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.

Email Address

Track this Cruise

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

Search Results

42 Matched Sailings

Departing	Itinerary and Ship	Length	Save to Favorites	Priced from
Feb 21, 2028 (Monday) Other Dates	22 Night Star Collector Caribbean Charms to Iberian Shores Cruise Star Legend Windstar Cruises Starts: San Juan, Puerto Rico Ends: Lisbon, Portugal Ports of Call: San Juan, St George's, Bequia, Mayreau, Iles des Saintes, Marigot, San Juan, Agadir, Casablanca... (see itinerary)	22 Nights	Add to Favorites Compare Favorites	from $2,451 per person (double occupancy) Includes taxes & fees Learn More
Mar 19, 2028 (Sunday) Other Dates	15 Night Ocean Crossing Cruise Wind Surf Windstar Cruises Starts: Philipsburg (St. Maarten), Netherlands Antilles Ends: Lisbon, Portugal Ports of Call: Philipsburg (St. Maarten), Horta, Ponta Delgada, Lisbon (see itinerary) The Signature Collection - Exclusive Amenities	15 Nights	Add to Favorites Compare Favorites	from $2,580 per person (double occupancy) Includes taxes & fees Learn More
Nov 05, 2027 (Friday) Other Dates	15 Night Ocean Crossing Cruise Wind Surf Windstar Cruises Starts: Lisbon, Portugal Ends: Philipsburg (St. Maarten), Netherlands Antilles Ports of Call: Lisbon, Madeira, Great Harbour, Philipsburg (St. Maarten) (see itinerary) Special Promotions Up to $300 Reduced Deposit Free All-Inclusive Package	15 Nights	Add to Favorites Compare Favorites	from $2,580 per person (double occupancy) Includes taxes & fees Learn More
May 20, 2027 (Thursday) Other Dates	12 Night Ocean Crossing Cruise Star Seeker Windstar Cruises Starts: Tokyo, Japan Ends: Seward, Alaska Ports of Call: Tokyo, Crossing the International Date Line, Seward (see itinerary) Special Promotions Up to $300 Reduced Deposit Free All-Inclusive Package	12 Nights	Add to Favorites Compare Favorites	from $2,619 per person (double occupancy) Includes taxes & fees Learn More
May 25, 2029 (Friday) Other Dates	12 Night Ocean Crossing Cruise Star Seeker Windstar Cruises Starts: Tokyo, Japan Ends: Seward, Alaska Ports of Call: Tokyo, Crossing the International Date Line, Seward (see itinerary)	12 Nights	Add to Favorites Compare Favorites	from $2,619 per person (double occupancy) Includes taxes & fees Learn More
Apr 03, 2028 (Monday) Other Dates	16 Night Ocean Crossing Cruise Star Pride Windstar Cruises Starts: San Juan, Puerto Rico Ends: Amsterdam, Netherlands Ports of Call: San Juan, Lisbon, Brest, Amsterdam (see itinerary) The Signature Collection - Exclusive Amenities	16 Nights	Add to Favorites Compare Favorites	from $2,760 per person (double occupancy) Includes taxes & fees Learn More
Mar 30, 2027 (Tuesday) Other Dates	16 Night Ocean Crossing Cruise Star Pride Windstar Cruises Starts: San Juan, Puerto Rico Ends: London, United Kingdom Ports of Call: San Juan, Lisbon, London (see itinerary) Special Promotions Solo Traveler Offer Up to $300 Reduced Deposit Free All-Inclusive Package	16 Nights	Add to Favorites Compare Favorites	from $2,760 per person (double occupancy) Includes taxes & fees Learn More
Mar 02, 2027 (Tuesday) Other Dates	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 (see itinerary) Special Promotions Up to $300 Reduced Deposit Free All-Inclusive Package	15 Nights	Add to Favorites Compare Favorites	from $2,796 per person (double occupancy) Includes taxes & fees Learn More
Mar 27, 2027 (Saturday) Other Dates	15 Night Ocean Crossing Cruise Wind Surf Windstar Cruises Starts: Philipsburg (St. Maarten), Netherlands Antilles Ends: Lisbon, Portugal Ports of Call: Philipsburg (St. Maarten), Madeira, PORTO SANTO, Lisbon (see itinerary) Special Promotions Up to $300 Reduced Deposit Free All-Inclusive Package The Signature Collection - Exclusive Amenities	15 Nights	Add to Favorites Compare Favorites	from $3,030 per person (double occupancy) Includes taxes & fees Learn More
Nov 12, 2026 (Thursday) Other Dates	15 Night Ocean Crossing Cruise Star Legend Windstar Cruises Starts: Malaga, Spain Ends: Bridgetown, Barbados Ports of Call: Malaga, Tangier, Casablanca, Madeira, Bridgetown (see itinerary) Special Promotions Solo Traveler Offer The Signature Collection - Exclusive Amenities	15 Nights	Add to Favorites Compare Favorites	from $3,304 per person (double occupancy) Includes taxes & fees Learn More
Sep 01, 2027 (Wednesday) Other Dates	12 Night Ocean Crossing Cruise Star Seeker Windstar Cruises Starts: Seward, Alaska Ends: Otaru, Japan Ports of Call: Seward, Otaru (see itinerary) Special Promotions Up to $300 Reduced Deposit Free All-Inclusive Package	12 Nights	Add to Favorites Compare Favorites	from $3,725 per person (double occupancy) Includes taxes & fees Learn More
Aug 30, 2028 (Wednesday) Other Dates	12 Night Ocean Crossing Cruise Star Seeker Windstar Cruises Starts: Seward, Alaska Ends: Tokyo, Japan Ports of Call: Seward, Tokyo (see itinerary)	12 Nights	Add to Favorites Compare Favorites	from $3,790 per person (double occupancy) Includes taxes & fees Learn More
Sep 02, 2026 (Wednesday) Other Dates	13 Night Ocean Crossing Cruise Star Seeker Windstar Cruises Starts: Seward, Alaska Ends: Tokyo, Japan Ports of Call: Seward, Tokyo (see itinerary)	13 Nights	Add to Favorites Compare Favorites	from $4,226 per person (double occupancy) Includes taxes & fees Learn More
Nov 10, 2026 (Tuesday) Other Dates	14 Night Knot Your Average Crossing Cruise Wind Star Windstar Cruises Starts: Lisbon, Portugal Ends: Bridgetown, Barbados Ports of Call: Lisbon, Bridgetown (see itinerary) The Signature Collection - Exclusive Amenities Knot Your Average Crossing	14 Nights	Add to Favorites Compare Favorites	from $4,226 per person (double occupancy) Includes taxes & fees Learn More
Mar 27, 2028 (Monday) Other Dates	23 Night Star Collector Tropical Horizons to Historic Amsterdam Cruise Star Pride Windstar Cruises Starts: San Juan, Puerto Rico Ends: Amsterdam, Netherlands Ports of Call: San Juan, St George's, Bequia, Mayreau, Iles des Saintes, Marigot, San Juan, Lisbon, Brest... (see itinerary)	23 Nights	Add to Favorites Compare Favorites	from $4,719 per person (double occupancy) Includes taxes & fees Learn More
Mar 12, 2028 (Sunday) Other Dates	22 Night Star Collector Hearty Ports and Rum Punches A Transatlantic Crossing Cruise Wind Surf Windstar Cruises Starts: Philipsburg (St. Maarten), Netherlands Antilles Ends: Lisbon, Portugal Ports of Call: Philipsburg (St. Maarten), St John's, Road Bay, Sopers Hole, Great Harbour... (see itinerary)	22 Nights	Add to Favorites Compare Favorites	from $4,731 per person (double occupancy) Includes taxes & fees Learn More
Nov 05, 2027 (Friday) Other Dates	23 Night Star Collector Hearty Ports and Rum Punches A Transatlantic Crossing Cruise Wind Surf Windstar Cruises Starts: Lisbon, Portugal Ends: Philipsburg (St. Maarten), Netherlands Antilles Ports of Call: Lisbon, Madeira, Great Harbour, Philipsburg (St. Maarten), Gustavia St. Barts, St John's, Deshaies... (see itinerary) Special Promotions Up to $300 Reduced Deposit Free All-Inclusive Package	23 Nights	Add to Favorites Compare Favorites	from $4,731 per person (double occupancy) Includes taxes & fees Learn More
Mar 27, 2027 (Saturday) Other Dates	23 Night Star Collector Atlantic Interludes and Iberian Indulgences Cruise Wind Surf Windstar Cruises Starts: Philipsburg (St. Maarten), Netherlands Antilles Ends: Tarragona, Spain Ports of Call: Philipsburg (St. Maarten), Madeira, PORTO SANTO, Lisbon, Cadiz (Seville), Gibraltar, Malaga... (see itinerary) Special Promotions Up to $300 Reduced Deposit Free All-Inclusive Package	23 Nights	Add to Favorites Compare Favorites	from $4,822 per person (double occupancy) Includes taxes & fees Learn More
Mar 02, 2027 (Tuesday) Other Dates	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... (see itinerary) Special Promotions Up to $300 Reduced Deposit Free All-Inclusive Package	23 Nights	Add to Favorites Compare Favorites	from $4,822 per person (double occupancy) Includes taxes & fees Learn More
Nov 12, 2026 (Thursday) Other Dates	22 Night Star Collector Caribbean Beats and Transatlantic Treats Cruise Star Legend Windstar Cruises Starts: Malaga, Spain Ends: Bridgetown, Barbados Ports of Call: Malaga, Tangier, Casablanca, Madeira, Bridgetown, Anse Mitan, Rodney Bay, Castries, The Pitons... (see itinerary) The Signature Collection - Exclusive Amenities	22 Nights	Add to Favorites Compare Favorites	from $5,491 per person (double occupancy) Includes taxes & fees Learn More
Nov 04, 2026 (Wednesday) Other Dates	23 Night Star Collector Spanish Mystery and Atlantic Crossing Cruise Star Legend Windstar Cruises Starts: Barcelona, Spain Ends: Bridgetown, Barbados Ports of Call: Barcelona, To Be Announced, Malaga, Tangier, Casablanca, Madeira, Bridgetown (see itinerary)	23 Nights	Add to Favorites Compare Favorites	from $6,535 per person (double occupancy) Includes taxes & fees Learn More
Dec 06, 2027 (Monday) Other Dates	14 Night Ocean Crossing Cruise Star Legend Windstar Cruises Starts: Lisbon, Portugal Ends: San Juan, Puerto Rico Ports of Call: Lisbon, Madeira, Great Harbour, San Juan (see itinerary) Special Promotions Up to $300 Reduced Deposit Free All-Inclusive Package The Signature Collection - Exclusive Amenities	14 Nights	Add to Favorites Compare Favorites	from $7,784 per person (double occupancy) Includes taxes & fees Learn More
May 25, 2028 (Thursday) Other Dates	24 Night Star Collector Alaskan Adventures and Wonders of Japan Cruise Star Seeker Windstar Cruises Starts: Osaka, Japan Ends: Vancouver, Canada Ports of Call: Osaka, Crossing the International Date Line, Seward, Kenai Fjords National Park, Juneau, Haines... (see itinerary)	24 Nights	Add to Favorites Compare Favorites	from $8,170 per person (double occupancy) Includes taxes & fees Learn More
May 20, 2027 (Thursday) Other Dates	24 Night Star Collector Alaska Discovery and Pacific Crossing Cruise Star Seeker Windstar Cruises Starts: Tokyo, Japan Ends: Vancouver, Canada Ports of Call: Tokyo, Crossing the International Date Line, Seward, Kenai Fjords National Park, Sitka... (see itinerary) Special Promotions Up to $300 Reduced Deposit Free All-Inclusive Package	24 Nights	Add to Favorites Compare Favorites	from $8,213 per person (double occupancy) Includes taxes & fees Learn More
May 15, 2029 (Tuesday) Other Dates	22 Night Star Collector Japan and North Pacific Crossing Cruise Star Seeker Windstar Cruises Starts: Osaka, Japan Ends: Seward, Alaska Ports of Call: Osaka, Takamatsu, Tomonoura, Hiroshima, Karatsu Japan, Busan (Pusan), Hashima Island, Nagasaki... (see itinerary)	22 Nights	Add to Favorites Compare Favorites	from $8,234 per person (double occupancy) Includes taxes & fees Learn More