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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Where to? tap as many as you like 1 selected · clear 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
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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 North America ×Celebrity ×Oceania × Clear all
Showing 26 of 26 sailings
Celebrity · Celebrity SilhouetteOne-way
Europe 14 nights Aug 22 – Sep 5, 2026 from Reykjavik, Iceland to Boston, Massachusetts
Reykjavik, Iceland · Isafjord, Iceland · … · Boston, Massachusetts9 ports
Reykjavik, Iceland · Isafjord, Iceland · Akureyri, Iceland · Prins Christian Sund(cruise) · Qaqortoq, Greenland · St. Johns, Newfoundland · Halifax, Nova Scotia · Sydney, Nova Scotia · Boston, Massachusetts
★ Bucket-list Inside the VolcanoDynjandi WaterfallPeggy's Cove & LunenburgBridgeClimb Sydney +1 more
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from $1,787
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Celebrity · Celebrity SilhouetteRound-trip
North America 12 nights Sep 5 – Sep 17, 2026 from Boston, Massachusetts
Boston, Massachusetts · Rockland, Maine · … · Boston, Massachusetts9 ports
Boston, Massachusetts · Rockland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Quebec City, Quebec · Charlottetown, Prince Edward Island · Portland, Maine · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $3,432
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Oceania · Oceania VistaOne-way
North America 11 nights Sep 14 – Sep 25, 2026 from New York, New York to Montreal, Quebec
New York, New York · Halifax, Nova Scotia · … · Montreal, Quebec9 ports
New York, New York · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Gaspe, Quebec · Baie-Commeau, Quebec · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Manhattan Helicopter TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $5,480
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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 TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $2,052
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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 BridgeClimb SydneyManhattan Helicopter Tour
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from $7,349
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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 TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $2,449
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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 TourPrivate Luxury Boston TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $6,460
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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 TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $1,635
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Oceania · Oceania VistaOne-way
North America 11 nights Oct 17 – Oct 28, 2026 from Montreal, Quebec to New York, New York
Montreal, Quebec · Quebec City, Quebec · … · New York, New York11 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Baie-Commeau, Quebec · Sept-Iles, Canada · Havre St. Pierre, Quebec · Corner Brook, Newfoundland · Sydney, Nova Scotia · Halifax, Nova Scotia · Bay of Fundy, Canada · New York, New York
★ Bucket-list BridgeClimb SydneyPeggy's Cove & LunenburgManhattan Helicopter Tour
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from $4,830
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Celebrity · Celebrity SilhouetteRepositioning
Caribbean 10 nights Oct 20 – Oct 30, 2026 from Boston, Massachusetts to Fort Lauderdale (Port Everglades), Florida
Boston, Massachusetts · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Port of Oranjestad, Aruba, Caribbean · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Private Luxury Boston TourPrivate Full-Day Curaçao Island Tour with Local Ex…Klein BonaireAruba +1 more
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from $898
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Celebrity · Celebrity SilhouetteOne-way
Europe 12 nights Aug 21 – Sep 2, 2027 from Reykjavik, Iceland to Boston, Massachusetts
Reykjavik, Iceland · Isafjord, Iceland · … · Boston, Massachusetts8 ports
Reykjavik, Iceland · Isafjord, Iceland · Akureyri, Iceland · Prins Christian Sund(cruise) · Qaqortoq, Greenland · St. Johns, Newfoundland · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list Inside the VolcanoDynjandi WaterfallPeggy's Cove & LunenburgPrivate Luxury Boston Tour
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from $2,616
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Celebrity · Celebrity SilhouetteRound-trip
North America 11 nights Sep 2 – Sep 13, 2027 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 TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $3,171
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Oceania · Oceania VistaOne-way
Middle East 11 nights Sep 7 – Sep 18, 2027 from New York, New York to Montreal, Quebec
New York, New York · Newport, Rhode Island · … · Montreal, Quebec10 ports
New York, New York · Newport, Rhode Island · Portland, Maine · Bay of Fundy, Canada · Halifax, Nova Scotia · Sydney, Nova Scotia · Suez Canal, Egypt · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Manhattan Helicopter TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $5,949
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Celebrity · Celebrity SilhouetteRound-trip
North America 11 nights Sep 13 – Sep 24, 2027 from Boston, Massachusetts
Boston, Massachusetts · Rockland, Maine · … · Boston, Massachusetts8 ports
Boston, Massachusetts · Rockland, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Quebec City, Quebec · Portland, Maine · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $3,171
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Celebrity · Celebrity SummitRepositioning
Caribbean 18 nights Sep 18 – Oct 6, 2027 from Los Angeles, California to Boston, Massachusetts
Los Angeles, California · Puerto Vallarta, Mexico · … · Boston, Massachusetts8 ports
Los Angeles, California · Puerto Vallarta, Mexico · Puerto Quetzal, Guatemala · Puntarenas, Costa Rica · Panama Canal, Panama · Cartagena, Colombia · Grand Turk, Turks and Caicos · Boston, Massachusetts
★ Bucket-list Warner Bros. Studio Tour HollywoodHidden Beach at Marietas IslandsThe Roman Theatre of Cartagena with the Rafael Mon…Gibbs Cay Private Stingray Swim & Reef Snorkel +1 more
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from $2,184
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Oceania · Oceania VistaOne-way
North America 11 nights Sep 18 – Sep 29, 2027 from Montreal, Quebec to Boston, Massachusetts
Montreal, Quebec · Saguenay Fjord, Canada · … · Boston, Massachusetts10 ports
Montreal, Quebec · Saguenay Fjord, Canada · Baie-Commeau, Quebec · Sept-Iles, Canada · Havre St. Pierre, Quebec · Corner Brook, Newfoundland · Halifax, Nova Scotia · Bay of Fundy, Canada · Portland, Maine · Boston, Massachusetts
★ Bucket-list Peggy's Cove & LunenburgPrivate Luxury Boston Tour
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from $6,649
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Oceania · Oceania SirenaOne-way
North America 12 nights Sep 19 – Oct 1, 2027 from New York, New York to Montreal, Quebec
New York, New York · Newport, Rhode Island · … · Montreal, Quebec12 ports
New York, New York · Newport, Rhode Island · Portland, Maine · Bay of Fundy, Canada · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Gaspe, Quebec · Sept-Iles, Canada · Baie-Commeau, Quebec · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Manhattan Helicopter TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $5,449
Book This Cruise@ Cruisebound
Celebrity · Celebrity SilhouetteRound-trip
North America 11 nights Sep 24 – Oct 5, 2027 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 TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $2,438
Book This Cruise@ Cruisebound
Oceania · Oceania VistaOne-way
North America 11 nights Sep 29 – Oct 10, 2027 from Boston, Massachusetts to Montreal, Quebec
Boston, Massachusetts · Portland, Maine · … · Montreal, Quebec11 ports
Boston, Massachusetts · Portland, Maine · Bay of Fundy, Canada · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Havre St. Pierre, Quebec · Sept-Iles, Canada · Baie-Commeau, Quebec · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $6,199
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Oceania · Oceania SirenaOne-way
North America 12 nights Oct 1 – Oct 13, 2027 from Montreal, Quebec to New York, New York
Montreal, Quebec · Quebec City, Quebec · … · New York, New York11 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Baie-Commeau, Quebec · Havre St. Pierre, Quebec · Corner Brook, Newfoundland · Sydney, Nova Scotia · Halifax, Nova Scotia · Bay of Fundy, Canada · Portland, Maine · New York, New York
★ Bucket-list BridgeClimb SydneyPeggy's Cove & LunenburgManhattan Helicopter Tour
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from $5,199
Book This Cruise@ Cruisebound
Celebrity · Celebrity SilhouetteRound-trip
North America 11 nights Oct 5 – Oct 16, 2027 from Boston, Massachusetts
Boston, Massachusetts · Portland, Maine · … · Boston, Massachusetts8 ports
Boston, Massachusetts · Portland, Maine · Rockland, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Quebec City, Quebec · Charlottetown, Prince Edward Island · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $3,229
Book This Cruise@ Cruisebound
Oceania · Oceania VistaOne-way
Bermuda 14 nights Oct 10 – Oct 24, 2027 from Montreal, Quebec to Miami, Florida
Montreal, Quebec · Quebec City, Quebec · … · Miami, Florida12 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Sept-Iles, Canada · Havre St. Pierre, Quebec · Corner Brook, Newfoundland · Sydney, Nova Scotia · Halifax, Nova Scotia · Royal Naval Dockyard, Bermuda · Suez Canal, Egypt · Nassau, Bahamas · Miami, Florida
★ Bucket-list BridgeClimb SydneyPeggy's Cove & LunenburgPrivate Island Wrap-Around Van Tour of BermudaSwim With the Wild Exuma Pigs +1 more
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from $7,349
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Oceania · Oceania SirenaOne-way
Mediterranean 12 nights Oct 13 – Oct 25, 2027 from New York, New York to Montreal, Quebec
New York, New York · Suez Canal, Egypt · … · Montreal, Quebec13 ports
New York, New York · Suez Canal, Egypt · Boston, Massachusetts · Portland, Maine · Bay of Fundy, Canada · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Gaspe, Quebec · Sept-Iles, Canada · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Manhattan Helicopter TourPrivate Luxury Boston TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $4,999
Book This Cruise@ Cruisebound
Celebrity · Celebrity SilhouetteRepositioning
Caribbean 10 nights Oct 16 – Oct 26, 2027 from Boston, Massachusetts to Fort Lauderdale (Port Everglades), Florida
Boston, Massachusetts · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Private Luxury Boston TourArubaPrivate Full-Day Curaçao Island Tour with Local Ex…Klein Bonaire +1 more
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from $755
Book This Cruise@ Cruisebound
Celebrity · Celebrity SummitRepositioning
Caribbean 9 nights Oct 20 – Oct 29, 2027 from Boston, Massachusetts to San Juan, Puerto Rico
Boston, Massachusetts · Puerto Plata, Dominican Republic · … · San Juan, Puerto Rico7 ports
Boston, Massachusetts · Puerto Plata, Dominican Republic · Samana, Dominican Republic · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. John's, Antigua · Tortola, B.V.I. · San Juan, Puerto Rico
★ Bucket-list Private Luxury Boston TourThe full 27 jumps at the Damajagua WaterfallsPrivate Full-Day Boat CharterPrivate Half-Day Island Adventure & Trunk Bay Beach +2 more
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from $806
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Oceania · Oceania SirenaRepositioning
Caribbean 27 nights Oct 25 – Nov 21, 2027 from Montreal, Quebec to Miami, Florida
Montreal, Quebec · Quebec City, Quebec · … · Miami, Florida21 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Baie-Commeau, Quebec · Havre St. Pierre, Quebec · Corner Brook, Newfoundland · Sydney, Nova Scotia · Halifax, Nova Scotia · Bay of Fundy, Canada · Portland, Maine · New York, New York · Tortola, B.V.I. · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Kralendijk, Bonaire, Dutch Antilles · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Ocho Rios, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Suez Canal, Egypt · Miami, Florida
★ Bucket-list BridgeClimb SydneyPeggy's Cove & LunenburgManhattan Helicopter TourJost Van Dyke +7 more
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from $8,749
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