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
- Caribbean
Travel Dates
Narrow Date Range
Departure Port
- All Departure Ports
Cruise Length
- All Durations
Cruise Line
- Windstar Cruises
Cruise Ships
- All Cruise Ships

Cruises in December 2024


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

Dec 07, 2024

(Saturday)

7 Night Jewels of the Windward Islands Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
Starts: Bridgetown, Barbados
Ends: Bridgetown, Barbados
Ports of Call:
Bridgetown, Pigeon Island, Castries, The Pitons, Kingstown, Mayreau, St George's, Bequia, Bridgetown

7 Nights


Add to Favorites
Compare Favorites
Lowest from

$2,199

per person
(double occupancy)
Learn More

Dec 07, 2024

(Saturday)

7 Night Winter Antilles Escape Cruise

Star Pride
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: Bridgetown, Barbados
Ports of Call:
San Juan, Charlotte Amalie (St Thomas), Gustavia St. Barts, Basseterre, Roseau, Pigeon Island...

7 Nights


Add to Favorites
Compare Favorites
Lowest from

$2,199

per person
(double occupancy)
Learn More

Dec 14, 2024

(Saturday)

7 Night Windward Islands Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
Starts: Bridgetown, Barbados
Ends: Bridgetown, Barbados
Ports of Call:
Bridgetown, Basseterre, Iles des Saintes, Roseau, Anse Mitan, Pigeon Island, Bridgetown

7 Nights


Add to Favorites
Compare Favorites
Lowest from

$2,199

per person
(double occupancy)
Learn More

Dec 14, 2024

(Saturday)

7 Night Windward Ways and Tobago Cays Cruise

Star Pride
Windstar Cruises
Starts: Bridgetown, Barbados
Ends: Oranjestad, Aruba
Ports of Call:
Bridgetown, Man of War Bay, Mayreau, Soufriere , St George's, Willemstad (Curacao), Oranjestad

7 Nights


Add to Favorites
Compare Favorites
Lowest from

$2,199

per person
(double occupancy)
Learn More

Dec 21, 2024

(Saturday)

7 Night Jewels of the Windward Islands Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
Starts: Bridgetown, Barbados
Ends: Bridgetown, Barbados
Ports of Call:
Bridgetown, Pigeon Island, Castries, The Pitons, Kingstown, Mayreau, St George's, Bequia, Bridgetown

7 Nights


Add to Favorites
Compare Favorites
Lowest from

$2,599

per person
(double occupancy)
Learn More

Dec 21, 2024

(Saturday)

7 Night Classic Caribbean Cruise

Wind Surf
Windstar Cruises
4.3 based on 8 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), Charlestown, Roseau, Pigeon Island, Iles des Saintes, Basseterre...

7 Nights


Add to Favorites
Compare Favorites
Lowest from

$2,599

per person
(double occupancy)
Learn More

Dec 28, 2024

(Saturday)

7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise

Wind Surf
Windstar Cruises
4.3 based on 8 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), Falmouth Harbour, Road Bay, Sopers Hole, Great Harbour, Virgin Gorda...

7 Nights


Add to Favorites
Compare Favorites
Lowest from

$2,599

per person
(double occupancy)
Learn More

Dec 28, 2024

(Saturday)

7 Night Windward Islands Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
Starts: Bridgetown, Barbados
Ends: Bridgetown, Barbados
Ports of Call:
Bridgetown, St John's, Roseau, Castries, Anse Mitan, Pigeon Island, Bridgetown

7 Nights


Add to Favorites
Compare Favorites
Lowest from

$2,599

per person
(double occupancy)
Learn More

Dec 07, 2024

(Saturday)

14 Night Star Collector Windward Treasures An Antilles Odyssey Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
Starts: Bridgetown, Barbados
Ends: Bridgetown, Barbados
Ports of Call:
Bridgetown, Pigeon Island, Castries, The Pitons, Kingstown, Mayreau, St George's, Bequia...

14 Nights


Add to Favorites
Compare Favorites
Lowest from

$3,499

per person
(double occupancy)
Learn More

Dec 07, 2024

(Saturday)

14 Night Star Collector White Sands of the Windward Islands Cruise

Star Pride
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: Oranjestad, Aruba
Ports of Call:
San Juan, Charlotte Amalie (St Thomas), Gustavia St. Barts, Basseterre, Roseau, Pigeon Island...

14 Nights


Add to Favorites
Compare Favorites
Lowest from

$3,499

per person
(double occupancy)
Learn More

Dec 14, 2024

(Saturday)

14 Night Star Collector Windward Treasures An Antilles Odyssey Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
Starts: Bridgetown, Barbados
Ends: Bridgetown, Barbados
Ports of Call:
Bridgetown, Basseterre, Iles des Saintes, Roseau, Anse Mitan, Pigeon Island, Bridgetown...

14 Nights


Add to Favorites
Compare Favorites
Lowest from

$3,799

per person
(double occupancy)
Learn More

Dec 28, 2024

(Saturday)

14 Night Star Collector Caribbean Explorations Cruise

Wind Surf
Windstar Cruises
4.3 based on 8 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), Falmouth Harbour, Road Bay, Sopers Hole, Great Harbour, Virgin Gorda...

14 Nights


Add to Favorites
Compare Favorites
Lowest from

$3,799

per person
(double occupancy)
Learn More

Dec 28, 2024

(Saturday)

14 Night Star Collector Windward Treasures An Antilles Odyssey Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
Starts: Bridgetown, Barbados
Ends: Bridgetown, Barbados
Ports of Call:
Bridgetown, St John's, Roseau, Castries, Anse Mitan, Pigeon Island, Bridgetown, Pigeon Island...

14 Nights


Add to Favorites
Compare Favorites
Lowest from

$3,799

per person
(double occupancy)
Learn More

Dec 21, 2024

(Saturday)

14 Night Star Collector Windward Treasures An Antilles Odyssey Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
Starts: Bridgetown, Barbados
Ends: Bridgetown, Barbados
Ports of Call:
Bridgetown, Pigeon Island, Castries, The Pitons, Kingstown, Mayreau, St George's, Bequia...

14 Nights


Add to Favorites
Compare Favorites
Lowest from

$4,099

per person
(double occupancy)
Learn More

Dec 21, 2024

(Saturday)

14 Night Star Collector Caribbean Explorations Cruise

Wind Surf
Windstar Cruises
4.3 based on 8 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), Charlestown, Roseau, Pigeon Island, Iles des Saintes, Basseterre...

14 Nights


Add to Favorites
Compare Favorites
Lowest from

$4,099

per person
(double occupancy)
Learn More

Dec 14, 2024

(Saturday)

14 Night Star Collector Windward Islands and Spanish New World Cruise

Star Pride
Windstar Cruises
Starts: Bridgetown, Barbados
Ends: Fuerte Amador, Panama
Ports of Call:
Bridgetown, Man of War Bay, Mayreau, Soufriere , St George's, Willemstad (Curacao), Oranjestad...

14 Nights


Add to Favorites
Compare Favorites
Lowest from

$4,099

per person
(double occupancy)
Learn More

Dec 21, 2024

(Saturday)

7 Night Panama Canal Cartagena San Blas Islands and More Cruise

Star Pride
Windstar Cruises
Starts: Oranjestad, Aruba
Ends: Fuerte Amador, Panama
Ports of Call:
Oranjestad, Cartagena, San Blas Islands, Bocas Del Toro, Cruising the Panama Canal, Fuerte Amador

7 Nights


Add to Favorites
Compare Favorites
Lowest from

$6,399

per person
(double occupancy)
Learn More

Dec 28, 2024

(Saturday)

7 Night Panama Canal Cartagena San Blas Islands and More Cruise

Star Pride
Windstar Cruises
Starts: Fuerte Amador, Panama
Ends: Oranjestad, Aruba
Ports of Call:
Fuerte Amador, Cruising the Panama Canal, Bocas Del Toro, San Blas Islands, Cartagena, Oranjestad

7 Nights


Add to Favorites
Compare Favorites
Lowest from

$6,399

per person
(double occupancy)
Learn More

Dec 28, 2024

(Saturday)

14 Night Star Collector Windward Islands and Spanish New World Cruise

Star Pride
Windstar Cruises
Starts: Fuerte Amador, Panama
Ends: Bridgetown, Barbados
Ports of Call:
Fuerte Amador, Cruising the Panama Canal, Bocas Del Toro, San Blas Islands, Cartagena, Oranjestad...

14 Nights


Add to Favorites
Compare Favorites
Lowest from

$10,599

per person
(double occupancy)
Learn More

Dec 07, 2024

(Saturday)

14 Night Ocean Crossing Cruise

Wind Surf
Windstar Cruises
4.3 based on 8 ratings
Starts: Lisbon, Portugal
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Lisbon, St John's, Philipsburg (St. Maarten)

14 Nights


Add to Favorites
Compare Favorites

Pricing On
Request

Learn More



Overlay Title