Bucket-List Cruise Adventures

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Bucket-list adventures at every port — where to fly in, and what to do the day(s) before and after.

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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 17 of 17 sailings
Disney · Disney DreamRound-trip
Bahamas 7 nights Oct 2 – Oct 9, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Disney Lookout Cay · … · Fort Lauderdale (Port Everglades), Florida6 ports
Fort Lauderdale (Port Everglades), Florida · Disney Lookout Cay · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Castaway Cay, Bahamas · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowPrivate Historical & Cultural SUV Tour of EleutheraWalk El Morro & Old San Juan's City WallsThe full 27 jumps at the Damajagua Waterfalls +1 more
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from $2,047
Book This Cruise@ Cruisebound
Disney · Disney DestinyRound-trip
Bahamas 7 nights Oct 17 – Oct 24, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Disney Lookout Cay · … · Fort Lauderdale (Port Everglades), Florida6 ports
Fort Lauderdale (Port Everglades), Florida · Disney Lookout Cay · Castaway Cay, Bahamas · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowPrivate Historical & Cultural SUV Tour of EleutheraAbaco Backcountry Fishing AdventureWalk El Morro & Old San Juan's City Walls +1 more
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from $2,558
Book This Cruise@ Cruisebound
Disney · Disney DreamRound-trip
Caribbean 7 nights Nov 13 – Nov 20, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Disney Lookout Cay · … · Fort Lauderdale (Port Everglades), Florida6 ports
Fort Lauderdale (Port Everglades), Florida · Disney Lookout Cay · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Castaway Cay, Bahamas · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowPrivate Historical & Cultural SUV Tour of EleutheraWalk El Morro & Old San Juan's City WallsThe full 27 jumps at the Damajagua Waterfalls +1 more
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from $2,432
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationOne-way
Caribbean 8 nights Nov 20 – Nov 28, 2026 from Miami, Florida to Bridgetown, Barbados
Miami, Florida · San Juan, Puerto Rico · … · Bridgetown, Barbados7 ports
Miami, Florida · San Juan, Puerto Rico · Great Harbor, Peter Island, BVI · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Roseau, Dominica · Port Elizabeth, Saint Vincent · Bridgetown, Barbados
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsMt. Liamuiga Volcano Crater HikeBoiling Lake Hike +2 more
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from $4,098
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Seabourn · Seabourn QuestRound-trip
Caribbean 14 nights Nov 22 – Dec 6, 2026 from Miami, Florida
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida11 ports
Miami, Florida · San Juan, Puerto Rico · Road Bay, Anguilla · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Roseau, Dominica · Fort-de-France, Martinique · Terre-de-haut, Guadeloupe · Little Bay, Montserrat, Leeward Islands · Virgin Gorda, British Virgin Islands · 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 HikeBoiling Lake Hike +2 more
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from $7,753
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationOne-way
Caribbean 14 nights Dec 5 – Dec 19, 2026 from Philipsburg, St. Maarten to Bridgetown, Barbados
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · … · Bridgetown, Barbados13 ports
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Trois Ilets, Martinique · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Bridgetown, Barbados · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Terre-de-haut, Guadeloupe · Saint-Pierre, Newfoundland, Canada · Roseau, Dominica · Rodney Bay, St. Lucia · Bridgetown, Barbados
★ Bucket-list Random Wind 'Paradise Day Sail'Mt. Liamuiga Volcano Crater HikeSchotia Private Game ReserveGrenada Private Taxi Tour +2 more
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from $6,798
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Seabourn · Seabourn QuestRound-trip
Caribbean 14 nights Dec 6 – Dec 20, 2026 from Miami, Florida
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida11 ports
Miami, Florida · San Juan, Puerto Rico · Virgin Gorda, British Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Roseau, Dominica · Fort-de-France, Martinique · Terre-de-haut, Guadeloupe · Little Bay, Montserrat, Leeward Islands · Road Bay, Anguilla · 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 WallsThe Baths National ParkMt. Liamuiga Volcano Crater Hike +2 more
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from $5,498
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationRound-trip
Caribbean 7 nights Dec 12 – Dec 19, 2026 from Bridgetown, Barbados
Bridgetown, Barbados · Port of Basseterre, St. Kitts, St. Kitts and Nevis · … · Bridgetown, Barbados7 ports
Bridgetown, Barbados · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Terre-de-haut, Guadeloupe · Saint-Pierre, Newfoundland, Canada · Roseau, Dominica · Rodney Bay, St. Lucia · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Mt. Liamuiga Volcano Crater HikeBoiling Lake Hike
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from $3,798
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Seabourn · Seabourn QuestRound-trip
Caribbean 16 nights Dec 20 – Jan 5, 2027 from Miami, Florida
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida13 ports
Miami, Florida · San Juan, Puerto Rico · Road Bay, Anguilla · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Marigot, Saint Martin · Terre-de-haut, Guadeloupe · Fort-de-France, Martinique · Rodney Bay, St. Lucia · Roseau, Dominica · Little Bay, Montserrat, Leeward Islands · St. John's, Antigua · 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 HikeMount Pelée & Saint-Pierre +2 more
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from $10,998
Book This Cruise@ Cruisebound
Disney · Disney DestinyRound-trip
Caribbean 7 nights Feb 6 – Feb 13, 2027 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Disney Lookout Cay · … · Fort Lauderdale (Port Everglades), Florida6 ports
Fort Lauderdale (Port Everglades), Florida · Disney Lookout Cay · Castaway Cay, Bahamas · Puerto Plata, Dominican Republic · Nassau, Bahamas · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowPrivate Historical & Cultural SUV Tour of EleutheraAbaco Backcountry Fishing AdventureThe full 27 jumps at the Damajagua Waterfalls +1 more
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from $2,768
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationRound-trip
Caribbean 7 nights Feb 6 – Feb 13, 2027 from Bridgetown, Barbados
Bridgetown, Barbados · Port of Basseterre, St. Kitts, St. Kitts and Nevis · … · Bridgetown, Barbados7 ports
Bridgetown, Barbados · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Saint-Pierre, Newfoundland, Canada · Roseau, Dominica · Terre-de-haut, Guadeloupe · Rodney Bay, St. Lucia · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Mt. Liamuiga Volcano Crater HikeBoiling Lake Hike
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from $5,998
Book This Cruise@ Cruisebound
Seabourn · Seabourn QuestRepositioning
Mediterranean 20 nights May 30 – Jun 19, 2027 from Miami, Florida to Dover (London), England
Miami, Florida · Funchal, Madeira, Portugal · … · Dover (London), England9 ports
Miami, Florida · Funchal, Madeira, Portugal · Lisbon, Portugal · Leixoes (Oporto), Portugal · Bilbao, Spain · St. Jean de Luz, France · St. Malo, France · Portsmouth, Dominica · Dover (London), England
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Pico do Arieiro to Pico RuivoSintraGuggenheim Bilbao +1 more
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from $8,898
Book This Cruise@ Cruisebound
Seabourn · Seabourn QuestOne-way
Northern Europe 22 nights Jun 11 – Jul 3, 2027 from Lisbon, Portugal to Dover (London), England
Lisbon, Portugal · Leixoes (Oporto), Portugal · … · Dover (London), England16 ports
Lisbon, Portugal · Leixoes (Oporto), Portugal · Bilbao, Spain · St. Jean de Luz, France · St. Malo, France · Portsmouth, Dominica · Dover (London), England · Trondheim, Norway · Bronnoysund, Norway · Svolvaer, Norway · Tromso, Norway · Honningsvag (North Cape), Norway · Olden, Norway · Bergen, Norway · Amsterdam, The Netherlands · Dover (London), England
★ Bucket-list SintraGuggenheim BilbaoWhite Cliffs of DoverNidaros Cathedral +5 more
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from $11,775
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Disney · Disney DestinyRound-trip
Bahamas 7 nights Jun 26 – Jul 3, 2027 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Castaway Cay, Bahamas · … · Fort Lauderdale (Port Everglades), Florida6 ports
Fort Lauderdale (Port Everglades), Florida · Castaway Cay, Bahamas · Disney Lookout Cay · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowAbaco Backcountry Fishing AdventurePrivate Historical & Cultural SUV Tour of EleutheraWalk El Morro & Old San Juan's City Walls +1 more
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from $3,139
Book This Cruise@ Cruisebound
Disney · Disney DestinyRound-trip
Bahamas 7 nights Aug 7 – Aug 14, 2027 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Castaway Cay, Bahamas · … · Fort Lauderdale (Port Everglades), Florida6 ports
Fort Lauderdale (Port Everglades), Florida · Castaway Cay, Bahamas · Disney Lookout Cay · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowAbaco Backcountry Fishing AdventurePrivate Historical & Cultural SUV Tour of EleutheraWalk El Morro & Old San Juan's City Walls +1 more
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from $2,726
Book This Cruise@ Cruisebound
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 WallsBoiling Lake HikeMt. Liamuiga Volcano Crater Hike
View →
from $5,098
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…Mt. Liamuiga Volcano Crater HikeMount Pelée & Saint-PierreBoiling Lake Hike +1 more
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from $7,298
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