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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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 ×Round trip ×Repositioning × Clear all
Showing 36 of 81 sailings
Norwegian · Norwegian BreakawayRound-trip
Bermuda 7 nights Jun 14 – Jun 21, 2026 from Boston, Massachusetts
Boston, Massachusetts · Halifax, Nova Scotia · Royal Naval Dockyard, Bermuda · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgPrivate Island Wrap-Around Van Tour of Bermuda
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from $610
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Norwegian · Norwegian BreakawayRound-trip
Bermuda 7 nights Jun 21 – Jun 28, 2026 from Boston, Massachusetts
Boston, Massachusetts · Halifax, Nova Scotia · Royal Naval Dockyard, Bermuda · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgPrivate Island Wrap-Around Van Tour of Bermuda
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from $764
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Norwegian · Norwegian BreakawayRound-trip
Bermuda 7 nights Jun 28 – Jul 5, 2026 from Boston, Massachusetts
Boston, Massachusetts · Halifax, Nova Scotia · Royal Naval Dockyard, Bermuda · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgPrivate Island Wrap-Around Van Tour of Bermuda
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from $801
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Holland America · ZuiderdamRound-trip
North America 7 nights Jul 4 – Jul 11, 2026 from Boston, Massachusetts
Boston, Massachusetts · Saint John, New Brunswick · Norfolk, Virginia · New York, New York · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourManhattan Helicopter Tour
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from $1,479
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Norwegian · Norwegian BreakawayRound-trip
Bermuda 7 nights Jul 5 – Jul 12, 2026 from Boston, Massachusetts
Boston, Massachusetts · Halifax, Nova Scotia · Royal Naval Dockyard, Bermuda · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgPrivate Island Wrap-Around Van Tour of Bermuda
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from $826
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Norwegian · Norwegian BreakawayRound-trip
Bermuda 7 nights Jul 12 – Jul 19, 2026 from Boston, Massachusetts
Boston, Massachusetts · Royal Naval Dockyard, Bermuda · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPrivate Island Wrap-Around Van Tour of Bermuda
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from $1,113
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Norwegian · Norwegian BreakawayRound-trip
Bermuda 7 nights Jul 19 – Jul 26, 2026 from Boston, Massachusetts
Boston, Massachusetts · Halifax, Nova Scotia · Royal Naval Dockyard, Bermuda · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgPrivate Island Wrap-Around Van Tour of Bermuda
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from $883
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Norwegian · Norwegian BreakawayRound-trip
Bermuda 7 nights Jul 26 – Aug 2, 2026 from Boston, Massachusetts
Boston, Massachusetts · Royal Naval Dockyard, Bermuda · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPrivate Island Wrap-Around Van Tour of Bermuda
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from $1,088
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Norwegian · Norwegian BreakawayRound-trip
Bermuda 7 nights Aug 2 – Aug 9, 2026 from Boston, Massachusetts
Boston, Massachusetts · Halifax, Nova Scotia · Royal Naval Dockyard, Bermuda · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgPrivate Island Wrap-Around Van Tour of Bermuda
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from $842
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Norwegian · Norwegian BreakawayRound-trip
Bermuda 7 nights Aug 9 – Aug 16, 2026 from Boston, Massachusetts
Boston, Massachusetts · Halifax, Nova Scotia · Royal Naval Dockyard, Bermuda · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgPrivate Island Wrap-Around Van Tour of Bermuda
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from $867
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Norwegian · Norwegian BreakawayRound-trip
Bermuda 7 nights Aug 16 – Aug 23, 2026 from Boston, Massachusetts
Boston, Massachusetts · Halifax, Nova Scotia · Royal Naval Dockyard, Bermuda · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgPrivate Island Wrap-Around Van Tour of Bermuda
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from $823
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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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Norwegian · Norwegian BreakawayRound-trip
North America 7 nights Aug 23 – Aug 30, 2026 from Boston, Massachusetts
Boston, Massachusetts · Portland, Maine · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Portland, Maine · Bar Harbor, Maine · Halifax, Nova Scotia · Saint John, New Brunswick · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPeggy's Cove & Lunenburg
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from $838
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Azamara · Azamara JourneyRepositioning
North America 16 nights Aug 26 – Sep 11, 2026 from Montreal, Quebec to Reykjavik, Iceland
Montreal, Quebec · Quebec City, Quebec · … · Reykjavik, Iceland10 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Havre St. Pierre, Quebec · Nuuk, Greenland · Paamiut (Frederickshaab), Greenland · Qaqortoq, Greenland · Prince Christian Sund, Greenland · Grundarfjordur, Iceland · Reykjavik, Iceland
★ Bucket-list Inside the Volcano
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from $5,769
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Norwegian · Norwegian BreakawayRound-trip
North America 7 nights Aug 30 – Sep 6, 2026 from Boston, Massachusetts
Boston, Massachusetts · Portland, Maine · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Portland, Maine · Bar Harbor, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPeggy's Cove & Lunenburg
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from $838
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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
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from $3,432
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Norwegian · Norwegian BreakawayRound-trip
North America 7 nights Sep 6 – Sep 13, 2026 from Boston, Massachusetts
Boston, Massachusetts · Portland, Maine · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Portland, Maine · Bar Harbor, Maine · Halifax, Nova Scotia · Saint John, New Brunswick · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPeggy's Cove & Lunenburg
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from $731
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Norwegian · Norwegian BreakawayRound-trip
North America 7 nights Sep 13 – Sep 20, 2026 from Boston, Massachusetts
Boston, Massachusetts · Portland, Maine · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Portland, Maine · Bar Harbor, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPeggy's Cove & Lunenburg
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from $690
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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
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from $2,052
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Norwegian · Norwegian BreakawayRound-trip
North America 7 nights Sep 20 – Sep 27, 2026 from Boston, Massachusetts
Boston, Massachusetts · Portland, Maine · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Portland, Maine · Bar Harbor, Maine · Eastport, Maine, United States · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPeggy's Cove & Lunenburg
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from $690
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Seabourn · Seabourn OvationRound-trip
North America 12 nights Sep 25 – Oct 7, 2026 from Montreal, Quebec
Montreal, Quebec · Havre St. Pierre, Quebec · … · Montreal, Quebec9 ports
Montreal, Quebec · Havre St. Pierre, Quebec · LAnse Aux Meadows, Newfoundland · St. Johns, Newfoundland · St Pierre et Miquelon · Cap-Aux-Meules, Canada · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
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from $9,859
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Norwegian · Norwegian BreakawayRound-trip
North America 7 nights Sep 27 – Oct 4, 2026 from Boston, Massachusetts
Boston, Massachusetts · Portland, Maine · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Portland, Maine · Bar Harbor, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPeggy's Cove & Lunenburg
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from $989
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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
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from $2,449
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Holland America · ZuiderdamRound-trip
North America 7 nights Oct 3 – Oct 10, 2026 from Boston, Massachusetts
Boston, Massachusetts · Eastport, Maine, United States · … · Boston, Massachusetts7 ports
Boston, Massachusetts · Eastport, Maine, United States · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Portland, Maine · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $1,429
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Cunard · Queen Mary 2Repositioning
Northern Europe 16 nights Oct 4 – Oct 20, 2026 from Quebec City, Quebec to Hamburg, Germany
Quebec City, Quebec · Saguenay Fjord, Canada · … · Hamburg, Germany7 ports
Quebec City, Quebec · Saguenay Fjord, Canada · Sept-Iles, Canada · Halifax, Nova Scotia · New York, New York · Southampton, England · Hamburg, Germany
★ Bucket-list Peggy's Cove & LunenburgManhattan Helicopter TourStand Inside Stonehenge & See the Original 1215 Ma…Private Full-Day Hamburg Shore Excursion with Loca…
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from $2,679
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Norwegian · Norwegian BreakawayRound-trip
North America 7 nights Oct 4 – Oct 11, 2026 from Boston, Massachusetts
Boston, Massachusetts · Portland, Maine · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Portland, Maine · Bar Harbor, Maine · Eastport, Maine, United States · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPeggy's Cove & Lunenburg
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from $797
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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
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from $1,635
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Norwegian · Norwegian BreakawayRound-trip
North America 7 nights Oct 11 – Oct 18, 2026 from Boston, Massachusetts
Boston, Massachusetts · Newport, Rhode Island · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Newport, Rhode Island · Bar Harbor, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPeggy's Cove & Lunenburg
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from $957
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Norwegian · Norwegian BreakawayRound-trip
Bermuda 7 nights Oct 18 – Oct 25, 2026 from Boston, Massachusetts
Boston, Massachusetts · Halifax, Nova Scotia · Royal Naval Dockyard, Bermuda · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgPrivate Island Wrap-Around Van Tour of Bermuda
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from $745
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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
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from $898
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Norwegian · Norwegian BreakawayRound-trip
Bermuda 7 nights Oct 25 – Nov 1, 2026 from Boston, Massachusetts
Boston, Massachusetts · Halifax, Nova Scotia · Royal Naval Dockyard, Bermuda · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgPrivate Island Wrap-Around Van Tour of Bermuda
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from $693
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Norwegian · Norwegian BreakawayRound-trip
Bermuda 7 nights Nov 1 – Nov 8, 2026 from Boston, Massachusetts
Boston, Massachusetts · Halifax, Nova Scotia · Royal Naval Dockyard, Bermuda · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgPrivate Island Wrap-Around Van Tour of Bermuda
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from $707
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Norwegian · Norwegian BreakawayRepositioning
Caribbean 14 nights Nov 8 – Nov 22, 2026 from Boston, Massachusetts to New Orleans, Louisiana
Boston, Massachusetts · St. Thomas, U.S. Virgin Islands · … · New Orleans, Louisiana8 ports
Boston, Massachusetts · St. Thomas, U.S. Virgin Islands · St. Lucia, Caribbean · St. Georges, Grenada, West Indies · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Georgetown, Grand Cayman, Cayman Islands · New Orleans, Louisiana
★ Bucket-list Private Luxury Boston TourPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Grenada Private Taxi TourPrivate Full-Day Curaçao Island Tour with Local Ex… +3 more
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from $970
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Norwegian · Norwegian BreakawayRepositioning
Caribbean 14 nights Apr 4 – Apr 18, 2027 from New Orleans, Louisiana to Boston, Massachusetts
New Orleans, Louisiana · Georgetown, Grand Cayman, Cayman Islands · … · Boston, Massachusetts9 ports
New Orleans, Louisiana · Georgetown, Grand Cayman, Cayman Islands · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · St. Georges, Grenada, West Indies · St. Lucia, Caribbean · Tortola, B.V.I. · Boston, Massachusetts
★ Bucket-list Steamboat NatchezStingray City SandbarArubaPrivate Full-Day Curaçao Island Tour with Local Ex… +4 more
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from $1,726
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Norwegian · Norwegian BreakawayRound-trip
Bermuda 7 nights Apr 18 – Apr 25, 2027 from Boston, Massachusetts
Boston, Massachusetts · Halifax, Nova Scotia · Royal Naval Dockyard, Bermuda · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgPrivate Island Wrap-Around Van Tour of Bermuda
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from $849
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Norwegian · Norwegian BreakawayRound-trip
Bermuda 7 nights Apr 25 – May 2, 2027 from Boston, Massachusetts
Boston, Massachusetts · Halifax, Nova Scotia · Royal Naval Dockyard, Bermuda · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgPrivate Island Wrap-Around Van Tour of Bermuda
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from $849
Book This Cruise@ Cruisebound
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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.

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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