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
- All Departure Ports
Cruise Length
- All Durations
Cruise Line
- Windstar Cruises
Cruise Ships
- All Cruise Ships

Search Results


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

May 06, 2026

(Wednesday)

1 Night One Day Pacific Adventure Cruise

Star Seeker
Windstar Cruises
Starts: Seattle, Washington
Ends: Vancouver, Canada
Ports of Call:
Seattle, Vancouver

1 Nights


Add to Favorites
Compare Favorites
from

$314

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

Jan 02, 2025

(Thursday)

14 Night Ocean Crossing Cruise

Star Breeze
Windstar Cruises
4.2 based on 5 ratings
Starts: Papeete, French Polynesia
Ends: Puerto Caldera, Costa Rica
Ports of Call:
Papeete, Puerto Caldera
Special Promotions

14 Nights


Add to Favorites
Compare Favorites
from

$2,008

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

Feb 02, 2025

(Sunday)

14 Night Ocean Crossing Cruise

Star Breeze
Windstar Cruises
4.2 based on 5 ratings
Starts: Puerto Caldera, Costa Rica
Ends: Papeete, French Polynesia
Ports of Call:
Puerto Caldera, Papeete
Special Promotions

14 Nights


Add to Favorites
Compare Favorites
from

$2,008

per person
(double occupancy)
Includes taxes & fees
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
Special Promotions

7 Nights


Add to Favorites
Compare Favorites
from

$2,018

per person
(double occupancy)
Includes taxes & fees
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...
Special Promotions

7 Nights


Add to Favorites
Compare Favorites
from

$2,040

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

Dec 02, 2025

(Tuesday)

5 Night Barefoot Break in the British Virgin Islands 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), Sopers Hole, Great Harbour, Prickly Pear British Virgin Islands...

5 Nights


Add to Favorites
Compare Favorites
from

$2,050

per person
(double occupancy)
Includes taxes & fees
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
Special Promotions

7 Nights


Add to Favorites
Compare Favorites
from

$2,140

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

Apr 28, 2026

(Tuesday)

8 Night Ocean Crossing Cruise

Star Seeker
Windstar Cruises
Starts: Puerto Vallarta, Mexico
Ends: Seattle, Washington
Ports of Call:
Puerto Vallarta, Seattle

8 Nights


Add to Favorites
Compare Favorites
from

$2,218

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

Nov 23, 2024

(Saturday)

7 Night Windward Islands Surf and Sunsets Cruise

Star Pride
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: San Juan, Puerto Rico
Ports of Call:
San Juan, St George's, Bequia, Pigeon Island, Iles des Saintes, Philipsburg (St. Maarten), San Juan
Special Promotions

7 Nights


Add to Favorites
Compare Favorites
from

$2,288

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

Dec 07, 2024

(Saturday)

9 Night Southern Spain Winter Escapes Cruise

Star Legend
Windstar Cruises
4.6 based on 5 ratings
Starts: Barcelona, Spain
Ends: Barcelona, Spain
Ports of Call:
Barcelona, Valencia, Cartagena, Gibraltar, Malaga, Palma de Mallorca, Barcelona
Special Promotions

9 Nights


Add to Favorites
Compare Favorites
from

$2,318

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

Mar 21, 2026

(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, Mayreau, Iles des Saintes, Basseterre...

7 Nights


Add to Favorites
Compare Favorites
from

$2,351

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

Dec 07, 2025

(Sunday)

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, Mayreau, Iles des Saintes, Basseterre...

7 Nights


Add to Favorites
Compare Favorites
from

$2,351

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

Apr 05, 2025

(Saturday)

10 Night Ocean Crossing Cruise

Star Pride
Windstar Cruises
Starts: Bridgetown, Barbados
Ends: Santa Cruz de Tenerife, Spain
Ports of Call:
Bridgetown, Santa Cruz de Tenerife

10 Nights


Add to Favorites
Compare Favorites
from

$2,404

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

Mar 26, 2025

(Wednesday)

15 Night Ocean Crossing Cruise

Wind Star
Windstar Cruises
4.2 based on 5 ratings
Starts: Bridgetown, Barbados
Ends: Lisbon, Portugal
Ports of Call:
Bridgetown, Lisbon
Special Promotions

15 Nights


Add to Favorites
Compare Favorites
from

$2,425

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

Nov 07, 2025

(Friday)

7 Night Southern Spain Winter Escapes Cruise

Star Legend
Windstar Cruises
4.6 based on 5 ratings
Starts: Barcelona, Spain
Ends: Malaga, Spain
Ports of Call:
Barcelona, Palma de Mallorca, Valencia, Cartagena, Gibraltar, Malaga

7 Nights


Add to Favorites
Compare Favorites
from

$2,442

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

Nov 22, 2024

(Friday)

8 Night Winter Italy and the Dalmatian Coast Cruise

Star Legend
Windstar Cruises
4.6 based on 5 ratings
Starts: Venice, Italy
Ends: Civitavecchia (Rome), Italy
Ports of Call:
Venice, Zadar, Dubrovnik, Messina, Naples, Civitavecchia (Rome)
Special Promotions

8 Nights


Add to Favorites
Compare Favorites
from

$2,457

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

Nov 30, 2024

(Saturday)

7 Night Europes Winter Riviera Cruise

Star Legend
Windstar Cruises
4.6 based on 5 ratings
Starts: Civitavecchia (Rome), Italy
Ends: Barcelona, Spain
Ports of Call:
Civitavecchia (Rome), Livorno, Genoa, Cannes, Nice, Barcelona
Special Promotions

7 Nights


Add to Favorites
Compare Favorites
from

$2,466

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

Dec 14, 2025

(Sunday)

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...

7 Nights


Add to Favorites
Compare Favorites
from

$2,467

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

Mar 14, 2026

(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...

7 Nights


Add to Favorites
Compare Favorites
from

$2,467

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

Mar 28, 2026

(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), St John's, Road Bay, Sopers Hole, Great Harbour...

7 Nights


Add to Favorites
Compare Favorites
from

$2,467

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

Feb 28, 2026

(Saturday)

7 Night Lush and Lovely Islands of the Lesser Antilles Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Bridgetown, Barbados
Ports of Call:
Philipsburg (St. Maarten), Basseterre, Gustavia St. Barts, St John's, Iles des Saintes, Roseau...

7 Nights


Add to Favorites
Compare Favorites
from

$2,520

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

Mar 28, 2026

(Saturday)

15 Night Ocean Crossing Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
Starts: Bridgetown, Barbados
Ends: Lisbon, Portugal
Ports of Call:
Bridgetown, Lisbon

15 Nights


Add to Favorites
Compare Favorites
from

$2,525

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

Nov 04, 2025

(Tuesday)

14 Night Ocean Crossing Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
Starts: Lisbon, Portugal
Ends: Bridgetown, Barbados
Ports of Call:
Lisbon, Bridgetown

14 Nights


Add to Favorites
Compare Favorites
from

$2,525

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

Mar 29, 2025

(Saturday)

14 Night Ocean Crossing and Ponta Delgada Azores Cruise

Wind Surf
Windstar Cruises
4.3 based on 8 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Lisbon, Portugal
Ports of Call:
Philipsburg (St. Maarten), Ponta Delgada, Lisbon
Special Promotions

14 Nights


Add to Favorites
Compare Favorites
from

$2,526

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

Dec 16, 2024

(Monday)

7 Night Europes Winter Riviera Cruise

Star Legend
Windstar Cruises
4.6 based on 5 ratings
Starts: Barcelona, Spain
Ends: Civitavecchia (Rome), Italy
Ports of Call:
Barcelona, Nice, Genoa, Livorno, Civitavecchia (Rome)
Special Promotions

7 Nights


Add to Favorites
Compare Favorites
from

$2,546

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



Overlay Title