Bucket-List Cruise Adventures

Pick your sailing — we plan the whole adventure

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

When are you free? — only cruises that fit entirely inside your dates
My result then click any cruise row to open it
Where to? tap as many as you like Caribbean Mediterranean Alaska Bahamas Mexico Northern Europe Hawaii Bermuda Europe Asia Australia & South Pacific Panama Canal South America North America Pacific Middle East Africa
Trip tap one or more Round-trip One-way Repositioning
Length tap one or more 3–5 nights 6–8 nights 9–12 nights 13+ nights
Cruise level tap one or more Luxury Premium Contemporary River
+ pick specific cruise lines · 2 selected
Luxury Azamara Oceania Regent Seabourn Viking Ocean River AmaWaterways Avalon Viking River Premium Celebrity Cunard Disney Holland America Princess Virgin Voyages Contemporary Carnival Costa MSC Cruises Norwegian Royal Caribbean
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Filtering Seabourn ×Viking Ocean ×Visits Puerto Montt × Clear all
Showing 14 of 14 sailings
Viking Ocean · Viking JupiterOne-way
South America 17 nights Dec 2 – Dec 19, 2026 from Buenos Aires, Argentina to Valparaiso (Santiago), Chile
Buenos Aires, Argentina · Montevideo, Uruguay · … · Valparaiso (Santiago), Chile15 ports
Buenos Aires, Argentina · Montevideo, Uruguay · Sail the Atlantic Ocean · Puerto Madryn, Argentina · Sail the Atlantic Ocean · Port Stanley, Falkland Islands · Sail the Atlantic Ocean · Scenic Sailing: Cape Horn · Ushuaia, Argentina · Punta Arenas, Chile · Scenic Sailing: Amalia Glacier · Scenic Sailing: Chilean Fjords · Puerto Montt, Chile · Sail the Pacific Ocean · Valparaiso (Santiago), Chile
★ Bucket-list El Teatro ColónMercado del PuertoPrivate Full-Day Península ValdésIsla Martillo +2 more
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from $9,299
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Viking Ocean · Viking JupiterOne-way
South America 17 nights Dec 19 – Jan 5, 2027 from Valparaiso (Santiago), Chile to Buenos Aires, Argentina
Valparaiso (Santiago), Chile · Sail the Pacific Ocean · … · Buenos Aires, Argentina15 ports
Valparaiso (Santiago), Chile · Sail the Pacific Ocean · Puerto Montt, Chile · Scenic Sailing: Chilean Fjords · Scenic Sailing: Amalia Glacier · Sail the Pacific Ocean · Ushuaia, Argentina · Scenic Sailing: Cape Horn · Sail the Atlantic Ocean · Port Stanley, Falkland Islands · Sail the Atlantic Ocean · Puerto Madryn, Argentina · Sail the Atlantic Ocean · Montevideo, Uruguay · Buenos Aires, Argentina
★ Bucket-list Private Osorno Volcano & Petrohué Falls Shore Excu…Isla MartilloPrivate Full-Day Península ValdésMercado del Puerto +1 more
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from $9,699
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Viking Ocean · Viking JupiterOne-way
South America 17 nights Jan 5 – Jan 22, 2027 from Buenos Aires, Argentina to Valparaiso (Santiago), Chile
Buenos Aires, Argentina · Montevideo, Uruguay · … · Valparaiso (Santiago), Chile15 ports
Buenos Aires, Argentina · Montevideo, Uruguay · Sail the Atlantic Ocean · Puerto Madryn, Argentina · Sail the Atlantic Ocean · Port Stanley, Falkland Islands · Sail the Atlantic Ocean · Scenic Sailing: Cape Horn · Ushuaia, Argentina · Punta Arenas, Chile · Scenic Sailing: Amalia Glacier · Scenic Sailing: Chilean Fjords · Puerto Montt, Chile · Sail the Pacific Ocean · Valparaiso (Santiago), Chile
★ Bucket-list El Teatro ColónMercado del PuertoPrivate Full-Day Península ValdésIsla Martillo +2 more
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from $10,599
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Viking Ocean · Viking JupiterOne-way
South America 17 nights Jan 22 – Feb 8, 2027 from Valparaiso (Santiago), Chile to Buenos Aires, Argentina
Valparaiso (Santiago), Chile · Sail the Pacific Ocean · … · Buenos Aires, Argentina15 ports
Valparaiso (Santiago), Chile · Sail the Pacific Ocean · Puerto Montt, Chile · Scenic Sailing: Chilean Fjords · Scenic Sailing: Amalia Glacier · Punta Arenas, Chile · Ushuaia, Argentina · Scenic Sailing: Cape Horn · Sail the Atlantic Ocean · Port Stanley, Falkland Islands · Sail the Atlantic Ocean · Puerto Madryn, Argentina · Sail the Atlantic Ocean · Montevideo, Uruguay · Buenos Aires, Argentina
★ Bucket-list Private Osorno Volcano & Petrohué Falls Shore Excu…Full-Day King Penguin Colony & Tierra del Fuego Ex…Isla MartilloPrivate Full-Day Península Valdés +2 more
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from $10,899
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Viking Ocean · Viking JupiterOne-way
South America 17 nights Feb 8 – Feb 25, 2027 from Buenos Aires, Argentina to Valparaiso (Santiago), Chile
Buenos Aires, Argentina · Montevideo, Uruguay · … · Valparaiso (Santiago), Chile15 ports
Buenos Aires, Argentina · Montevideo, Uruguay · Sail the Atlantic Ocean · Puerto Madryn, Argentina · Sail the Atlantic Ocean · Port Stanley, Falkland Islands · Sail the Atlantic Ocean · Scenic Sailing: Cape Horn · Ushuaia, Argentina · Punta Arenas, Chile · Scenic Sailing: Amalia Glacier · Scenic Sailing: Chilean Fjords · Puerto Montt, Chile · Sail the Pacific Ocean · Valparaiso (Santiago), Chile
★ Bucket-list El Teatro ColónMercado del PuertoPrivate Full-Day Península ValdésIsla Martillo +2 more
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from $11,099
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Viking Ocean · Viking JupiterOne-way
South America 17 nights Feb 25 – Mar 14, 2027 from Valparaiso (Santiago), Chile to Buenos Aires, Argentina
Valparaiso (Santiago), Chile · Sail the Pacific Ocean · … · Buenos Aires, Argentina15 ports
Valparaiso (Santiago), Chile · Sail the Pacific Ocean · Puerto Montt, Chile · Scenic Sailing: Chilean Fjords · Scenic Sailing: Amalia Glacier · Punta Arenas, Chile · Ushuaia, Argentina · Scenic Sailing: Cape Horn · Sail the Atlantic Ocean · Port Stanley, Falkland Islands · Sail the Atlantic Ocean · Puerto Madryn, Argentina · Sail the Atlantic Ocean · Montevideo, Uruguay · Buenos Aires, Argentina
★ Bucket-list Private Osorno Volcano & Petrohué Falls Shore Excu…Full-Day King Penguin Colony & Tierra del Fuego Ex…Isla MartilloPrivate Full-Day Península Valdés +2 more
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from $10,499
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Viking Ocean · Viking JupiterOne-way
South America 17 nights Dec 4 – Dec 21, 2027 from Buenos Aires, Argentina to Valparaiso (Santiago), Chile
Buenos Aires, Argentina · Montevideo, Uruguay · … · Valparaiso (Santiago), Chile15 ports
Buenos Aires, Argentina · Montevideo, Uruguay · Sail the Atlantic Ocean · Puerto Madryn, Argentina · Sail the Atlantic Ocean · Port Stanley, Falkland Islands · Sail the Atlantic Ocean · Scenic Sailing: Cape Horn · Ushuaia, Argentina · Punta Arenas, Chile · Scenic Sailing: Amalia Glacier · Scenic Sailing: Chilean Fjords · Puerto Montt, Chile · Sail the Pacific Ocean · Valparaiso (Santiago), Chile
★ Bucket-list El Teatro ColónMercado del PuertoPrivate Full-Day Península ValdésIsla Martillo +2 more
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from $8,899
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Viking Ocean · Viking JupiterOne-way
South America 17 nights Dec 21 – Jan 7, 2028 from Valparaiso (Santiago), Chile to Buenos Aires, Argentina
Valparaiso (Santiago), Chile · Sail the Pacific Ocean · … · Buenos Aires, Argentina15 ports
Valparaiso (Santiago), Chile · Sail the Pacific Ocean · Puerto Montt, Chile · Scenic Sailing: Chilean Fjords · Scenic Sailing: Amalia Glacier · Punta Arenas, Chile · Ushuaia, Argentina · Scenic Sailing: Cape Horn · Sail the Atlantic Ocean · Port Stanley, Falkland Islands · Sail the Atlantic Ocean · Puerto Madryn, Argentina · Sail the Atlantic Ocean · Montevideo, Uruguay · Buenos Aires, Argentina
★ Bucket-list Private Osorno Volcano & Petrohué Falls Shore Excu…Full-Day King Penguin Colony & Tierra del Fuego Ex…Isla MartilloPrivate Full-Day Península Valdés +2 more
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from $8,099
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Seabourn · Seabourn QuestRepositioning
Mediterranean 112 nights Jan 7 – Apr 28, 2028 from Miami, Florida to Lisbon, Portugal
Miami, Florida · Fuerte Amador, Panama · … · Lisbon, Portugal52 ports
Miami, Florida · Fuerte Amador, Panama · Guayaquil (Quito), Ecuador · Salaverry (Trujillo), Peru · Callao (Lima), Peru · General San Martin, Peru · Easter Island, Chile · Robinson Crusoe Island, Chile · Santa Clara Island, Chile · Valparaiso (Santiago), Chile · Puerto Montt, Chile · Castro, Chile · Puerto Chacabuco, Chile · Pio Xi (Bruggen) Glacier · Amalia (Skua) Glacier, Chile · Strait OF Magellan · Punta Arenas, Chile · Garibaldi Glacier, Chile · Ushuaia, Argentina · The Seabourn Antarctic Experience (day 1) · The Seabourn Antarctic Experience (day 2) · The Seabourn Antarctic Experience (day 3) · The Seabourn Antarctic Experience (day 4) · The Seabourn Antarctic Experience (day 5) · The Seabourn Falkland Island Experience (day 1) · The Seabourn Falkland Island Experience (day 2) · Stanley, Falkland Islands · Montevideo, Uruguay · Buenos Aires, Argentina · Inaccessible Island, Tristan da Cunha · Nightingale Island, Tristan da Cunha · Richards Bay, South Africa · Maputo, Mozambique · Durban, South Africa · Port Elizabeth, South Africa · Mossel Bay, South Africa · Cape Town, South Africa · Luderitz, Namibia · Walvis Bay, Namibia · Luanda, Angola · Principe Island, Sao Tome and Principe · Cotonou, Benin · Tema (Accra), Ghana · Takoradi, Ghana · Dakar, Senegal · Mindelo, Cape Verde Island · Las Palmas, Gran Canaria, Canary Islands · Arrecife, Lanzarote, Canary Islands · Casablanca, Morocco · Tangier, Morocco · Cadiz (Seville), Spain · Lisbon, Portugal
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Full-Island Moai & Sacred Sites Tour with…Private Osorno Volcano & Petrohué Falls Shore Excu…Full-Day King Penguin Colony & Tierra del Fuego Ex… +10 more
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from $72,799
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Viking Ocean · Viking JupiterOne-way
South America 17 nights Jan 7 – Jan 24, 2028 from Buenos Aires, Argentina to Valparaiso (Santiago), Chile
Buenos Aires, Argentina · Montevideo, Uruguay · … · Valparaiso (Santiago), Chile15 ports
Buenos Aires, Argentina · Montevideo, Uruguay · Sail the Atlantic Ocean · Puerto Madryn, Argentina · Sail the Atlantic Ocean · Port Stanley, Falkland Islands · Sail the Atlantic Ocean · Scenic Sailing: Cape Horn · Ushuaia, Argentina · Punta Arenas, Chile · Scenic Sailing: Amalia Glacier · Scenic Sailing: Chilean Fjords · Puerto Montt, Chile · Sail the Pacific Ocean · Valparaiso (Santiago), Chile
★ Bucket-list El Teatro ColónMercado del PuertoPrivate Full-Day Península ValdésIsla Martillo +2 more
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from $9,899
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Viking Ocean · Viking JupiterOne-way
South America 17 nights Jan 24 – Feb 10, 2028 from Valparaiso (Santiago), Chile to Buenos Aires, Argentina
Valparaiso (Santiago), Chile · Sail the Pacific Ocean · … · Buenos Aires, Argentina15 ports
Valparaiso (Santiago), Chile · Sail the Pacific Ocean · Puerto Montt, Chile · Scenic Sailing: Chilean Fjords · Scenic Sailing: Amalia Glacier · Punta Arenas, Chile · Ushuaia, Argentina · Scenic Sailing: Cape Horn · Sail the Atlantic Ocean · Port Stanley, Falkland Islands · Sail the Atlantic Ocean · Puerto Madryn, Argentina · Sail the Atlantic Ocean · Montevideo, Uruguay · Buenos Aires, Argentina
★ Bucket-list Private Osorno Volcano & Petrohué Falls Shore Excu…Full-Day King Penguin Colony & Tierra del Fuego Ex…Isla MartilloPrivate Full-Day Península Valdés +2 more
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from $9,899
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Seabourn · Seabourn QuestRepositioning
Northern Europe 53 nights Feb 5 – Mar 29, 2028 from Valparaiso (Santiago), Chile to Cape Town, South Africa
Valparaiso (Santiago), Chile · Puerto Montt, Chile · … · Cape Town, South Africa28 ports
Valparaiso (Santiago), Chile · Puerto Montt, Chile · Castro, Chile · Puerto Chacabuco, Chile · Pio Xi (Bruggen) Glacier · Amalia (Skua) Glacier, Chile · Punta Arenas, Chile · Strait OF Magellan · Garibaldi Glacier, Chile · Ushuaia, Argentina · The Seabourn Antarctic Experience (day 1) · The Seabourn Antarctic Experience (day 2) · The Seabourn Antarctic Experience (day 3) · The Seabourn Antarctic Experience (day 4) · The Seabourn Antarctic Experience (day 5) · The Seabourn Falkland Island Experience (day 1) · The Seabourn Falkland Island Experience (day 2) · Stanley, Falkland Islands · Montevideo, Uruguay · Buenos Aires, Argentina · Inaccessible Island, Tristan da Cunha · Nightingale Island, Tristan da Cunha · Richards Bay, South Africa · Maputo, Mozambique · Durban, South Africa · Port Elizabeth, South Africa · Mossel Bay, South Africa · Cape Town, South Africa
★ Bucket-list Private Osorno Volcano & Petrohué Falls Shore Excu…Full-Day King Penguin Colony & Tierra del Fuego Ex…Isla MartilloPrivate Stanley Highlights & Gentoo Penguin Colony… +2 more
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from $35,598
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Viking Ocean · Viking JupiterOne-way
South America 17 nights Feb 10 – Feb 27, 2028 from Buenos Aires, Argentina to Valparaiso (Santiago), Chile
Buenos Aires, Argentina · Montevideo, Uruguay · … · Valparaiso (Santiago), Chile15 ports
Buenos Aires, Argentina · Montevideo, Uruguay · Sail the Atlantic Ocean · Puerto Madryn, Argentina · Sail the Atlantic Ocean · Port Stanley, Falkland Islands · Sail the Atlantic Ocean · Scenic Sailing: Cape Horn · Ushuaia, Argentina · Punta Arenas, Chile · Scenic Sailing: Amalia Glacier · Scenic Sailing: Chilean Fjords · Puerto Montt, Chile · Sail the Pacific Ocean · Valparaiso (Santiago), Chile
★ Bucket-list El Teatro ColónMercado del PuertoPrivate Full-Day Península ValdésIsla Martillo +2 more
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from $9,799
Book This Cruise@ Cruisebound
Viking Ocean · Viking JupiterOne-way
South America 17 nights Feb 27 – Mar 15, 2028 from Valparaiso (Santiago), Chile to Buenos Aires, Argentina
Valparaiso (Santiago), Chile · Sail the Pacific Ocean · … · Buenos Aires, Argentina15 ports
Valparaiso (Santiago), Chile · Sail the Pacific Ocean · Puerto Montt, Chile · Scenic Sailing: Chilean Fjords · Scenic Sailing: Amalia Glacier · Punta Arenas, Chile · Ushuaia, Argentina · Scenic Sailing: Cape Horn · Sail the Atlantic Ocean · Port Stanley, Falkland Islands · Sail the Atlantic Ocean · Puerto Madryn, Argentina · Sail the Atlantic Ocean · Montevideo, Uruguay · Buenos Aires, Argentina
★ Bucket-list Private Osorno Volcano & Petrohué Falls Shore Excu…Full-Day King Penguin Colony & Tierra del Fuego Ex…Isla MartilloPrivate Full-Day Península Valdés +2 more
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from $9,899
Book This Cruise@ Cruisebound

Itineraries from the Cruisebound catalog + our enrichment; schedules cross-checked against official port authorities. Booking via Cruisebound and CruiseDirect — we may earn a commission, at no extra cost to you.

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MSC Cruises Royal Caribbean Carnival Viking River Costa Norwegian AmaWaterways Princess Celebrity Viking Ocean Avalon Disney Holland America Oceania Virgin Voyages Regent Cunard Seabourn Azamara