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 Bahamas ×Visits Antigua ×Repositioning × Clear all
Showing 8 of 8 sailings
Cunard · Queen ElizabethRepositioning
Mexico 33 nights Sep 24 – Oct 27, 2026 from Seattle, Washington to Miami, Florida
Seattle, Washington · Los Angeles, California · … · Miami, Florida16 ports
Seattle, Washington · Los Angeles, California · Cabo San Lucas, Mexico · Puerto Quetzal, Guatemala · Fuerte Amador, Panama · Panama Canal, Panama · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Miami, Florida · San Juan, Puerto Rico · Antigua, Antigua & Barbuda · St. Lucia, Caribbean · Bridgetown, Barbados · Philipsburg, St. Maarten · Road Town, Tortola, B.V.I. · Miami, Florida
★ Bucket-list Space Needle & Chihuly Garden of GlassWarner Bros. Studio Tour HollywoodEl Arco & Lover's BeachPrivate Antigua Colonial City & Jade Factory Full-… +10 more
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from $2,499
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Oceania · Oceania VistaRepositioning
Caribbean 14 nights Oct 28 – Nov 11, 2026 from New York, New York to Miami, Florida
New York, New York · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · Miami, Florida10 ports
New York, New York · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Castries, St. Lucia · St. Georges, Grenada, West Indies · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Miami, Florida
★ Bucket-list Manhattan Helicopter TourPrivate Full-Day Boat CharterJost Van DykePrivate Half-Day Island Adventure & Trunk Bay Beach +6 more
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from $3,412
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Cunard · Queen ElizabethRepositioning
Mexico 33 nights Dec 17 – Jan 19, 2027 from Miami, Florida to Southampton, England
Miami, Florida · San Juan, Puerto Rico · … · Southampton, England16 ports
Miami, Florida · San Juan, Puerto Rico · Antigua, Antigua & Barbuda · St. Lucia, Caribbean · Bridgetown, Barbados · Philipsburg, St. Maarten · Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Montego Bay, Jamaica · Roatan, Honduras · Costa Maya, Mexico · Cozumel, Mexico · Miami, Florida · Praia da Vitoria, Portugal · Ponta Delgada, Azores, Portugal · Southampton, England
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsAdventure AntiguaGros Piton Summit Hike +10 more
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from $5,999
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Oceania · Oceania InsigniaRepositioning
Caribbean 54 nights Feb 14 – Apr 9, 2027 from Valparaiso (Santiago), Chile to Miami, Florida
Valparaiso (Santiago), Chile · Puerto Montt, Chile · … · Miami, Florida33 ports
Valparaiso (Santiago), Chile · Puerto Montt, Chile · Castro, Chile · Puerto Chacabuco, Chile · Laguna San Raphael, Chile · Kiel Canal, Germany · Punta Arenas, Chile · Ushuaia, Argentina · Kiel Canal, Germany · Port Stanley, Falkland Islands · Puerto Madryn, Argentina · Buenos Aires, Argentina · Montevideo, Uruguay · Punta del Este, Uruguay · Rio Grande, Rio Grande do Sul, Brazil · Florianopolis, Brazil · Itajai, Brazil · Santos (Sao Paulo), Brazil · Paraty, Brazil · Ilha Grande, Brazil · Buzios, Brazil · Rio de Janeiro, Brazil · Kiel Canal, Germany · Alter do Chao, Brazil · Boca da Valeria, Brazil · Manaus, Brazil · Parintins, Brazil · Santarem, Brazil · Kiel Canal, Germany · Bridgetown, Barbados · St. John's, Antigua · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Miami, Florida
★ Bucket-list Private Osorno Volcano & Petrohué Falls Shore Excu…Full-Day King Penguin Colony & Tierra del Fuego Ex…Isla MartilloPrivate Full-Day Península Valdés +8 more
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from $16,399
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Oceania · Oceania InsigniaRepositioning
Caribbean 21 nights Mar 19 – Apr 9, 2027 from Rio de Janeiro, Brazil to Miami, Florida
Rio de Janeiro, Brazil · Kiel Canal, Germany · … · Miami, Florida12 ports
Rio de Janeiro, Brazil · Kiel Canal, Germany · Alter do Chao, Brazil · Boca da Valeria, Brazil · Manaus, Brazil · Parintins, Brazil · Santarem, Brazil · Kiel Canal, Germany · Bridgetown, Barbados · St. John's, Antigua · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Miami, Florida
★ Bucket-list Private Full-Day Rio HighlightsSwim with wild green sea turtles + two shipwrecks…Private Half-Day Island Adventure & Trunk Bay BeachPrivate Full-Day Boat Charter +1 more
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from $6,299
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Oceania · Oceania SirenaRepositioning
Caribbean 27 nights Oct 25 – Nov 21, 2027 from Montreal, Quebec to Miami, Florida
Montreal, Quebec · Quebec City, Quebec · … · Miami, Florida21 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Baie-Commeau, Quebec · Havre St. Pierre, Quebec · Corner Brook, Newfoundland · Sydney, Nova Scotia · Halifax, Nova Scotia · Bay of Fundy, Canada · Portland, Maine · New York, New York · Tortola, B.V.I. · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Kralendijk, Bonaire, Dutch Antilles · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Ocho Rios, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Suez Canal, Egypt · Miami, Florida
★ Bucket-list Old Québec Private Walking Tour with Expert Local…Daniel-Johnson DamMingan ArchipelagoBridgeClimb Sydney +12 more
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from $8,749
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Oceania · Oceania SirenaRepositioning
Caribbean 15 nights Nov 6 – Nov 21, 2027 from New York, New York to Miami, Florida
New York, New York · Tortola, B.V.I. · … · Miami, Florida10 ports
New York, New York · Tortola, B.V.I. · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Kralendijk, Bonaire, Dutch Antilles · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Ocho Rios, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Miami, Florida
★ Bucket-list Manhattan Helicopter TourJost Van DykePrivate Half-Day Island Adventure & Trunk Bay BeachMt. Liamuiga Volcano Crater Hike +6 more
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from $4,199
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Princess · Regal PrincessRepositioning
Caribbean 14 nights Nov 6 – Nov 20, 2027 from New York, New York to Miami, Florida
New York, New York · St. Thomas, U.S. Virgin Islands · … · Miami, Florida9 ports
New York, New York · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Antigua, Antigua & Barbuda · St. Lucia, Caribbean · Bridgetown, Barbados · Port of Oranjestad, Aruba, Caribbean · Grand Turk, Turks and Caicos · Miami, Florida
★ Bucket-list Manhattan Helicopter TourPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Mt. Liamuiga Volcano Crater HikeAdventure Antigua +5 more
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from $1,324
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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