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
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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
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Luxury Azamara Explora Journeys Oceania Regent Seabourn Silversea Viking Ocean Windstar River AmaWaterways Avalon Viking River Premium Celebrity Cunard Disney Holland America Princess Virgin Virgin Voyages Contemporary Carnival Costa MSC Cruises Norwegian Royal Caribbean
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Showing 36 of 686 sailings
Celebrity · Celebrity SilhouetteRound-trip
North America 11 nights Sep 17 – Sep 28, 2026 from Boston, Massachusetts
Boston, Massachusetts · Rockland, Maine · … · Boston, Massachusetts8 ports
Boston, Massachusetts · Rockland, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Quebec City, Quebec · Charlottetown, Prince Edward Island · Portland, Maine · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourLuxury Camden Sailing Experience on Penobscot BayPeggy's Cove & LunenburgBridgeClimb Sydney +3 more
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from $2,507
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Regent · Seven Seas SplendorOne-way
North America 11 nights Sep 17 – Sep 28, 2026 from Montreal, Quebec to Boston, Massachusetts
Montreal, Quebec · Quebec City, Quebec · … · Boston, Massachusetts11 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Sept-Iles, Canada · Havre St. Pierre, Quebec · Willis Island · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Saint John, New Brunswick · Boston, Massachusetts
★ Bucket-list Notre-Dame BasilicaOld Québec Private Walking Tour with Expert Local…Sept-Îles Archipelago Zodiac ExpeditionMingan Archipelago +6 more
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from $15,899
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Carnival · Carnival AdventureRound-trip
Australia & South Pacific 3 nights Sep 18, 2026 from Sydney, Australia
Sydney, Australia
★ Bucket-list BridgeClimb Sydney
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from $282
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Cunard · Queen Mary 2One-way
Northern Europe 15 nights Sep 19 – Oct 4, 2026 from Southampton, England to Quebec City, Quebec
Southampton, England · New York, New York · Boston, Massachusetts · Sydney, Nova Scotia · Quebec City, Quebec
★ Bucket-list Stand Inside Stonehenge & See the Original 1215 Ma…Manhattan Helicopter TourPrivate Luxury Boston TourBridgeClimb Sydney +1 more
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from $2,649
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Holland America · VolendamOne-way
North America 7 nights Sep 19 – Sep 26, 2026 from Boston, Massachusetts to Montreal, Quebec
Boston, Massachusetts · Eastport, Maine, United States · … · Montreal, Quebec7 ports
Boston, Massachusetts · Eastport, Maine, United States · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Private Luxury Boston TourCampobello IslandPeggy's Cove & LunenburgBridgeClimb Sydney +3 more
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from $1,319
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Holland America · ZuiderdamOne-way
North America 7 nights Sep 19 – Sep 26, 2026 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgBridgeClimb SydneyGreen Gables House & Anne of Green Gables Island E… +1 more
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from $1,469
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Norwegian · Norwegian EscapeRound-trip
North America 7 nights Sep 19 – Sep 26, 2026 from New York, New York
New York, New York · Newport, Rhode Island · … · New York, New York6 ports
New York, New York · Newport, Rhode Island · Boston, Massachusetts · Sydney, Nova Scotia · Halifax, Nova Scotia · New York, New York
★ Bucket-list Manhattan Helicopter TourThe BreakersPrivate Luxury Boston TourBridgeClimb Sydney +1 more
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from $1,269
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Carnival · Carnival AdventureRound-trip
Australia & South Pacific 4 nights Sep 21, 2026 from Sydney, Australia
Sydney, Australia · Moreton Island, Australia · Sydney, Australia
★ Bucket-list BridgeClimb SydneyWild Dolphin Feeding at Dusk
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from $341
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Princess · Sapphire PrincessOne-way
North America 10 nights Sep 23 – Oct 3, 2026 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Portland, Maine · … · Quebec City, Quebec8 ports
Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Saguenay Fjord, Canada · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg +3 more
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from $1,229
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Azamara · Azamara JourneyOne-way
North America 12 nights Sep 25 – Oct 7, 2026 from Montreal, Quebec to New York, New York
Montreal, Quebec · Quebec City, Quebec · … · New York, New York13 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Lunenburg, Nova Scotia · Saint John, New Brunswick · Portland, Maine · Cape Cod, Massachusetts · Boston, Massachusetts · Marthas Vineyard, Massachusetts · New York, New York
★ Bucket-list Notre-Dame BasilicaOld Québec Private Walking Tour with Expert Local…Green Gables House & Anne of Green Gables Island E…BridgeClimb Sydney +8 more
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from $3,649
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Carnival · Carnival AdventureRound-trip
Australia & South Pacific 4 nights Sep 25, 2026 from Sydney, Australia
Sydney, Australia · Moreton Island, Australia · Sydney, Australia
★ Bucket-list BridgeClimb SydneyWild Dolphin Feeding at Dusk
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from $434
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Oceania · Oceania VistaOne-way
North America 11 nights Sep 25 – Oct 6, 2026 from Montreal, Quebec to New York, New York
Montreal, Quebec · Quebec City, Quebec · … · New York, New York10 ports
Montreal, Quebec · Quebec City, Quebec · Baie-Commeau, Quebec · Sept-Iles, Canada · Havre St. Pierre, Quebec · Corner Brook, Newfoundland · Sydney, Nova Scotia · Bay of Fundy, Canada · Portland, Maine · New York, New York
★ Bucket-list Notre-Dame BasilicaOld Québec Private Walking Tour with Expert Local…Daniel-Johnson DamSept-Îles Archipelago Zodiac Expedition +6 more
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from $7,799
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Cunard · Queen Mary 2Round-trip
North America 15 nights Sep 26 – Oct 11, 2026 from New York, New York
New York, New York · Boston, Massachusetts · … · New York, New York8 ports
New York, New York · Boston, Massachusetts · Sydney, Nova Scotia · Quebec City, Quebec · Saguenay Fjord, Canada · Sept-Iles, Canada · Halifax, Nova Scotia · New York, New York
★ Bucket-list Manhattan Helicopter TourPrivate Luxury Boston TourBridgeClimb SydneyOld Québec Private Walking Tour with Expert Local… +2 more
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from $1,719
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Holland America · VolendamOne-way
North America 12 nights Sep 26 – Oct 8, 2026 from Montreal, Quebec to New York, New York
Montreal, Quebec · Quebec City, Quebec · … · New York, New York10 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Baie-Commeau, Quebec · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Boston, Massachusetts · Oak Bluffs, Massachusetts · New York, New York
★ Bucket-list Notre-Dame BasilicaOld Québec Private Walking Tour with Expert Local…Daniel-Johnson DamGreen Gables House & Anne of Green Gables Island E… +5 more
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from $1,529
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Norwegian · Norwegian EscapeRepositioning
Mediterranean 16 nights Sep 26 – Oct 12, 2026 from New York, New York to Barcelona, Spain
New York, New York · Halifax, Nova Scotia · … · Barcelona, Spain11 ports
New York, New York · Halifax, Nova Scotia · Sydney, Nova Scotia · Ponta Delgada, Azores, Portugal · Funchal, Madeira, Portugal · Gibraltar, British Territory · Motril, Spain · Melilla, Morocco · Ibiza, Spain · Palma de Mallorca, Spain · Barcelona, Spain
★ Bucket-list Manhattan Helicopter TourPeggy's Cove & LunenburgBridgeClimb SydneySete Cidades Twin Lakes +7 more
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from $1,169
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Norwegian · Norwegian JewelOne-way
North America 11 nights Sep 26 – Oct 7, 2026 from Philadelphia, Pennsylvania to Quebec City, Quebec
Philadelphia, Pennsylvania · Portland, Maine · … · Quebec City, Quebec9 ports
Philadelphia, Pennsylvania · Portland, Maine · Bar Harbor, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · La Baie, Canada · Quebec City, Quebec
★ Bucket-list Portland Head Light & Casco Bay Scenic Lighthouse…Private Acadia National Park Van Tour with Expert…Reversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg +4 more
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from $949
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Carnival · Carnival SplendorRound-trip
Australia & South Pacific 4 nights Sep 27, 2026 from Sydney, Australia
Sydney, Australia · Moreton Island, Australia · Sydney, Australia
★ Bucket-list BridgeClimb SydneyWild Dolphin Feeding at Dusk
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from $465
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Celebrity · Celebrity EdgeRepositioning
Australia & South Pacific 18 nights Sep 28 – Oct 16, 2026 from Honolulu, Oahu, Hawaii to Sydney, Australia
Honolulu, Oahu, Hawaii · Moorea, French Polynesia · … · Sydney, Australia8 ports
Honolulu, Oahu, Hawaii · Moorea, French Polynesia · Raiatea, French Polynesia · Papeete, Tahiti, French Polynesia · International Dateline · Tauranga, New Zealand · Bay of Islands (Paihia), New Zealand · Sydney, Australia
★ Bucket-list Pearl HarborPrivate Lagoon SafariTaputapuatea MaraeTeahupo'o +3 more
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from $2,081
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Celebrity · Celebrity SilhouetteRound-trip
North America 11 nights Sep 28 – Oct 9, 2026 from Boston, Massachusetts
Boston, Massachusetts · Rockland, Maine · … · Boston, Massachusetts8 ports
Boston, Massachusetts · Rockland, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Quebec City, Quebec · Charlottetown, Prince Edward Island · Portland, Maine · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourLuxury Camden Sailing Experience on Penobscot BayPeggy's Cove & LunenburgBridgeClimb Sydney +3 more
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from $8,793
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Regent · Seven Seas SplendorOne-way
North America 11 nights Sep 28 – Oct 9, 2026 from Boston, Massachusetts to Montreal, Quebec
Boston, Massachusetts · Portland, Maine · … · Montreal, Quebec12 ports
Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Willis Island · Gaspe, Quebec · Sept-Iles, Canada · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg +7 more
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from $15,799
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Carnival · Carnival AdventureRound-trip
Australia & South Pacific 9 nights Sep 29, 2026 from Sydney, Australia
Sydney, Australia · Noumea, New Caledonia · Mystery Island Vanuatu · Port Vila, Vanuatu · Sydney, Australia
★ Bucket-list BridgeClimb SydneyAmédée Island Day TripClear Kayak & SnorkelLelepa Island
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from $822
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Carnival · Carnival SplendorRound-trip
Australia & South Pacific 4 nights Oct 1, 2026 from Sydney, Australia
Sydney, Australia · Moreton Island, Australia · Sydney, Australia
★ Bucket-list BridgeClimb SydneyWild Dolphin Feeding at Dusk
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from $469
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Holland America · ZuiderdamRound-trip
North America 7 nights Oct 3 – Oct 10, 2026 from Boston, Massachusetts
Boston, Massachusetts · Eastport, Maine, United States · … · Boston, Massachusetts7 ports
Boston, Massachusetts · Eastport, Maine, United States · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Portland, Maine · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourCampobello IslandReversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg +2 more
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from $1,714
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Princess · Crown PrincessOne-way
Australia & South Pacific 4 nights Oct 3 – Oct 7, 2026 from Auckland, New Zealand to Sydney, Australia
Auckland, New Zealand · Sydney, Australia
★ Bucket-list Waiheke Island Private Wine TourBridgeClimb Sydney
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from $1,034
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Princess · Sapphire PrincessOne-way
North America 10 nights Oct 3 – Oct 13, 2026 from Quebec City, Quebec to Boston, Massachusetts
Quebec City, Quebec · Saguenay Fjord, Canada · … · Boston, Massachusetts8 ports
Quebec City, Quebec · Saguenay Fjord, Canada · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Saint John, New Brunswick · Portland, Maine · Boston, Massachusetts
★ Bucket-list Old Québec Private Walking Tour with Expert Local…Green Gables House & Anne of Green Gables Island E…BridgeClimb SydneyPeggy's Cove & Lunenburg +3 more
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from $1,421
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Carnival · Carnival SplendorRound-trip
Australia & South Pacific 4 nights Oct 5, 2026 from Sydney, Australia
Sydney, Australia · Moreton Island, Australia · Sydney, Australia
★ Bucket-list BridgeClimb SydneyWild Dolphin Feeding at Dusk
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from $555
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Princess · Grand PrincessRepositioning
Australia & South Pacific 28 nights Oct 5 – Nov 2, 2026 from Los Angeles, California to Sydney, Australia
Los Angeles, California · Hilo, Hawaii · … · Sydney, Australia14 ports
Los Angeles, California · Hilo, Hawaii · Kona, Hawaii · Kauai, Hawaii · Honolulu, Oahu, Hawaii · Cross International Date Line · Apia, Western Samoa · Lautoka, Fiji · Suva, Fiji Islands · Dravuni Island, Fiji · Mystery Island Vanuatu · Port Vila, Vanuatu · Noumea, New Caledonia · Sydney, Australia
★ Bucket-list Warner Bros. Studio Tour HollywoodPrivate Big Island Volcanoes & Lava Fields Tour fr…Big Island Manta Ray Night SnorkelDoors-Off Helicopter Tour +9 more
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from $2,548
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Oceania · Oceania VistaOne-way
Europe 11 nights Oct 6 – Oct 17, 2026 from New York, New York to Montreal, Quebec
New York, New York · Newport, Rhode Island · … · Montreal, Quebec11 ports
New York, New York · Newport, Rhode Island · Boston, Massachusetts · Bay of Fundy, Canada · Halifax, Nova Scotia · Sydney, Nova Scotia · Corner Brook, Newfoundland · Kiel Canal, Germany · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Manhattan Helicopter TourThe BreakersPrivate Luxury Boston TourHopewell Rocks +6 more
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from $6,460
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Explora Journeys · EXPLORA IIIRound-trip
North America 15 nights Oct 7, 2026 from New York, New York
New York, New York · Portland, Maine · … · New York, New York12 ports
New York, New York · Portland, Maine · Saint John, New Brunswick · Cap-Aux-Meules, Canada · Havre St. Pierre, Quebec · Baie-Commeau, Quebec · Quebec City, Quebec · La Baie, Canada · Sept-Iles, Canada · Sydney, Nova Scotia · Halifax, Nova Scotia · New York, New York
★ Bucket-list Manhattan Helicopter TourPortland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal BoreArchipelago Flavours +7 more
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from $13,160
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Norwegian · Norwegian JewelOne-way
North America 10 nights Oct 7 – Oct 17, 2026 from Quebec City, Quebec to Philadelphia, Pennsylvania
Quebec City, Quebec · La Baie, Canada · … · Philadelphia, Pennsylvania9 ports
Quebec City, Quebec · La Baie, Canada · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Bar Harbor, Maine · Portland, Maine · Boston, Massachusetts · Philadelphia, Pennsylvania
★ Bucket-list Old Québec Private Walking Tour with Expert Local…Saguenay Fjord Zodiac Whale-Watching with NaturalistGreen Gables House & Anne of Green Gables Island E…BridgeClimb Sydney +4 more
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from $1,079
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Princess · Crown PrincessOne-way
Australia & South Pacific 11 nights Oct 7 – Oct 18, 2026 from Sydney, Australia to Fremantle, Australia
Sydney, Australia · Newcastle, Australia · … · Fremantle, Australia7 ports
Sydney, Australia · Newcastle, Australia · Melbourne, Australia · Adelaide, Australia · Albany, Australia · Margaret River, Australia · Fremantle, Australia
★ Bucket-list BridgeClimb SydneyHunter Valley Private Boutique Wine Tour from Newc…Great Ocean Road & 12 ApostlesBarossa Valley +3 more
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from $3,074
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Carnival · Carnival AdventureRound-trip
Australia & South Pacific 4 nights Oct 8, 2026 from Sydney, Australia
Sydney, Australia · Moreton Island, Australia · Sydney, Australia
★ Bucket-list BridgeClimb SydneyWild Dolphin Feeding at Dusk
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from $496
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Carnival · Carnival SplendorRound-trip
Australia & South Pacific 3 nights Oct 9, 2026 from Sydney, Australia
Sydney, Australia
★ Bucket-list BridgeClimb Sydney
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from $1,058
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Celebrity · Celebrity SilhouetteRound-trip
North America 11 nights Oct 9 – Oct 20, 2026 from Boston, Massachusetts
Boston, Massachusetts · Rockland, Maine · … · Boston, Massachusetts8 ports
Boston, Massachusetts · Rockland, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Quebec City, Quebec · Charlottetown, Prince Edward Island · Portland, Maine · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourLuxury Camden Sailing Experience on Penobscot BayPeggy's Cove & LunenburgBridgeClimb Sydney +3 more
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from $17,608
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Regent · Seven Seas SplendorOne-way
North America 11 nights Oct 9 – Oct 20, 2026 from Montreal, Quebec to New York, New York
Montreal, Quebec · Quebec City, Quebec · … · New York, New York12 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Baie-Commeau, Quebec · Willis Island · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Saint John, New Brunswick · Eastport, Maine, United States · Willis Island · New York, New York
★ Bucket-list Notre-Dame BasilicaOld Québec Private Walking Tour with Expert Local…Daniel-Johnson DamZodiac Circumnavigation of Willis Island +6 more
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from $13,249
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Holland America · ZuiderdamOne-way
North America 7 nights Oct 10 – Oct 17, 2026 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Portland, Maine · … · Quebec City, Quebec6 ports
Boston, Massachusetts · Portland, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Peggy's Cove & LunenburgBridgeClimb Sydney +2 more
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from $1,331
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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.

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