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 · 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
Must visit a specific port
Reset
Filtering North America ×Viking Ocean ×Celebrity × Clear all
Showing 24 of 24 sailings
Viking Ocean · Viking NeptuneOne-way
Europe 14 nights Jun 20 – Jul 4, 2026 from Reykjavik, Iceland to Boston, Massachusetts
Reykjavik, Iceland · Heimaey, Iceland · … · Boston, Massachusetts15 ports
Reykjavik, Iceland · Heimaey, Iceland · Djupivogur, Iceland · Seydisfjordur, Iceland · Akureyri, Iceland · Isafjord, Iceland · Sail the Atlantic Ocean · Nanortalik, Greenland · Qaqortoq, Greenland · Sail the Labrador Sea · LAnse Aux Meadows, Newfoundland · Sail the Gulf of St. Lawrence · Halifax, Nova Scotia · Sail the Atlantic Ocean · Boston, Massachusetts
★ Bucket-list Inside the VolcanoDynjandi WaterfallPeggy's Cove & LunenburgPrivate Luxury Boston Tour
View →
from $10,499
Book This Cruise@ Cruisebound
Viking Ocean · Viking NeptuneOne-way
North America 14 nights Jul 4 – Jul 18, 2026 from Boston, Massachusetts to Reykjavik, Iceland
Boston, Massachusetts · Sail the Atlantic Ocean · … · Reykjavik, Iceland15 ports
Boston, Massachusetts · Sail the Atlantic Ocean · Halifax, Nova Scotia · Sail the Gulf of St. Lawrence · LAnse Aux Meadows, Newfoundland · Sail the Labrador Sea · Qaqortoq, Greenland · Nanortalik, Greenland · Sail the Atlantic Ocean · Isafjord, Iceland · Akureyri, Iceland · Seydisfjordur, Iceland · Djupivogur, Iceland · Heimaey, Iceland · Reykjavik, Iceland
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgDynjandi WaterfallInside the Volcano
View →
from $10,499
Book This Cruise@ Cruisebound
Celebrity · Celebrity SilhouetteOne-way
Europe 14 nights Aug 22 – Sep 5, 2026 from Reykjavik, Iceland to Boston, Massachusetts
Reykjavik, Iceland · Isafjord, Iceland · … · Boston, Massachusetts9 ports
Reykjavik, Iceland · Isafjord, Iceland · Akureyri, Iceland · Prins Christian Sund(cruise) · Qaqortoq, Greenland · St. Johns, Newfoundland · Halifax, Nova Scotia · Sydney, Nova Scotia · Boston, Massachusetts
★ Bucket-list Inside the VolcanoDynjandi WaterfallPeggy's Cove & LunenburgBridgeClimb Sydney +1 more
View →
from $1,787
Book This Cruise@ Cruisebound
Viking Ocean · Viking MarsOne-way
North America 12 nights Aug 31 – Sep 12, 2026 from New York, New York to Montreal, Quebec
New York, New York · Boston, Massachusetts · … · Montreal, Quebec10 ports
New York, New York · Boston, Massachusetts · Sail the Nova Scotia Coast · Halifax, Nova Scotia · Sail the Gulf of St. Lawrence · Gaspe, Quebec · Sail the Gulf of St. Lawrence · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Manhattan Helicopter TourPrivate Luxury Boston TourPeggy's Cove & Lunenburg
View →
from $8,299
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 TourPeggy's Cove & LunenburgBridgeClimb Sydney
View →
from $3,432
Book This Cruise@ Cruisebound
Viking Ocean · Viking MarsOne-way
North America 12 nights Sep 12 – Sep 24, 2026 from Montreal, Quebec to Brooklyn, NY
Montreal, Quebec · Quebec City, Quebec · … · Brooklyn, NY10 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Sail the Gulf of St. Lawrence · Gaspe, Quebec · Sail the Gulf of St. Lawrence · Halifax, Nova Scotia · Sail the Nova Scotia Coast · Boston, Massachusetts · Brooklyn, NY
★ Bucket-list Peggy's Cove & LunenburgPrivate Luxury Boston Tour
View →
from $9,999
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 TourPeggy's Cove & LunenburgBridgeClimb Sydney
View →
from $2,052
Book This Cruise@ Cruisebound
Viking Ocean · Viking MarsOne-way
North America 12 nights Sep 24 – Oct 6, 2026 from Brooklyn, NY to Montreal, Quebec
Brooklyn, NY · Boston, Massachusetts · … · Montreal, Quebec10 ports
Brooklyn, NY · Boston, Massachusetts · Sail the Nova Scotia Coast · Halifax, Nova Scotia · Sail the Gulf of St. Lawrence · Gaspe, Quebec · Sail the Gulf of St. Lawrence · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Private Luxury Boston TourPeggy's Cove & Lunenburg
View →
from $10,099
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 TourPeggy's Cove & LunenburgBridgeClimb Sydney
View →
from $2,449
Book This Cruise@ Cruisebound
Viking Ocean · Viking MarsOne-way
North America 14 nights Oct 6 – Oct 20, 2026 from Montreal, Quebec to Fort Lauderdale (Port Everglades), Florida
Montreal, Quebec · Quebec City, Quebec · … · Fort Lauderdale (Port Everglades), Florida13 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Sail the Gulf of St. Lawrence · Charlottetown, Prince Edward Island · Scenic Sailing: St. Lawrence Seaway · Sail the Nova Scotia Coast · Saint John, New Brunswick · Eastport, Maine, United States · Portland, Maine · Newport, Rhode Island · Sail the Atlantic Ocean · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live Show
View →
from $9,099
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 TourPeggy's Cove & LunenburgBridgeClimb Sydney
View →
from $1,635
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
Celebrity · Celebrity SilhouetteOne-way
Europe 12 nights Aug 21 – Sep 2, 2027 from Reykjavik, Iceland to Boston, Massachusetts
Reykjavik, Iceland · Isafjord, Iceland · … · Boston, Massachusetts8 ports
Reykjavik, Iceland · Isafjord, Iceland · Akureyri, Iceland · Prins Christian Sund(cruise) · Qaqortoq, Greenland · St. Johns, Newfoundland · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list Inside the VolcanoDynjandi WaterfallPeggy's Cove & LunenburgPrivate Luxury Boston Tour
View →
from $2,616
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 TourPeggy's Cove & LunenburgBridgeClimb Sydney
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 TourPeggy's Cove & LunenburgBridgeClimb Sydney
View →
from $3,171
Book This Cruise@ Cruisebound
Viking Ocean · Viking MarsOne-way
North America 12 nights Sep 16 – Sep 28, 2027 from New York, New York to Montreal, Quebec
New York, New York · Boston, Massachusetts · … · Montreal, Quebec10 ports
New York, New York · Boston, Massachusetts · Sail the Nova Scotia Coast · Halifax, Nova Scotia · Sail the Gulf of St. Lawrence · Gaspe, Quebec · Scenic Sailing: St. Lawrence Seaway · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Manhattan Helicopter TourPrivate Luxury Boston TourPeggy's Cove & Lunenburg
View →
from $8,299
Book This Cruise@ Cruisebound
Celebrity · Celebrity SummitRepositioning
Caribbean 18 nights Sep 18 – Oct 6, 2027 from Los Angeles, California to Boston, Massachusetts
Los Angeles, California · Puerto Vallarta, Mexico · … · Boston, Massachusetts8 ports
Los Angeles, California · Puerto Vallarta, Mexico · Puerto Quetzal, Guatemala · Puntarenas, Costa Rica · Panama Canal, Panama · Cartagena, Colombia · Grand Turk, Turks and Caicos · Boston, Massachusetts
★ Bucket-list Warner Bros. Studio Tour HollywoodHidden Beach at Marietas IslandsThe Roman Theatre of Cartagena with the Rafael Mon…Gibbs Cay Private Stingray Swim & Reef Snorkel +1 more
View →
from $2,184
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 TourPeggy's Cove & LunenburgBridgeClimb Sydney
View →
from $2,438
Book This Cruise@ Cruisebound
Viking Ocean · Viking MarsOne-way
North America 12 nights Sep 28 – Oct 10, 2027 from Montreal, Quebec to New York, New York
Montreal, Quebec · Quebec City, Quebec · … · New York, New York10 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Scenic Sailing: St. Lawrence Seaway · Gaspe, Quebec · Sail the Gulf of St. Lawrence · Halifax, Nova Scotia · Sail the Nova Scotia Coast · Boston, Massachusetts · New York, New York
★ Bucket-list Peggy's Cove & LunenburgPrivate Luxury Boston TourManhattan Helicopter Tour
View →
from $8,199
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 TourPeggy's Cove & LunenburgBridgeClimb Sydney
View →
from $3,229
Book This Cruise@ Cruisebound
Viking Ocean · Viking MarsOne-way
North America 12 nights Oct 10 – Oct 22, 2027 from New York, New York to Montreal, Quebec
New York, New York · Boston, Massachusetts · … · Montreal, Quebec10 ports
New York, New York · Boston, Massachusetts · Sail the Nova Scotia Coast · Halifax, Nova Scotia · Sail the Gulf of St. Lawrence · Gaspe, Quebec · Scenic Sailing: St. Lawrence Seaway · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Manhattan Helicopter TourPrivate Luxury Boston TourPeggy's Cove & Lunenburg
View →
from $7,999
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
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 WaterfallsPrivate Full-Day Boat CharterPrivate Half-Day Island Adventure & Trunk Bay Beach +2 more
View →
from $806
Book This Cruise@ Cruisebound
Viking Ocean · Viking MarsOne-way
North America 14 nights Oct 22 – Nov 5, 2027 from Montreal, Quebec to Fort Lauderdale (Port Everglades), Florida
Montreal, Quebec · Quebec City, Quebec · … · Fort Lauderdale (Port Everglades), Florida13 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Scenic Sailing: St. Lawrence Seaway · Charlottetown, Prince Edward Island · Sail the Gulf of St. Lawrence · Sail the Nova Scotia Coast · Saint John, New Brunswick · Bar Harbor, Maine · Portland, Maine · Newport, Rhode Island · Sail the Atlantic Ocean · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live Show
View →
from $8,299
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