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
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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 Visits Portland ×Round trip ×13+ nights × Clear all
Showing 12 of 12 sailings
Seabourn · Seabourn OvationRound-trip
Northern Europe 14 nights Jun 27 – Jul 11, 2026 from Dover (London), England
Dover (London), England · Portland, England · … · Dover (London), England12 ports
Dover (London), England · Portland, England · Ringaskiddy, Ireland · Fishguard, Wales · Douglas, Isle Of Man · Belfast, Northern Ireland · Greenock (Glasgow), Scotland · Greencastle, Ireland · Oban, Scotland · Leith/Edinburgh, Scotland · NEWHAVEN, United Kingdom · Dover (London), England
★ Bucket-list White Cliffs of DoverPortland Head Light & Casco Bay Scenic Lighthouse…Giant's Causeway Private Luxury Day Tour from Belf…
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from $6,799
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Oceania · Oceania VistaRound-trip
Northern Europe 67 nights Jul 9 – Sep 14, 2026 from New York, New York
New York, New York · Halifax, Nova Scotia · … · New York, New York50 ports
New York, New York · Halifax, Nova Scotia · Sydney, Nova Scotia · St. Pierre, St. Pierre and Miquelon · St. Johns, Newfoundland · Grundarfjordur, Iceland · Akureyri, Iceland · Siglufjordur, Iceland · Isafjord, Iceland · Reykjavik, Iceland · Heimaey, Iceland · Djupivogur, Iceland · Alesund, Norway · Maloy, Norway · Haugesund, Norway · Amsterdam, The Netherlands · Zeebrugge (Bruges), Belgium · Southampton, England · Portland, England · Falmouth, Cornwall, England · Dingle, Ireland · Bantry Bay, Ireland · Cobh (Cork), Ireland · Waterford, Ireland · Holyhead, Wales · Liverpool · Dun Laoghaire, Dublin, Ireland · Belfast, Northern Ireland · Douglas, Isle Of Man · Greencastle, Ireland · Ullapool, Scotland · Scrabster, Scotland · Invergordon, Scotland · Kristiansand · Copenhagen, Denmark · Berlin, Germany · Ronne, Denmark · Aarhus, Denmark · Southampton, England · Le Havre (Paris), France · Saint Malo, France · Falmouth, Cornwall, England · Ringaskiddy, Ireland · Holyhead, Wales · Greenock (Glasgow), Scotland · Killybegs Ireland · Corner Brook, Newfoundland · Sydney, Nova Scotia · Boston, Massachusetts · New York, New York
★ Bucket-list Manhattan Helicopter TourPeggy's Cove & LunenburgBridgeClimb SydneyÎle aux Marins +15 more
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from $38,049
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Princess · Sky PrincessRound-trip
Northern Europe 14 nights Aug 29 – Sep 12, 2026 from Southampton, England
Southampton, England · Portland, England · … · Southampton, England11 ports
Southampton, England · Portland, England · Cobh (Cork), Ireland · Reykjavik, Iceland · Grundarfjordur, Iceland · Isafjord, Iceland · Akureyri, Iceland · Lerwick, Shetland Islands · Kirkwall, Scotland · Zeebrugge (Bruges), Belgium · Southampton, England
★ Bucket-list Stand Inside Stonehenge & See the Original 1215 Ma…Portland Head Light & Casco Bay Scenic Lighthouse…Inside the VolcanoDynjandi Waterfall +3 more
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from $2,833
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Holland America · Nieuw StatendamRound-trip
Mediterranean 42 nights Jun 26 – Aug 7, 2027 from Rotterdam, The Netherlands
Rotterdam, The Netherlands · Copenhagen, Denmark · … · Rotterdam, The Netherlands28 ports
Rotterdam, The Netherlands · Copenhagen, Denmark · Aarhus, Denmark · Warnemunde, Germany · Tallinn, Estonia · Helsinki, Finland · Stockholm, Sweden · Visby, Sweden · Oslo, Norway · Dover (London), England · Rotterdam, The Netherlands · Copenhagen, Denmark · Aarhus, Denmark · Tilbury (London), England · Portland, England · Le Havre (Paris), France · Le Verdon, France · Bilbao, Spain · Lisbon, Portugal · Cadiz (Seville), Spain · Tangier, Morocco · Malaga, Spain · Barcelona, Spain · Gibraltar, British Territory · Solar Eclipse · Leixoes (Oporto), Portugal · Dover (London), England · Rotterdam, The Netherlands
★ Bucket-list All-Inclusive Private Windmill Tour to Kinderdijk…Private Copenhagen Walking Tour with a Local ExpertBerlin Private Full-Day Shore Excursion from Warne…Private Half-Day Tallinn Old Town & City Sightseei… +11 more
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from $8,014
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Holland America · VolendamRound-trip
North America 14 nights Jun 26 – Jul 10, 2027 from Montreal, Quebec
Montreal, Quebec · Quebec City, Quebec · … · Montreal, Quebec13 ports
Montreal, Quebec · Quebec City, Quebec · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Portland, Maine · Boston, Massachusetts · Portland, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Old Québec Private Walking Tour with Expert Local…Green Gables House & Anne of Green Gables Island E…BridgeClimb SydneyPeggy's Cove & Lunenburg +2 more
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from $3,369
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Holland America · VolendamRound-trip
North America 14 nights Jul 3 – Jul 17, 2027 from Boston, Massachusetts
Boston, Massachusetts · Portland, Maine · … · Boston, Massachusetts13 ports
Boston, Massachusetts · Portland, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Quebec City, Quebec · Montreal, Quebec · Quebec City, Quebec · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Portland, Maine · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Peggy's Cove & LunenburgBridgeClimb Sydney +2 more
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from $3,454
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Princess · Regal PrincessRound-trip
Northern Europe 27 nights Jul 3 – Jul 30, 2027 from Southampton, England
Southampton, England · Zeebrugge (Bruges), Belgium · … · Southampton, England23 ports
Southampton, England · Zeebrugge (Bruges), Belgium · Amsterdam, The Netherlands · Hamburg, Germany · Skagen, Denmark · Copenhagen, Denmark · Kristiansund, Norway · Skagen, Denmark · Stavanger, Norway · Nordfjordeid, Norway · Molde, Norway · Akureyri, Iceland · Isafjord, Iceland · Grundarfjordur, Iceland · Reykjavik, Iceland · Grundarfjordur, Iceland · Isafjord, Iceland · Akureyri, Iceland · Seydisfjordur, Iceland · Stornoway, Scotland · Greenock (Glasgow), Scotland · Portland, England · Southampton, England
★ Bucket-list Stand Inside Stonehenge & See the Original 1215 Ma…Private Bruges Full-Day Shore Excursion with Canal…Walk Into the Secret Annex - Anne Frank HousePrivate Full-Day Hamburg Shore Excursion with Loca… +6 more
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from $3,422
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Holland America · Nieuw StatendamRound-trip
Northern Europe 28 nights Jul 9 – Aug 6, 2027 from Dover (London), England
Dover (London), England · Rotterdam, The Netherlands · … · Dover (London), England18 ports
Dover (London), England · Rotterdam, The Netherlands · Copenhagen, Denmark · Aarhus, Denmark · Tilbury (London), England · Portland, England · Le Havre (Paris), France · Le Verdon, France · Bilbao, Spain · Lisbon, Portugal · Cadiz (Seville), Spain · Tangier, Morocco · Malaga, Spain · Barcelona, Spain · Gibraltar, British Territory · Solar Eclipse · Leixoes (Oporto), Portugal · Dover (London), England
★ Bucket-list White Cliffs of DoverAll-Inclusive Private Windmill Tour to Kinderdijk…Private Copenhagen Walking Tour with a Local ExpertPortland Head Light & Casco Bay Scenic Lighthouse… +7 more
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from $5,634
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Holland America · Nieuw StatendamRound-trip
Northern Europe 28 nights Jul 10 – Aug 7, 2027 from Rotterdam, The Netherlands
Rotterdam, The Netherlands · Copenhagen, Denmark · … · Rotterdam, The Netherlands18 ports
Rotterdam, The Netherlands · Copenhagen, Denmark · Aarhus, Denmark · Tilbury (London), England · Portland, England · Le Havre (Paris), France · Le Verdon, France · Bilbao, Spain · Lisbon, Portugal · Cadiz (Seville), Spain · Tangier, Morocco · Malaga, Spain · Barcelona, Spain · Gibraltar, British Territory · Solar Eclipse · Leixoes (Oporto), Portugal · Dover (London), England · Rotterdam, The Netherlands
★ Bucket-list All-Inclusive Private Windmill Tour to Kinderdijk…Private Copenhagen Walking Tour with a Local ExpertPortland Head Light & Casco Bay Scenic Lighthouse…Private Paris Highlights & Seine River Cruise from… +7 more
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from $5,619
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Holland America · VolendamRound-trip
Northern Europe 35 nights Jul 17 – Aug 21, 2027 from Boston, Massachusetts
Boston, Massachusetts · Portland, Maine · … · Boston, Massachusetts21 ports
Boston, Massachusetts · Portland, Maine · Sydney, Nova Scotia · Corner Brook, Newfoundland · Red Bay, Canada · Paamiut (Frederickshaab), Greenland · Nanortalik, Greenland · Isafjord, Iceland · Akureyri, Iceland · Eidfjord, Norway · Rotterdam, The Netherlands · Cobh (Cork), Ireland · Dun Laoghaire, Dublin, Ireland · Belfast, Northern Ireland · Reykjavik, Iceland · Grundarfjordur, Iceland · Qaqortoq, Greenland · St. Anthony, Newfoundland · St. Johns, Newfoundland · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…BridgeClimb SydneyKuannersooq Fjord +8 more
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from $9,214
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Holland America · ZuiderdamRound-trip
North America 14 nights Oct 2 – Oct 16, 2027 from Quebec City, Quebec
Quebec City, Quebec · Charlottetown, Prince Edward Island · … · Quebec City, Quebec11 ports
Quebec City, Quebec · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Portland, Maine · Boston, Massachusetts · Portland, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Quebec City, Quebec
★ Bucket-list Old Québec Private Walking Tour with Expert Local…Green Gables House & Anne of Green Gables Island E…BridgeClimb SydneyPeggy's Cove & Lunenburg +2 more
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from $3,464
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Princess · Coral PrincessRound-trip
Mediterranean 42 nights Oct 15 – Nov 26, 2027 from New York, New York
New York, New York · Halifax, Nova Scotia · … · New York, New York24 ports
New York, New York · Halifax, Nova Scotia · St. Johns, Newfoundland · Cobh (Cork), Ireland · Holyhead, Wales · Greenock (Glasgow), Scotland · Belfast, Northern Ireland · Liverpool, England · Portland, England · Tilbury (London), England · Hamburg, Germany · Amsterdam, The Netherlands · Zeebrugge (Bruges), Belgium · Paris, France · Bilbao, Spain · La Coruna, Spain · Leixoes (Oporto), Portugal · Lisbon, Portugal · Seville, Spain · Ceuta, Spain · Casablanca, Morocco · Funchal, Madeira, Portugal · Azores Islands, Portugal · New York, New York
★ Bucket-list Manhattan Helicopter TourPeggy's Cove & LunenburgCape St. Mary's Ecological ReserveGiant's Causeway Private Luxury Day Tour from Belf… +8 more
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from $7,272
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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