Bucket-List Cruise Adventures

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Showing 23 of 23 sailings
Oceania · Oceania VistaRound-trip
Caribbean 12 nights Nov 25 – Dec 7, 2026 from Miami, Florida
Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · Miami, Florida9 ports
Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · Gustavia, St. Barts · Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe · St. John's, Antigua · Tortola, B.V.I. · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Full-Day Boat CharterRandom Wind 'Paradise Day Sail'Private Open-Top Mini Moke Island Tour of St. Barts +4 more
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from $3,360
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Regent · Seven Seas GrandeurRound-trip
Bahamas 10 nights Nov 29 – Dec 9, 2026 from Miami, Florida
Miami, Florida · Willis Island · … · Miami, Florida10 ports
Miami, Florida · Willis Island · San Juan, Puerto Rico · Gustavia, St. Barts · Philipsburg, St. Maarten · Frederikstad, St. Croix · La Romana, Dominican Republic · Willis Island · Nassau, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandWalk El Morro & Old San Juan's City WallsPrivate Open-Top Mini Moke Island Tour of St. Barts +3 more
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from $6,949
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Oceania · Oceania AlluraRound-trip
Caribbean 10 nights Dec 2 – Dec 12, 2026 from Miami, Florida
Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · Miami, Florida7 ports
Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Gustavia, St. Barts · Philipsburg, St. Maarten · Frederikstad, St. Croix · Tortola, B.V.I. · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Full-Day Boat CharterPrivate Open-Top Mini Moke Island Tour of St. BartsRandom Wind 'Paradise Day Sail' +1 more
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from $3,815
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Oceania · Oceania MarinaRound-trip
Caribbean 12 nights Dec 10 – Dec 22, 2026 from Miami, Florida
Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · Miami, Florida9 ports
Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Gustavia, St. Barts · St. John's, Antigua · Fort-de-France, Martinique · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · Tortola, B.V.I. · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Full-Day Boat CharterPrivate Open-Top Mini Moke Island Tour of St. BartsPrivate Half-Day Island Adventure & Trunk Bay Beach +4 more
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from $2,697
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Oceania · Oceania AlluraRound-trip
Caribbean 9 nights Dec 12 – Dec 21, 2026 from Miami, Florida
Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · Miami, Florida6 ports
Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · Gustavia, St. Barts · Tortola, B.V.I. · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Full-Day Boat CharterRandom Wind 'Paradise Day Sail'Private Open-Top Mini Moke Island Tour of St. Barts +1 more
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from $2,555
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Oceania · Oceania AlluraRound-trip
Mexico 17 nights Dec 21 – Jan 7, 2027 from Miami, Florida
Miami, Florida · Costa Maya, Mexico · … · Miami, Florida12 ports
Miami, Florida · Costa Maya, Mexico · Roatan, Honduras · Harvest Caye, Belize · Cozumel, Mexico · Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Chacchoben Mayan RuinsHold a Sloth at Daniel Johnson's Monkey & Sloth Ha…Lamanai Mayan Ruins +6 more
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from $10,049
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Oceania · Oceania AlluraRound-trip
Caribbean 10 nights Dec 28 – Jan 7, 2027 from Miami, Florida
Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · Miami, Florida7 ports
Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Full-Day Boat CharterRandom Wind 'Paradise Day Sail'Private Open-Top Mini Moke Island Tour of St. Barts +2 more
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from $6,649
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Oceania · Oceania AlluraRound-trip
Caribbean 10 nights Mar 11 – Mar 21, 2027 from Miami, Florida
Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · Miami, Florida7 ports
Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Full-Day Boat CharterRandom Wind 'Paradise Day Sail'Private Open-Top Mini Moke Island Tour of St. Barts +2 more
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from $3,899
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Oceania · Oceania AlluraRound-trip
Caribbean 10 nights Mar 21 – Mar 31, 2027 from Miami, Florida
Miami, Florida · Port of Basseterre, St. Kitts, St. Kitts and Nevis · … · Miami, Florida7 ports
Miami, Florida · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · Gustavia, St. Barts · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Mt. Liamuiga Volcano Crater HikeRandom Wind 'Paradise Day Sail'Private Open-Top Mini Moke Island Tour of St. Barts +2 more
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from $3,735
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Regent · Seven Seas MarinerRound-trip
Australia & South Pacific 15 nights Mar 26 – Apr 10, 2027 from Miami, Florida
Miami, Florida · Willis Island · … · Miami, Florida15 ports
Miami, Florida · Willis Island · Tortola, B.V.I. · Gustavia, St. Barts · Fort-de-France, Martinique · Port of Kingstown, St. Vincent & the Grenadines · Bridgetown, Barbados · St. Georges, Grenada, West Indies · Willis Island · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Willis Island · Puerto Plata, Dominican Republic · Willis Island · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandJost Van DykePrivate Open-Top Mini Moke Island Tour of St. Barts +7 more
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from $10,299
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Seabourn · Seabourn QuestRound-trip
Caribbean 10 nights Nov 13 – Nov 23, 2027 from Miami, Florida
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida7 ports
Miami, Florida · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Little Bay, Montserrat, Leeward Islands · Gustavia, St. Barts · Great Harbor, Peter Island, BVI · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsMt. Liamuiga Volcano Crater HikePrivate Open-Top Mini Moke Island Tour of St. Barts
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from $4,498
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Seabourn · Seabourn QuestRound-trip
Caribbean 11 nights Nov 23 – Dec 4, 2027 from Miami, Florida
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida8 ports
Miami, Florida · San Juan, Puerto Rico · Gustavia, St. Barts · Little Bay, Montserrat, Leeward Islands · Roseau, Dominica · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Great Harbor, Peter Island, BVI · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsPrivate Open-Top Mini Moke Island Tour of St. BartsBoiling Lake Hike +1 more
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from $5,098
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Regent · Seven Seas GrandeurRound-trip
Caribbean 10 nights Nov 28 – Dec 8, 2027 from Miami, Florida
Miami, Florida · Willis Island · … · Miami, Florida10 ports
Miami, Florida · Willis Island · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · Gustavia, St. Barts · Tortola, B.V.I. · Willis Island · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandThe full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City Walls +4 more
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from $5,999
Book This Cruise@ Cruisebound
Seabourn · Seabourn QuestRound-trip
Caribbean 14 nights Dec 4 – Dec 18, 2027 from Miami, Florida
Miami, Florida · Cruz Bay, St. John, U.S. Virgin Islands · … · Miami, Florida11 ports
Miami, Florida · Cruz Bay, St. John, U.S. Virgin Islands · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Fort-de-France, Martinique · Roseau, Dominica · Little Bay, Montserrat, Leeward Islands · St. John's, Antigua · Road Bay, Anguilla · Great Harbor, Peter Island, BVI · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Open-Top Mini Moke Island Tour of St. BartsMt. Liamuiga Volcano Crater HikeMount Pelée & Saint-Pierre +2 more
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from $7,298
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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 +5 more
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from $3,499
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Regent · Seven Seas VoyagerRound-trip
Mediterranean 25 nights Dec 19 – Jan 13, 2028 from Miami, Florida
Miami, Florida · Willis Island · … · Miami, Florida26 ports
Miami, Florida · Willis Island · Tortola, B.V.I. · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · Roseau, Dominica · Castries, St. Lucia · Bridgetown, Barbados · St. Georges, Grenada, West Indies · Willis Island · Oranjestad, Sint Eustatius · Kralendijk, Bonaire, Dutch Antilles · Willemstad, Curacao · Willis Island · Cartagena, Spain · Panama Canal, Panama · Colon, Panama · Puerto Limon, Costa Rica · Willis Island · Falmouth, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Willis Island · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandJost Van DykePrivate Full-Day Boat Charter +16 more
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from $14,049
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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 +4 more
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from $3,099
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Seabourn · Seabourn QuestRound-trip
Caribbean 10 nights Dec 28 – Jan 7, 2028 from Miami, Florida
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida7 ports
Miami, Florida · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Little Bay, Montserrat, Leeward Islands · Gustavia, St. Barts · Great Harbor, Peter Island, BVI · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsMt. Liamuiga Volcano Crater HikePrivate Open-Top Mini Moke Island Tour of St. Barts
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from $5,498
Book This Cruise@ Cruisebound
Regent · Seven Seas PrestigeRound-trip
Caribbean 10 nights Jan 7 – Jan 17, 2028 from Miami, Florida
Miami, Florida · Willis Island · … · Miami, Florida9 ports
Miami, Florida · Willis Island · Philipsburg, St. Maarten · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · Gustavia, St. Barts · Tortola, B.V.I. · Willis Island · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandRandom Wind 'Paradise Day Sail'Mt. Liamuiga Volcano Crater Hike +3 more
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from $7,299
Book This Cruise@ Cruisebound
Regent · Seven Seas PrestigeRound-trip
Caribbean 10 nights Jan 17 – Jan 27, 2028 from Miami, Florida
Miami, Florida · Willis Island · … · Miami, Florida10 ports
Miami, Florida · Willis Island · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Philipsburg, St. Maarten · Gustavia, St. Barts · St. John's, Antigua · Tortola, B.V.I. · Willis Island · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandThe full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City Walls +4 more
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from $7,699
Book This Cruise@ Cruisebound
Regent · Seven Seas PrestigeRound-trip
Caribbean 9 nights Jan 27 – Feb 5, 2028 from Miami, Florida
Miami, Florida · Willis Island · … · Miami, Florida8 ports
Miami, Florida · Willis Island · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Castries, St. Lucia · Philipsburg, St. Maarten · Willis Island · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandPrivate Open-Top Mini Moke Island Tour of St. BartsMt. Liamuiga Volcano Crater Hike +2 more
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from $7,099
Book This Cruise@ Cruisebound
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 +2 more
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from $3,099
Book This Cruise@ Cruisebound
Regent · Seven Seas GrandeurRound-trip
Caribbean 12 nights Mar 20 – Apr 1, 2028 from Miami, Florida
Miami, Florida · Willis Island · … · Miami, Florida12 ports
Miami, Florida · Willis Island · Puerto Plata, Dominican Republic · Cayo Levantado, Dominican Republic · San Juan, Puerto Rico · Gustavia, St. Barts · Roseau, Dominica · Pointe-a-Pitre, Guadeloupe · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · Willis Island · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandThe full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City Walls +5 more
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from $7,599
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