | Kralendijk | Man-O-War Bay | Mayreau | Oranjestad | Soufriere | Willemstad | $1,599 Up To $200 Onboard Credit | |
10 reviews ![]() | Feb 18, 2023 | Windstar | Star Pride | San Juan | San Juan | 14 Nights | Bequia | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Pigeon Island | San Juan | St. George's | St. Maarten | St. Thomas | Virgin Gorda | $2,599 Up To $300 Onboard Credit | |
10 reviews ![]() | Feb 18, 2023 | Windstar | Star Pride | San Juan | San Juan | 7 Nights | Bequia | Les Saintes | Pigeon Island | San Juan | St. George's | St. Maarten | $1,599 Up To $200 Onboard Credit | |
24 reviews ![]() | Feb 18, 2023 | Windstar | Wind Surf | Philipsburg | Philipsburg | 7 Nights | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Soper's Hole | St. Maarten | Virgin Gorda | $1,999 Up To $200 Onboard Credit | |
24 reviews ![]() | Feb 18, 2023 | Windstar | Wind Surf | Philipsburg | Bridgetown | 14 Nights | Basseterre | Bridgetown | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Pigeon Island | Roseau | Soper's Hole | St. Maarten | Virgin Gorda | $2,999 Up To $300 Onboard Credit | Onboard Credit! |
3 reviews ![]() | Feb 18, 2023 | Windstar | Star Legend | Bridgetown | Oranjestad | 7 Nights | Bridgetown | Kralendijk | Man-O-War Bay | Mayreau | Oranjestad | Soufriere | Willemstad | $1,599 Up To $200 Onboard Credit | Suite! |
3 reviews ![]() | Feb 18, 2023 | Windstar | Star Legend | Bridgetown | Balboa | 14 Nights | Balboa / Fuerte Amador | Bocas del Toro | Bridgetown | Cartagena | Kralendijk | Man-O-War Bay | Mayreau | Oranjestad | Panama Canal | San Blas | Santa Marta | Soufriere | Willemstad | $2,499 Up To $250 Onboard Credit | Suite! |
10 reviews ![]() | Feb 25, 2023 | Windstar | Star Pride | San Juan | San Juan | 14 Nights | Bequia | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Pigeon Island | San Juan | St. George's | St. Maarten | St. Thomas | Virgin Gorda | $2,799 Up To $300 Onboard Credit | Suite! |
10 reviews ![]() | Feb 25, 2023 | Windstar | Star Pride | San Juan | San Juan | 7 Nights | Gustavia | Jost Van Dyke, Great Harbour | Little Bay | San Juan | St. Maarten | St. Thomas | Virgin Gorda | $1,599 Up To $200 Onboard Credit | |
9 reviews ![]() | Feb 25, 2023 | Windstar | Wind Star | Puerto Caldera | Colon | 7 Nights | Balboa / Fuerte Amador | Colón | Golfo Dulce | Isla Parida | Panama Canal | Puerto Caldera | Quepos | $1,599 Up To $200 Onboard Credit | Onboard Credit! |
24 reviews ![]() | Feb 25, 2023 | Windstar | Wind Surf | Philipsburg | Bridgetown | 7 Nights | Basseterre | Bridgetown | Gustavia | Les Saintes | Little Bay | Pigeon Island | Roseau | St. Maarten | $1,499 Up To $150 Onboard Credit Welcome Reception Exclusive Amenity Distinctive Host | *Distinctive Voyage |
24 reviews ![]() | Feb 25, 2023 | Windstar | Wind Surf | Philipsburg | Bridgetown | 14 Nights | Anse Mitan | Basseterre | Bequia | Bridgetown | Castries | Gustavia | Les Saintes | Little Bay | Mayreau | Pigeon Island | Roseau | St. George's | St. Maarten | The Pitons | $2,399 Up To $250 Onboard Credit | Onboard Credit! |
3 reviews ![]() | Feb 25, 2023 | Windstar | Star Legend | Oranjestad | Balboa | 7 Nights | Balboa / Fuerte Amador | Bocas del Toro | Cartegena | Oranjestad | Panama Canal | San Blas | Santa Marta | $1,599 Up To $200 Onboard Credit | |
10 reviews ![]() | Mar 04, 2023 | Windstar | Star Pride | San Juan | San Juan | 14 Nights | Bequia | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Pigeon Island | San Juan | St. George's | St. Maarten | St. Thomas | Virgin Gorda | $3,199 Up To $500 Onboard Credit | Suite! |
10 reviews ![]() | Mar 04, 2023 | Windstar | Star Pride | San Juan | San Juan | 7 Nights | Bequia | Les Saintes | Pigeon Island | San Juan | St. George's | St. Maarten | $1,599 Up To $200 Onboard Credit |
Departure Ports
- Papeete, French Polynesia Cruises (156)
- Athens (Piraeus), Greece Cruises (119)
- Philipsburg, St. Maarten Cruises (74)
- Civitavecchia, Italy Cruises (45)
- Bridgetown, Barbados Cruises (38)
- Barcelona, Spain Cruises (37)
- Puerto Caldera, Costa Rica Cruises (36)
- Reykjavik, Iceland Cruises (35)
- Lisbon, Portugal Cruises (30)
- Venice, Italy Cruises (28)
- Colon, Panama Cruises (26)
- San Juan, Puerto Rico Cruises (21)
Destinations
- Europe - All Cruises (330)
- Mediterranean Cruises (291)
- Greek Isles Cruises (174)
- Europe - Western Cruises (169)
- Tahiti Cruises (162)
- Caribbean - All Cruises (111)
- Asia Cruises (103)
- Black Sea Cruises (102)
- Caribbean - Southern Cruises (91)
- Caribbean - Eastern Cruises (89)
- Europe - Northern Cruises (74)
- Central America Cruises (72)
Departure
- 2023 Cruises
- 2024 Cruises
- 2025 Cruises
- Feb 2023 Cruises
- Mar 2023 Cruises
- Apr 2023 Cruises
- May 2023 Cruises
- Jun 2023 Cruises
- Jul 2023 Cruises
- Aug 2023 Cruises
- Sep 2023 Cruises
- Oct 2023 Cruises
- Nov 2023 Cruises
- Dec 2023 Cruises
- Jan 2024 Cruises
- Feb 2024 Cruises
- Mar 2024 Cruises
- Apr 2024 Cruises
- May 2024 Cruises
- Jun 2024 Cruises
- Jul 2024 Cruises
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!