Get FREE Price Alerts

Subscribe to our weekly cruise deals email and enjoy FREE price change alerts and updates for this cruise and others like it.

We promise to protect your privacy and personal data. You can review our privacy policy here.

Modify Your Choices
Vacation Type


Filters
Destination
- Any Destination
Travel Dates
Narrow Date Range
Departure Port
- Bridgetown, Barbados
Cruise Length
- All Durations
Cruise Line
- Windstar Cruises
Cruise Ships
- All Cruise Ships

Cruises from Bridgetown


Sailings per page
8 Matched Sailings
Departing
Itinerary and Ship
Length
Save to
Favorites
Priced from

Nov 27, 2026

(Friday)

7 Night Jewels of the Windward Islands Cruise

Star Legend
Windstar Cruises
Starts: Bridgetown, Barbados
Ends: Bridgetown, Barbados
Ports of Call:
Bridgetown, Anse Mitan, Rodney Bay, Castries, The Pitons, Mayreau, St George's, Bequia, Bridgetown

7 Nights


Add to Favorites
Compare Favorites
from

$2,838

per person
(double occupancy)
Includes taxes & fees
Learn More

Dec 04, 2026

(Friday)

8 Night Windward Ways and Tobago Cays Cruise

Star Legend
Windstar Cruises
Starts: Bridgetown, Barbados
Ends: Oranjestad, Aruba
Ports of Call:
Bridgetown, The Pitons, Scarborough, Bequia, Mayreau, St George's, Willemstad (Curacao), Oranjestad

8 Nights


Add to Favorites
Compare Favorites
from

$3,519

per person
(double occupancy)
Includes taxes & fees
Learn More

Mar 02, 2027

(Tuesday)

15 Night Knot Your Average Crossing Cruise

Star Legend
Windstar Cruises
Starts: Bridgetown, Barbados
Ends: Lisbon, Portugal
Ports of Call:
Bridgetown, Madeira, PORTO SANTO, Casablanca, Lisbon
Special Promotions

15 Nights


Add to Favorites
Compare Favorites
from

$3,770

per person
(double occupancy)
Includes taxes & fees
Learn More

Nov 27, 2026

(Friday)

15 Night Star Collector Captivating Caribbean Cruise

Star Legend
Windstar Cruises
Starts: Bridgetown, Barbados
Ends: Oranjestad, Aruba
Ports of Call:
Bridgetown, Anse Mitan, Rodney Bay, Castries, The Pitons, Mayreau, St George's, Bequia, Bridgetown...

15 Nights


Add to Favorites
Compare Favorites
from

$5,358

per person
(double occupancy)
Includes taxes & fees
Learn More

Dec 04, 2026

(Friday)

16 Night Star Collector Windward Islands and Spanish New World Cruise

Star Legend
Windstar Cruises
Starts: Bridgetown, Barbados
Ends: Fuerte Amador, Panama
Ports of Call:
Bridgetown, The Pitons, Scarborough, Bequia, Mayreau, St George's, Willemstad (Curacao), Oranjestad...

16 Nights


Add to Favorites
Compare Favorites
from

$5,611

per person
(double occupancy)
Includes taxes & fees
Learn More

Nov 24, 2026

(Tuesday)

11 Night Colombian and Southern Caribbean Coastlines Cruise

Wind Star
Windstar Cruises
Starts: Bridgetown, Barbados
Ends: Colon, Panama
Ports of Call:
Bridgetown, Bequia, St George's, Bonaire, Willemstad (Curacao), Oranjestad, Cartagena...
Special Promotions

11 Nights


Add to Favorites
Compare Favorites
from

$5,730

per person
(double occupancy)
Includes taxes & fees
Learn More

Mar 02, 2027

(Tuesday)

23 Night Star Collector Spanish Shores Transatlantic Crossing Cruise

Star Legend
Windstar Cruises
Starts: Bridgetown, Barbados
Ends: Barcelona, Spain
Ports of Call:
Bridgetown, Madeira, PORTO SANTO, Casablanca, Lisbon, Cadiz (Seville), Gibraltar, Malaga, Almeria...

23 Nights


Add to Favorites
Compare Favorites
from

$6,350

per person
(double occupancy)
Includes taxes & fees
Learn More

Nov 24, 2026

(Tuesday)

18 Night Star Collector Reefs and Rainforests the Caribbean Colombia Panama and Costa Rica via the Panama Canal Cruise

Wind Star
Windstar Cruises
Starts: Bridgetown, Barbados
Ends: Puerto Caldera, Costa Rica
Ports of Call:
Bridgetown, Bequia, St George's, Bonaire, Willemstad (Curacao), Oranjestad, Cartagena...
Special Promotions

18 Nights


Add to Favorites
Compare Favorites

Pricing On
Request

Learn More



Overlay Title