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 · 2 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 Costa ×Regent ×Visits Portland × Clear all
Showing 5 of 5 sailings
Regent · Seven Seas SplendorOne-way
Australia & South Pacific 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 +5 more
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from $11,899
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Regent · Seven Seas ExplorerRound-trip
Australia & South Pacific 10 nights Dec 19 – Dec 29, 2026 from Sydney, Australia
Sydney, Australia · Eden, Australia · … · Sydney, Australia10 ports
Sydney, Australia · Eden, Australia · Willis Island · Melbourne, Australia · Phillip Island, Australia · Portland, Maine · Willis Island · Hobart, Australia · Willis Island · Sydney, Australia
★ Bucket-list BridgeClimb SydneyZodiac Circumnavigation of Willis IslandPortland Head Light & Casco Bay Scenic Lighthouse…
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from $10,199
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Costa · Costa FavolosaRound-trip
Northern Europe 11 nights Aug 25 – Sep 5, 2027 from Hamburg, Germany
Hamburg, Germany · Portland, England · … · Hamburg, Germany9 ports
Hamburg, Germany · Portland, England · Falmouth, Cornwall, England · Cork (ireland) · Dun Laoghaire, Dublin, Ireland · Liverpool, England · Greenock (Glasgow), Scotland · Alesund, Norway · Hamburg, Germany
★ Bucket-list Private Full-Day Hamburg Shore Excursion with Loca…Portland Head Light & Casco Bay Scenic Lighthouse…Blue Hole & Secret FallsTrollstigen & Geiranger Fjord
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from $2,119
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Regent · Seven Seas GrandeurOne-way
Australia & South Pacific 11 nights Sep 10 – Sep 21, 2027 from Montreal, Quebec to New York, New York
Montreal, Quebec · Quebec City, Quebec · … · New York, New York11 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Willis Island · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Bar Harbor, Maine · Portland, Maine · Willis Island · New York, New York
★ Bucket-list Old Québec Private Walking Tour with Expert Local…Zodiac Circumnavigation of Willis IslandGreen Gables House & Anne of Green Gables Island E…BridgeClimb Sydney +4 more
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from $10,799
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Regent · Seven Seas SplendorOne-way
Australia & South Pacific 21 nights Mar 5 – Mar 26, 2028 from Melbourne, Australia to Singapore, Singapore
Melbourne, Australia · Portland, Maine · … · Singapore, Singapore18 ports
Melbourne, Australia · Portland, Maine · Kangaroo Island, Australia · Adelaide, Australia · Willis Island · Esperance, Australia · Albany, Australia · Busselton, Australia · Perth (Fremantle), Australia · Willis Island · Komodo Island, Indonesia · Bali, Indonesia · Lombok, Indonesia · Surabaya, Java, Indonesia · Semarang, Java, Indonesia · Jakarta, Java, Indonesia · Willis Island · Singapore, Singapore
★ Bucket-list Portland Head Light & Casco Bay Scenic Lighthouse…Zodiac Circumnavigation of Willis IslandGardens by the Bay
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from $22,399
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.

19 lines
aboard
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