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? From to — 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 1 selected · clear 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

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 Bermuda ×Visits Portland ×6–8 nights × Clear all

Showing 15 of 15 sailings

Norwegian · Norwegian EscapeRound-trip

North America 7 nights Aug 29 – Sep 5, 2026 from New York, New York

New York, New York · Boston, Massachusetts · … · New York, New York6 ports

New York, New York · Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · New York, New York

★ Bucket-list Manhattan Helicopter Tour Private Luxury Boston Tour Portland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal Bore +1 more

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from $956

Book This Cruise@ Cruisebound

Norwegian · Norwegian EscapeRound-trip

North America 7 nights Sep 5 – Sep 12, 2026 from New York, New York

New York, New York · Sydney, Nova Scotia · … · New York, New York7 ports

New York, New York · Sydney, Nova Scotia · Halifax, Nova Scotia · Portland, Maine · Boston, Massachusetts · Newport, Rhode Island · New York, New York

★ Bucket-list Manhattan Helicopter Tour BridgeClimb Sydney Peggy's Cove & Lunenburg Portland Head Light & Casco Bay Scenic Lighthouse… +2 more

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from $915

Book This Cruise@ Cruisebound

Norwegian · Norwegian EscapeRound-trip

North America 7 nights Sep 12 – Sep 19, 2026 from New York, New York

New York, New York · Halifax, Nova Scotia · … · New York, New York7 ports

New York, New York · Halifax, Nova Scotia · Saint John, New Brunswick · Boston, Massachusetts · Portland, Maine · Newport, Rhode Island · New York, New York

★ Bucket-list Manhattan Helicopter Tour Peggy's Cove & Lunenburg Reversing Falls & Fundy Tidal Bore Private Luxury Boston Tour +2 more

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from $935

Book This Cruise@ Cruisebound

Princess · Majestic PrincessRound-trip

North America 7 nights Oct 10 – Oct 17, 2026 from New York, New York

New York, New York · Newport, Rhode Island · … · New York, New York7 ports

New York, New York · Newport, Rhode Island · Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · New York, New York

★ Bucket-list Manhattan Helicopter Tour The Breakers Private Luxury Boston Tour Portland Head Light & Casco Bay Scenic Lighthouse… +2 more

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from $1,404

Book This Cruise@ Cruisebound

Princess · Majestic PrincessRound-trip

North America 7 nights Oct 17 – Oct 24, 2026 from New York, New York

New York, New York · Newport, Rhode Island · … · New York, New York7 ports

New York, New York · Newport, Rhode Island · Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · New York, New York

★ Bucket-list Manhattan Helicopter Tour The Breakers Private Luxury Boston Tour Portland Head Light & Casco Bay Scenic Lighthouse… +2 more

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from $1,418

Book This Cruise@ Cruisebound

Princess · Majestic PrincessRound-trip

North America 7 nights Oct 24 – Oct 31, 2026 from New York, New York

New York, New York · Newport, Rhode Island · … · New York, New York7 ports

New York, New York · Newport, Rhode Island · Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · New York, New York

★ Bucket-list Manhattan Helicopter Tour The Breakers Private Luxury Boston Tour Portland Head Light & Casco Bay Scenic Lighthouse… +2 more

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from $1,187

Book This Cruise@ Cruisebound

Princess · Majestic PrincessRound-trip

North America 7 nights Oct 31 – Nov 7, 2026 from New York, New York

New York, New York · Newport, Rhode Island · … · New York, New York7 ports

New York, New York · Newport, Rhode Island · Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · New York, New York

★ Bucket-list Manhattan Helicopter Tour The Breakers Private Luxury Boston Tour Portland Head Light & Casco Bay Scenic Lighthouse… +2 more

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from $1,145

Book This Cruise@ Cruisebound

Princess · Regal PrincessRound-trip

North America 7 nights Aug 21 – Aug 28, 2027 from New York, New York

New York, New York · Boston, Massachusetts · … · New York, New York6 ports

New York, New York · Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · New York, New York

★ Bucket-list Manhattan Helicopter Tour Private Luxury Boston Tour Portland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal Bore +1 more

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from $829

Book This Cruise@ Cruisebound

Princess · Regal PrincessRound-trip

North America 7 nights Sep 18 – Sep 25, 2027 from New York, New York

New York, New York · Newport, Rhode Island · … · New York, New York7 ports

New York, New York · Newport, Rhode Island · Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · New York, New York

★ Bucket-list Manhattan Helicopter Tour The Breakers Private Luxury Boston Tour Portland Head Light & Casco Bay Scenic Lighthouse… +2 more

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from $889

Book This Cruise@ Cruisebound

Princess · Regal PrincessRound-trip

North America 7 nights Sep 25 – Oct 2, 2027 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 · Portland, Maine · Halifax, Nova Scotia · New York, New York

★ Bucket-list Manhattan Helicopter Tour The Breakers Private Luxury Boston Tour Portland Head Light & Casco Bay Scenic Lighthouse… +1 more

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from $749

Book This Cruise@ Cruisebound

Princess · Regal PrincessRound-trip

North America 7 nights Oct 2 – Oct 9, 2027 from New York, New York

New York, New York · Newport, Rhode Island · … · New York, New York7 ports

New York, New York · Newport, Rhode Island · Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · New York, New York

★ Bucket-list Manhattan Helicopter Tour The Breakers Private Luxury Boston Tour Portland Head Light & Casco Bay Scenic Lighthouse… +2 more

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from $1,449

Book This Cruise@ Cruisebound

Princess · Regal PrincessRound-trip

North America 7 nights Oct 9 – Oct 16, 2027 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 · Portland, Maine · Halifax, Nova Scotia · New York, New York

★ Bucket-list Manhattan Helicopter Tour The Breakers Private Luxury Boston Tour Portland Head Light & Casco Bay Scenic Lighthouse… +1 more

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from $1,049

Book This Cruise@ Cruisebound

Princess · Regal PrincessRound-trip

North America 7 nights Oct 16 – Oct 23, 2027 from New York, New York

New York, New York · Newport, Rhode Island · … · New York, New York7 ports

New York, New York · Newport, Rhode Island · Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · New York, New York

★ Bucket-list Manhattan Helicopter Tour The Breakers Private Luxury Boston Tour Portland Head Light & Casco Bay Scenic Lighthouse… +2 more

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from $769

Book This Cruise@ Cruisebound

Princess · Regal PrincessRound-trip

North America 7 nights Oct 23 – Oct 30, 2027 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 · Portland, Maine · Halifax, Nova Scotia · New York, New York

★ Bucket-list Manhattan Helicopter Tour The Breakers Private Luxury Boston Tour Portland Head Light & Casco Bay Scenic Lighthouse… +1 more

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from $899

Book This Cruise@ Cruisebound

Princess · Regal PrincessRound-trip

North America 7 nights Oct 30 – Nov 6, 2027 from New York, New York

New York, New York · Newport, Rhode Island · … · New York, New York7 ports

New York, New York · Newport, Rhode Island · Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · New York, New York

★ Bucket-list Manhattan Helicopter Tour The Breakers Private Luxury Boston Tour Portland Head Light & Casco Bay Scenic Lighthouse… +2 more

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from $806

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