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 ×Oceania ×Visits Puerto Montt × Clear all
Showing 6 of 6 sailings
Oceania · Oceania InsigniaOne-way
Europe 21 nights Jan 3 – Jan 24, 2027 from Lima, Peru to Buenos Aires, Argentina
Lima, Peru · Pisco (Puerto San Martin), Peru · … · Buenos Aires, Argentina15 ports
Lima, Peru · Pisco (Puerto San Martin), Peru · Coquimbo (La Serena), Chile · San Antonio, Santiago, Chile · Puerto Montt, Chile · Puerto Chacabuco, Chile · Laguna San Raphael, Chile · Kiel Canal, Germany · Punta Arenas, Chile · Kiel Canal, Germany · Ushuaia, Argentina · Port Stanley, Falkland Islands · Puerto Madryn, Argentina · Punta del Este, Uruguay · Buenos Aires, Argentina
★ Bucket-list Private Santiago City TourPrivate Osorno Volcano & Petrohué Falls Shore Excu…Full-Day King Penguin Colony & Tierra del Fuego Ex…Isla Martillo +2 more
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from $6,699
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Oceania · Oceania InsigniaOne-way
Europe 21 nights Jan 24 – Feb 14, 2027 from Buenos Aires, Argentina to Valparaiso (Santiago), Chile
Buenos Aires, Argentina · Puerto Madryn, Argentina · … · Valparaiso (Santiago), Chile12 ports
Buenos Aires, Argentina · Puerto Madryn, Argentina · Port Stanley, Falkland Islands · Kiel Canal, Germany · Ushuaia, Argentina · Punta Arenas, Chile · Kiel Canal, Germany · Laguna San Raphael, Chile · Puerto Chacabuco, Chile · Castro, Chile · Puerto Montt, Chile · Valparaiso (Santiago), Chile
★ Bucket-list El Teatro ColónPrivate Full-Day Península ValdésIsla MartilloFull-Day King Penguin Colony & Tierra del Fuego Ex… +1 more
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from $6,699
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Oceania · Oceania InsigniaRepositioning
Caribbean 54 nights Feb 14 – Apr 9, 2027 from Valparaiso (Santiago), Chile to Miami, Florida
Valparaiso (Santiago), Chile · Puerto Montt, Chile · … · Miami, Florida33 ports
Valparaiso (Santiago), Chile · Puerto Montt, Chile · Castro, Chile · Puerto Chacabuco, Chile · Laguna San Raphael, Chile · Kiel Canal, Germany · Punta Arenas, Chile · Ushuaia, Argentina · Kiel Canal, Germany · Port Stanley, Falkland Islands · Puerto Madryn, Argentina · Buenos Aires, Argentina · Montevideo, Uruguay · Punta del Este, Uruguay · Rio Grande, Rio Grande do Sul, Brazil · Florianopolis, Brazil · Itajai, Brazil · Santos (Sao Paulo), Brazil · Paraty, Brazil · Ilha Grande, Brazil · Buzios, Brazil · Rio de Janeiro, Brazil · Kiel Canal, Germany · Alter do Chao, Brazil · Boca da Valeria, Brazil · Manaus, Brazil · Parintins, Brazil · Santarem, Brazil · Kiel Canal, Germany · Bridgetown, Barbados · St. John's, Antigua · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Miami, Florida
★ Bucket-list Private Osorno Volcano & Petrohué Falls Shore Excu…Full-Day King Penguin Colony & Tierra del Fuego Ex…Isla MartilloPrivate Full-Day Península Valdés +8 more
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from $16,399
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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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Oceania · Oceania SirenaOne-way
Asia 14 nights Jan 19 – Feb 2, 2028 from Lima, Peru to Punta Arenas, Chile
Lima, Peru · Pisco (Puerto San Martin), Peru · … · Punta Arenas, Chile12 ports
Lima, Peru · Pisco (Puerto San Martin), Peru · Suez Canal, Egypt · Arica, Chile · Antofagasta, Chile · Valparaiso (Santiago), Chile · Suez Canal, Egypt · Puerto Montt, Chile · Castro, Chile · Puerto Chacabuco, Chile · Chilean, Fjords · Punta Arenas, Chile
★ Bucket-list Private Osorno Volcano & Petrohué Falls Shore Excu…Full-Day King Penguin Colony & Tierra del Fuego Ex…
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from $4,549
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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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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