5 reviews | Aug 02, 2024 | Windstar | Star Legend | Baltic | Stockholm | Copenhagen | 10 Nights | Copenhagen | Gdansk | Helsinki | Klaipeda | Riga | Sassnitz, Germany | Stockholm | Tallinn | Visby | Warnemünde (Berlin) | $4,799 Up To $500 Onboard Credit | | Suite! |
11 reviews | Nov 18, 2025 | Windstar | Wind Spirit | Caribbean | Bridgetown | Puerto Caldera | 18 Nights | Balboa / Fuerte Amador | Bequia | Bridgetown | Cartagena | Colón | Golfo Dulce | Isla Parida | Kralendijk | Mayreau | Oranjestad | Panama Canal | Puerto Caldera | Quepos | St. George's | Willemstad | $5,299 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
15 reviews | Dec 07, 2025 | Windstar | Star Pride | Caribbean | San Juan | Colon | 6 Nights | Cartagena | Colón | San Blas | San Juan | Santo Domingo | $2,899 Up To $300 Onboard Credit | | |
5 reviews | Dec 13, 2025 | Windstar | Star Legend | Caribbean | Malaga | Rome | 14 Nights | Barcelona | Cartagena | Genoa, Italy | Gibraltar | Livorno | Málaga | Nice | Palma de Mallorca | Rome | Valencia | $5,299 Up To $750 Onboard Credit | | |
Need Help Planning A Cruise?
Our cruise experts can help you:
- Find the best discounts
- Hold a cabin for 24 hours for free
- Receive personalized recommendations
- Book handicap accessible cabins
|
24 reviews | Jan 04, 2026 | Windstar | Wind Surf | Caribbean | Philipsburg | Oranjestad | 28 Nights | Anse Mitan | Basseterre | Bequia | Bridgetown | Castries | Deshaies | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Kralendijk | Little Bay | Man-O-War Bay | Mayreau | Oranjestad | Pigeon Island | Road Bay | Roseau | Soper's Hole | Soufriere | St. George's | St. Maarten | Virgin Gorda / Prickly Pear | Willemstad | $7,899 Up To $1000 Onboard Credit | | Onboard Credit! |
24 reviews | Jan 04, 2026 | Windstar | Wind Surf | Caribbean | Philipsburg | Philipsburg | 55 Nights | Anse Mitan | Basseterre | Belize City | Bequia | Bocas del Toro | Bridgetown | Cartagena | Castries | Cayman Brac | Colón | Costa Maya | Cozumel | Deshaies | Falmouth Harbour | Grand Cayman | Gustavia | Isla San Andres | Jost Van Dyke, Great Harbour | Kralendijk | La Romana | Little Bay | Man-O-War Bay | Mayreau | Oranjestad | Pigeon Island | Port Antonio | Road Bay | Roatan | Roseau | Santa Marta | Santo Domingo | Soper's Hole | Soufriere | St. George's | St. Maarten | Virgin Gorda / Prickly Pear | Willemstad | $16,599 Up To $1000 Onboard Credit | | Onboard Credit! |
5 reviews | Jan 12, 2026 | Windstar | Star Legend | Caribbean | Rome | Barcelona | 16 Nights | Barcelona | Cartagena | Genoa, Italy | Gibraltar | Livorno | Málaga | Nice | Palma de Mallorca | Rome | Valencia | $5,299 Up To $750 Onboard Credit | | Suite! |
24 reviews | Jan 18, 2026 | Windstar | Wind Surf | Caribbean | Bridgetown | Oranjestad | 14 Nights | Anse Mitan | Bequia | Bridgetown | Castries | Kralendijk | Man-O-War Bay | Mayreau | Oranjestad | Pigeon Island | Soufriere | St. George's | Willemstad | $4,099 Up To $500 Onboard Credit | | |
5 reviews | Jan 19, 2026 | Windstar | Star Legend | Caribbean | Barcelona | Rome | 16 Nights | Barcelona | Cartagena | Genoa, Italy | Gibraltar | Livorno | Málaga | Nice | Palma de Mallorca | Rome | Valencia | $5,299 Up To $750 Onboard Credit | | |
24 reviews | Jan 25, 2026 | Windstar | Wind Surf | Caribbean | Bridgetown | Oranjestad | 7 Nights | Bridgetown | Kralendijk | Man-O-War Bay | Mayreau | Oranjestad | Soufriere | Willemstad | $2,699 Up To $300 Onboard Credit | | Onboard Credit! |
24 reviews | Feb 01, 2026 | Windstar | Wind Surf | Caribbean | Oranjestad | Colon | 8 Nights | Bocas del Toro | Cartagena | Colón | Oranjestad | Santa Marta | $3,199 Up To $500 Onboard Credit | | Onboard Credit! |
24 reviews | Feb 01, 2026 | Windstar | Wind Surf | Caribbean | Oranjestad | Cozumel | 16 Nights | Belize City | Bocas del Toro | Cartagena | Colón | Costa Maya | Cozumel | Isla San Andres | Oranjestad | Roatan | Santa Marta | $5,099 Up To $750 Onboard Credit | | |
5 reviews | Feb 20, 2026 | Windstar | Star Legend | Caribbean | Rome | Barcelona | 16 Nights | Barcelona | Cartagena | Genoa, Italy | Gibraltar | Livorno | Málaga | Nice | Palma de Mallorca | Rome | Valencia | $5,299 Up To $750 Onboard Credit | | |
5 reviews | Feb 27, 2026 | Windstar | Star Legend | Caribbean | Barcelona | Rome | 16 Nights | Barcelona | Cartagena | Genoa, Italy | Gibraltar | Livorno | Málaga | Nice | Palma de Mallorca | Rome | Valencia | $5,299 Up To $750 Onboard Credit | | Suite! |
11 reviews | Nov 18, 2025 | Windstar | Wind Spirit | Caribbean - Southern | Bridgetown | Colon | 11 Nights | Bequia | Bridgetown | Cartagena | Colón | Kralendijk | Mayreau | Oranjestad | St. George's | Willemstad | $3,499 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Jun 07, 2024 | Windstar | Wind Surf | Europe | Rome | Venice | 8 Nights | Dubrovnik | Giardini Naxos | Kotor | Rome | Rovinj | Sorrento | Split | Venice | $3,399 Up To $500 Onboard Credit | | |
15 reviews | Jun 10, 2024 | Windstar | Star Pride | Europe | Edinburgh | Reykjavik | 18 Nights | Akureyri | Alesund | Bergen | Edinburgh | Geiranger | Grundarfjordur | Heimaey Island, | Isafjordur | Kirkwall | Molde | Reykjavik | Seydisfjordur | Surtsey Island | Torshavn | $9,459 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Jul 03, 2024 | Windstar | Wind Surf | Europe | Venice | Rome | 18 Nights | Amalfi | Catania | Dubrovnik | Giardini Naxos | Gozo | Kotor | Lipari | Porto Empedocle | Rome | Rovinj | Sorrento | Split | Trapani | Valletta | Venice | $7,259 Up To $750 Onboard Credit | | |
24 reviews | Jul 03, 2024 | Windstar | Wind Surf | Europe | Venice | Rome | 8 Nights | Dubrovnik | Giardini Naxos | Kotor | Rome | Rovinj | Sorrento | Split | Venice | $3,959 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Jul 11, 2024 | Windstar | Wind Surf | Europe | Rome | Barcelona | 17 Nights | Amalfi | Barcelona | Cannes | Catania | Gozo | Lipari | Monte Carlo | Palamos | Porto Empedocle | Portoferraio | Portofino | Rome | Sanary-sur-Mer | Sorrento | Trapani | Valletta | $7,189 Up To $750 Onboard Credit | | Onboard Credit! |