Bucket-List Cruise Adventures

Windstar Cruises

Showing 253 Windstar sailings. Every line →

253 sailings, each one priced and planned end to end: the ports it calls at, the one unmissable thing to do at each, and the flights and nights either side. Leaving within three weeks?

Bucket-list adventures at every port — where to fly in, and what to do the day(s) before and after.

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Showing 36 of 253 sailings
Windstar · Star LegendRound-trip
Mediterranean 8 nights Sep 25 – Oct 3, 2026 from Piraeus (Athens), Greece
Piraeus (Athens), Greece · Kusadasi (Ephesus), Turkey · … · Piraeus (Athens), Greece7 ports
Piraeus (Athens), Greece · Kusadasi (Ephesus), Turkey · Kavala, Greece · Ouranoupoli, Greece · Volos, Greece · Skopelos Island, Greece · Piraeus (Athens), Greece
★ Bucket-list The Acropolis & Parthenon, Guided Skip-the-LineEphesus + the Terrace Houses with a licensed archa…Ancient PhilippiMount Athos Sacred Coast +2 more
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from $4,334
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Windstar · Star LegendRound-trip
Mediterranean 8 nights Oct 3 – Oct 11, 2026 from Piraeus (Athens), Greece
Piraeus (Athens), Greece · Kusadasi (Ephesus), Turkey · … · Piraeus (Athens), Greece7 ports
Piraeus (Athens), Greece · Kusadasi (Ephesus), Turkey · Kavala, Greece · Ouranoupoli, Greece · Volos, Greece · Skopelos Island, Greece · Piraeus (Athens), Greece
★ Bucket-list The Acropolis & Parthenon, Guided Skip-the-LineEphesus + the Terrace Houses with a licensed archa…Ancient PhilippiMount Athos Sacred Coast +2 more
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from $3,248
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Windstar · Star SeekerOne-way
Asia 10 nights Oct 6 – Oct 16, 2026 from Yokohama, Japan to Osaka (Kyoto and Nara), Japan
Yokohama, Japan · Shimizu, Japan · … · Osaka (Kyoto and Nara), Japan11 ports
Yokohama, Japan · Shimizu, Japan · Shingu, Japan · Kagoshima, Kyushu, Japan · 210 · Nagasaki, Japan · Busan (Kyongju), South Korea · Karatsu, Japan · Hiroshima, Japan · Takamatsu, Japan · Osaka (Kyoto and Nara), Japan
★ Bucket-list Private Full-Day Tokyo Highlights from YokohamaPrivate Mt. Fuji & Hakone Full-Day Tour from Shimi…Nachi Falls & Kumano Nachi TaishaSakurajima +6 more
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from $8,619
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Windstar · Wind SurfOne-way
Mediterranean 8 nights Oct 7 – Oct 15, 2026 from Civitavecchia (Rome), Italy to Venice, Italy
Civitavecchia (Rome), Italy · Sorrento, Italy · … · Venice, Italy8 ports
Civitavecchia (Rome), Italy · Sorrento, Italy · Giardini Naxos, Sicily · Kotor, Montenegro · Dubrovnik, Croatia · Trogir, Croatia · Rovinj, Croatia · Venice, Italy
★ Bucket-list Vatican, Sistine Chapel & Colosseum in One DayPompeii Private Excavation Tour with Archaeologist…Ancient Theatre of TaorminaClimb the City Walls to San Giovanni Fortress +4 more
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from $10,408
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Windstar · Star BreezeRound-trip
Hawaii 7 nights Oct 15 – Oct 22, 2026 from Papeete, Tahiti, French Polynesia
Papeete, Tahiti, French Polynesia · Fakarava, Tahiti · … · Papeete, Tahiti, French Polynesia6 ports
Papeete, Tahiti, French Polynesia · Fakarava, Tahiti · Rangiroa, Tahiti · Bora Bora, French Polynesia · Tahaa, French Polynesia · Papeete, Tahiti, French Polynesia
★ Bucket-list Teahupo'oFakarava South PassTiputa Pass Drift DivePrivate Lagoon Safari +1 more
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from $5,753
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Windstar · Wind StarOne-way
Mediterranean 7 nights Oct 24 – Oct 31, 2026 from Civitavecchia (Rome), Italy to Barcelona, Spain
Civitavecchia (Rome), Italy · Portoferraio (Elba), Italy · … · Barcelona, Spain7 ports
Civitavecchia (Rome), Italy · Portoferraio (Elba), Italy · Bastia, France · Calvi, France · Mahon, Minorca, Spain · Palma de Mallorca, Spain · Barcelona, Spain
★ Bucket-list Vatican, Sistine Chapel & Colosseum in One DayNapoleon's ElbaScandola Nature Reserve & GirolataScandola Nature Reserve & Calanches de Piana +3 more
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from $3,709
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Windstar · Wind SurfOne-way
Mediterranean 5 nights Oct 25 – Oct 30, 2026 from Civitavecchia (Rome), Italy to Barcelona, Spain
Civitavecchia (Rome), Italy · Portofino, Italy · … · Barcelona, Spain6 ports
Civitavecchia (Rome), Italy · Portofino, Italy · Monte Carlo, Monaco · Sanary-Sur-Mer, France · Palamos, Spain · Barcelona, Spain
★ Bucket-list Vatican, Sistine Chapel & Colosseum in One DayPrivate Yacht CharterCasino de Monte-CarloPrivate Full-Day Cassis Calanques & Village Tour f… +2 more
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from $2,286
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Windstar · Star LegendOne-way
Mediterranean 8 nights Oct 27 – Nov 4, 2026 from Piraeus (Athens), Greece to Barcelona, Spain
Piraeus (Athens), Greece · Delphi, Greece · … · Barcelona, Spain9 ports
Piraeus (Athens), Greece · Delphi, Greece · Corinth, Greece · Corfu, Greece · Argostoli, Kephalonia · Messina, Sicily, Italy · Trapani, Italy · Cagliari, Sardinia, Italy · Barcelona, Spain
★ Bucket-list The Acropolis & Parthenon, Guided Skip-the-LinePrivate Oracle ExperienceAcrocorinthPaleokastritsa Blue Caves & coves by speedboat +5 more
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from $10,340
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Windstar · Star PrideRound-trip
Caribbean 11 nights Oct 28 – Nov 8, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Cruz Bay, St. John · … · San Juan, Puerto Rico11 ports
San Juan, Puerto Rico · Cruz Bay, St. John · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Falmouth Harbour, Antigua · Les Saintes, Guadeloupe · Rodney Bay, St. Lucia · St. Georges, Grenada, West Indies · Jost Van Dyke, British Virgin Islands · Virgin Gorda, British Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsTrunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. BartsMt. Liamuiga Volcano Crater Hike +6 more
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from $3,930
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Windstar · Star BreezeRound-trip
Hawaii 7 nights Oct 29 – Nov 5, 2026 from Papeete, Tahiti, French Polynesia
Papeete, Tahiti, French Polynesia · Moorea, French Polynesia · … · Papeete, Tahiti, French Polynesia7 ports
Papeete, Tahiti, French Polynesia · Moorea, French Polynesia · Raiatea, French Polynesia · Tahaa, French Polynesia · Bora Bora, French Polynesia · Huahine, French Polynesia · Papeete, Tahiti, French Polynesia
★ Bucket-list Teahupo'oPrivate Lagoon SafariTaputapuatea MaraeTahaa Coral Garden Snorkel by Private Outrigger +2 more
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from $5,021
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Windstar · Wind SpiritOne-way
Mediterranean 10 nights Oct 30 – Nov 9, 2026 from Barcelona, Spain to Lisbon, Portugal
Barcelona, Spain · Palma de Mallorca, Spain · … · Lisbon, Portugal8 ports
Barcelona, Spain · Palma de Mallorca, Spain · Tarragona, Spain · Valencia, Spain · Cartagena, Spain · Malaga, Spain · Tangier, Morocco · Lisbon, Portugal
★ Bucket-list Sagrada FamiliaLa Seu Cathedral + Rooftop Terraces ClimbPrivate Roman TarracoOceanografic +4 more
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from $4,624
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Windstar · Wind SurfOne-way
Mediterranean 8 nights Oct 30 – Nov 7, 2026 from Barcelona, Spain to Lisbon, Portugal
Barcelona, Spain · Palma de Mallorca, Spain · … · Lisbon, Portugal8 ports
Barcelona, Spain · Palma de Mallorca, Spain · Cartagena, Spain · Almeria, Spain · Malaga, Spain · Gibraltar, British Territory · Cadiz (Seville), Spain · Lisbon, Portugal
★ Bucket-list Sagrada FamiliaLa Seu Cathedral + Rooftop Terraces ClimbThe Roman Theatre of Cartagena with the Rafael Mon…Private Alhambra Palace & Generalife Gardens from… +4 more
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from $2,877
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Windstar · Wind StarOne-way
Mediterranean 10 nights Oct 31 – Nov 10, 2026 from Barcelona, Spain to Lisbon, Portugal
Barcelona, Spain · Palma de Mallorca, Spain · … · Lisbon, Portugal8 ports
Barcelona, Spain · Palma de Mallorca, Spain · Tarragona, Spain · Valencia, Spain · Cartagena, Spain · Malaga, Spain · Tangier, Morocco · Lisbon, Portugal
★ Bucket-list Sagrada FamiliaLa Seu Cathedral + Rooftop Terraces ClimbPrivate Roman TarracoOceanografic +4 more
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from $4,064
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Windstar · Star LegendOne-way
Mediterranean 8 nights Nov 4 – Nov 12, 2026 from Barcelona, Spain to Malaga, Spain
Barcelona, Spain · 001 · … · Malaga, Spain9 ports
Barcelona, Spain · 001 · 002 · 003 · 004 · 005 · 006 · 007 · Malaga, Spain
★ Bucket-list Sagrada FamiliaGranada & the Alhambra
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from $2,931
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Windstar · Star BreezeRound-trip
Hawaii 7 nights Nov 5 – Nov 12, 2026 from Papeete, Tahiti, French Polynesia
Papeete, Tahiti, French Polynesia · Moorea, French Polynesia · … · Papeete, Tahiti, French Polynesia7 ports
Papeete, Tahiti, French Polynesia · Moorea, French Polynesia · Raiatea, French Polynesia · Tahaa, French Polynesia · Bora Bora, French Polynesia · Huahine, French Polynesia · Papeete, Tahiti, French Polynesia
★ Bucket-list Teahupo'oPrivate Lagoon SafariTaputapuatea MaraeTahaa Coral Garden Snorkel by Private Outrigger +2 more
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from $4,146
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Windstar · Star SeekerOne-way
Asia 10 nights Nov 5 – Nov 15, 2026 from Osaka (Kyoto and Nara), Japan to Ha Long Bay, Vietnam
Osaka (Kyoto and Nara), Japan · Amami Oshima, Japan · … · Ha Long Bay, Vietnam7 ports
Osaka (Kyoto and Nara), Japan · Amami Oshima, Japan · Okinawa (Naha), Japan · Ishigaki, Ryukyu Island · Keelung (Taipei), Taiwan · Hong Kong, Hong Kong SAR, China · Ha Long Bay, Vietnam
★ Bucket-list Fushimi Inari at DawnKuroshio no Mori Mangrove Kayak at DawnShuri CastleKabira Bay Glass-Bottom Boat & Private Snorkel Saf… +3 more
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from $5,205
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Windstar · Star PrideRound-trip
Caribbean 7 nights Nov 8 – Nov 15, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Georges, Grenada, West Indies · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · St. Georges, Grenada, West Indies · Bequia, Grenadines · Mayreau, Grenadines · Les Saintes, Guadeloupe · Marmaris, Turkey · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsGrenada Private Taxi TourTobago Cays & Mystique Full-Day Private SailSalt Whistle Bay +2 more
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from $2,411
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Windstar · Wind SpiritOne-way
Mediterranean 8 nights Nov 9 – Nov 17, 2026 from Lisbon, Portugal to Santa Cruz de Tenerife, Canary Islands
Lisbon, Portugal · Funchal, Madeira, Portugal · … · Santa Cruz de Tenerife, Canary Islands6 ports
Lisbon, Portugal · Funchal, Madeira, Portugal · San Sebastian, Spain · Santa Cruz de La Palma, Spain · Las Palmas, Gran Canaria, Canary Islands · Santa Cruz de Tenerife, Canary Islands
★ Bucket-list SintraPico do Arieiro to Pico RuivoPrivate Pintxos & Txakoli Wine Crawl in Parte ViejaTajogaite Volcano +2 more
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from $3,322
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Windstar · Star BreezeRound-trip
Hawaii 11 nights Nov 12 – Nov 23, 2026 from Papeete, Tahiti, French Polynesia
Papeete, Tahiti, French Polynesia · Fakarava, Tahiti · … · Papeete, Tahiti, French Polynesia8 ports
Papeete, Tahiti, French Polynesia · Fakarava, Tahiti · Fatu Hiva, French Polynesia · Hiva Oa, Marquesas, French Polynesia · Taiohae, Nuku Hiva, Marquesas · Rangiroa, Tahiti · Bora Bora, French Polynesia · Papeete, Tahiti, French Polynesia
★ Bucket-list Teahupo'oFakarava South PassBay of Virgins at DawnPuamau Sacred Valley & Te I'ipona Tiki Site +3 more
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from $4,197
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Windstar · Star PrideRound-trip
Caribbean 7 nights Nov 15 – Nov 22, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Cruz Bay, St. John · … · San Juan, Puerto Rico8 ports
San Juan, Puerto Rico · Cruz Bay, St. John · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Philipsburg, St. Maarten · Jost Van Dyke, British Virgin Islands · Virgin Gorda, British Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsTrunk Bay Underwater Snorkel Trail & VI National P…Mt. Liamuiga Volcano Crater HikePrivate Open-Top Mini Moke Island Tour of St. Barts +3 more
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from $6,153
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Windstar · Wind StarOne-way
Caribbean 11 nights Nov 24 – Dec 5, 2026 from Bridgetown, Barbados to Colon, Panama
Bridgetown, Barbados · Bequia, Grenadines · … · Colon, Panama9 ports
Bridgetown, Barbados · Bequia, Grenadines · St. Georges, Grenada, West Indies · Kralendijk, Bonaire · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Cartagena, Colombia · San Blas Islands, Panama · Colon, Panama
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Tobago Cays & Mystique Full-Day Private SailGrenada Private Taxi TourKlein Bonaire +5 more
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from $7,896
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Windstar · Star SeekerOne-way
Asia 11 nights Nov 25 – Dec 6, 2026 from Bangkok, Thailand to Phuket, Thailand
Bangkok, Thailand · 101 · … · Phuket, Thailand10 ports
Bangkok, Thailand · 101 · Ko Kood, Thailand · Ko Samui, Thailand · Singapore, Singapore · Port Klang (Kuala Lumpur), Malaysia · Penang, Malaysia · Krabi, Thailand · Ko Yao Noi · Phuket, Thailand
★ Bucket-list Grand Palace & Emerald BuddhaHTMS Chang Wreck & Coral Reef Private Scuba DiveAng Thong National Marine ParkGardens by the Bay +4 more
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from $5,512
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Windstar · Star LegendRound-trip
Mediterranean 7 nights Nov 27 – Dec 4, 2026 from Bridgetown, Barbados
Bridgetown, Barbados · Anses D'arlet, Martinique · … · Bridgetown, Barbados8 ports
Bridgetown, Barbados · Anses D'arlet, Martinique · Rodney Bay, St. Lucia · Casablanca, Morocco · Mayreau, Grenadines · St. Georges, Grenada, West Indies · Bequia, Grenadines · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Small-Boat Snorkel with Wild Sea Turtles, Anse NoireFull-Day Private Catamaran Sail to Soufrière & the…Private Guided Tour of Casablanca with Hassan II M… +3 more
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from $2,594
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Windstar · Wind SpiritRound-trip
Mediterranean 10 nights Nov 27 – Dec 7, 2026 from Santa Cruz de Tenerife, Canary Islands
Santa Cruz de Tenerife, Canary Islands · Fuerteventura, Canary Islands · … · Santa Cruz de Tenerife, Canary Islands8 ports
Santa Cruz de Tenerife, Canary Islands · Fuerteventura, Canary Islands · Funchal, Madeira, Portugal · M6e · Santa Cruz de La Palma, Spain · Hie · San Sebastian, Spain · Santa Cruz de Tenerife, Canary Islands
★ Bucket-list Teide National ParkPrivate Boat to Isla de LobosPico do Arieiro to Pico RuivoTajogaite Volcano +1 more
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from $3,320
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Windstar · Star PrideRound-trip
Caribbean 7 nights Nov 29 – Dec 6, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Cruz Bay, St. John · … · San Juan, Puerto Rico8 ports
San Juan, Puerto Rico · Cruz Bay, St. John · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · Jost Van Dyke, British Virgin Islands · Virgin Gorda, British Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsTrunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. BartsMt. Liamuiga Volcano Crater Hike +3 more
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from $3,913
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Windstar · Star BreezeRound-trip
Hawaii 7 nights Dec 3 – Dec 10, 2026 from Papeete, Tahiti, French Polynesia
Papeete, Tahiti, French Polynesia · Moorea, French Polynesia · … · Papeete, Tahiti, French Polynesia7 ports
Papeete, Tahiti, French Polynesia · Moorea, French Polynesia · Raiatea, French Polynesia · Tahaa, French Polynesia · Bora Bora, French Polynesia · Huahine, French Polynesia · Papeete, Tahiti, French Polynesia
★ Bucket-list Teahupo'oPrivate Lagoon SafariTaputapuatea MaraeTahaa Coral Garden Snorkel by Private Outrigger +2 more
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from $3,306
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Windstar · Star LegendOne-way
Caribbean 8 nights Dec 4 – Dec 12, 2026 from Bridgetown, Barbados to Port of Oranjestad, Aruba, Caribbean
Bridgetown, Barbados · Rodney Bay, St. Lucia · … · Port of Oranjestad, Aruba, Caribbean8 ports
Bridgetown, Barbados · Rodney Bay, St. Lucia · Sca · Bequia, Grenadines · Mayreau, Grenadines · St. Georges, Grenada, West Indies · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Full-Day Private Catamaran Sail to Soufrière & the…Tobago Cays & Mystique Full-Day Private SailSalt Whistle Bay +3 more
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from $2,940
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Windstar · Star PrideRound-trip
Caribbean 7 nights Dec 6 – Dec 13, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Georges, Grenada, West Indies · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · St. Georges, Grenada, West Indies · Bequia, Grenadines · Mayreau, Grenadines · Deshaies, Guadeloupe · Marmaris, Turkey · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsGrenada Private Taxi TourTobago Cays & Mystique Full-Day Private SailSalt Whistle Bay +2 more
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from $3,636
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Windstar · Wind SpiritRound-trip
Mediterranean 10 nights Dec 7 – Dec 17, 2026 from Santa Cruz de Tenerife, Canary Islands
Santa Cruz de Tenerife, Canary Islands · Santa Cruz de La Palma, Spain · … · Santa Cruz de Tenerife, Canary Islands8 ports
Santa Cruz de Tenerife, Canary Islands · Santa Cruz de La Palma, Spain · Hie · San Sebastian, Spain · M6e · Funchal, Madeira, Portugal · Arrecife, Lanzarote, Canary Islands · Santa Cruz de Tenerife, Canary Islands
★ Bucket-list Teide National ParkTajogaite VolcanoPrivate Pintxos & Txakoli Wine Crawl in Parte ViejaPico do Arieiro to Pico Ruivo +1 more
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from $3,370
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Windstar · Star BreezeRound-trip
Hawaii 7 nights Dec 10 – Dec 17, 2026 from Papeete, Tahiti, French Polynesia
Papeete, Tahiti, French Polynesia · Moorea, French Polynesia · … · Papeete, Tahiti, French Polynesia7 ports
Papeete, Tahiti, French Polynesia · Moorea, French Polynesia · Raiatea, French Polynesia · Tahaa, French Polynesia · Bora Bora, French Polynesia · Huahine, French Polynesia · Papeete, Tahiti, French Polynesia
★ Bucket-list Teahupo'oPrivate Lagoon SafariTaputapuatea MaraeTahaa Coral Garden Snorkel by Private Outrigger +2 more
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from $2,851
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Windstar · Star LegendOne-way
Caribbean 8 nights Dec 12 – Dec 20, 2026 from Port of Oranjestad, Aruba, Caribbean to Balboa, Panama
Port of Oranjestad, Aruba, Caribbean · Cartagena, Colombia · … · Balboa, Panama6 ports
Port of Oranjestad, Aruba, Caribbean · Cartagena, Colombia · Bocas Del Toro, Panama · San Blas Islands, Panama · Panama Canal, Panama · Balboa, Panama
★ Bucket-list ArubaThe Roman Theatre of Cartagena with the Rafael Mon…Isla ZapatillasGuna Yala by Private Panga +2 more
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from $3,246
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Windstar · Wind StarOne-way
Pacific 7 nights Dec 12 – Dec 19, 2026 from Puerto Caldera, Costa Rica to Colon, Panama
Puerto Caldera, Costa Rica · Quepos, Costa Rica · … · Colon, Panama7 ports
Puerto Caldera, Costa Rica · Quepos, Costa Rica · Puerto Jimenez, Costa Rica · Isla Parida, Panama · Balboa, Panama · Panama Canal, Panama · Colon, Panama
★ Bucket-list Isla Tortuga VIPManuel Antonio National ParkCorcovado's Sirena StationPanama Canal Partial Transit +2 more
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from $4,360
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Windstar · Star PrideRound-trip
Caribbean 7 nights Dec 13 – Dec 20, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Cruz Bay, St. John · … · San Juan, Puerto Rico8 ports
San Juan, Puerto Rico · Cruz Bay, St. John · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · Jost Van Dyke, British Virgin Islands · Virgin Gorda, British Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsTrunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. BartsMt. Liamuiga Volcano Crater Hike +3 more
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from $3,983
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Windstar · Wind StarOne-way
Panama Canal 7 nights Dec 26 – Jan 2, 2027 from Puerto Caldera, Costa Rica to Colon, Panama
Puerto Caldera, Costa Rica · Quepos, Costa Rica · … · Colon, Panama7 ports
Puerto Caldera, Costa Rica · Quepos, Costa Rica · Puerto Jimenez, Costa Rica · Isla Parida, Panama · Balboa, Panama · Panama Canal, Panama · Colon, Panama
★ Bucket-list Isla Tortuga VIPManuel Antonio National ParkCorcovado's Sirena StationPanama Canal Partial Transit +2 more
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from $4,395
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Windstar · Wind SurfRound-trip
Asia 7 nights Dec 26 – Jan 2, 2027 from Philipsburg, St. Maarten
Philipsburg, St. Maarten · Gustavia, St. Barts · … · Philipsburg, St. Maarten8 ports
Philipsburg, St. Maarten · Gustavia, St. Barts · Jeju Island South Korea · Roseau, Dominica · Mayreau, Grenadines · Les Saintes, Guadeloupe · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten
★ Bucket-list Random Wind 'Paradise Day Sail'Private Open-Top Mini Moke Island Tour of St. BartsSeongsan IlchulbongBoiling Lake Hike +3 more
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from $3,377
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Windstar · Star PrideRound-trip
Caribbean 7 nights Dec 27 – Jan 3, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Cruz Bay, St. John · … · San Juan, Puerto Rico8 ports
San Juan, Puerto Rico · Cruz Bay, St. John · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · Jost Van Dyke, British Virgin Islands · Virgin Gorda, British Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsTrunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. BartsMt. Liamuiga Volcano Crater Hike +3 more
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from $3,563
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