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
Must visit a specific port clear
Reset
Filtering Visits Charlottetown ×Repositioning ×Round trip × Clear all
Showing 15 of 15 sailings
Princess · Crown PrincessRepositioning
Australia & South Pacific 59 nights Jul 4 – Sep 1, 2026 from Dover (London), England to Sydney, Australia
Dover (London), England · Lerwick, Shetland Islands · … · Sydney, Australia26 ports
Dover (London), England · Lerwick, Shetland Islands · Reykjavik, Iceland · Grundarfjordur, Iceland · Isafjord, Iceland · St. Johns, Newfoundland · Corner Brook, Newfoundland · Quebec City, Quebec · Saguenay Fjord, Canada · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · New York, New York · Miami, Florida · Cartagena, Colombia · Panama Canal Full Transit New Locks · Manta (Quito), Ecuador · Callao (Lima), Peru · Pisco (Puerto San Martin), Peru · Easter Island, Chile · Adamstown, Pitcairn Island · Papeete, Tahiti, French Polynesia · Moorea, French Polynesia · Cross International Date Line · Auckland, New Zealand · Sydney, Australia
★ Bucket-list White Cliffs of DoverInside the VolcanoDynjandi WaterfallCape St. Mary's Ecological Reserve +11 more
View →
from $13,924
Book This Cruise@ Cruisebound
Celebrity · Celebrity SilhouetteRound-trip
North America 12 nights Sep 5 – Sep 17, 2026 from Boston, Massachusetts
Boston, Massachusetts · Rockland, Maine · … · Boston, Massachusetts9 ports
Boston, Massachusetts · Rockland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Quebec City, Quebec · Charlottetown, Prince Edward Island · Portland, Maine · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourLuxury Camden Sailing Experience on Penobscot BayReversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg +4 more
View →
from $3,432
Book This Cruise@ Cruisebound
Celebrity · Celebrity SilhouetteRound-trip
North America 11 nights Sep 17 – Sep 28, 2026 from Boston, Massachusetts
Boston, Massachusetts · Rockland, Maine · … · Boston, Massachusetts8 ports
Boston, Massachusetts · Rockland, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Quebec City, Quebec · Charlottetown, Prince Edward Island · Portland, Maine · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourLuxury Camden Sailing Experience on Penobscot BayPeggy's Cove & LunenburgBridgeClimb Sydney +3 more
View →
from $2,052
Book This Cruise@ Cruisebound
Celebrity · Celebrity SilhouetteRound-trip
North America 11 nights Sep 28 – Oct 9, 2026 from Boston, Massachusetts
Boston, Massachusetts · Rockland, Maine · … · Boston, Massachusetts8 ports
Boston, Massachusetts · Rockland, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Quebec City, Quebec · Charlottetown, Prince Edward Island · Portland, Maine · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourLuxury Camden Sailing Experience on Penobscot BayPeggy's Cove & LunenburgBridgeClimb Sydney +3 more
View →
from $2,449
Book This Cruise@ Cruisebound
Celebrity · Celebrity SilhouetteRound-trip
North America 11 nights Oct 9 – Oct 20, 2026 from Boston, Massachusetts
Boston, Massachusetts · Rockland, Maine · … · Boston, Massachusetts8 ports
Boston, Massachusetts · Rockland, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Quebec City, Quebec · Charlottetown, Prince Edward Island · Portland, Maine · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourLuxury Camden Sailing Experience on Penobscot BayPeggy's Cove & LunenburgBridgeClimb Sydney +3 more
View →
from $1,635
Book This Cruise@ Cruisebound
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
View →
from $3,369
Book This Cruise@ Cruisebound
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
View →
from $3,454
Book This Cruise@ Cruisebound
Holland America · VolendamRound-trip
North America 10 nights Sep 1 – Sep 11, 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
★ Bucket-list Old Québec Private Walking Tour with Expert Local…Green Gables House & Anne of Green Gables Island E…Cape St. Mary's Ecological ReserveÎle aux Marins
View →
from $3,039
Book This Cruise@ Cruisebound
Celebrity · Celebrity SilhouetteRound-trip
North America 11 nights Sep 2 – Sep 13, 2027 from Boston, Massachusetts
Boston, Massachusetts · Rockland, Maine · … · Boston, Massachusetts8 ports
Boston, Massachusetts · Rockland, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Quebec City, Quebec · Charlottetown, Prince Edward Island · Portland, Maine · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourLuxury Camden Sailing Experience on Penobscot BayPeggy's Cove & LunenburgBridgeClimb Sydney +3 more
View →
from $3,171
Book This Cruise@ Cruisebound
Celebrity · Celebrity SilhouetteRound-trip
North America 11 nights Sep 13 – Sep 24, 2027 from Boston, Massachusetts
Boston, Massachusetts · Rockland, Maine · … · Boston, Massachusetts8 ports
Boston, Massachusetts · Rockland, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Quebec City, Quebec · Portland, Maine · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourLuxury Camden Sailing Experience on Penobscot BayPeggy's Cove & LunenburgBridgeClimb Sydney +3 more
View →
from $3,171
Book This Cruise@ Cruisebound
Cunard · Queen Mary 2Repositioning
Northern Europe 24 nights Sep 17 – Oct 11, 2027 from New York, New York to Hamburg, Germany
New York, New York · Boston, Massachusetts · … · Hamburg, Germany12 ports
New York, New York · Boston, Massachusetts · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Quebec City, Quebec · Saguenay Fjord, Canada · Sept-Iles, Canada · Halifax, Nova Scotia · New York, New York · Southampton, England · Zeebrugge (Bruges), Belgium · Hamburg, Germany
★ Bucket-list Manhattan Helicopter TourPrivate Luxury Boston TourBridgeClimb SydneyGreen Gables House & Anne of Green Gables Island E… +5 more
View →
from $4,659
Book This Cruise@ Cruisebound
Celebrity · Celebrity SilhouetteRound-trip
North America 11 nights Sep 24 – Oct 5, 2027 from Boston, Massachusetts
Boston, Massachusetts · Rockland, Maine · … · Boston, Massachusetts8 ports
Boston, Massachusetts · Rockland, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Quebec City, Quebec · Charlottetown, Prince Edward Island · Portland, Maine · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourLuxury Camden Sailing Experience on Penobscot BayPeggy's Cove & LunenburgBridgeClimb Sydney +3 more
View →
from $2,438
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
View →
from $3,464
Book This Cruise@ Cruisebound
Celebrity · Celebrity SilhouetteRound-trip
North America 11 nights Oct 5 – Oct 16, 2027 from Boston, Massachusetts
Boston, Massachusetts · Portland, Maine · … · Boston, Massachusetts8 ports
Boston, Massachusetts · Portland, Maine · Rockland, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Quebec City, Quebec · Charlottetown, Prince Edward Island · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Luxury Camden Sailing Experience on Penobscot BayPeggy's Cove & Lunenburg +3 more
View →
from $3,229
Book This Cruise@ Cruisebound
Norwegian · Norwegian PearlRound-trip
North America 11 nights Oct 19 – Oct 30, 2027 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Boston, Massachusetts · … · Philadelphia, Pennsylvania9 ports
Philadelphia, Pennsylvania · Boston, Massachusetts · Eastport, Maine, United States · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Portland, Maine · Philadelphia, Pennsylvania
★ Bucket-list Private Luxury Boston TourReversing Falls & Fundy Tidal BorePeggy's Cove & LunenburgBridgeClimb Sydney +2 more
View →
from $1,459
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