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
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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
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+ 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
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Filtering North America ×Princess ×Regent × Clear all
Showing 27 of 27 sailings
Princess · Sapphire PrincessRepositioning
Northern Europe 15 nights Aug 19 – Sep 3, 2026 from Copenhagen, Denmark to Boston, Massachusetts
Copenhagen, Denmark · Lerwick, Shetland Islands · … · Boston, Massachusetts9 ports
Copenhagen, Denmark · Lerwick, Shetland Islands · Stornoway, Scotland · Belfast, Northern Ireland · Liverpool, England · Cobh (Cork), Ireland · Sydney, Nova Scotia · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list Private Copenhagen Walking Tour with a Local ExpertGiant's Causeway Private Luxury Day Tour from Belf…BridgeClimb SydneyPeggy's Cove & Lunenburg +1 more
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from $1,455
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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 TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $1,344
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Regent · Seven Seas SplendorOne-way
Australia & South Pacific 11 nights Sep 6 – Sep 17, 2026 from New York, New York to Montreal, Quebec
New York, New York · Willis Island · … · Montreal, Quebec12 ports
New York, New York · Willis Island · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Willis Island · Gaspe, Quebec · Baie-Commeau, Quebec · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Manhattan Helicopter TourZodiac Circumnavigation of Willis IslandPeggy's Cove & LunenburgBridgeClimb Sydney
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from $14,780
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Princess · Sapphire PrincessOne-way
North America 10 nights Sep 13 – Sep 23, 2026 from Quebec City, Quebec to Boston, Massachusetts
Quebec City, Quebec · Saguenay Fjord, Canada · … · Boston, Massachusetts7 ports
Quebec City, Quebec · Saguenay Fjord, Canada · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Saint John, New Brunswick · Boston, Massachusetts
★ Bucket-list BridgeClimb SydneyPeggy's Cove & LunenburgPrivate Luxury Boston Tour
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from $1,137
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Regent · Seven Seas SplendorOne-way
Australia & South Pacific 11 nights Sep 17 – Sep 28, 2026 from Montreal, Quebec to Boston, Massachusetts
Montreal, Quebec · Quebec City, Quebec · … · Boston, Massachusetts11 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Sept-Iles, Canada · Havre St. Pierre, Quebec · Willis Island · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Saint John, New Brunswick · Boston, Massachusetts
★ Bucket-list Zodiac Circumnavigation of Willis IslandBridgeClimb SydneyPeggy's Cove & LunenburgPrivate Luxury Boston Tour
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from $13,199
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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 TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $1,229
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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 TourPeggy's Cove & LunenburgBridgeClimb SydneyZodiac Circumnavigation of Willis Island
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from $11,899
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Princess · Sapphire PrincessOne-way
North America 10 nights Oct 3 – Oct 13, 2026 from Quebec City, Quebec to Boston, Massachusetts
Quebec City, Quebec · Saguenay Fjord, Canada · … · Boston, Massachusetts8 ports
Quebec City, Quebec · Saguenay Fjord, Canada · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Saint John, New Brunswick · Portland, Maine · Boston, Massachusetts
★ Bucket-list BridgeClimb SydneyPeggy's Cove & LunenburgPrivate Luxury Boston Tour
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from $1,421
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Regent · Seven Seas SplendorOne-way
Australia & South Pacific 11 nights Oct 9 – Oct 20, 2026 from Montreal, Quebec to New York, New York
Montreal, Quebec · Quebec City, Quebec · … · New York, New York12 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Baie-Commeau, Quebec · Willis Island · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Saint John, New Brunswick · Eastport, Maine, United States · Willis Island · New York, New York
★ Bucket-list Zodiac Circumnavigation of Willis IslandBridgeClimb SydneyPeggy's Cove & LunenburgManhattan Helicopter Tour
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from $11,399
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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 TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $1,074
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Regent · Seven Seas SplendorOne-way
Australia & South Pacific 10 nights Oct 20 – Oct 30, 2026 from New York, New York to Montreal, Quebec
New York, New York · Willis Island · … · Montreal, Quebec11 ports
New York, New York · Willis Island · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Willis Island · Baie-Commeau, Quebec · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Manhattan Helicopter TourZodiac Circumnavigation of Willis IslandPeggy's Cove & LunenburgBridgeClimb Sydney
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from $12,450
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Princess · Sapphire PrincessOne-way
Bahamas 14 nights Oct 23 – Nov 6, 2026 from Quebec City, Quebec to Fort Lauderdale (Port Everglades), Florida
Quebec City, Quebec · Saguenay Fjord, Canada · … · Fort Lauderdale (Port Everglades), Florida10 ports
Quebec City, Quebec · Saguenay Fjord, Canada · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Boston, Massachusetts · Newport, Rhode Island · New York, New York · Nassau, Bahamas · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list BridgeClimb SydneyPeggy's Cove & LunenburgPrivate Luxury Boston TourManhattan Helicopter Tour +2 more
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from $1,345
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Regent · Seven Seas SplendorOne-way
Australia & South Pacific 16 nights Oct 30 – Nov 15, 2026 from Montreal, Quebec to Miami, Florida
Montreal, Quebec · Quebec City, Quebec · … · Miami, Florida14 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Willis Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Willis Island · Philipsburg, St. Maarten · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · San Juan, Puerto Rico · Willis Island · Miami, Florida
★ Bucket-list Zodiac Circumnavigation of Willis IslandBridgeClimb SydneyPeggy's Cove & LunenburgRandom Wind 'Paradise Day Sail' +5 more
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from $11,950
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Princess · Caribbean PrincessRepositioning
Northern Europe 28 nights Aug 10 – Sep 7, 2027 from Copenhagen, Denmark to Boston, Massachusetts
Copenhagen, Denmark · Visby, Sweden · … · Boston, Massachusetts20 ports
Copenhagen, Denmark · Visby, Sweden · Stockholm, Sweden · Helsinki, Finland · Tallinn, Estonia · Riga, Latvia · Klaipeda, Lithuania · Gdansk, Poland · Oslo, Norway · Skagen, Denmark · Copenhagen, Denmark · Gothenburg, Sweden · Runavik, Faroe Islands · Seydisfjordur, Iceland · Akureyri, Iceland · Isafjord, Iceland · Reykjavik, Iceland · St. Johns, Newfoundland · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list Private Copenhagen Walking Tour with a Local ExpertVasa MuseumPrivate Half-Day Tallinn Old Town & City Sightseei…Private Oslo Highlights & Hidden Gems with a Local… +4 more
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from $5,263
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Princess · Caribbean PrincessRepositioning
Northern Europe 16 nights Aug 22 – Sep 7, 2027 from Copenhagen, Denmark to Boston, Massachusetts
Copenhagen, Denmark · Gothenburg, Sweden · … · Boston, Massachusetts10 ports
Copenhagen, Denmark · Gothenburg, Sweden · Runavik, Faroe Islands · Seydisfjordur, Iceland · Akureyri, Iceland · Isafjord, Iceland · Reykjavik, Iceland · St. Johns, Newfoundland · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list Private Copenhagen Walking Tour with a Local ExpertDynjandi WaterfallInside the VolcanoPeggy's Cove & Lunenburg +1 more
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from $1,759
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Regent · Seven Seas GrandeurOne-way
Northern Europe 14 nights Aug 27 – Sep 10, 2027 from Southampton, England to Montreal, Quebec
Southampton, England · Fowey, Cornwall, England · … · Montreal, Quebec11 ports
Southampton, England · Fowey, Cornwall, England · Cobh (Cork), Ireland · Liverpool, England · Dun Laoghaire, Dublin, Ireland · Willis Island · St. Johns, Newfoundland · Willis Island · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Stand Inside Stonehenge & See the Original 1215 Ma…Zodiac Circumnavigation of Willis Island
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from $9,249
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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 TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $1,200
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Regent · Seven Seas GrandeurOne-way
Australia & South Pacific 11 nights Sep 10 – Sep 21, 2027 from Montreal, Quebec to New York, New York
Montreal, Quebec · Quebec City, Quebec · … · New York, New York11 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Willis Island · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Bar Harbor, Maine · Portland, Maine · Willis Island · New York, New York
★ Bucket-list Zodiac Circumnavigation of Willis IslandBridgeClimb SydneyPeggy's Cove & LunenburgManhattan Helicopter Tour
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from $10,799
Book This Cruise@ Cruisebound
Princess · Caribbean PrincessOne-way
North America 11 nights Sep 17 – Sep 28, 2027 from Quebec City, Quebec to Boston, Massachusetts
Quebec City, Quebec · Saguenay Fjord, Canada · … · Boston, Massachusetts8 ports
Quebec City, Quebec · Saguenay Fjord, Canada · Sept-Iles, Canada · Corner Brook, Newfoundland · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list BridgeClimb SydneyPeggy's Cove & LunenburgPrivate Luxury Boston Tour
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from $1,126
Book This Cruise@ Cruisebound
Regent · Seven Seas GrandeurOne-way
Australia & South Pacific 11 nights Sep 21 – Oct 2, 2027 from New York, New York to Montreal, Quebec
New York, New York · Willis Island · … · Montreal, Quebec11 ports
New York, New York · Willis Island · Boston, Massachusetts · Bar Harbor, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Willis Island · Sept-Iles, Canada · Saguenay Fjord, Canada · Montreal, Quebec
★ Bucket-list Manhattan Helicopter TourZodiac Circumnavigation of Willis IslandPrivate Luxury Boston TourPeggy's Cove & Lunenburg +1 more
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from $11,099
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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 TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $1,199
Book This Cruise@ Cruisebound
Regent · Seven Seas GrandeurOne-way
Australia & South Pacific 11 nights Oct 2 – Oct 13, 2027 from Montreal, Quebec to Boston, Massachusetts
Montreal, Quebec · Quebec City, Quebec · … · Boston, Massachusetts11 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Willis Island · Gaspe, Quebec · Willis Island · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Saint John, New Brunswick · Boston, Massachusetts
★ Bucket-list Zodiac Circumnavigation of Willis IslandBridgeClimb SydneyPeggy's Cove & LunenburgPrivate Luxury Boston Tour
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from $13,149
Book This Cruise@ Cruisebound
Princess · Caribbean PrincessOne-way
North America 11 nights Oct 8 – Oct 19, 2027 from Quebec City, Quebec to Boston, Massachusetts
Quebec City, Quebec · Saguenay Fjord, Canada · … · Boston, Massachusetts8 ports
Quebec City, Quebec · Saguenay Fjord, Canada · Sept-Iles, Canada · Corner Brook, Newfoundland · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list BridgeClimb SydneyPeggy's Cove & LunenburgPrivate Luxury Boston Tour
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from $1,204
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 TourPeggy's Cove & LunenburgBridgeClimb SydneyZodiac Circumnavigation of Willis Island
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from $13,249
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 TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $1,199
Book This Cruise@ Cruisebound
Regent · Seven Seas GrandeurOne-way
Australia & South Pacific 11 nights Oct 24 – Nov 4, 2027 from Montreal, Quebec to New York, New York
Montreal, Quebec · Quebec City, Quebec · … · New York, New York12 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Sept-Iles, Canada · Willis Island · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Bar Harbor, Maine · Boston, Massachusetts · Willis Island · New York, New York
★ Bucket-list Zodiac Circumnavigation of Willis IslandBridgeClimb SydneyPeggy's Cove & LunenburgPrivate Luxury Boston Tour +1 more
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from $10,949
Book This Cruise@ Cruisebound
Princess · Caribbean PrincessOne-way
North America 13 nights Oct 29 – Nov 11, 2027 from Quebec City, Quebec to Fort Lauderdale (Port Everglades), Florida
Quebec City, Quebec · Saguenay Fjord, Canada · … · Fort Lauderdale (Port Everglades), Florida10 ports
Quebec City, Quebec · Saguenay Fjord, Canada · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Portland, Maine · Boston, Massachusetts · Newport, Rhode Island · New York, New York · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list BridgeClimb SydneyPeggy's Cove & LunenburgPrivate Luxury Boston TourManhattan Helicopter Tour +1 more
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from $1,339
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