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 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
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
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 ×Repositioning ×13+ nights × Clear all
Showing 9 of 9 sailings
Princess · Sapphire PrincessRepositioning
Northern Europe 15 nights Aug 19 – Sep 3, 2026 from Copenhagen, Denmark to Boston, Massachusetts
Copenhagen, Denmark · Lerwick, Shetland Islands · … · Boston, Massachusetts9 ports
Copenhagen, Denmark · Lerwick, Shetland Islands · Stornoway, Scotland · Belfast, Northern Ireland · Liverpool, England · Cobh (Cork), Ireland · Sydney, Nova Scotia · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list Private Copenhagen Walking Tour with a Local ExpertGiant's Causeway Private Luxury Day Tour from Belf…BridgeClimb SydneyPeggy's Cove & Lunenburg +1 more
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from $1,455
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Azamara · Azamara JourneyRepositioning
North America 16 nights Aug 26 – Sep 11, 2026 from Montreal, Quebec to Reykjavik, Iceland
Montreal, Quebec · Quebec City, Quebec · … · Reykjavik, Iceland10 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Havre St. Pierre, Quebec · Nuuk, Greenland · Paamiut (Frederickshaab), Greenland · Qaqortoq, Greenland · Prince Christian Sund, Greenland · Grundarfjordur, Iceland · Reykjavik, Iceland
★ Bucket-list Inside the Volcano
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from $5,769
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Cunard · Queen Mary 2Repositioning
Northern Europe 16 nights Oct 4 – Oct 20, 2026 from Quebec City, Quebec to Hamburg, Germany
Quebec City, Quebec · Saguenay Fjord, Canada · … · Hamburg, Germany7 ports
Quebec City, Quebec · Saguenay Fjord, Canada · Sept-Iles, Canada · Halifax, Nova Scotia · New York, New York · Southampton, England · Hamburg, Germany
★ Bucket-list Peggy's Cove & LunenburgManhattan Helicopter TourStand Inside Stonehenge & See the Original 1215 Ma…Private Full-Day Hamburg Shore Excursion with Loca…
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from $2,679
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Norwegian · Norwegian BreakawayRepositioning
Caribbean 14 nights Nov 8 – Nov 22, 2026 from Boston, Massachusetts to New Orleans, Louisiana
Boston, Massachusetts · St. Thomas, U.S. Virgin Islands · … · New Orleans, Louisiana8 ports
Boston, Massachusetts · St. Thomas, U.S. Virgin Islands · St. Lucia, Caribbean · St. Georges, Grenada, West Indies · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Georgetown, Grand Cayman, Cayman Islands · New Orleans, Louisiana
★ Bucket-list Private Luxury Boston TourPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Grenada Private Taxi TourPrivate Full-Day Curaçao Island Tour with Local Ex… +3 more
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from $970
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Norwegian · Norwegian BreakawayRepositioning
Caribbean 14 nights Apr 4 – Apr 18, 2027 from New Orleans, Louisiana to Boston, Massachusetts
New Orleans, Louisiana · Georgetown, Grand Cayman, Cayman Islands · … · Boston, Massachusetts9 ports
New Orleans, Louisiana · Georgetown, Grand Cayman, Cayman Islands · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · St. Georges, Grenada, West Indies · St. Lucia, Caribbean · Tortola, B.V.I. · Boston, Massachusetts
★ Bucket-list Steamboat NatchezStingray City SandbarArubaPrivate Full-Day Curaçao Island Tour with Local Ex… +4 more
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from $1,726
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Princess · Caribbean PrincessRepositioning
Northern Europe 28 nights Aug 10 – Sep 7, 2027 from Copenhagen, Denmark to Boston, Massachusetts
Copenhagen, Denmark · Visby, Sweden · … · Boston, Massachusetts20 ports
Copenhagen, Denmark · Visby, Sweden · Stockholm, Sweden · Helsinki, Finland · Tallinn, Estonia · Riga, Latvia · Klaipeda, Lithuania · Gdansk, Poland · Oslo, Norway · Skagen, Denmark · Copenhagen, Denmark · Gothenburg, Sweden · Runavik, Faroe Islands · Seydisfjordur, Iceland · Akureyri, Iceland · Isafjord, Iceland · Reykjavik, Iceland · St. Johns, Newfoundland · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list Private Copenhagen Walking Tour with a Local ExpertVasa MuseumPrivate Half-Day Tallinn Old Town & City Sightseei…Private Oslo Highlights & Hidden Gems with a Local… +4 more
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from $5,263
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Princess · Caribbean PrincessRepositioning
Northern Europe 16 nights Aug 22 – Sep 7, 2027 from Copenhagen, Denmark to Boston, Massachusetts
Copenhagen, Denmark · Gothenburg, Sweden · … · Boston, Massachusetts10 ports
Copenhagen, Denmark · Gothenburg, Sweden · Runavik, Faroe Islands · Seydisfjordur, Iceland · Akureyri, Iceland · Isafjord, Iceland · Reykjavik, Iceland · St. Johns, Newfoundland · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list Private Copenhagen Walking Tour with a Local ExpertDynjandi WaterfallInside the VolcanoPeggy's Cove & Lunenburg +1 more
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from $1,759
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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 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
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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.

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