Windstar Cruises January 2026
Showing 1 to 10 of total 42
From Sat 3 Jan 2026
(To Sun 11 Jan 2026)
8 Night Naturally Costa Rica
Ship Star Pride
More details at
(To Sun 11 Jan 2026)
8 Night Naturally Costa Rica
Ship Star Pride
More details at
Cruise Prices
From $2,158
Cruise Itinerary: Puerto Caldera, Costa Rica (03 Jan d1800); Playa Flamingo, Costa Rica (04 Jan 0700-1800); Curu, Costa Rica (05 Jan 0700-1800); Herradura, Costa Rica (06 Jan 0700-2100); Quepos, Costa Rica (07 Jan 0600-1800); Golfito, Costa Rica (08 Jan 0600-1700); Isla Gamez, Panama (09 Jan 0700-1800); Panama City, Panama (11 Jan a0700) >>port loads
From $2,158
Cruise Itinerary: Puerto Caldera, Costa Rica (03 Jan d1800); Playa Flamingo, Costa Rica (04 Jan 0700-1800); Curu, Costa Rica (05 Jan 0700-1800); Herradura, Costa Rica (06 Jan 0700-2100); Quepos, Costa Rica (07 Jan 0600-1800); Golfito, Costa Rica (08 Jan 0600-1700); Isla Gamez, Panama (09 Jan 0700-1800); Panama City, Panama (11 Jan a0700) >>port loads
From Sun 4 Jan 2026
(To Mon 12 Jan 2026)
8 Night Winter Italy and the Dalmatian Coast
Ship Star Legend
More details at
(To Mon 12 Jan 2026)
8 Night Winter Italy and the Dalmatian Coast
Ship Star Legend
More details at
Cruise Prices
From $3,999
Cruise Itinerary: Venice, Italy (04 Jan embark(+1)d1700); Zadar, Croatia (06 Jan 0800-1700); Dubrovnik, Croatia (07 Jan 1200(+1)1800); Messina, Sicily (10 Jan 0700-1500); Naples, Italy (11 Jan 0800-1600); Civitavecchia (Rome), Italy (12 Jan a0800) >>port loads
From $3,999
Cruise Itinerary: Venice, Italy (04 Jan embark(+1)d1700); Zadar, Croatia (06 Jan 0800-1700); Dubrovnik, Croatia (07 Jan 1200(+1)1800); Messina, Sicily (10 Jan 0700-1500); Naples, Italy (11 Jan 0800-1600); Civitavecchia (Rome), Italy (12 Jan a0800) >>port loads
From Sun 4 Jan 2026
(To Mon 19 Jan 2026)
15 Night Star Collector: Winter in Europe's Rivieras & Croatia
Ship Star Legend
More details at
(To Mon 19 Jan 2026)
15 Night Star Collector: Winter in Europe's Rivieras & Croatia
Ship Star Legend
More details at
Cruise Prices
From $5,899
Cruise Itinerary: Venice, Italy (04 Jan embark(+1)d1700); Zadar, Croatia (06 Jan 0800-1700); Dubrovnik, Croatia (07 Jan 1200(+1)1800); Messina, Sicily (10 Jan 0700-1500); Naples, Italy (11 Jan 0800-1600); Civitavecchia (Rome), Italy (12 Jan 0800-1700); Livorno (Florence/Pisa), Italy (13 Jan 0800(+1)2200); Genoa, Italy (15 Jan 0800-2200); Villefranche (Nice), France (16 Jan 0800(+1)1300); Barcelona, Spain (18 Jan a1300(+1)disembark) >>port loads
From $5,899
Cruise Itinerary: Venice, Italy (04 Jan embark(+1)d1700); Zadar, Croatia (06 Jan 0800-1700); Dubrovnik, Croatia (07 Jan 1200(+1)1800); Messina, Sicily (10 Jan 0700-1500); Naples, Italy (11 Jan 0800-1600); Civitavecchia (Rome), Italy (12 Jan 0800-1700); Livorno (Florence/Pisa), Italy (13 Jan 0800(+1)2200); Genoa, Italy (15 Jan 0800-2200); Villefranche (Nice), France (16 Jan 0800(+1)1300); Barcelona, Spain (18 Jan a1300(+1)disembark) >>port loads
From Sun 4 Jan 2026
(To Wed 28 Jan 2026)
24 Night Star Collector: Winter Mediterranean Adventure
Ship Star Legend
More details at
(To Wed 28 Jan 2026)
24 Night Star Collector: Winter Mediterranean Adventure
Ship Star Legend
More details at
Cruise Prices
From $8,799
Cruise Itinerary: Venice, Italy (04 Jan embark(+1)d1700); Zadar, Croatia (06 Jan 0800-1700); Dubrovnik, Croatia (07 Jan 1200(+1)1800); Messina, Sicily (10 Jan 0700-1500); Naples, Italy (11 Jan 0800-1600); Civitavecchia (Rome), Italy (12 Jan 0800-1700); Livorno (Florence/Pisa), Italy (13 Jan 0800(+1)2200); Genoa, Italy (15 Jan 0800-2200); Villefranche (Nice), France (16 Jan 0800(+1)1300); Barcelona, Spain (18 Jan 1300(+2)1600); Valencia, Spain (21 Jan 0800-1700); Cartagena, Spain (22 Jan 0800-1500); Gibraltar, UK (23 Jan 1300-2200); Malaga, Spain (24 Jan 0800(+1)1800); Palma De Mallorca, Spain (27 Jan 0800-1700); Barcelona, Spain (28 Jan a0800) >>port loads
From $8,799
Cruise Itinerary: Venice, Italy (04 Jan embark(+1)d1700); Zadar, Croatia (06 Jan 0800-1700); Dubrovnik, Croatia (07 Jan 1200(+1)1800); Messina, Sicily (10 Jan 0700-1500); Naples, Italy (11 Jan 0800-1600); Civitavecchia (Rome), Italy (12 Jan 0800-1700); Livorno (Florence/Pisa), Italy (13 Jan 0800(+1)2200); Genoa, Italy (15 Jan 0800-2200); Villefranche (Nice), France (16 Jan 0800(+1)1300); Barcelona, Spain (18 Jan 1300(+2)1600); Valencia, Spain (21 Jan 0800-1700); Cartagena, Spain (22 Jan 0800-1500); Gibraltar, UK (23 Jan 1300-2200); Malaga, Spain (24 Jan 0800(+1)1800); Palma De Mallorca, Spain (27 Jan 0800-1700); Barcelona, Spain (28 Jan a0800) >>port loads
From Sun 4 Jan 2026
(To Wed 14 Jan 2026)
10 Night Sublime Southern Caribbean
Ship Wind Spirit
More details at
(To Wed 14 Jan 2026)
10 Night Sublime Southern Caribbean
Ship Wind Spirit
More details at
Cruise Prices
From NA
Cruise Itinerary: Bridgetown, Barbados (04 Jan d1800); Mayreau, Grenadines (05 Jan 0800-1700); Roseau, Dominica (06 Jan 1300-1800); Les Anses d'Arlet, Martinique (07 Jan 0700-1600); Nevis, St Kitts and Nevis (08 Jan 1300-2200); Basseterre, St. Kitts (09 Jan 0800-2100); St Johns, Antigua (10 Jan 0900-2300); Falmouth, Antigua (11 Jan 0800-1800); St Barthelemy (12 Jan 0900-2200); Anguilla (13 Jan 0700-1900); Philipsburg, St. Maarten (14 Jan a0600) >>port loads
From NA
Cruise Itinerary: Bridgetown, Barbados (04 Jan d1800); Mayreau, Grenadines (05 Jan 0800-1700); Roseau, Dominica (06 Jan 1300-1800); Les Anses d'Arlet, Martinique (07 Jan 0700-1600); Nevis, St Kitts and Nevis (08 Jan 1300-2200); Basseterre, St. Kitts (09 Jan 0800-2100); St Johns, Antigua (10 Jan 0900-2300); Falmouth, Antigua (11 Jan 0800-1800); St Barthelemy (12 Jan 0900-2200); Anguilla (13 Jan 0700-1900); Philipsburg, St. Maarten (14 Jan a0600) >>port loads
From Sun 4 Jan 2026
(To Sun 25 Jan 2026)
21 Night Star Collector: A Lesser Antilles Odyssey
Ship Wind Surf
More details at
(To Sun 25 Jan 2026)
21 Night Star Collector: A Lesser Antilles Odyssey
Ship Wind Surf
More details at
Cruise Prices
From $8,899
Cruise Itinerary: Philipsburg, St. Maarten (04 Jan d1900); Falmouth, Antigua (05 Jan 0800-1800); Anguilla (06 Jan 0800-1800); Tortola, British Virgin Islands (07 Jan 0800-1800); Jost Van Dyke, British Virgin Islands (07 Jan 1900(+1)2200); Virgin Gorda, British Virgin Islands (09 Jan 0800-1700); St Barthelemy (10 Jan 0800-2200); Philipsburg, St. Maarten (11 Jan 0600-1900); Basseterre, St. Kitts (12 Jan 0800-2100); St Barthelemy (13 Jan 0800-2200); St Johns, Antigua (14 Jan 0800-2200); Iles Des Saintes, Guadeloupe (15 Jan 0800-1700); Roseau, Dominica (16 Jan 0800-1600); Mayreau, Grenadines (17 Jan 0800-1700); Bridgetown, Barbados (18 Jan 0500-1800); Les Anses d'Arlet, Martinique (19 Jan 0900-2300); Castries, St Lucia (20 Jan 0800-1600); Pigeon Island, St Lucia (20 Jan 1800(+1)1800); Bequia, Grenadines (22 Jan 0800-2200); Mayreau, Grenadines (23 Jan 0800-1800); St Georges, Grenada (24 Jan 0700-1400); Bridgetown, Barbados (25 Jan a0600) >>port loads
From $8,899
Cruise Itinerary: Philipsburg, St. Maarten (04 Jan d1900); Falmouth, Antigua (05 Jan 0800-1800); Anguilla (06 Jan 0800-1800); Tortola, British Virgin Islands (07 Jan 0800-1800); Jost Van Dyke, British Virgin Islands (07 Jan 1900(+1)2200); Virgin Gorda, British Virgin Islands (09 Jan 0800-1700); St Barthelemy (10 Jan 0800-2200); Philipsburg, St. Maarten (11 Jan 0600-1900); Basseterre, St. Kitts (12 Jan 0800-2100); St Barthelemy (13 Jan 0800-2200); St Johns, Antigua (14 Jan 0800-2200); Iles Des Saintes, Guadeloupe (15 Jan 0800-1700); Roseau, Dominica (16 Jan 0800-1600); Mayreau, Grenadines (17 Jan 0800-1700); Bridgetown, Barbados (18 Jan 0500-1800); Les Anses d'Arlet, Martinique (19 Jan 0900-2300); Castries, St Lucia (20 Jan 0800-1600); Pigeon Island, St Lucia (20 Jan 1800(+1)1800); Bequia, Grenadines (22 Jan 0800-2200); Mayreau, Grenadines (23 Jan 0800-1800); St Georges, Grenada (24 Jan 0700-1400); Bridgetown, Barbados (25 Jan a0600) >>port loads
From Sun 4 Jan 2026
(To Sun 11 Jan 2026)
7 Night Beach Fun & Sun: A Remote Caribbean Getaway
Ship Wind Surf
More details at
(To Sun 11 Jan 2026)
7 Night Beach Fun & Sun: A Remote Caribbean Getaway
Ship Wind Surf
More details at
Cruise Prices
From $2,638
Cruise Itinerary: Philipsburg, St. Maarten (04 Jan d1900); Falmouth, Antigua (05 Jan 0800-1800); Anguilla (06 Jan 0800-1800); Tortola, British Virgin Islands (07 Jan 0800-1800); Jost Van Dyke, British Virgin Islands (07 Jan 1900(+1)2200); Virgin Gorda, British Virgin Islands (09 Jan 0800-1700); St Barthelemy (10 Jan 0800-2200); Philipsburg, St. Maarten (11 Jan a0600) >>port loads
From $2,638
Cruise Itinerary: Philipsburg, St. Maarten (04 Jan d1900); Falmouth, Antigua (05 Jan 0800-1800); Anguilla (06 Jan 0800-1800); Tortola, British Virgin Islands (07 Jan 0800-1800); Jost Van Dyke, British Virgin Islands (07 Jan 1900(+1)2200); Virgin Gorda, British Virgin Islands (09 Jan 0800-1700); St Barthelemy (10 Jan 0800-2200); Philipsburg, St. Maarten (11 Jan a0600) >>port loads
From Sun 4 Jan 2026
(To Sun 1 Feb 2026)
28 Night Star Collector: The Best of the Windward & Leeward Isles
Ship Wind Surf
More details at
(To Sun 1 Feb 2026)
28 Night Star Collector: The Best of the Windward & Leeward Isles
Ship Wind Surf
More details at
Cruise Prices
From $11,999
Cruise Itinerary: Philipsburg, St. Maarten (04 Jan d1900); Falmouth, Antigua (05 Jan 0800-1800); Anguilla (06 Jan 0800-1800); Tortola, British Virgin Islands (07 Jan 0800-1800); Jost Van Dyke, British Virgin Islands (07 Jan 1900(+1)2200); Virgin Gorda, British Virgin Islands (09 Jan 0800-1700); St Barthelemy (10 Jan 0800-2200); Philipsburg, St. Maarten (11 Jan 0600-1900); Basseterre, St. Kitts (12 Jan 0800-2100); St Barthelemy (13 Jan 0800-2200); St Johns, Antigua (14 Jan 0800-2200); Iles Des Saintes, Guadeloupe (15 Jan 0800-1700); Roseau, Dominica (16 Jan 0800-1600); Mayreau, Grenadines (17 Jan 0800-1700); Bridgetown, Barbados (18 Jan 0500-1800); Les Anses d'Arlet, Martinique (19 Jan 0900-2300); Castries, St Lucia (20 Jan 0800-1600); Pigeon Island, St Lucia (20 Jan 1800(+1)1800); Bequia, Grenadines (22 Jan 0800-2200); Mayreau, Grenadines (23 Jan 0800-1800); St Georges, Grenada (24 Jan 0700-1400); Bridgetown, Barbados (25 Jan 0600-1800); Bequia, Grenadines (26 Jan 0800-1700); Mayreau, Grenadines (27 Jan 0800-1800); Soufriere, St Lucia (28 Jan 0800-1600); Kralendijk, Bonaire (30 Jan 1300-2200); Willemstad, Curacao (31 Jan 0800-1800); Oranjestad, Aruba (01 Feb a0600) >>port loads
From $11,999
Cruise Itinerary: Philipsburg, St. Maarten (04 Jan d1900); Falmouth, Antigua (05 Jan 0800-1800); Anguilla (06 Jan 0800-1800); Tortola, British Virgin Islands (07 Jan 0800-1800); Jost Van Dyke, British Virgin Islands (07 Jan 1900(+1)2200); Virgin Gorda, British Virgin Islands (09 Jan 0800-1700); St Barthelemy (10 Jan 0800-2200); Philipsburg, St. Maarten (11 Jan 0600-1900); Basseterre, St. Kitts (12 Jan 0800-2100); St Barthelemy (13 Jan 0800-2200); St Johns, Antigua (14 Jan 0800-2200); Iles Des Saintes, Guadeloupe (15 Jan 0800-1700); Roseau, Dominica (16 Jan 0800-1600); Mayreau, Grenadines (17 Jan 0800-1700); Bridgetown, Barbados (18 Jan 0500-1800); Les Anses d'Arlet, Martinique (19 Jan 0900-2300); Castries, St Lucia (20 Jan 0800-1600); Pigeon Island, St Lucia (20 Jan 1800(+1)1800); Bequia, Grenadines (22 Jan 0800-2200); Mayreau, Grenadines (23 Jan 0800-1800); St Georges, Grenada (24 Jan 0700-1400); Bridgetown, Barbados (25 Jan 0600-1800); Bequia, Grenadines (26 Jan 0800-1700); Mayreau, Grenadines (27 Jan 0800-1800); Soufriere, St Lucia (28 Jan 0800-1600); Kralendijk, Bonaire (30 Jan 1300-2200); Willemstad, Curacao (31 Jan 0800-1800); Oranjestad, Aruba (01 Feb a0600) >>port loads
From Sun 4 Jan 2026
(To Sun 18 Jan 2026)
14 Night Star Collector: Leeward & Windward Caribbean Havens
Ship Wind Surf
More details at
(To Sun 18 Jan 2026)
14 Night Star Collector: Leeward & Windward Caribbean Havens
Ship Wind Surf
More details at
Cruise Prices
From $5,014
Cruise Itinerary: Philipsburg, St. Maarten (04 Jan d1900); Falmouth, Antigua (05 Jan 0800-1800); Anguilla (06 Jan 0800-1800); Tortola, British Virgin Islands (07 Jan 0800-1800); Jost Van Dyke, British Virgin Islands (07 Jan 1900(+1)2200); Virgin Gorda, British Virgin Islands (09 Jan 0800-1700); St Barthelemy (10 Jan 0800-2200); Philipsburg, St. Maarten (11 Jan 0600-1900); Basseterre, St. Kitts (12 Jan 0800-2100); St Barthelemy (13 Jan 0800-2200); St Johns, Antigua (14 Jan 0800-2200); Iles Des Saintes, Guadeloupe (15 Jan 0800-1700); Roseau, Dominica (16 Jan 0800-1600); Mayreau, Grenadines (17 Jan 0800-1700); Bridgetown, Barbados (18 Jan a0500) >>port loads
From $5,014
Cruise Itinerary: Philipsburg, St. Maarten (04 Jan d1900); Falmouth, Antigua (05 Jan 0800-1800); Anguilla (06 Jan 0800-1800); Tortola, British Virgin Islands (07 Jan 0800-1800); Jost Van Dyke, British Virgin Islands (07 Jan 1900(+1)2200); Virgin Gorda, British Virgin Islands (09 Jan 0800-1700); St Barthelemy (10 Jan 0800-2200); Philipsburg, St. Maarten (11 Jan 0600-1900); Basseterre, St. Kitts (12 Jan 0800-2100); St Barthelemy (13 Jan 0800-2200); St Johns, Antigua (14 Jan 0800-2200); Iles Des Saintes, Guadeloupe (15 Jan 0800-1700); Roseau, Dominica (16 Jan 0800-1600); Mayreau, Grenadines (17 Jan 0800-1700); Bridgetown, Barbados (18 Jan a0500) >>port loads
From Sun 4 Jan 2026
(To Sat 28 Feb 2026)
55 Night Star Collector: Grand Caribbean Adventure
Ship Wind Surf
More details at
(To Sat 28 Feb 2026)
55 Night Star Collector: Grand Caribbean Adventure
Ship Wind Surf
More details at
Cruise Prices
From NA
Cruise Itinerary: Philipsburg, St. Maarten (04 Jan d1900); Falmouth, Antigua (05 Jan 0800-1800); Anguilla (06 Jan 0800-1800); Tortola, British Virgin Islands (07 Jan 0800-1800); Jost Van Dyke, British Virgin Islands (07 Jan 1900(+1)2200); Virgin Gorda, British Virgin Islands (09 Jan 0800-1700); St Barthelemy (10 Jan 0800-2200); Philipsburg, St. Maarten (11 Jan 0600-1900); Basseterre, St. Kitts (12 Jan 0800-2100); St Barthelemy (13 Jan 0800-2200); St Johns, Antigua (14 Jan 0800-2200); Iles Des Saintes, Guadeloupe (15 Jan 0800-1700); Roseau, Dominica (16 Jan 0800-1600); Mayreau, Grenadines (17 Jan 0800-1700); Bridgetown, Barbados (18 Jan 0500-1800); Les Anses d'Arlet, Martinique (19 Jan 0900-2300); Castries, St Lucia (20 Jan 0800-1600); Pigeon Island, St Lucia (20 Jan 1800(+1)1800); Bequia, Grenadines (22 Jan 0800-2200); Mayreau, Grenadines (23 Jan 0800-1800); St Georges, Grenada (24 Jan 0700-1400); Bridgetown, Barbados (25 Jan 0600-1800); Bequia, Grenadines (26 Jan 0800-1700); Mayreau, Grenadines (27 Jan 0800-1800); Soufriere, St Lucia (28 Jan 0800-1600); Kralendijk, Bonaire (30 Jan 1300-2200); Willemstad, Curacao (31 Jan 0800-1800); Oranjestad, Aruba (01 Feb 0600-1800); Cartagena, Colombia (03 Feb 0800(+1)1300); San Blas Islands, Panama (05 Feb 1000-1800); Bocas Del Toro, Panama (07 Feb 0700-1500); Colon, Panama (08 Feb 0800(+1)1600); Bocas Del Toro, Panama (10 Feb 1000-1600); San Andres Island, Colombia (11 Feb 1300-1900); Roatan, Honduras (14 Feb 0900-1700); Belize City, Belize (15 Feb 0900-1900); Costa Maya, Mexico (16 Feb 0800-1700); Cozumel, Mexico (17 Feb 0800-1800); George Town, Grand Cayman (19 Feb 0800-1800); Cayman Brac (20 Feb 0700-1300); Ocho Rios, Jamaica (21 Feb 0830-1400); Santo Domingo, Dominican Republic (23 Feb 1300-2200); La Romana, Dominican Republic (24 Feb 0700-1700); Jost Van Dyke, British Virgin Islands (26 Feb 0800-2200); Virgin Gorda, British Virgin Islands (27 Feb 0800-1700); Philipsburg, St. Maarten (28 Feb a0600) >>port loads
From NA
Cruise Itinerary: Philipsburg, St. Maarten (04 Jan d1900); Falmouth, Antigua (05 Jan 0800-1800); Anguilla (06 Jan 0800-1800); Tortola, British Virgin Islands (07 Jan 0800-1800); Jost Van Dyke, British Virgin Islands (07 Jan 1900(+1)2200); Virgin Gorda, British Virgin Islands (09 Jan 0800-1700); St Barthelemy (10 Jan 0800-2200); Philipsburg, St. Maarten (11 Jan 0600-1900); Basseterre, St. Kitts (12 Jan 0800-2100); St Barthelemy (13 Jan 0800-2200); St Johns, Antigua (14 Jan 0800-2200); Iles Des Saintes, Guadeloupe (15 Jan 0800-1700); Roseau, Dominica (16 Jan 0800-1600); Mayreau, Grenadines (17 Jan 0800-1700); Bridgetown, Barbados (18 Jan 0500-1800); Les Anses d'Arlet, Martinique (19 Jan 0900-2300); Castries, St Lucia (20 Jan 0800-1600); Pigeon Island, St Lucia (20 Jan 1800(+1)1800); Bequia, Grenadines (22 Jan 0800-2200); Mayreau, Grenadines (23 Jan 0800-1800); St Georges, Grenada (24 Jan 0700-1400); Bridgetown, Barbados (25 Jan 0600-1800); Bequia, Grenadines (26 Jan 0800-1700); Mayreau, Grenadines (27 Jan 0800-1800); Soufriere, St Lucia (28 Jan 0800-1600); Kralendijk, Bonaire (30 Jan 1300-2200); Willemstad, Curacao (31 Jan 0800-1800); Oranjestad, Aruba (01 Feb 0600-1800); Cartagena, Colombia (03 Feb 0800(+1)1300); San Blas Islands, Panama (05 Feb 1000-1800); Bocas Del Toro, Panama (07 Feb 0700-1500); Colon, Panama (08 Feb 0800(+1)1600); Bocas Del Toro, Panama (10 Feb 1000-1600); San Andres Island, Colombia (11 Feb 1300-1900); Roatan, Honduras (14 Feb 0900-1700); Belize City, Belize (15 Feb 0900-1900); Costa Maya, Mexico (16 Feb 0800-1700); Cozumel, Mexico (17 Feb 0800-1800); George Town, Grand Cayman (19 Feb 0800-1800); Cayman Brac (20 Feb 0700-1300); Ocho Rios, Jamaica (21 Feb 0830-1400); Santo Domingo, Dominican Republic (23 Feb 1300-2200); La Romana, Dominican Republic (24 Feb 0700-1700); Jost Van Dyke, British Virgin Islands (26 Feb 0800-2200); Virgin Gorda, British Virgin Islands (27 Feb 0800-1700); Philipsburg, St. Maarten (28 Feb a0600) >>port loads