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
My result then click any cruise row to open it
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
Cruise level tap one or more Luxury Premium Contemporary River
+ 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 ×One-way ×9–12 nights × Clear all
Showing 12 of 12 sailings
Holland America · VolendamOne-way
North America 10 nights Aug 22 – Sep 1, 2026 from Boston, Massachusetts to Montreal, Quebec
Boston, Massachusetts · Eastport, Maine, United States · … · Montreal, Quebec10 ports
Boston, Massachusetts · Eastport, Maine, United States · Halifax, Nova Scotia · St. Johns, Newfoundland · St. Anthony, Newfoundland · Corner Brook, Newfoundland · Havre St. Pierre, Quebec · Baie-Commeau, Quebec · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Private Luxury Boston TourPeggy's Cove & Lunenburg
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from $1,999
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Holland America · OosterdamOne-way
Mediterranean 10 nights Sep 23 – Oct 3, 2026 from Trieste, Italy to Piraeus (Athens), Greece
Trieste, Italy · Rijeka, Croatia · … · Piraeus (Athens), Greece8 ports
Trieste, Italy · Rijeka, Croatia · Split, Croatia · Santorini (Thira), Greece · Bodrum, Turkey · Kusadasi (Ephesus), Turkey · Istanbul, Turkey · Piraeus (Athens), Greece
★ Bucket-list Miramare CastleDiocletian's PalaceSemi-Private Caldera Catamaran with Hot Springs &…Ephesus + the Terrace Houses with a licensed archa… +2 more
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from $2,149
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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 BridgeClimb SydneyPeggy's Cove & LunenburgPrivate Luxury Boston TourManhattan Helicopter Tour
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from $1,529
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Holland America · OosterdamOne-way
Mediterranean 10 nights May 15 – May 25, 2027 from Trieste, Italy to Barcelona, Spain
Trieste, Italy · Zadar, Croatia · … · Barcelona, Spain9 ports
Trieste, Italy · Zadar, Croatia · Dubrovnik, Croatia · Kotor, Montenegro · Kefalonia, Greece · Messina, Sicily, Italy · Naples, Italy · Civitavecchia (Rome), Italy · Barcelona, Spain
★ Bucket-list Miramare CastleKornati National Park & TelašćicaWalk Dubrovnik's Ancient City WallsClimb the City Walls to San Giovanni Fortress +4 more
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from $1,909
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Holland America · VolendamOne-way
North America 10 nights May 29 – Jun 8, 2027 from Montreal, Quebec
Montreal, Quebec · Quebec City, Quebec · … · Montreal, Quebec7 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Charlottetown, Prince Edward Island · St. Johns, Newfoundland · St. Pierre, St. Pierre and Miquelon · Montreal, Quebec
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from $2,999
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Holland America · VolendamOne-way
North America 11 nights Jun 8 – Jun 19, 2027 from Montreal, Quebec to Boston, Massachusetts
Montreal, Quebec · Quebec City, Quebec · … · Boston, Massachusetts10 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Baie-Commeau, Quebec · Havre St. Pierre, Quebec · Corner Brook, Newfoundland · St. Anthony, Newfoundland · St. Johns, Newfoundland · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list Peggy's Cove & LunenburgPrivate Luxury Boston Tour
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from $2,874
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Holland America · VolendamOne-way
North America 11 nights Aug 21 – Sep 1, 2027 from Boston, Massachusetts to Montreal, Quebec
Boston, Massachusetts · Eastport, Maine, United States · … · Montreal, Quebec11 ports
Boston, Massachusetts · Eastport, Maine, United States · Halifax, Nova Scotia · St. Johns, Newfoundland · St. Anthony, Newfoundland · Corner Brook, Newfoundland · Havre St. Pierre, Quebec · Baie-Commeau, Quebec · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Private Luxury Boston TourPeggy's Cove & Lunenburg
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from $2,839
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Holland America · OosterdamOne-way
Mediterranean 10 nights Sep 11 – Sep 21, 2027 from Civitavecchia (Rome), Italy to Trieste, Italy
Civitavecchia (Rome), Italy · Naples, Italy · … · Trieste, Italy9 ports
Civitavecchia (Rome), Italy · Naples, Italy · Palermo, Sicily, Italy · Messina, Sicily, Italy · Kefalonia, Greece · Kotor, Montenegro · Dubrovnik, Croatia · Split, Croatia · Trieste, Italy
★ Bucket-list Vatican, Sistine Chapel & Colosseum in One DayPompeii with a Licensed ArchaeologistCappella Palatina & the Norman PalaceTaormina's Ancient Greek Theatre, framed by Mount… +4 more
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from $1,902
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Holland America · OosterdamOne-way
Mediterranean 11 nights Sep 21 – Oct 2, 2027 from Trieste, Italy to Piraeus (Athens), Greece
Trieste, Italy · Split, Croatia · … · Piraeus (Athens), Greece9 ports
Trieste, Italy · Split, Croatia · Dubrovnik, Croatia · Santorini (Thira), Greece · Mykonos, Greece · Kos, Greece · Kusadasi (Ephesus), Turkey · Istanbul, Turkey · Piraeus (Athens), Greece
★ Bucket-list Miramare CastleDiocletian's PalaceWalk Dubrovnik's Ancient City WallsSemi-Private Caldera Catamaran with Hot Springs &… +4 more
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from $2,327
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Holland America · OosterdamOne-way
Mediterranean 10 nights Oct 2 – Oct 12, 2027 from Piraeus (Athens), Greece to Civitavecchia (Rome), Italy
Piraeus (Athens), Greece · Mykonos, Greece · … · Civitavecchia (Rome), Italy7 ports
Piraeus (Athens), Greece · Mykonos, Greece · Istanbul, Turkey · Santorini (Thira), Greece · Souda Bay · Messina, Sicily, Italy · Civitavecchia (Rome), Italy
★ Bucket-list The Acropolis & Parthenon, Guided Skip-the-LineDelosHagia Sophia + the upper gallery mosaics with a li…Semi-Private Caldera Catamaran with Hot Springs &… +2 more
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from $1,882
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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 BridgeClimb SydneyPeggy's Cove & LunenburgManhattan Helicopter Tour
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from $2,369
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Holland America · NoordamOne-way
Australia & South Pacific 12 nights Jan 4 – Jan 16, 2028 from Singapore, Singapore to Hong Kong, Hong Kong SAR, China
Singapore, Singapore · Ko Samui, Thailand · … · Hong Kong, Hong Kong SAR, China6 ports
Singapore, Singapore · Ko Samui, Thailand · Pattaya, Thailand · Phu My, Vietnam · Ha Long Bay, Vietnam · Hong Kong, Hong Kong SAR, China
★ Bucket-list Gardens by the BayVictoria Peak at Dusk
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from $1,504
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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