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
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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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Showing 12 of 12 sailings
Oceania · Oceania InsigniaRound-trip
Bahamas 25 nights Nov 24 – Dec 19, 2026 from Miami, Florida
Miami, Florida · Tortola, B.V.I. · … · Miami, Florida18 ports
Miami, Florida · Tortola, B.V.I. · St. John's, Antigua · Castries, St. Lucia · Scarborough, Tobago · Kiel Canal, Germany · Santarem, Brazil · Boca da Valeria, Brazil · Manaus, Brazil · Parintins, Brazil · Alter do Chao, Brazil · Kiel Canal, Germany · Bridgetown, Barbados · Roseau, Dominica · Philipsburg, St. Maarten · San Juan, Puerto Rico · Nassau, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Jost Van DykePrivate Half-Day Island Adventure & Trunk Bay BeachCosol Tours +5 more
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from $7,649
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Oceania · Oceania MarinaRound-trip
Caribbean 12 nights Feb 1 – Feb 13, 2027 from Miami, Florida
Miami, Florida · Port of Oranjestad, Aruba, Caribbean · … · Miami, Florida9 ports
Miami, Florida · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Port of Kingstown, St. Vincent & the Grenadines · Castries, St. Lucia · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…ArubaPrivate Full-Day Curaçao Island Tour with Local Ex…La Soufrière Volcano Summit Hike +4 more
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from $3,899
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Oceania · Oceania MarinaRound-trip
Caribbean 10 nights Feb 13 – Feb 23, 2027 from Miami, Florida
Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · Miami, Florida8 ports
Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. John's, Antigua · Philipsburg, St. Maarten · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Great Stirrup Cay, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Full-Day Boat CharterPrivate Half-Day Island Adventure & Trunk Bay BeachRandom Wind 'Paradise Day Sail' +3 more
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from $3,015
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Oceania · Oceania MarinaRound-trip
Caribbean 10 nights Feb 23 – Mar 5, 2027 from Miami, Florida
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida8 ports
Miami, Florida · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · Tortola, B.V.I. · Puerto Plata, Dominican Republic · Great Stirrup Cay, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsMt. Liamuiga Volcano Crater HikeRandom Wind 'Paradise Day Sail' +3 more
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from $2,760
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Oceania · Oceania AlluraRound-trip
Bahamas 12 nights Feb 27 – Mar 11, 2027 from Miami, Florida
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · … · Miami, Florida9 ports
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Falmouth, Jamaica · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Cabo Rojo, Dominican Republic · Nassau, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Stingray City SandbarBlue Hole & Secret FallsAruba +3 more
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from $5,949
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Oceania · Oceania SirenaRound-trip
Bahamas 12 nights Dec 10 – Dec 22, 2027 from Miami, Florida
Miami, Florida · Nassau, Bahamas · … · Miami, Florida10 ports
Miami, Florida · Nassau, Bahamas · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · Gustavia, St. Barts · Tortola, B.V.I. · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Swim With the Wild Exuma PigsThe full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City Walls +4 more
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from $3,499
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Oceania · Oceania SirenaRound-trip
Caribbean 14 nights Dec 22 – Jan 5, 2028 from Miami, Florida
Miami, Florida · Port of Oranjestad, Aruba, Caribbean · … · Miami, Florida11 ports
Miami, Florida · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · St. Georges, Grenada, West Indies · Port of Kingstown, St. Vincent & the Grenadines · Castries, St. Lucia · Fort-de-France, Martinique · Roseau, Dominica · Tortola, B.V.I. · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…ArubaPrivate Full-Day Curaçao Island Tour with Local Ex…Klein Bonaire +6 more
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from $4,399
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Oceania · Oceania MarinaRound-trip
Caribbean 10 nights Dec 27 – Jan 6, 2028 from Miami, Florida
Miami, Florida · Nassau, Bahamas · … · Miami, Florida9 ports
Miami, Florida · Nassau, Bahamas · San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Puerto Plata, Dominican Republic · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Swim With the Wild Exuma PigsWalk El Morro & Old San Juan's City WallsJost Van Dyke +3 more
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from $3,099
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Oceania · Oceania MarinaRound-trip
Bahamas 10 nights Feb 7 – Feb 17, 2028 from Miami, Florida
Miami, Florida · Nassau, Bahamas · … · Miami, Florida9 ports
Miami, Florida · Nassau, Bahamas · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · Philipsburg, St. Maarten · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Puerto Plata, Dominican Republic · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Swim With the Wild Exuma PigsWalk El Morro & Old San Juan's City WallsMt. Liamuiga Volcano Crater Hike +4 more
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from $3,099
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Oceania · Oceania MarinaRound-trip
Caribbean 10 nights Feb 17 – Feb 27, 2028 from Miami, Florida
Miami, Florida · Puerto Plata, Dominican Republic · … · Miami, Florida8 ports
Miami, Florida · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Frederikstad, St. Croix · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Philipsburg, St. Maarten · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…The full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsMt. Liamuiga Volcano Crater Hike +1 more
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from $3,099
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Oceania · Oceania SonataRound-trip
Caribbean 11 nights Feb 19 – Mar 1, 2028 from Miami, Florida
Miami, Florida · Puerto Plata, Dominican Republic · … · Miami, Florida9 ports
Miami, Florida · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · Philipsburg, St. Maarten · Tortola, B.V.I. · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…The full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsPrivate Full-Day Boat Charter +4 more
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from $5,299
Book This Cruise@ Cruisebound
Oceania · Oceania SonataRound-trip
Mexico 17 nights Mar 1 – Mar 18, 2028 from Miami, Florida
Miami, Florida · Puerto Plata, Dominican Republic · … · Miami, Florida13 ports
Miami, Florida · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · Tortola, B.V.I. · Miami, Florida · Cozumel, Mexico · Roatan, Honduras · Harvest Caye, Belize · Costa Maya, Mexico · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…The full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsPrivate Full-Day Boat Charter +7 more
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from $7,799
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
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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