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
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 Visits Portland ×Round trip ×6–8 nights × Clear all
Showing 34 of 34 sailings
Norwegian · Norwegian BreakawayRound-trip
North America 7 nights Aug 23 – Aug 30, 2026 from Boston, Massachusetts
Boston, Massachusetts · Portland, Maine · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Portland, Maine · Bar Harbor, Maine · Halifax, Nova Scotia · Saint John, New Brunswick · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Private Acadia National Park Van Tour with Expert…Peggy's Cove & Lunenburg +1 more
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from $838
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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 TourPrivate Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal Bore +1 more
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from $956
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Norwegian · Norwegian BreakawayRound-trip
North America 7 nights Aug 30 – Sep 6, 2026 from Boston, Massachusetts
Boston, Massachusetts · Portland, Maine · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Portland, Maine · Bar Harbor, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Private Acadia National Park Van Tour with Expert…Reversing Falls & Fundy Tidal Bore +1 more
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from $838
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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 TourBridgeClimb SydneyPeggy's Cove & LunenburgPortland Head Light & Casco Bay Scenic Lighthouse… +2 more
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from $915
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Norwegian · Norwegian BreakawayRound-trip
North America 7 nights Sep 6 – Sep 13, 2026 from Boston, Massachusetts
Boston, Massachusetts · Portland, Maine · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Portland, Maine · Bar Harbor, Maine · Halifax, Nova Scotia · Saint John, New Brunswick · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Private Acadia National Park Van Tour with Expert…Peggy's Cove & Lunenburg +1 more
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from $731
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Disney · Disney DreamRound-trip
Northern Europe 7 nights Sep 7 – Sep 14, 2026 from Southampton, England
Southampton, England · Liverpool, England · … · Southampton, England6 ports
Southampton, England · Liverpool, England · Greenock (Glasgow), Scotland · Cobh (Cork), Ireland · Portland, United Kingdom · Southampton, England
★ Bucket-list Stand Inside Stonehenge & See the Original 1215 Ma…Portland Head Light & Casco Bay Scenic Lighthouse…
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from $2,709
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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 TourPeggy's Cove & LunenburgReversing Falls & Fundy Tidal BorePrivate Luxury Boston Tour +2 more
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from $935
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Norwegian · Norwegian BreakawayRound-trip
North America 7 nights Sep 13 – Sep 20, 2026 from Boston, Massachusetts
Boston, Massachusetts · Portland, Maine · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Portland, Maine · Bar Harbor, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Private Acadia National Park Van Tour with Expert…Reversing Falls & Fundy Tidal Bore +1 more
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from $690
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Norwegian · Norwegian BreakawayRound-trip
North America 7 nights Sep 20 – Sep 27, 2026 from Boston, Massachusetts
Boston, Massachusetts · Portland, Maine · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Portland, Maine · Bar Harbor, Maine · Eastport, Maine, United States · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Private Acadia National Park Van Tour with Expert…Peggy's Cove & Lunenburg
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from $690
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Norwegian · Norwegian BreakawayRound-trip
North America 7 nights Sep 27 – Oct 4, 2026 from Boston, Massachusetts
Boston, Massachusetts · Portland, Maine · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Portland, Maine · Bar Harbor, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Private Acadia National Park Van Tour with Expert…Reversing Falls & Fundy Tidal Bore +1 more
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from $989
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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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Norwegian · Norwegian BreakawayRound-trip
North America 7 nights Oct 4 – Oct 11, 2026 from Boston, Massachusetts
Boston, Massachusetts · Portland, Maine · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Portland, Maine · Bar Harbor, Maine · Eastport, Maine, United States · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Private Acadia National Park Van Tour with Expert…Peggy's Cove & Lunenburg
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from $797
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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 TourThe BreakersPrivate Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse… +2 more
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from $1,404
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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 TourThe BreakersPrivate Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse… +2 more
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from $1,418
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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 TourThe BreakersPrivate Luxury Boston TourPortland 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 TourThe BreakersPrivate Luxury Boston TourPortland 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 TourPrivate Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal Bore +1 more
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from $829
Book This Cruise@ Cruisebound
Norwegian · Norwegian BreakawayRound-trip
North America 7 nights Aug 29 – Sep 5, 2027 from Boston, Massachusetts
Boston, Massachusetts · Portland, Maine · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Sydney, Nova Scotia · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal BoreBridgeClimb Sydney +1 more
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from $853
Book This Cruise@ Cruisebound
Disney · Disney WishRound-trip
Northern Europe 7 nights Sep 3 – Sep 10, 2027 from Southampton, England
Southampton, England · Greenock (Glasgow), Scotland · … · Southampton, England6 ports
Southampton, England · Greenock (Glasgow), Scotland · Liverpool, England · Belfast, Northern Ireland · Portland, United Kingdom · Southampton, England
★ Bucket-list Stand Inside Stonehenge & See the Original 1215 Ma…Giant's Causeway Private Luxury Day Tour from Belf…Portland Head Light & Casco Bay Scenic Lighthouse…
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from $2,981
Book This Cruise@ Cruisebound
Norwegian · Norwegian BreakawayRound-trip
North America 7 nights Sep 5 – Sep 12, 2027 from Boston, Massachusetts
Boston, Massachusetts · Portland, Maine · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Portland, Maine · Eastport, Maine, United States · Saint John, New Brunswick · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg
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from $816
Book This Cruise@ Cruisebound
Norwegian · Norwegian BreakawayRound-trip
North America 7 nights Sep 12 – Sep 19, 2027 from Boston, Massachusetts
Boston, Massachusetts · Portland, Maine · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Sydney, Nova Scotia · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal BoreBridgeClimb Sydney +1 more
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from $824
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
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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
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 TourThe BreakersPrivate Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse… +2 more
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from $889
Book This Cruise@ Cruisebound
Norwegian · Norwegian BreakawayRound-trip
North America 7 nights Sep 19 – Sep 26, 2027 from Boston, Massachusetts
Boston, Massachusetts · Eastport, Maine, United States · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Eastport, Maine, United States · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg
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from $816
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 TourThe BreakersPrivate Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse… +1 more
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from $749
Book This Cruise@ Cruisebound
Norwegian · Norwegian BreakawayRound-trip
North America 7 nights Sep 26 – Oct 3, 2027 from Boston, Massachusetts
Boston, Massachusetts · Eastport, Maine, United States · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Eastport, Maine, United States · Saint John, New Brunswick · Halifax, Nova Scotia · Portland, Maine · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourReversing Falls & Fundy Tidal BorePeggy's Cove & LunenburgPortland Head Light & Casco Bay Scenic Lighthouse…
View →
from $816
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 TourThe BreakersPrivate Luxury Boston TourPortland 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 TourThe BreakersPrivate Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse… +1 more
View →
from $1,049
Book This Cruise@ Cruisebound
Norwegian · Norwegian BreakawayRound-trip
North America 7 nights Oct 10 – Oct 17, 2027 from Boston, Massachusetts
Boston, Massachusetts · Saint John, New Brunswick · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Saint John, New Brunswick · Sydney, Nova Scotia · Halifax, Nova Scotia · Portland, Maine · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourReversing Falls & Fundy Tidal BoreBridgeClimb SydneyPeggy's Cove & Lunenburg +1 more
View →
from $816
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 TourThe BreakersPrivate Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse… +2 more
View →
from $769
Book This Cruise@ Cruisebound
Norwegian · Norwegian BreakawayRound-trip
North America 7 nights Oct 17 – Oct 24, 2027 from Boston, Massachusetts
Boston, Massachusetts · Eastport, Maine, United States · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Eastport, Maine, United States · Saint John, New Brunswick · Halifax, Nova Scotia · Portland, Maine · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourReversing Falls & Fundy Tidal BorePeggy's Cove & LunenburgPortland Head Light & Casco Bay Scenic Lighthouse…
View →
from $816
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 TourThe BreakersPrivate Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse… +1 more
View →
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 TourThe BreakersPrivate Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse… +2 more
View →
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.

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