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 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
Must visit a specific port
Reset
Filtering North America ×From Boston, Massachusetts ×9–12 nights × Clear all
Showing 23 of 23 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 TourCampobello IslandPeggy's Cove & LunenburgCape St. Mary's Ecological Reserve +6 more
View →
from $1,999
Book This Cruise@ Cruisebound
Princess · Sapphire PrincessOne-way
North America 10 nights Sep 3 – Sep 13, 2026 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Portland, Maine · … · Quebec City, Quebec8 ports
Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Saguenay Fjord, Canada · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg +3 more
View →
from $1,344
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
Princess · Sapphire PrincessOne-way
North America 10 nights Sep 23 – Oct 3, 2026 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Portland, Maine · … · Quebec City, Quebec8 ports
Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Saguenay Fjord, Canada · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg +3 more
View →
from $1,229
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
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 +7 more
View →
from $11,899
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
Princess · Sapphire PrincessOne-way
North America 10 nights Oct 13 – Oct 23, 2026 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Portland, Maine · … · Quebec City, Quebec8 ports
Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Saguenay Fjord, Canada · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg +3 more
View →
from $1,074
Book This Cruise@ Cruisebound
Celebrity · Celebrity SilhouetteRepositioning
Caribbean 10 nights Oct 20 – Oct 30, 2026 from Boston, Massachusetts to Fort Lauderdale (Port Everglades), Florida
Boston, Massachusetts · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Port of Oranjestad, Aruba, Caribbean · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Private Luxury Boston TourPrivate Full-Day Curaçao Island Tour with Local Ex…Klein BonaireAruba +1 more
View →
from $898
Book This Cruise@ Cruisebound
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 TourCampobello IslandPeggy's Cove & LunenburgCape St. Mary's Ecological Reserve +6 more
View →
from $2,839
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
Princess · Caribbean PrincessOne-way
North America 10 nights Sep 7 – Sep 17, 2027 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Portland, Maine · … · Quebec City, Quebec8 ports
Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Saguenay Fjord, Canada · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg +3 more
View →
from $1,200
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
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
Princess · Caribbean PrincessOne-way
North America 10 nights Sep 28 – Oct 8, 2027 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Portland, Maine · … · Quebec City, Quebec8 ports
Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Saguenay Fjord, Canada · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg +3 more
View →
from $1,199
Book This Cruise@ Cruisebound
Oceania · Oceania VistaOne-way
North America 11 nights Sep 29 – Oct 10, 2027 from Boston, Massachusetts to Montreal, Quebec
Boston, Massachusetts · Portland, Maine · … · Montreal, Quebec11 ports
Boston, Massachusetts · Portland, Maine · Bay of Fundy, Canada · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Havre St. Pierre, Quebec · Sept-Iles, Canada · Baie-Commeau, Quebec · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Hopewell RocksPeggy's Cove & Lunenburg +7 more
View →
from $6,199
Book This Cruise@ Cruisebound
Azamara · Azamara QuestOne-way
North America 12 nights Oct 4 – Oct 16, 2027 from Boston, Massachusetts to Montreal, Quebec
Boston, Massachusetts · Portland, Maine · … · Montreal, Quebec12 ports
Boston, Massachusetts · Portland, Maine · Rockland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Corner Brook, Newfoundland · Havre St. Pierre, Quebec · Sept-Iles, Canada · Saguenay Fjord, Canada · Quebec City, Quebec · Troisrivieres, Canada · Montreal, Quebec
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Luxury Camden Sailing Experience on Penobscot BayReversing Falls & Fundy Tidal Bore +7 more
View →
from $4,789
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
Regent · Seven Seas GrandeurOne-way
Australia & South Pacific 11 nights Oct 13 – Oct 24, 2027 from Boston, Massachusetts to Montreal, Quebec
Boston, Massachusetts · Bar Harbor, Maine · … · Montreal, Quebec12 ports
Boston, Massachusetts · Bar Harbor, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Willis Island · Gaspe, Quebec · Willis Island · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Private Luxury Boston TourPrivate Acadia National Park Van Tour with Expert…Reversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg +6 more
View →
from $13,249
Book This Cruise@ Cruisebound
Celebrity · Celebrity SilhouetteRepositioning
Caribbean 10 nights Oct 16 – Oct 26, 2027 from Boston, Massachusetts to Fort Lauderdale (Port Everglades), Florida
Boston, Massachusetts · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Private Luxury Boston TourArubaPrivate Full-Day Curaçao Island Tour with Local Ex…Klein Bonaire +1 more
View →
from $755
Book This Cruise@ Cruisebound
Princess · Caribbean PrincessOne-way
North America 10 nights Oct 19 – Oct 29, 2027 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Portland, Maine · … · Quebec City, Quebec8 ports
Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Saguenay Fjord, Canada · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg +3 more
View →
from $1,199
Book This Cruise@ Cruisebound
Celebrity · Celebrity SummitRepositioning
Caribbean 9 nights Oct 20 – Oct 29, 2027 from Boston, Massachusetts to San Juan, Puerto Rico
Boston, Massachusetts · Puerto Plata, Dominican Republic · … · San Juan, Puerto Rico7 ports
Boston, Massachusetts · Puerto Plata, Dominican Republic · Samana, Dominican Republic · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. John's, Antigua · Tortola, B.V.I. · San Juan, Puerto Rico
★ Bucket-list Private Luxury Boston TourThe full 27 jumps at the Damajagua WaterfallsHumpback Whale Watching in Samaná BayPrivate Full-Day Boat Charter +3 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