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 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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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 From New York, New York ×3–5 nights ×9–12 nights × Clear all
Showing 36 of 61 sailings
Norwegian · Norwegian EscapeRound-trip
Caribbean 10 nights Aug 19 – Aug 29, 2026 from New York, New York
New York, New York · San Juan, Puerto Rico · … · New York, New York7 ports
New York, New York · San Juan, Puerto Rico · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · Puerto Plata, Dominican Republic · New York, New York
★ Bucket-list Manhattan Helicopter TourWalk El Morro & Old San Juan's City WallsRandom Wind 'Paradise Day Sail'Private Catamaran Sail & Snorkel at Honeymoon Beac… +2 more
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from $1,264
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Norwegian · Norwegian AquaRound-trip
Bermuda 5 nights Aug 29 – Sep 3, 2026 from New York, New York
New York, New York · Royal Naval Dockyard, Bermuda · New York, New York
★ Bucket-list Manhattan Helicopter TourPrivate Island Wrap-Around Van Tour of Bermuda
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from $829
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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 & LunenburgPeggy's Cove & Lunenburg +4 more
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from $8,299
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Norwegian · Norwegian AquaRound-trip
Bermuda 5 nights Sep 3 – Sep 8, 2026 from New York, New York
New York, New York · Royal Naval Dockyard, Bermuda · New York, New York
★ Bucket-list Manhattan Helicopter TourPrivate Island Wrap-Around Van Tour of Bermuda
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from $852
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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 IslandReversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg +6 more
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from $14,780
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Norwegian · Norwegian AquaRound-trip
Bermuda 5 nights Sep 8 – Sep 13, 2026 from New York, New York
New York, New York · Royal Naval Dockyard, Bermuda · New York, New York
★ Bucket-list Manhattan Helicopter TourPrivate Island Wrap-Around Van Tour of Bermuda
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from $614
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Norwegian · Norwegian AquaRound-trip
Bermuda 5 nights Sep 13 – Sep 18, 2026 from New York, New York
New York, New York · Royal Naval Dockyard, Bermuda · New York, New York
★ Bucket-list Manhattan Helicopter TourPrivate Island Wrap-Around Van Tour of Bermuda
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from $570
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Seabourn · Seabourn OvationOne-way
North America 12 nights Sep 13 – Sep 25, 2026 from New York, New York to Montreal, Quebec
New York, New York · Newport, Rhode Island · … · Montreal, Quebec10 ports
New York, New York · Newport, Rhode Island · Transit The Cape Cod Canal · Boston, Massachusetts · Rockland, Maine · Halifax, Nova Scotia · Charlottetown, Prince Edward Island · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Manhattan Helicopter TourThe BreakersCape Cod Canal Sightseeing CruisePrivate Luxury Boston Tour +5 more
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from $7,649
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Oceania · Oceania VistaOne-way
North America 11 nights Sep 14 – Sep 25, 2026 from New York, New York to Montreal, Quebec
New York, New York · Halifax, Nova Scotia · … · Montreal, Quebec9 ports
New York, New York · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Gaspe, Quebec · Baie-Commeau, Quebec · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Manhattan Helicopter TourPeggy's Cove & LunenburgBridgeClimb SydneyGreen Gables House & Anne of Green Gables Island E… +4 more
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from $5,480
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Norwegian · Norwegian AquaRound-trip
Bermuda 5 nights Sep 18 – Sep 23, 2026 from New York, New York
New York, New York · Royal Naval Dockyard, Bermuda · New York, New York
★ Bucket-list Manhattan Helicopter TourPrivate Island Wrap-Around Van Tour of Bermuda
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from $664
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Norwegian · Norwegian AquaRound-trip
Bermuda 5 nights Sep 23 – Sep 28, 2026 from New York, New York
New York, New York · Royal Naval Dockyard, Bermuda · New York, New York
★ Bucket-list Manhattan Helicopter TourPrivate Island Wrap-Around Van Tour of Bermuda
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from $598
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Norwegian · Norwegian AquaRound-trip
Bermuda 5 nights Sep 28 – Oct 3, 2026 from New York, New York
New York, New York · Royal Naval Dockyard, Bermuda · New York, New York
★ Bucket-list Manhattan Helicopter TourPrivate Island Wrap-Around Van Tour of Bermuda
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from $606
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Norwegian · Norwegian AquaRound-trip
Bermuda 5 nights Oct 3 – Oct 8, 2026 from New York, New York
New York, New York · Royal Naval Dockyard, Bermuda · New York, New York
★ Bucket-list Manhattan Helicopter TourPrivate Island Wrap-Around Van Tour of Bermuda
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from $633
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Oceania · Oceania VistaOne-way
Europe 11 nights Oct 6 – Oct 17, 2026 from New York, New York to Montreal, Quebec
New York, New York · Newport, Rhode Island · … · Montreal, Quebec11 ports
New York, New York · Newport, Rhode Island · Boston, Massachusetts · Bay of Fundy, Canada · Halifax, Nova Scotia · Sydney, Nova Scotia · Corner Brook, Newfoundland · Kiel Canal, Germany · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Manhattan Helicopter TourThe BreakersPrivate Luxury Boston TourHopewell Rocks +6 more
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from $6,460
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Norwegian · Norwegian AquaRound-trip
Bermuda 5 nights Oct 8 – Oct 13, 2026 from New York, New York
New York, New York · Royal Naval Dockyard, Bermuda · New York, New York
★ Bucket-list Manhattan Helicopter TourPrivate Island Wrap-Around Van Tour of Bermuda
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from $683
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Seabourn · Seabourn OvationOne-way
North America 12 nights Oct 19 – Oct 31, 2026 from New York, New York to Montreal, Quebec
New York, New York · Newport, Rhode Island · … · Montreal, Quebec10 ports
New York, New York · Newport, Rhode Island · Transit The Cape Cod Canal · Boston, Massachusetts · Rockland, Maine · Halifax, Nova Scotia · Charlottetown, Prince Edward Island · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Manhattan Helicopter TourThe BreakersCape Cod Canal Sightseeing CruisePrivate Luxury Boston Tour +5 more
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from $6,204
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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 IslandReversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg +5 more
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from $12,450
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Azamara · Azamara JourneyOne-way
Bermuda 9 nights Oct 29 – Nov 7, 2026 from New York, New York to San Juan, Puerto Rico
New York, New York · Hamilton, Bermuda · Philipsburg, St. Maarten · Road Town, Tortola, B.V.I. · San Juan, Puerto Rico
★ Bucket-list Manhattan Helicopter TourRising Son CatamaranRandom Wind 'Paradise Day Sail'Norman Island +1 more
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from $1,609
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Princess · Majestic PrincessRepositioning
Caribbean 12 nights Nov 7 – Nov 19, 2026 from New York, New York to Fort Lauderdale (Port Everglades), Florida
New York, New York · St. Maarten, Netherlands Antilles · … · Fort Lauderdale (Port Everglades), Florida7 ports
New York, New York · St. Maarten, Netherlands Antilles · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Lucia, Caribbean · Curacao, Caribbean · Port of Oranjestad, Aruba, Caribbean · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Manhattan Helicopter TourMaho BeachMt. Liamuiga Volcano Crater HikeGros Piton Summit Hike +3 more
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from $811
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Norwegian · Norwegian BlissRound-trip
Caribbean 12 nights Nov 9 – Nov 21, 2026 from New York, New York
New York, New York · Puerto Plata, Dominican Republic · … · New York, New York8 ports
New York, New York · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · New York, New York
★ Bucket-list Manhattan Helicopter TourThe full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsMt. Liamuiga Volcano Crater Hike +3 more
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from $1,127
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Cunard · Queen Mary 2Round-trip
Caribbean 11 nights Nov 17 – Nov 28, 2026 from New York, New York
New York, New York · St. Thomas, U.S. Virgin Islands · … · New York, New York6 ports
New York, New York · St. Thomas, U.S. Virgin Islands · Road Town, Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · New York, New York
★ Bucket-list Manhattan Helicopter TourPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Norman IslandMt. Liamuiga Volcano Crater Hike +1 more
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from $1,199
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Norwegian · Norwegian BlissRound-trip
Caribbean 12 nights Nov 29 – Dec 11, 2026 from New York, New York
New York, New York · Puerto Plata, Dominican Republic · … · New York, New York8 ports
New York, New York · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · New York, New York
★ Bucket-list Manhattan Helicopter TourThe full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsMt. Liamuiga Volcano Crater Hike +3 more
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from $945
Book This Cruise@ Cruisebound
Norwegian · Norwegian BlissRound-trip
Caribbean 12 nights Dec 11 – Dec 23, 2026 from New York, New York
New York, New York · Puerto Plata, Dominican Republic · … · New York, New York8 ports
New York, New York · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · New York, New York
★ Bucket-list Manhattan Helicopter TourThe full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsMt. Liamuiga Volcano Crater Hike +3 more
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from $887
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Norwegian · Norwegian BlissRound-trip
Caribbean 12 nights Dec 23 – Jan 4, 2027 from New York, New York
New York, New York · Puerto Plata, Dominican Republic · … · New York, New York8 ports
New York, New York · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · Philipsburg, St. Maarten · New York, New York
★ Bucket-list Manhattan Helicopter TourThe full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsMt. Liamuiga Volcano Crater Hike +3 more
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from $1,860
Book This Cruise@ Cruisebound
Cunard · Queen Mary 2Repositioning
Northern Europe 9 nights Jan 2 – Jan 11, 2027 from New York, New York to Southampton, England
New York, New York · Southampton, England
★ Bucket-list Manhattan Helicopter TourStand Inside Stonehenge & See the Original 1215 Ma…
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from $979
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Norwegian · Norwegian BlissRound-trip
Caribbean 12 nights Jan 4 – Jan 16, 2027 from New York, New York
New York, New York · Puerto Plata, Dominican Republic · … · New York, New York8 ports
New York, New York · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · New York, New York
★ Bucket-list Manhattan Helicopter TourThe full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsMt. Liamuiga Volcano Crater Hike +3 more
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from $1,157
Book This Cruise@ Cruisebound
Norwegian · Norwegian BlissRound-trip
Caribbean 12 nights Feb 1 – Feb 13, 2027 from New York, New York
New York, New York · Puerto Plata, Dominican Republic · … · New York, New York8 ports
New York, New York · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · New York, New York
★ Bucket-list Manhattan Helicopter TourThe full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac… +3 more
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from $1,305
Book This Cruise@ Cruisebound
Norwegian · Norwegian BlissRound-trip
Caribbean 12 nights Mar 1 – Mar 13, 2027 from New York, New York
New York, New York · Puerto Plata, Dominican Republic · … · New York, New York8 ports
New York, New York · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · New York, New York
★ Bucket-list Manhattan Helicopter TourThe full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsMt. Liamuiga Volcano Crater Hike +3 more
View →
from $1,379
Book This Cruise@ Cruisebound
Norwegian · Norwegian BlissRound-trip
Bermuda 5 nights Apr 4 – Apr 9, 2027 from New York, New York
New York, New York · Royal Naval Dockyard, Bermuda · New York, New York
★ Bucket-list Manhattan Helicopter TourPrivate Island Wrap-Around Van Tour of Bermuda
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from $731
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Norwegian · Norwegian LunaRound-trip
Bermuda 4 nights Apr 6 – Apr 10, 2027 from New York, New York
New York, New York · Royal Naval Dockyard, Bermuda · New York, New York
★ Bucket-list Manhattan Helicopter TourPrivate Island Wrap-Around Van Tour of Bermuda
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from $706
Book This Cruise@ Cruisebound
Cunard · Queen Mary 2Repositioning
Northern Europe 9 nights May 19 – May 28, 2027 from New York, New York to Hamburg, Germany
New York, New York · Southampton, England · Hamburg, Germany
★ Bucket-list Manhattan Helicopter TourStand Inside Stonehenge & See the Original 1215 Ma…Private Full-Day Hamburg Shore Excursion with Loca…
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from $1,999
Book This Cruise@ Cruisebound
Norwegian · Norwegian LunaRound-trip
Bermuda 5 nights Aug 28 – Sep 2, 2027 from New York, New York
New York, New York · Royal Naval Dockyard, Bermuda · New York, New York
★ Bucket-list Manhattan Helicopter TourPrivate Island Wrap-Around Van Tour of Bermuda
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from $948
Book This Cruise@ Cruisebound
Norwegian · Norwegian LunaRound-trip
Bermuda 5 nights Sep 2 – Sep 7, 2027 from New York, New York
New York, New York · Royal Naval Dockyard, Bermuda · New York, New York
★ Bucket-list Manhattan Helicopter TourPrivate Island Wrap-Around Van Tour of Bermuda
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from $1,099
Book This Cruise@ Cruisebound
Norwegian · Norwegian LunaRound-trip
Bermuda 5 nights Sep 7 – Sep 12, 2027 from New York, New York
New York, New York · Royal Naval Dockyard, Bermuda · New York, New York
★ Bucket-list Manhattan Helicopter TourPrivate Island Wrap-Around Van Tour of Bermuda
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from $790
Book This Cruise@ Cruisebound
Oceania · Oceania VistaOne-way
Middle East 11 nights Sep 7 – Sep 18, 2027 from New York, New York to Montreal, Quebec
New York, New York · Newport, Rhode Island · … · Montreal, Quebec10 ports
New York, New York · Newport, Rhode Island · Portland, Maine · Bay of Fundy, Canada · Halifax, Nova Scotia · Sydney, Nova Scotia · Suez Canal, Egypt · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Manhattan Helicopter TourThe BreakersPortland Head Light & Casco Bay Scenic Lighthouse…Hopewell Rocks +5 more
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from $5,949
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Azamara · Azamara QuestOne-way
North America 12 nights Sep 10 – Sep 22, 2027 from New York, New York to Montreal, Quebec
New York, New York · Cape Cod, Massachusetts · … · Montreal, Quebec14 ports
New York, New York · Cape Cod, Massachusetts · Marthas Vineyard, Massachusetts · Boston, Massachusetts · Bar Harbor, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Cap-Aux-Meules, Canada · Gaspe, Quebec · Sept-Iles, Canada · Cruise Saguenay River · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Manhattan Helicopter TourProvincetown Whale WatchAquinnah Cliffs & Gay Head LighthousePrivate Luxury Boston Tour +9 more
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from $5,019
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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