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.

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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
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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 Princess ×Seabourn ×Visits Portland × Clear all
Showing 32 of 32 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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Princess · Majestic PrincessRound-trip
Northern Europe 12 nights Jul 9 – Jul 21, 2026 from Southampton, England
Southampton, England · Portland, England · … · Southampton, England11 ports
Southampton, England · Portland, England · Cornwall, England · Cobh (Cork), Ireland · Dublin, Ireland · Belfast, Northern Ireland · Greenock (Glasgow), Scotland · Invergordon, Scotland · South Queensferry, Scotland · Paris, France · Southampton, England
★ Bucket-list Stand Inside Stonehenge & See the Original 1215 Ma…Portland Head Light & Casco Bay Scenic Lighthouse…Giant's Causeway Private Luxury Day Tour from Belf…Loch Ness & Urquhart Castle +1 more
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from $1,641
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Princess · Majestic PrincessRound-trip
Northern Europe 12 nights Aug 14 – Aug 26, 2026 from Southampton, England
Southampton, England · Portland, England · … · Southampton, England11 ports
Southampton, England · Portland, England · Cornwall, England · Cobh (Cork), Ireland · Dublin, Ireland · Liverpool, England · Greenock (Glasgow), Scotland · Invergordon, Scotland · South Queensferry, Scotland · Paris, France · Southampton, England
★ Bucket-list Stand Inside Stonehenge & See the Original 1215 Ma…Portland Head Light & Casco Bay Scenic Lighthouse…Loch Ness & Urquhart CastleEiffel Tower
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from $1,528
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Seabourn · Seabourn OvationOne-way
Europe 22 nights Aug 22 – Sep 13, 2026 from Reykjavik, Iceland to New York, New York
Reykjavik, Iceland · Grundarfjordur, Iceland · … · New York, New York15 ports
Reykjavik, Iceland · Grundarfjordur, Iceland · Isafjord, Iceland · Akureyri, Iceland · Qaqortoq, Greenland · Nanortalik, Greenland · LAnse Aux Meadows, Newfoundland · Gaspe, Quebec · Cap-Aux-Meules, Canada · Sydney, Nova Scotia · Halifax, Nova Scotia · Shelburne, Nova Scotia · Portland, Maine · Boston, Massachusetts · New York, New York
★ Bucket-list Inside the VolcanoDynjandi WaterfallMývatn Nature BathsTasermiut Fjord Full-Day Boat Expedition +6 more
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from $8,479
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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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Princess · Sapphire PrincessOne-way
North America 10 nights Sep 3 – Sep 13, 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 $1,344
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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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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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Seabourn · Seabourn OvationOne-way
North America 12 nights Oct 7 – Oct 19, 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 · Charlottetown, Prince Edward Island · Halifax, Nova Scotia · Portland, Maine · Transit The Cape Cod Canal · Boston, Massachusetts · Newport, Rhode Island · New York, New York
★ Bucket-list Old Québec Private Walking Tour with Expert Local…Green Gables House & Anne of Green Gables Island E…Peggy's Cove & LunenburgPortland Head Light & Casco Bay Scenic Lighthouse… +4 more
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from $8,924
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Princess · Majestic PrincessRound-trip
North America 7 nights Oct 10 – Oct 17, 2026 from New York, New York
New York, New York · Newport, Rhode Island · … · New York, New York7 ports
New York, New York · Newport, Rhode Island · Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · New York, New York
★ Bucket-list Manhattan Helicopter TourThe BreakersPrivate Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse… +2 more
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from $1,404
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Princess · Sapphire PrincessOne-way
North America 10 nights Oct 13 – Oct 23, 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 $1,074
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Princess · Majestic PrincessRound-trip
North America 7 nights Oct 17 – Oct 24, 2026 from New York, New York
New York, New York · Newport, Rhode Island · … · New York, New York7 ports
New York, New York · Newport, Rhode Island · Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · New York, New York
★ Bucket-list Manhattan Helicopter TourThe BreakersPrivate Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse… +2 more
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from $1,418
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Princess · Majestic PrincessRound-trip
North America 7 nights Oct 24 – Oct 31, 2026 from New York, New York
New York, New York · Newport, Rhode Island · … · New York, New York7 ports
New York, New York · Newport, Rhode Island · Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · New York, New York
★ Bucket-list Manhattan Helicopter TourThe BreakersPrivate Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse… +2 more
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from $1,187
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Princess · Majestic PrincessRound-trip
North America 7 nights Oct 31 – Nov 7, 2026 from New York, New York
New York, New York · Newport, Rhode Island · … · New York, New York7 ports
New York, New York · Newport, Rhode Island · Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · New York, New York
★ Bucket-list Manhattan Helicopter TourThe BreakersPrivate Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse… +2 more
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from $1,145
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Princess · Sky PrincessRepositioning
Northern Europe 15 nights Nov 5 – Nov 20, 2026 from Southampton, England to Port Canaveral, Florida
Southampton, England · Portland, England · … · Port Canaveral, Florida6 ports
Southampton, England · Portland, England · Vigo, Spain · Funchal, Madeira, Portugal · Santa Cruz de Tenerife, Canary Islands · Port Canaveral, Florida
★ Bucket-list Stand Inside Stonehenge & See the Original 1215 Ma…Portland Head Light & Casco Bay Scenic Lighthouse…Pico do Arieiro to Pico RuivoTeide National Park +1 more
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from $767
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Princess · Majestic PrincessRound-trip
Northern Europe 12 nights May 25 – Jun 6, 2027 from Southampton, England
Southampton, England · Portland, England · … · Southampton, England11 ports
Southampton, England · Portland, England · Cornwall, England · Cobh (Cork), Ireland · Dublin, Ireland · Belfast, Northern Ireland · Holyhead, Wales · Greenock (Glasgow), Scotland · South Queensferry, Scotland · Paris, France · Southampton, England
★ Bucket-list Stand Inside Stonehenge & See the Original 1215 Ma…Portland Head Light & Casco Bay Scenic Lighthouse…Giant's Causeway Private Luxury Day Tour from Belf…Eiffel Tower
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from $1,783
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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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Princess · Regal PrincessOne-way
Northern Europe 17 nights Jul 20 – Aug 6, 2027 from Reykjavik, Iceland to Southampton, England
Reykjavik, Iceland · Grundarfjordur, Iceland · … · Southampton, England14 ports
Reykjavik, Iceland · Grundarfjordur, Iceland · Isafjord, Iceland · Akureyri, Iceland · Seydisfjordur, Iceland · Stornoway, Scotland · Greenock (Glasgow), Scotland · Portland, England · Southampton, England · Haugesund, Norway · Nordfjordeid, Norway · Skjolden, Norway · Stavanger, Norway · Southampton, England
★ Bucket-list Inside the VolcanoDynjandi WaterfallMývatn Nature BathsPortland Head Light & Casco Bay Scenic Lighthouse… +2 more
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from $2,220
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Princess · Regal PrincessRound-trip
North America 7 nights Aug 21 – Aug 28, 2027 from New York, New York
New York, New York · Boston, Massachusetts · … · New York, New York6 ports
New York, New York · Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · New York, New York
★ Bucket-list Manhattan Helicopter TourPrivate Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal Bore +1 more
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from $829
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Princess · Caribbean PrincessOne-way
North America 10 nights Sep 7 – Sep 17, 2027 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 $1,200
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Princess · Regal PrincessRound-trip
North America 7 nights Sep 18 – Sep 25, 2027 from New York, New York
New York, New York · Newport, Rhode Island · … · New York, New York7 ports
New York, New York · Newport, Rhode Island · Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · New York, New York
★ Bucket-list Manhattan Helicopter TourThe BreakersPrivate Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse… +2 more
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from $889
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Princess · Regal PrincessRound-trip
North America 7 nights Sep 25 – Oct 2, 2027 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 · Portland, Maine · Halifax, Nova Scotia · New York, New York
★ Bucket-list Manhattan Helicopter TourThe BreakersPrivate Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse… +1 more
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from $749
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Princess · Caribbean PrincessOne-way
North America 10 nights Sep 28 – Oct 8, 2027 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 $1,199
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Princess · Regal PrincessRound-trip
North America 7 nights Oct 2 – Oct 9, 2027 from New York, New York
New York, New York · Newport, Rhode Island · … · New York, New York7 ports
New York, New York · Newport, Rhode Island · Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · New York, New York
★ Bucket-list Manhattan Helicopter TourThe BreakersPrivate Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse… +2 more
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from $1,449
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Princess · Regal PrincessRound-trip
North America 7 nights Oct 9 – Oct 16, 2027 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 · Portland, Maine · Halifax, Nova Scotia · New York, New York
★ Bucket-list Manhattan Helicopter TourThe BreakersPrivate Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse… +1 more
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from $1,049
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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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Princess · Regal PrincessRound-trip
North America 7 nights Oct 16 – Oct 23, 2027 from New York, New York
New York, New York · Newport, Rhode Island · … · New York, New York7 ports
New York, New York · Newport, Rhode Island · Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · New York, New York
★ Bucket-list Manhattan Helicopter TourThe BreakersPrivate Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse… +2 more
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from $769
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Princess · Caribbean PrincessOne-way
North America 10 nights Oct 19 – Oct 29, 2027 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 $1,199
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Princess · Regal PrincessRound-trip
North America 7 nights Oct 23 – Oct 30, 2027 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 · Portland, Maine · Halifax, Nova Scotia · New York, New York
★ Bucket-list Manhattan Helicopter TourThe BreakersPrivate Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse… +1 more
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from $899
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Princess · Caribbean PrincessOne-way
North America 13 nights Oct 29 – Nov 11, 2027 from Quebec City, Quebec to Fort Lauderdale (Port Everglades), Florida
Quebec City, Quebec · Saguenay Fjord, Canada · … · Fort Lauderdale (Port Everglades), Florida10 ports
Quebec City, Quebec · Saguenay Fjord, Canada · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Portland, Maine · Boston, Massachusetts · Newport, Rhode Island · New York, New York · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Old Québec Private Walking Tour with Expert Local…Green Gables House & Anne of Green Gables Island E…BridgeClimb SydneyPeggy's Cove & Lunenburg +5 more
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from $1,339
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Princess · Regal PrincessRound-trip
North America 7 nights Oct 30 – Nov 6, 2027 from New York, New York
New York, New York · Newport, Rhode Island · … · New York, New York7 ports
New York, New York · Newport, Rhode Island · Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · New York, New York
★ Bucket-list Manhattan Helicopter TourThe BreakersPrivate Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse… +2 more
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from $806
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Seabourn · Seabourn QuestOne-way
Northern Europe 14 nights May 6 – May 20, 2028 from Southampton, England to Copenhagen, Denmark
Southampton, England · Portland, England · … · Copenhagen, Denmark13 ports
Southampton, England · Portland, England · St Helier, Isle of Jersey · Cherbourg, France · Zeebrugge (Bruges), Belgium · Antwerp, Belgium · Hamburg, Germany · Farsund,norway · Oslo, Norway · Gothenburg, Sweden · Skagen, Denmark · Wismar, Germany · Copenhagen, Denmark
★ Bucket-list Stand Inside Stonehenge & See the Original 1215 Ma…Portland Head Light & Casco Bay Scenic Lighthouse…Private Bruges Full-Day Shore Excursion with Canal…Private Full-Day Hamburg Shore Excursion with Loca… +2 more
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from $7,919
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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
aboard
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