Bucket-List Cruise Adventures

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

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Filtering South America ×Hawaii ×Visits Valparaiso (Santiago) × Clear all
Showing 20 of 20 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 PuertoARC Transatlantic RallyPrivate Full-Day Península Valdés +6 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 Custom ValparaísoPrivate Catamaran Sail & SnorkelPrivate Osorno Volcano & Petrohué Falls Shore Excu…Isla Martillo +5 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 PuertoARC Transatlantic RallyPrivate Full-Day Península Valdés +6 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 Custom ValparaísoPrivate Catamaran Sail & SnorkelPrivate Osorno Volcano & Petrohué Falls Shore Excu…Full-Day King Penguin Colony & Tierra del Fuego Ex… +6 more
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from $10,899
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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 ValdésBertha's Beach Private 4×4 Gentoo Penguin ExpeditionPrivate Expert Walking Tour of Kiel +5 more
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from $6,699
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MSC Cruises · MSC MagnificaRepositioning
Northern Europe 99 nights Jan 26 – May 5, 2027 from Buenos Aires, Argentina to Civitavecchia (Rome), Italy
Buenos Aires, Argentina · Puerto Madryn, Argentina · … · Civitavecchia (Rome), Italy37 ports
Buenos Aires, Argentina · Puerto Madryn, Argentina · Port Stanley, Falkland Islands · Ushuaia, Argentina · Puerto Montt, Chile · Valparaiso (Santiago), Chile · Easter Island, Chile · Pitcairn Island, United Kingdom · Papeete, Tahiti, French Polynesia · Moorea, French Polynesia · Aitutaki, Cook Islands · Rarotonga, Cook Islands · Bay of Islands (Paihia), New Zealand · Auckland, New Zealand · Tauranga, New Zealand · Bluff, New Zealand · Dunedin, New Zealand · Hobart, Australia · Sydney, Australia · Noumea, New Caledonia · Luganville, Vanuatu · Apia, Western Samoa · Pago Pago, American Samoa · Honolulu, Oahu, Hawaii · Hilo, Hawaii · Los Angeles, California · Cabo San Lucas, Mexico · Puntarenas, Costa Rica · Balboa, Panama · Panama Canal (transit) Panama · La Romana, Dominican Republic · Road Town, Tortola, B.V.I. · Philipsburg, St. Maarten · Las Palmas, Gran Canaria, Canary Islands · Ibiza, Spain · Naples, Italy · Civitavecchia (Rome), Italy
★ Bucket-list El Teatro ColónPrivate Full-Day Península ValdésBertha's Beach Private 4×4 Gentoo Penguin ExpeditionIsla Martillo +33 more
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from $14,299
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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 PuertoARC Transatlantic RallyPrivate Full-Day Península Valdés +6 more
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from $11,099
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MSC Cruises · MSC MagnificaRepositioning
Mediterranean 86 nights Feb 10 – May 7, 2027 from Valparaiso (Santiago), Chile to Marseille, France
Valparaiso (Santiago), Chile · Easter Island, Chile · … · Marseille, France33 ports
Valparaiso (Santiago), Chile · Easter Island, Chile · Pitcairn Island, United Kingdom · Papeete, Tahiti, French Polynesia · Moorea, French Polynesia · Aitutaki, Cook Islands · Rarotonga, Cook Islands · Bay of Islands (Paihia), New Zealand · Auckland, New Zealand · Tauranga, New Zealand · Bluff, New Zealand · Dunedin, New Zealand · Hobart, Australia · Sydney, Australia · Noumea, New Caledonia · Luganville, Vanuatu · Apia, Western Samoa · Pago Pago, American Samoa · Honolulu, Oahu, Hawaii · Hilo, Hawaii · Los Angeles, California · Cabo San Lucas, Mexico · Puntarenas, Costa Rica · Balboa, Panama · La Romana, Dominican Republic · Road Town, Tortola, B.V.I. · Philipsburg, St. Maarten · Las Palmas, Gran Canaria, Canary Islands · Ibiza, Spain · Naples, Italy · Civitavecchia (Rome), Italy · Genoa, Italy · Marseille, France
★ Bucket-list Private Custom ValparaísoPrivate Full-Island Moai & Sacred Sites Tour with…Bounty Bay Landing & AdamstownTeahupo'o +29 more
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from $12,459
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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 Custom ValparaísoPrivate Osorno Volcano & Petrohué Falls Shore Excu…Laguna San Rafael GlacierPrivate Expert Walking Tour of Kiel +24 more
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from $16,399
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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 Custom ValparaísoPrivate Catamaran Sail & SnorkelPrivate Osorno Volcano & Petrohué Falls Shore Excu…Full-Day King Penguin Colony & Tierra del Fuego Ex… +6 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 PuertoARC Transatlantic RallyPrivate Full-Day Península Valdés +6 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 Custom ValparaísoPrivate Catamaran Sail & SnorkelPrivate Osorno Volcano & Petrohué Falls Shore Excu…Full-Day King Penguin Colony & Tierra del Fuego Ex… +6 more
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from $8,099
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Azamara · Azamara QuestOne-way
Panama Canal 19 nights Jan 5 – Jan 24, 2028 from Miami, Florida to Valparaiso (Santiago), Chile
Miami, Florida · Cozumel, Mexico · … · Valparaiso (Santiago), Chile13 ports
Miami, Florida · Cozumel, Mexico · Belize City, Belize · Roatan, Honduras · Puerto Limon, Costa Rica · Bocas Del Toro, Panama · Panama Canal, Panama · Panama City, Panama · Manta (Quito), Ecuador · Callao (Lima), Peru · Pisco (Puerto San Martin), Peru · Coquimbo (La Serena), Chile · Valparaiso (Santiago), Chile
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…El Cielo + Palancar + Columbia 3-Stop SnorkelGreat Blue Hole Flightseeing & Lighthouse Reef Sno…Hold a Sloth at Daniel Johnson's Monkey & Sloth Ha… +8 more
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from $8,839
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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 PuertoARC Transatlantic RallyPrivate Full-Day Península Valdés +6 more
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from $9,899
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Azamara · Azamara QuestOne-way
Panama Canal 10 nights Jan 14 – Jan 24, 2028 from Panama City, Panama to Valparaiso (Santiago), Chile
Panama City, Panama · Manta (Quito), Ecuador · … · Valparaiso (Santiago), Chile6 ports
Panama City, Panama · Manta (Quito), Ecuador · Callao (Lima), Peru · Pisco (Puerto San Martin), Peru · Coquimbo (La Serena), Chile · Valparaiso (Santiago), Chile
★ Bucket-list Panama Canal Miraflores LocksPacoche Wildlife RefugePalomino IslandsBallestas Islands +2 more
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from $3,799
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Azamara · Azamara QuestOne-way
South America 23 nights Jan 24 – Feb 16, 2028 from Valparaiso (Santiago), Chile to Buenos Aires, Argentina
Valparaiso (Santiago), Chile · Puerto Montt, Chile · … · Buenos Aires, Argentina12 ports
Valparaiso (Santiago), Chile · Puerto Montt, Chile · Castro, Chile · Puerto Chacabuco, Chile · Sailing IN The Chilean Fjords · Punta Arenas, Chile · Ushuaia, Argentina · Sailing IN The Antarctic Peninsula · Port Stanley, Falkland Islands · Punta del Este, Uruguay · Montevideo, Uruguay · Buenos Aires, Argentina
★ Bucket-list Private Custom ValparaísoPrivate Osorno Volcano & Petrohué Falls Shore Excu…Laguna San Rafael GlacierFull-Day King Penguin Colony & Tierra del Fuego Ex… +5 more
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from $10,421
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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 Custom ValparaísoPrivate Catamaran Sail & SnorkelPrivate Osorno Volcano & Petrohué Falls Shore Excu…Full-Day King Penguin Colony & Tierra del Fuego Ex… +6 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 Custom ValparaísoPrivate Osorno Volcano & Petrohué Falls Shore Excu…Laguna San Rafael GlacierFull-Day King Penguin Colony & Tierra del Fuego Ex… +9 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 PuertoARC Transatlantic RallyPrivate Full-Day Península Valdés +6 more
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from $9,799
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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 Custom ValparaísoPrivate Catamaran Sail & SnorkelPrivate Osorno Volcano & Petrohué Falls Shore Excu…Full-Day King Penguin Colony & Tierra del Fuego Ex… +6 more
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from $9,899
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19 lines
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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