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 Explora Journeys Oceania Regent Seabourn Silversea Viking Ocean Windstar River AmaWaterways Avalon Viking River Premium Celebrity Cunard Disney Holland America Princess Virgin Virgin Voyages Contemporary Carnival Costa MSC Cruises Norwegian Royal Caribbean
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Showing 12 of 12 sailings
Explora Journeys · EXPLORA IIIRound-trip
Caribbean 7 nights Nov 8, 2026 from Miami, Florida
Miami, Florida · Providenciales, Turks & Caicos · … · Miami, Florida13 ports
Miami, Florida · Providenciales, Turks & Caicos · Puerto Plata, Dominican Republic · La Romana, Dominican Republic · Jost Van Dyke, British Virgin Islands · Gustavia, St. Barts · San Juan, Puerto Rico · Road Bay, Anguilla · St. John's, Antigua · Frederikstad, St. Croix · Ain Sokhna, Egypt · Puerto Plata, Dominican Republic · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Iguana Island & ReefThe full 27 jumps at the Damajagua WaterfallsSaona Island Private Speedboat & Natural Pool Day +6 more
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from $8,735
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Explora Journeys · EXPLORA IIIRound-trip
Caribbean 7 nights Nov 15, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Road Bay, Anguilla · … · San Juan, Puerto Rico12 ports
San Juan, Puerto Rico · Road Bay, Anguilla · St. John's, Antigua · Frederikstad, St. Croix · Ain Sokhna, Egypt · Puerto Plata, Dominican Republic · Miami, Florida · Saint John/cruz Bay · St. John's, Antigua · Terre-de-haut, Guadeloupe · Philipsburg, St. Maarten · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Island HoppingPrivate Half-Day Island Adventure & Trunk Bay BeachPrivate Pyramids of Giza, Sphinx & Grand Egyptian… +4 more
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from $10,200
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Explora Journeys · EXPLORA IIIRound-trip
Caribbean 15 nights Dec 13, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Road Bay, Anguilla · … · San Juan, Puerto Rico12 ports
San Juan, Puerto Rico · Road Bay, Anguilla · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Grand Turk, Turks and Caicos · Miami, Florida · Ocho Rios, Jamaica · Ain Sokhna, Egypt · Jost Van Dyke, British Virgin Islands · Philipsburg, St. Maarten · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Island HoppingPrivate Half-Day Island Adventure & Trunk Bay BeachMt. Liamuiga Volcano Crater Hike +7 more
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from $12,600
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Explora Journeys · EXPLORA IRound-trip
Caribbean 15 nights Dec 20, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · … · San Juan, Puerto Rico13 ports
San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Road Town, Tortola, B.V.I. · Gustavia, St. Barts · Road Bay, Anguilla · Miami, Florida · Puerto Plata, Dominican Republic · Ain Sokhna, Egypt · Saint John/cruz Bay · Jost Van Dyke, British Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsMt. Liamuiga Volcano Crater HikeNorman IslandPrivate Open-Top Mini Moke Island Tour of St. Barts +6 more
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from $12,365
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Explora Journeys · EXPLORA IIIOne-way
Caribbean 16 nights Dec 20, 2026 from Miami, Florida to San Juan, Puerto Rico
Miami, Florida · Ocho Rios, Jamaica · … · San Juan, Puerto Rico7 ports
Miami, Florida · Ocho Rios, Jamaica · Ain Sokhna, Egypt · Jost Van Dyke, British Virgin Islands · Philipsburg, St. Maarten · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Blue HolePrivate Pyramids of Giza, Sphinx & Grand Egyptian…Private Catamaran Charter +3 more
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from $5,285
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Explora Journeys · EXPLORA IOne-way
Caribbean 8 nights Dec 27, 2026 from Miami, Florida to San Juan, Puerto Rico
Miami, Florida · Puerto Plata, Dominican Republic · … · San Juan, Puerto Rico8 ports
Miami, Florida · Puerto Plata, Dominican Republic · Ain Sokhna, Egypt · Saint John/cruz Bay · Jost Van Dyke, British Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…The full 27 jumps at the Damajagua WaterfallsPrivate Pyramids of Giza, Sphinx & Grand Egyptian…Private Catamaran Charter +3 more
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from $7,095
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Norwegian · Norwegian SunRepositioning
Middle East 21 nights Sep 5 – Sep 26, 2027 from Piraeus (Athens), Greece to Dubai, United Arab Emirates
Piraeus (Athens), Greece · Rhodes, Greece · … · Dubai, United Arab Emirates15 ports
Piraeus (Athens), Greece · Rhodes, Greece · Limassol, Cyprus · Alexandria, Egypt · Port Said (Cairo), Egypt · Suez Canal, Egypt · Ain Sokhna, Egypt · Safaga (Luxor, Karnak), Egypt · Sharm-el-Sheikh, Egypt · Aqaba, Jordan · Jeddah, Saudi Arabia · Muscat, Oman · Doha, Qatar · Abu Dhabi, United Arab Emirates · Dubai, United Arab Emirates
★ Bucket-list The Acropolis & Parthenon, Guided Skip-the-LinePrivate Full-Day Rhodes Island Highlights & LindosAncient Kourion & Apollo SanctuaryPrivate Full-Day Cairo +11 more
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from $7,069
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Explora Journeys · EXPLORA IVOne-way
Caribbean 7 nights Nov 13, 2027 from San Juan, Puerto Rico to Miami, Florida
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · Miami, Florida7 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Ain Sokhna, Egypt · Puerto Plata, Dominican Republic · Key West, Florida · Ocean Cay, Bahamas · Miami, Florida
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterPrivate Pyramids of Giza, Sphinx & Grand Egyptian…The full 27 jumps at the Damajagua Waterfalls +3 more
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from $4,200
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Explora Journeys · EXPLORA IIOne-way
Caribbean 7 nights Dec 12, 2027 from Miami, Florida to San Juan, Puerto Rico
Miami, Florida · Puerto Plata, Dominican Republic · … · San Juan, Puerto Rico7 ports
Miami, Florida · Puerto Plata, Dominican Republic · Ain Sokhna, Egypt · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. John's, Antigua · Marigot Bay, St. Lucia · San Juan, Puerto Rico
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…The full 27 jumps at the Damajagua WaterfallsPrivate Pyramids of Giza, Sphinx & Grand Egyptian…Private Full-Day Boat Charter +2 more
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from $4,020
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Explora Journeys · EXPLORA IIOne-way
Caribbean 7 nights Dec 26, 2027 from Miami, Florida to San Juan, Puerto Rico
Miami, Florida · Puerto Plata, Dominican Republic · … · San Juan, Puerto Rico7 ports
Miami, Florida · Puerto Plata, Dominican Republic · Ain Sokhna, Egypt · Frederikstad, St. Croix · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Jost Van Dyke, British Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…The full 27 jumps at the Damajagua WaterfallsPrivate Pyramids of Giza, Sphinx & Grand Egyptian…Private Full-Day Boat Charter +2 more
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from $5,350
Book This Cruise@ Cruisebound
Explora Journeys · EXPLORA IIOne-way
Caribbean 7 nights Jan 9, 2028 from Miami, Florida to San Juan, Puerto Rico
Miami, Florida · Puerto Plata, Dominican Republic · … · San Juan, Puerto Rico7 ports
Miami, Florida · Puerto Plata, Dominican Republic · Ain Sokhna, Egypt · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Marigot Bay, St. Lucia · Saint John/cruz Bay · San Juan, Puerto Rico
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…The full 27 jumps at the Damajagua WaterfallsPrivate Pyramids of Giza, Sphinx & Grand Egyptian…Private Full-Day Boat Charter +1 more
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from $4,020
Book This Cruise@ Cruisebound
Explora Journeys · EXPLORA IIOne-way
Caribbean 7 nights Jan 30, 2028 from Miami, Florida to San Juan, Puerto Rico
Miami, Florida · Puerto Plata, Dominican Republic · … · San Juan, Puerto Rico7 ports
Miami, Florida · Puerto Plata, Dominican Republic · Ain Sokhna, Egypt · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Road Bay, Anguilla · Saint John/cruz Bay · San Juan, Puerto Rico
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…The full 27 jumps at the Damajagua WaterfallsPrivate Pyramids of Giza, Sphinx & Grand Egyptian…Private Full-Day Boat Charter +2 more
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from $4,020
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 Norwegian AmaWaterways Costa Princess Celebrity Avalon Disney Viking Ocean Holland America Silversea Oceania Virgin Regent Explora Journeys Cunard Azamara Windstar Seabourn Virgin Voyages