• We forecast future price movements.
  • We find the best deals in the market.
  • We inform you about every price change.

Never miss the right time to book your perfect cruise with us!


14 Night Caribbean

  • Summary
  • Ship
  • Itinerary
  • Price History
  • Dates & Future Prices
  • Book Now
© Windstar
Wind Surf © Windstar
Wind Surf © Windstar
Wind Surf Oceanview Stateroom © Windstar
Wind Surf Suite © Windstar
Wind Surf Suite © Windstar
Wind Surf Suite © Windstar
Wind Surf Suite © Windstar
Restaurant Amphora on Wind Surf © Windstar
Pool on Wind Surf © Windstar
Wind Surf Oceanview
Wind Surf Oceanview © Windstar
Wind Surf Pool
Wind Surf Pool © Windstar
Ship facts
? The Quality Score is our combined rating balancing professional reviews and customer feedback on a ship level. The score can range from 0 (everybody hates it) to 100 (everybody loves it).
0.6
Customer : Crew Ratio
310
Passengers
178
Crew
1989
Construction Year
47.6
Customer : Space Ratio
6
Passenger Decks
155
Cabins
Small
Ship Size
Ship is pretty good!
? The Quality Score is our combined rating balancing professional reviews and customer feedback on a ship level. The score can range from 0 (everybody hates it) to 100 (everybody loves it).

Laid back yet upscale, Wind Surf offers comfort and class to passengers cruising below its five masts of billowing sails. The ship itself is older, and exudes romance and a little nostalgia, and its clubby yet inclusive feel is only further emphasized by the genuine friendliness of the crew.
More... Current Position

Overall rating
? The Overall Rating is our combined rating for each cruise ship based on balancing their professional reviews and customer feedback.
Ship is pretty good!
55/100
Professional Reviews
? See how the various aspects of this cruise ship compares to all other ships in our database.
Ship Facilities are good
Accomodation is fantastic
Beverage is good
Entertainment is good
Service is good
Cruise is good
Customer Reviews
? Customer reviews give you a good overview of how much customers like this cruise ship.
2.1/5
people think it's OK
bad
7
acceptable
16
ok
37
good
49
excellent
175
overall
42%
of passengers would recommend this ship
Ship facts
? The Quality Score is our combined rating balancing professional reviews and customer feedback on a ship level. The score can range from 0 (everybody hates it) to 100 (everybody loves it).
0.6
Customer : Crew Ratio
310
Passengers
178
Crew
1989
Construction Year
47.6
Customer : Space Ratio
6
Passenger Decks
155
Cabins
Small
Ship Size



From

Philipsburg, Saint-Martin

to

Bridgetown

Day Port Arrival Departure
0 		Philipsburg, Saint-Martin - -
1 		Falmouth, Cornwall, England 08:00 18:00
2 		Road Bay, Anguilla 08:00 18:00
3 		Soper's Hole, Tortola, B.V.I. 08:00 18:00
4-5 		Jost Van Dyke - -
6 		Prickly Pear Island, B.V.I. 08:00 17:00
7 		Gustavia 08:00 22:00
8 		Philipsburg, Saint-Martin 06:00 19:00
9 		Basseterre 08:00 21:00
10 		Gustavia 08:00 22:00
11 		St. John's, Antigua 08:00 22:00
12 		Iles Des Saintes (West Indies) 08:00 17:00
13 		Roseau 08:00 16:00
14 		Mayreau, Grenadines 08:00 17:00
15 		Bridgetown 05:00 00:00



Prices for other Dates and Cabins

Jan 04, 2026

Choose other date/cabin type to see alternatives
min. $874
cheaper
costlier
max. $24379
Jan 04, 2026
Interior
-4830
Ocean
-4630
Balcony
-3950
Suite
-3650
Jan 04, 2026
Ocean
-1400
Suite
$6299
Interior
Sold Out
Balcony
Sold Out
Jan 04, 2026
Interior
Sold Out
Ocean
Sold Out
Balcony
Sold Out
Suite
Sold Out
Jan 08, 2026
Interior
-4850
Ocean
-4650
Balcony
-3970
Suite
Sold Out
Jan 08, 2026
Interior
-4810
Ocean
-4600
Balcony
-3920
Suite
-3620
Value for money:
? The colors below indicate what you get for your money.
A steal
Fair
Expensive
N/A




N/A
No price rating data
Set price alert
$4899
$350 p.P./ night
Slightly expensive
Set price alert
N/A
No price rating data
Set price alert
$6299
$450 p.P./ night
Expensive
Set price alert
dasda Interior Oceanview Balcony Suite
Current Price - $4899 - $6299
Price per Day - $350 - $450
Previous Price - $4599 - $5899
Change in $ - $300 - $400
Change in % - 6.12% - 6.35%
Updated Jan 09, 2025 Jul 27, 2025 Jan 09, 2025 Jun 28, 2025
Initial Price - $4099 - $5799
Lowest Price Ever - $4099 - $5799
Our Opinion Slightly expensive Expensive
Historic prices Interior cabin price history Oceanview cabin price history Balcony cabin price history Suite cabin price history
Book Now Book Now Book Now Book Now



Interior cabin, departing on Jan 04, 2026.

We don’t have enough data to show any prediction or the accuracy is not high enough. We are sorry, please try again another day.

Jan 04, 2026 Departure

We don’t have enough data to show any prediction or the accuracy is not high enough. We are sorry, please try again another day.

Jan 04, 2026 Departure

We don’t have enough data to show any prediction or the accuracy is not high enough. We are sorry, please try again another day.

Jan 04, 2026 Departure

We don’t have enough data to show any prediction or the accuracy is not high enough. We are sorry, please try again another day.

Jan 04, 2026 Departure

Don't miss a price drop!
Set an alert now!

SET ALERT
Wind Surf Oceanview
Wind Surf Oceanview © Windstar
Why we like this 14 Night Caribbean
  • Ecstatic customers.
  • One of the best customer recommendation ratios in the market.
  • Caribbean generally offers great beaches, fun excursions and ample shopping opportunities.
  • Great passenger to crew ratio - you will get pampered!
  • Plenty of space on board.