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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Showing 36 of 274 sailings
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 TourLuxury Camden Sailing Experience on Penobscot BayPeggy's Cove & LunenburgBridgeClimb Sydney +3 more
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from $2,507
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Regent · Seven Seas SplendorOne-way
North America 11 nights Sep 17 – Sep 28, 2026 from Montreal, Quebec to Boston, Massachusetts
Montreal, Quebec · Quebec City, Quebec · … · Boston, Massachusetts11 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Sept-Iles, Canada · Havre St. Pierre, Quebec · Willis Island · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Saint John, New Brunswick · Boston, Massachusetts
★ Bucket-list Notre-Dame BasilicaOld Québec Private Walking Tour with Expert Local…Sept-Îles Archipelago Zodiac ExpeditionMingan Archipelago +6 more
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from $15,899
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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 $770
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Carnival · Carnival SunshineRound-trip
North America 8 nights Sep 19, 2026 from Norfolk, Virginia
Norfolk, Virginia · Saint John, New Brunswick · Halifax, Nova Scotia · St. Johns, Newfoundland · Norfolk, Virginia
★ Bucket-list Battleship WisconsinReversing Falls & Fundy Tidal BorePeggy's Cove & LunenburgCape St. Mary's Ecological Reserve
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from $875
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Holland America · VolendamOne-way
North America 7 nights Sep 19 – Sep 26, 2026 from Boston, Massachusetts to Montreal, Quebec
Boston, Massachusetts · Eastport, Maine, United States · … · Montreal, Quebec7 ports
Boston, Massachusetts · Eastport, Maine, United States · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Private Luxury Boston TourCampobello IslandPeggy's Cove & LunenburgBridgeClimb Sydney +3 more
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from $1,319
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Holland America · ZuiderdamOne-way
North America 7 nights Sep 19 – Sep 26, 2026 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgBridgeClimb SydneyGreen Gables House & Anne of Green Gables Island E… +1 more
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from $1,469
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Norwegian · Norwegian EscapeRound-trip
North America 7 nights Sep 19 – Sep 26, 2026 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 · Sydney, Nova Scotia · Halifax, Nova Scotia · New York, New York
★ Bucket-list Manhattan Helicopter TourThe BreakersPrivate Luxury Boston TourBridgeClimb Sydney +1 more
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from $1,269
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Princess · Majestic PrincessRepositioning
Northern Europe 14 nights Sep 19 – Oct 3, 2026 from Southampton, England to New York, New York
Southampton, England · Stavanger, Norway · … · New York, New York7 ports
Southampton, England · Stavanger, Norway · Haugesund, Norway · Skjolden, Norway · Reykjavik, Iceland · Halifax, Nova Scotia · New York, New York
★ Bucket-list Stand Inside Stonehenge & See the Original 1215 Ma…Lysefjorden & Pulpit Rock RIB SafariPrivate RIB SpeedboatSognefjord RIB Speedboat +3 more
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from $2,296
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Virgin · Valiant LadyRound-trip
North America 8 nights Sep 19, 2026 from Brooklyn, NY
Brooklyn, NY · Gloucester, Massachusetts · … · Brooklyn, NY6 ports
Brooklyn, NY · Gloucester, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Brooklyn, NY
★ Bucket-list NYC Private VIP Tour by VehicleWhale Watch ExpeditionPortland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal Bore +1 more
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from $1,192
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Norwegian · Norwegian BreakawayRound-trip
North America 7 nights Sep 20 – Sep 27, 2026 from Boston, Massachusetts
Boston, Massachusetts · Portland, Maine · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Portland, Maine · Bar Harbor, Maine · Eastport, Maine, United States · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Private Acadia National Park Van Tour with Expert…Campobello Island +1 more
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from $639
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Silversea · Silver ShadowOne-way
North America 11 nights Sep 21 – Oct 2, 2026 from Cape Liberty (Bayonne), New Jersey to Montreal, Quebec
Cape Liberty (Bayonne), New Jersey · Newport, Rhode Island · … · Montreal, Quebec10 ports
Cape Liberty (Bayonne), New Jersey · Newport, Rhode Island · Boston, Massachusetts · Cape Cod, Massachusetts · Portland, Maine · Halifax, Nova Scotia · Charlottetown, Prince Edward Island · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Statue of Liberty & Ellis IslandThe BreakersPrivate Luxury Boston TourProvincetown Whale Watch +5 more
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from $9,750
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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 National AquariumPrivate Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal Bore +1 more
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from $949
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Viking Ocean · Viking MarsOne-way
North America 12 nights Sep 24 – Oct 6, 2026 from Brooklyn, NY to Montreal, Quebec
Brooklyn, NY · Boston, Massachusetts · … · Montreal, Quebec10 ports
Brooklyn, NY · Boston, Massachusetts · Sail the Nova Scotia Coast · Halifax, Nova Scotia · Sail the Gulf of St. Lawrence · Gaspe, Quebec · Sail the Gulf of St. Lawrence · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list NYC Private VIP Tour by VehiclePrivate Luxury Boston TourPeggy's Cove & LunenburgPercé Rock & Bonaventure Island +2 more
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from $10,699
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Azamara · Azamara JourneyOne-way
North America 12 nights Sep 25 – Oct 7, 2026 from Montreal, Quebec to New York, New York
Montreal, Quebec · Quebec City, Quebec · … · New York, New York13 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Lunenburg, Nova Scotia · Saint John, New Brunswick · Portland, Maine · Cape Cod, Massachusetts · Boston, Massachusetts · Marthas Vineyard, Massachusetts · New York, New York
★ Bucket-list Notre-Dame BasilicaOld Québec Private Walking Tour with Expert Local…Green Gables House & Anne of Green Gables Island E…BridgeClimb Sydney +8 more
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from $3,649
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Cunard · Queen Mary 2Round-trip
North America 15 nights Sep 26 – Oct 11, 2026 from New York, New York
New York, New York · Boston, Massachusetts · … · New York, New York8 ports
New York, New York · Boston, Massachusetts · Sydney, Nova Scotia · Quebec City, Quebec · Saguenay Fjord, Canada · Sept-Iles, Canada · Halifax, Nova Scotia · New York, New York
★ Bucket-list Manhattan Helicopter TourPrivate Luxury Boston TourBridgeClimb SydneyOld Québec Private Walking Tour with Expert Local… +2 more
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from $1,719
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Holland America · VolendamOne-way
North America 12 nights Sep 26 – Oct 8, 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 · Baie-Commeau, Quebec · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Boston, Massachusetts · Oak Bluffs, Massachusetts · New York, New York
★ Bucket-list Notre-Dame BasilicaOld Québec Private Walking Tour with Expert Local…Daniel-Johnson DamGreen Gables House & Anne of Green Gables Island E… +5 more
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from $1,529
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Norwegian · Norwegian EscapeRepositioning
Mediterranean 16 nights Sep 26 – Oct 12, 2026 from New York, New York to Barcelona, Spain
New York, New York · Halifax, Nova Scotia · … · Barcelona, Spain11 ports
New York, New York · Halifax, Nova Scotia · Sydney, Nova Scotia · Ponta Delgada, Azores, Portugal · Funchal, Madeira, Portugal · Gibraltar, British Territory · Motril, Spain · Melilla, Morocco · Ibiza, Spain · Palma de Mallorca, Spain · Barcelona, Spain
★ Bucket-list Manhattan Helicopter TourPeggy's Cove & LunenburgBridgeClimb SydneySete Cidades Twin Lakes +7 more
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from $1,169
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Norwegian · Norwegian JewelOne-way
North America 11 nights Sep 26 – Oct 7, 2026 from Philadelphia, Pennsylvania to Quebec City, Quebec
Philadelphia, Pennsylvania · Portland, Maine · … · Quebec City, Quebec9 ports
Philadelphia, Pennsylvania · Portland, Maine · Bar Harbor, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · La Baie, Canada · Quebec City, Quebec
★ Bucket-list Portland Head Light & Casco Bay Scenic Lighthouse…Private Acadia National Park Van Tour with Expert…Reversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg +4 more
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from $949
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Norwegian · Norwegian BreakawayRound-trip
North America 7 nights Sep 27 – Oct 4, 2026 from Boston, Massachusetts
Boston, Massachusetts · Portland, Maine · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Portland, Maine · Bar Harbor, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Private Acadia National Park Van Tour with Expert…Reversing Falls & Fundy Tidal Bore +1 more
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from $1,089
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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 TourLuxury Camden Sailing Experience on Penobscot BayPeggy's Cove & LunenburgBridgeClimb Sydney +3 more
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from $8,793
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Regent · Seven Seas SplendorOne-way
North America 11 nights Sep 28 – Oct 9, 2026 from Boston, Massachusetts to Montreal, Quebec
Boston, Massachusetts · Portland, Maine · … · Montreal, Quebec12 ports
Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Willis Island · Gaspe, Quebec · Sept-Iles, Canada · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg +7 more
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from $15,799
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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 $1,422
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Carnival · Carnival SunshineRound-trip
North America 8 nights Oct 3, 2026 from Norfolk, Virginia
Norfolk, Virginia · Saint John, New Brunswick · Halifax, Nova Scotia · St. Johns, Newfoundland · Norfolk, Virginia
★ Bucket-list Battleship WisconsinReversing Falls & Fundy Tidal BorePeggy's Cove & LunenburgCape St. Mary's Ecological Reserve
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from $796
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Holland America · ZuiderdamRound-trip
North America 7 nights Oct 3 – Oct 10, 2026 from Boston, Massachusetts
Boston, Massachusetts · Eastport, Maine, United States · … · Boston, Massachusetts7 ports
Boston, Massachusetts · Eastport, Maine, United States · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Portland, Maine · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourCampobello IslandReversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg +2 more
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from $1,714
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Princess · Majestic PrincessRound-trip
North America 7 nights Oct 3 – Oct 10, 2026 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 · Saint John, New Brunswick · Halifax, Nova Scotia · New York, New York
★ Bucket-list Manhattan Helicopter TourThe BreakersPrivate Luxury Boston TourReversing Falls & Fundy Tidal Bore +1 more
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from $2,185
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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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Cunard · Queen Mary 2One-way
North America 7 nights Oct 4 – Oct 11, 2026 from Quebec City, Quebec to New York, New York
Quebec City, Quebec · Saguenay Fjord, Canada · Sept-Iles, Canada · Halifax, Nova Scotia · New York, New York
★ Bucket-list Old Québec Private Walking Tour with Expert Local…Sept-Îles Archipelago Zodiac ExpeditionPeggy's Cove & LunenburgManhattan Helicopter Tour
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from $1,439
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Norwegian · Norwegian BreakawayRound-trip
North America 7 nights Oct 4 – Oct 11, 2026 from Boston, Massachusetts
Boston, Massachusetts · Portland, Maine · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Portland, Maine · Bar Harbor, Maine · Eastport, Maine, United States · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Private Acadia National Park Van Tour with Expert…Campobello Island +1 more
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from $959
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Seabourn · Seabourn VentureOne-way
Caribbean 8 nights Oct 5 – Oct 13, 2026 from Halifax, Nova Scotia to Bridgetown, Barbados
Halifax, Nova Scotia · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Little Bay, Montserrat, Leeward Islands · Rodney Bay, St. Lucia · Bridgetown, Barbados
★ Bucket-list Peggy's Cove & LunenburgMt. Liamuiga Volcano Crater HikeSoufrière Hills Volcano Exclusion Zone Helicopter…Full-Day Private Catamaran Sail to Soufrière & the… +1 more
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from $3,569
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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 TourThe BreakersPrivate Luxury Boston TourHopewell Rocks +6 more
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from $6,460
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Explora Journeys · EXPLORA IIIRound-trip
North America 15 nights Oct 7, 2026 from New York, New York
New York, New York · Portland, Maine · … · New York, New York12 ports
New York, New York · Portland, Maine · Saint John, New Brunswick · Cap-Aux-Meules, Canada · Havre St. Pierre, Quebec · Baie-Commeau, Quebec · Quebec City, Quebec · La Baie, Canada · Sept-Iles, Canada · Sydney, Nova Scotia · Halifax, Nova Scotia · New York, New York
★ Bucket-list Manhattan Helicopter TourPortland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal BoreArchipelago Flavours +7 more
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from $13,160
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Norwegian · Norwegian JewelOne-way
North America 10 nights Oct 7 – Oct 17, 2026 from Quebec City, Quebec to Philadelphia, Pennsylvania
Quebec City, Quebec · La Baie, Canada · … · Philadelphia, Pennsylvania9 ports
Quebec City, Quebec · La Baie, Canada · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Bar Harbor, Maine · Portland, Maine · Boston, Massachusetts · Philadelphia, Pennsylvania
★ Bucket-list Old Québec Private Walking Tour with Expert Local…Saguenay Fjord Zodiac Whale-Watching with NaturalistGreen Gables House & Anne of Green Gables Island E…BridgeClimb Sydney +4 more
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from $1,079
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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 Notre-Dame BasilicaOld Québec Private Walking Tour with Expert Local…Green Gables House & Anne of Green Gables Island E…Peggy's Cove & Lunenburg +4 more
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from $9,048
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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 National AquariumPrivate Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal Bore +1 more
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from $3,511
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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 TourLuxury Camden Sailing Experience on Penobscot BayPeggy's Cove & LunenburgBridgeClimb Sydney +3 more
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from $17,608
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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.

23 lines
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MSC Cruises Royal Caribbean Carnival Viking River Norwegian AmaWaterways Costa Princess Celebrity Avalon Disney Viking Ocean Holland America Silversea Oceania Virgin Regent Explora Journeys Cunard Azamara Windstar Seabourn Virgin Voyages