Bucket-List Cruise Adventures

Pick your sailing — we plan the whole adventure

Bucket-list adventures at every port — where to fly in, and what to do the day(s) before and after.

When are you free? — only cruises that fit entirely inside your dates
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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
Trip tap one or more Round-trip One-way Repositioning
Length tap one or more 3–5 nights 6–8 nights 9–12 nights 13+ nights
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+ pick specific cruise lines · 1 selected
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 Holland America ×Visits Portland ×Round trip × Clear all
Showing 10 of 10 sailings
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 · 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 · 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 · 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
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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 · ZuiderdamRound-trip
North America 14 nights Oct 2 – Oct 16, 2027 from Quebec City, Quebec
Quebec City, Quebec · Charlottetown, Prince Edward Island · … · Quebec City, Quebec11 ports
Quebec City, Quebec · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Portland, Maine · Boston, Massachusetts · Portland, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Quebec City, Quebec
★ Bucket-list Old Québec Private Walking Tour with Expert Local…Green Gables House & Anne of Green Gables Island E…BridgeClimb SydneyPeggy's Cove & Lunenburg +2 more
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from $3,464
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