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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Filtering Royal Caribbean ×Princess ×Visits Portland × Clear all
Showing 36 of 44 sailings
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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Royal Caribbean · Vision of the SeasRound-trip
North America 9 nights Aug 27 – Sep 5, 2026 from Baltimore, Maryland
Baltimore, Maryland · Boston, Massachusetts · … · Baltimore, Maryland6 ports
Baltimore, Maryland · Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Baltimore, Maryland
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg
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from $1,033
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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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Royal Caribbean · Independence of the SeasRound-trip
North America 9 nights Sep 3 – Sep 12, 2026 from Cape Liberty (Bayonne), New Jersey
Cape Liberty (Bayonne), New Jersey · Boston, Massachusetts · … · Cape Liberty (Bayonne), New Jersey6 ports
Cape Liberty (Bayonne), New Jersey · Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Sydney, Nova Scotia · Cape Liberty (Bayonne), New Jersey
★ Bucket-list Statue of Liberty & Ellis IslandPrivate Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal Bore +1 more
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from $1,032
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Royal Caribbean · Vision of the SeasRound-trip
North America 9 nights Sep 10 – Sep 19, 2026 from Baltimore, Maryland
Baltimore, Maryland · Boston, Massachusetts · … · Baltimore, Maryland6 ports
Baltimore, Maryland · Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Baltimore, Maryland
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg
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from $995
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Royal Caribbean · Independence of the SeasRound-trip
North America 9 nights Sep 17 – Sep 26, 2026 from Cape Liberty (Bayonne), New Jersey
Cape Liberty (Bayonne), New Jersey · Boston, Massachusetts · … · Cape Liberty (Bayonne), New Jersey6 ports
Cape Liberty (Bayonne), New Jersey · Boston, Massachusetts · Portland, Maine · Halifax, Nova Scotia · Saint John, New Brunswick · Cape Liberty (Bayonne), New Jersey
★ Bucket-list Statue of Liberty & Ellis IslandPrivate Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Peggy's Cove & Lunenburg +1 more
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from $1,292
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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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Royal Caribbean · Vision of the SeasRound-trip
North America 9 nights Sep 24 – Oct 3, 2026 from Baltimore, Maryland
Baltimore, Maryland · Boston, Massachusetts · … · Baltimore, Maryland6 ports
Baltimore, Maryland · Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Baltimore, Maryland
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg
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from $999
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Royal Caribbean · Independence of the SeasRound-trip
North America 9 nights Oct 1 – Oct 10, 2026 from Cape Liberty (Bayonne), New Jersey
Cape Liberty (Bayonne), New Jersey · Boston, Massachusetts · … · Cape Liberty (Bayonne), New Jersey6 ports
Cape Liberty (Bayonne), New Jersey · Boston, Massachusetts · Portland, Maine · Halifax, Nova Scotia · Saint John, New Brunswick · Cape Liberty (Bayonne), New Jersey
★ Bucket-list Statue of Liberty & Ellis IslandPrivate Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Peggy's Cove & Lunenburg +1 more
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from $1,116
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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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Royal Caribbean · Vision of the SeasRound-trip
North America 9 nights Oct 8 – Oct 17, 2026 from Baltimore, Maryland
Baltimore, Maryland · Boston, Massachusetts · … · Baltimore, Maryland6 ports
Baltimore, Maryland · Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Baltimore, Maryland
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg
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from $1,031
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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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Royal Caribbean · Independence of the SeasRound-trip
North America 9 nights Oct 15 – Oct 24, 2026 from Cape Liberty (Bayonne), New Jersey
Cape Liberty (Bayonne), New Jersey · Boston, Massachusetts · … · Cape Liberty (Bayonne), New Jersey6 ports
Cape Liberty (Bayonne), New Jersey · Boston, Massachusetts · Portland, Maine · Halifax, Nova Scotia · Saint John, New Brunswick · Cape Liberty (Bayonne), New Jersey
★ Bucket-list Statue of Liberty & Ellis IslandPrivate Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Peggy's Cove & Lunenburg +1 more
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from $1,223
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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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Royal Caribbean · Vision of the SeasRound-trip
North America 9 nights Aug 26 – Sep 4, 2027 from Baltimore, Maryland
Baltimore, Maryland · Boston, Massachusetts · … · Baltimore, Maryland6 ports
Baltimore, Maryland · Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Baltimore, Maryland
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg
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from $894
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Royal Caribbean · Independence of the SeasRound-trip
North America 9 nights Sep 2 – Sep 11, 2027 from Cape Liberty (Bayonne), New Jersey
Cape Liberty (Bayonne), New Jersey · Boston, Massachusetts · … · Cape Liberty (Bayonne), New Jersey7 ports
Cape Liberty (Bayonne), New Jersey · Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Sydney, Nova Scotia · Halifax, Nova Scotia · Cape Liberty (Bayonne), New Jersey
★ Bucket-list Statue of Liberty & Ellis IslandPrivate Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal Bore +2 more
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from $905
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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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Royal Caribbean · Vision of the SeasRound-trip
North America 9 nights Sep 9 – Sep 18, 2027 from Baltimore, Maryland
Baltimore, Maryland · Boston, Massachusetts · … · Baltimore, Maryland7 ports
Baltimore, Maryland · Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Baltimore, Maryland
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg +1 more
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from $932
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Royal Caribbean · Independence of the SeasRound-trip
North America 9 nights Sep 16 – Sep 25, 2027 from Cape Liberty (Bayonne), New Jersey
Cape Liberty (Bayonne), New Jersey · Boston, Massachusetts · … · Cape Liberty (Bayonne), New Jersey7 ports
Cape Liberty (Bayonne), New Jersey · Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Cape Liberty (Bayonne), New Jersey
★ Bucket-list Statue of Liberty & Ellis IslandPrivate Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal Bore +2 more
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from $883
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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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Royal Caribbean · Vision of the SeasRound-trip
North America 9 nights Sep 23 – Oct 2, 2027 from Baltimore, Maryland
Baltimore, Maryland · Boston, Massachusetts · … · Baltimore, Maryland7 ports
Baltimore, Maryland · Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Baltimore, Maryland
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg +1 more
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from $912
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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
Book This Cruise@ Cruisebound
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
Book This Cruise@ Cruisebound
Royal Caribbean · Independence of the SeasRound-trip
North America 9 nights Sep 30 – Oct 9, 2027 from Cape Liberty (Bayonne), New Jersey
Cape Liberty (Bayonne), New Jersey · Boston, Massachusetts · … · Cape Liberty (Bayonne), New Jersey7 ports
Cape Liberty (Bayonne), New Jersey · Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Cape Liberty (Bayonne), New Jersey
★ Bucket-list Statue of Liberty & Ellis IslandPrivate Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal Bore +2 more
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from $882
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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
Book This Cruise@ Cruisebound
Royal Caribbean · Vision of the SeasRound-trip
North America 9 nights Oct 7 – Oct 16, 2027 from Baltimore, Maryland
Baltimore, Maryland · Boston, Massachusetts · … · Baltimore, Maryland6 ports
Baltimore, Maryland · Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Baltimore, Maryland
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg
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from $910
Book This Cruise@ Cruisebound
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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