Bucket-List Cruise Adventures

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Filtering Holland America ×Visits Portland × Clear all
Showing 28 of 28 sailings
Holland America · ZuiderdamOne-way
North America 7 nights Jun 20 – Jun 27, 2026 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Portland, Maine · … · Quebec City, Quebec6 ports
Boston, Massachusetts · Portland, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Peggy's Cove & LunenburgBridgeClimb Sydney +2 more
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from $889
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Holland America · ZuiderdamOne-way
North America 7 nights Aug 22 – Aug 29, 2026 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Portland, Maine · … · Quebec City, Quebec6 ports
Boston, Massachusetts · Portland, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Peggy's Cove & LunenburgBridgeClimb Sydney +2 more
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from $1,159
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Holland America · ZuiderdamOne-way
North America 7 nights Sep 12 – Sep 19, 2026 from Quebec City, Quebec to Boston, Massachusetts
Quebec City, Quebec · Charlottetown, Prince Edward Island · … · Boston, Massachusetts6 ports
Quebec City, Quebec · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · 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 +2 more
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from $1,189
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Holland America · ZuiderdamOne-way
North America 7 nights Sep 26 – Oct 3, 2026 from Quebec City, Quebec to Boston, Massachusetts
Quebec City, Quebec · Saguenay Fjord, Canada · … · Boston, Massachusetts6 ports
Quebec City, Quebec · Saguenay Fjord, Canada · Cap-Aux-Meules, Canada · Charlottetown, Prince Edward Island · Portland, Maine · Boston, Massachusetts
★ Bucket-list Old Québec Private Walking Tour with Expert Local…Green Gables House & Anne of Green Gables Island E…Portland Head Light & Casco Bay Scenic Lighthouse…Private Luxury Boston Tour
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from $1,409
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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 TourReversing Falls & Fundy Tidal BorePeggy's Cove & LunenburgBridgeClimb Sydney +1 more
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from $1,429
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Holland America · ZuiderdamOne-way
North America 7 nights Oct 10 – Oct 17, 2026 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Portland, Maine · … · Quebec City, Quebec6 ports
Boston, Massachusetts · Portland, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Peggy's Cove & LunenburgBridgeClimb Sydney +2 more
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from $1,399
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Holland America · RotterdamRepositioning
Bermuda 13 nights Oct 18 – Oct 31, 2026 from Amsterdam, The Netherlands to Fort Lauderdale (Port Everglades), Florida
Amsterdam, The Netherlands · Zeebrugge (Bruges), Belgium · … · Fort Lauderdale (Port Everglades), Florida6 ports
Amsterdam, The Netherlands · Zeebrugge (Bruges), Belgium · Portland, England · Cornwall, England · Kings Wharf, Bermuda · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Walk Into the Secret Annex - Anne Frank HousePrivate Bruges Full-Day Shore Excursion with Canal…Portland Head Light & Casco Bay Scenic Lighthouse…Everglades Airboat Skim + Gator Boys Live Show
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from $1,119
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Holland America · Nieuw StatendamRepositioning
Northern Europe 15 nights Dec 5 – Dec 20, 2026 from Rotterdam, The Netherlands to Fort Lauderdale (Port Everglades), Florida
Rotterdam, The Netherlands · Zeebrugge (Bruges), Belgium · … · Fort Lauderdale (Port Everglades), Florida7 ports
Rotterdam, The Netherlands · Zeebrugge (Bruges), Belgium · Dover (London), England · Cherbourg, France · Le Havre (Paris), France · Portland, England · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list All-Inclusive Private Windmill Tour to Kinderdijk…Private Bruges Full-Day Shore Excursion with Canal…White Cliffs of DoverPrivate Paris Highlights & Seine River Cruise from… +2 more
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from $1,149
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Holland America · Nieuw StatendamRepositioning
Mediterranean 26 nights Apr 4 – Apr 30, 2027 from Fort Lauderdale (Port Everglades), Florida to Dover (London), England
Fort Lauderdale (Port Everglades), Florida · Kings Wharf, Bermuda · … · Dover (London), England12 ports
Fort Lauderdale (Port Everglades), Florida · Kings Wharf, Bermuda · Portland, England · Dover (London), England · Rotterdam, The Netherlands · Casablanca, Morocco · Agadir, Morocco · Lanzarote, Canary Islands, Spain · Santa Cruz de Tenerife, Canary Islands · Funchal, Madeira, Portugal · Lisbon, Portugal · Dover (London), England
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowPortland Head Light & Casco Bay Scenic Lighthouse…White Cliffs of DoverAll-Inclusive Private Windmill Tour to Kinderdijk… +4 more
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from $3,384
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Holland America · VolendamOne-way
North America 14 nights May 15 – May 29, 2027 from Fort Lauderdale (Port Everglades), Florida to Montreal, Quebec
Fort Lauderdale (Port Everglades), Florida · Norfolk, Virginia · … · Montreal, Quebec9 ports
Fort Lauderdale (Port Everglades), Florida · Norfolk, Virginia · Boston, Massachusetts · Portland, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowPrivate Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Peggy's Cove & Lunenburg +3 more
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from $2,059
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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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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 · VolendamOne-way
North America 7 nights Jul 10 – Jul 17, 2027 from Montreal, Quebec to Boston, Massachusetts
Montreal, Quebec · Quebec City, Quebec · … · Boston, Massachusetts7 ports
Montreal, Quebec · Quebec City, Quebec · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · 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 +2 more
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from $1,654
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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 · ZuiderdamOne-way
Northern Europe 28 nights Aug 7 – Sep 4, 2027 from Amsterdam, The Netherlands to Boston, Massachusetts
Amsterdam, The Netherlands · Aarhus, Denmark · … · Boston, Massachusetts20 ports
Amsterdam, The Netherlands · Aarhus, Denmark · Warnemunde, Germany · Ronne, Denmark · Copenhagen, Denmark · Amsterdam, The Netherlands · Lerwick, Shetland Islands · Seydisfjordur, Iceland · Akureyri, Iceland · Husavik, Iceland · Isafjord, Iceland · Grundarfjordur, Iceland · Reykjavik, Iceland · Nanortalik, Greenland · Qaqortoq, Greenland · St. Anthony, Newfoundland · St. Johns, Newfoundland · Halifax, Nova Scotia · Portland, Maine · Boston, Massachusetts
★ Bucket-list Walk Into the Secret Annex - Anne Frank HouseBerlin Private Full-Day Shore Excursion from Warne…Private Copenhagen Walking Tour with a Local ExpertMývatn Nature Baths +7 more
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from $5,354
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Holland America · ZuiderdamOne-way
Northern Europe 21 nights Aug 14 – Sep 4, 2027 from Amsterdam, The Netherlands to Boston, Massachusetts
Amsterdam, The Netherlands · Lerwick, Shetland Islands · … · Boston, Massachusetts15 ports
Amsterdam, The Netherlands · Lerwick, Shetland Islands · Seydisfjordur, Iceland · Akureyri, Iceland · Husavik, Iceland · Isafjord, Iceland · Grundarfjordur, Iceland · Reykjavik, Iceland · Nanortalik, Greenland · Qaqortoq, Greenland · St. Anthony, Newfoundland · St. Johns, Newfoundland · Halifax, Nova Scotia · Portland, Maine · Boston, Massachusetts
★ Bucket-list Walk Into the Secret Annex - Anne Frank HouseMývatn Nature BathsDynjandi WaterfallInside the Volcano +5 more
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from $4,264
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Holland America · ZuiderdamOne-way
North America 7 nights Sep 4 – Sep 11, 2027 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Portland, Maine · … · Quebec City, Quebec6 ports
Boston, Massachusetts · Portland, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Peggy's Cove & LunenburgBridgeClimb Sydney +2 more
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from $1,709
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Holland America · VolendamOne-way
North America 7 nights Sep 11 – Sep 18, 2027 from Montreal, Quebec to Boston, Massachusetts
Montreal, Quebec · Quebec City, Quebec · … · Boston, Massachusetts7 ports
Montreal, Quebec · Quebec City, Quebec · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · 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 +2 more
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from $1,689
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Holland America · ZuiderdamOne-way
North America 7 nights Sep 11 – Sep 18, 2027 from Quebec City, Quebec to Boston, Massachusetts
Quebec City, Quebec · Charlottetown, Prince Edward Island · … · Boston, Massachusetts6 ports
Quebec City, Quebec · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · 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 +2 more
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from $1,709
Book This Cruise@ Cruisebound
Holland America · VolendamRound-trip
North America 7 nights Sep 18 – Sep 25, 2027 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 TourReversing Falls & Fundy Tidal BorePeggy's Cove & LunenburgBridgeClimb Sydney +1 more
View →
from $1,709
Book This Cruise@ Cruisebound
Holland America · ZuiderdamRound-trip
North America 7 nights Sep 18 – Sep 25, 2027 from Boston, Massachusetts
Boston, Massachusetts · Saint John, New Brunswick · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Portland, Maine · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourReversing Falls & Fundy Tidal BorePeggy's Cove & LunenburgBridgeClimb Sydney +1 more
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from $1,804
Book This Cruise@ Cruisebound
Holland America · ZuiderdamOne-way
North America 7 nights Sep 25 – Oct 2, 2027 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Portland, Maine · … · Quebec City, Quebec6 ports
Boston, Massachusetts · Portland, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Peggy's Cove & LunenburgBridgeClimb Sydney +2 more
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from $1,784
Book This Cruise@ Cruisebound
Holland America · VolendamOne-way
North America 9 nights Oct 2 – Oct 11, 2027 from Montreal, Quebec to New York, New York
Montreal, Quebec · Quebec City, Quebec · … · New York, New York8 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Portland, Maine · New York, New York
★ 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 $2,369
Book This Cruise@ Cruisebound
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
View →
from $3,464
Book This Cruise@ Cruisebound
Holland America · ZuiderdamOne-way
North America 7 nights Oct 9 – Oct 16, 2027 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Portland, Maine · … · Quebec City, Quebec6 ports
Boston, Massachusetts · Portland, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Peggy's Cove & LunenburgBridgeClimb Sydney +2 more
View →
from $1,784
Book This Cruise@ Cruisebound

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