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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Showing 36 of 313 sailings
Royal Caribbean · Star of the SeasRound-trip
Bahamas 7 nights Jun 14 – Jun 21, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Perfect Day at CocoCay · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexDaredevil's PeakPrivate Full-Day Boat CharterMt. Liamuiga Volcano Crater Hike
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from $1,584
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Royal Caribbean · Star of the SeasRound-trip
Bahamas 7 nights Jun 21 – Jun 28, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Perfect Day at CocoCay · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexDaredevil's PeakPrivate Full-Day Boat CharterRandom Wind 'Paradise Day Sail'
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from $1,133
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Royal Caribbean · Adventure of the SeasRound-trip
Bahamas 8 nights Jun 26 – Jul 4, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Perfect Day at CocoCay · … · Port Canaveral, Florida6 ports
Port Canaveral, Florida · Perfect Day at CocoCay · San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. Croix, U.S. Virgin Islands · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexDaredevil's PeakWalk El Morro & Old San Juan's City WallsPrivate Full-Day Boat Charter +1 more
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from $1,286
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Royal Caribbean · Icon of the SeasRound-trip
Bahamas 7 nights Jun 27 – Jul 4, 2026 from Miami, Florida
Miami, Florida · Philipsburg, St. Maarten · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Perfect Day at CocoCay · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Random Wind 'Paradise Day Sail'Private Full-Day Boat CharterDaredevil's Peak
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from $1,316
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Royal Caribbean · Star of the SeasRound-trip
Bahamas 7 nights Jul 5 – Jul 12, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Perfect Day at CocoCay · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexDaredevil's PeakPrivate Full-Day Boat CharterMt. Liamuiga Volcano Crater Hike
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from $1,108
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Royal Caribbean · Icon of the SeasRound-trip
Bahamas 7 nights Jul 11 – Jul 18, 2026 from Miami, Florida
Miami, Florida · Philipsburg, St. Maarten · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Perfect Day at CocoCay · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Random Wind 'Paradise Day Sail'Private Full-Day Boat CharterDaredevil's Peak
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from $1,292
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Royal Caribbean · Icon of the SeasRound-trip
Bahamas 7 nights Jul 18 – Jul 25, 2026 from Miami, Florida
Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico · Perfect Day at CocoCay · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Full-Day Boat CharterWalk El Morro & Old San Juan's City WallsDaredevil's Peak
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from $1,196
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Royal Caribbean · Adventure of the SeasRound-trip
Caribbean 8 nights Jul 24 – Aug 1, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Perfect Day at CocoCay · … · Port Canaveral, Florida6 ports
Port Canaveral, Florida · Perfect Day at CocoCay · San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. Croix, U.S. Virgin Islands · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexDaredevil's PeakWalk El Morro & Old San Juan's City WallsPrivate Full-Day Boat Charter +1 more
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from $874
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Royal Caribbean · Allure of the SeasRound-trip
Bahamas 8 nights Jul 25 – Aug 2, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Port of Basseterre, St. Kitts, St. Kitts and Nevis · … · Fort Lauderdale (Port Everglades), Florida6 ports
Fort Lauderdale (Port Everglades), Florida · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Perfect Day at CocoCay · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowMt. Liamuiga Volcano Crater HikeRandom Wind 'Paradise Day Sail'Private Full-Day Boat Charter +1 more
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from $1,125
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Royal Caribbean · Star of the SeasRound-trip
Caribbean 7 nights Jul 26 – Aug 2, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Perfect Day at CocoCay · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexDaredevil's PeakPrivate Full-Day Boat CharterMt. Liamuiga Volcano Crater Hike
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from $1,162
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Royal Caribbean · Icon of the SeasRound-trip
Caribbean 7 nights Aug 1 – Aug 8, 2026 from Miami, Florida
Miami, Florida · Philipsburg, St. Maarten · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Perfect Day at CocoCay · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Random Wind 'Paradise Day Sail'Private Full-Day Boat CharterDaredevil's Peak
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from $1,126
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Royal Caribbean · Icon of the SeasRound-trip
Bahamas 7 nights Aug 8 – Aug 15, 2026 from Miami, Florida
Miami, Florida · Philipsburg, St. Maarten · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Perfect Day at CocoCay · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Random Wind 'Paradise Day Sail'Private Full-Day Boat CharterDaredevil's Peak
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from $1,184
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Royal Caribbean · Star of the SeasRound-trip
Caribbean 7 nights Aug 16 – Aug 23, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Perfect Day at CocoCay · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexDaredevil's PeakPrivate Full-Day Boat CharterMt. Liamuiga Volcano Crater Hike
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from $887
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Royal Caribbean · Adventure of the SeasRound-trip
Bahamas 8 nights Aug 21 – Aug 29, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Perfect Day at CocoCay · … · Port Canaveral, Florida6 ports
Port Canaveral, Florida · Perfect Day at CocoCay · San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. Croix, U.S. Virgin Islands · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexDaredevil's PeakWalk El Morro & Old San Juan's City WallsPrivate Full-Day Boat Charter +1 more
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from $877
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Royal Caribbean · Harmony of the SeasRound-trip
Bahamas 7 nights Aug 22 – Aug 29, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Perfect Day at CocoCay · Nassau, Bahamas · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexPrivate Full-Day Boat CharterDaredevil's PeakSwim With the Wild Exuma Pigs
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from $729
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Royal Caribbean · Icon of the SeasRound-trip
Bahamas 7 nights Aug 22 – Aug 29, 2026 from Miami, Florida
Miami, Florida · Philipsburg, St. Maarten · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Perfect Day at CocoCay · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Random Wind 'Paradise Day Sail'Private Full-Day Boat CharterDaredevil's Peak
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from $1,542
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Royal Caribbean · Icon of the SeasRound-trip
Caribbean 7 nights Aug 29 – Sep 5, 2026 from Miami, Florida
Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico · Perfect Day at CocoCay · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Full-Day Boat CharterWalk El Morro & Old San Juan's City WallsDaredevil's Peak
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from $804
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Royal Caribbean · Star of the SeasRound-trip
Bahamas 7 nights Sep 6 – Sep 13, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Perfect Day at CocoCay · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexDaredevil's PeakPrivate Full-Day Boat CharterMt. Liamuiga Volcano Crater Hike
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from $1,138
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Royal Caribbean · Icon of the SeasRound-trip
Bahamas 7 nights Sep 12 – Sep 19, 2026 from Miami, Florida
Miami, Florida · Philipsburg, St. Maarten · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Perfect Day at CocoCay · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Random Wind 'Paradise Day Sail'Private Full-Day Boat CharterDaredevil's Peak
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from $1,156
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Royal Caribbean · Adventure of the SeasRound-trip
Caribbean 8 nights Sep 18 – Sep 26, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · St. Croix, U.S. Virgin Islands · … · Port Canaveral, Florida6 ports
Port Canaveral, Florida · St. Croix, U.S. Virgin Islands · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico · Perfect Day at CocoCay · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexBuck Island ReefPrivate Full-Day Boat CharterWalk El Morro & Old San Juan's City Walls +1 more
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from $731
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Royal Caribbean · Harmony of the SeasRound-trip
Caribbean 7 nights Sep 19 – Sep 26, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Perfect Day at CocoCay · Nassau, Bahamas · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexPrivate Full-Day Boat CharterDaredevil's PeakSwim With the Wild Exuma Pigs
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from $686
Book This Cruise@ Cruisebound
Royal Caribbean · Icon of the SeasRound-trip
Caribbean 7 nights Sep 19 – Sep 26, 2026 from Miami, Florida
Miami, Florida · Philipsburg, St. Maarten · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Perfect Day at CocoCay · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Random Wind 'Paradise Day Sail'Private Full-Day Boat CharterDaredevil's Peak
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from $1,092
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Royal Caribbean · Star of the SeasRound-trip
Caribbean 7 nights Sep 27 – Oct 4, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Perfect Day at CocoCay · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexDaredevil's PeakPrivate Full-Day Boat CharterMt. Liamuiga Volcano Crater Hike
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from $1,078
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Royal Caribbean · Icon of the SeasRound-trip
Bahamas 7 nights Oct 3 – Oct 10, 2026 from Miami, Florida
Miami, Florida · Philipsburg, St. Maarten · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Perfect Day at CocoCay · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Random Wind 'Paradise Day Sail'Private Full-Day Boat CharterDaredevil's Peak
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from $1,081
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Royal Caribbean · Icon of the SeasRound-trip
Bahamas 7 nights Oct 10 – Oct 17, 2026 from Miami, Florida
Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico · Perfect Day at CocoCay · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Full-Day Boat CharterWalk El Morro & Old San Juan's City WallsDaredevil's Peak
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from $1,151
Book This Cruise@ Cruisebound
Royal Caribbean · Adventure of the SeasRound-trip
Caribbean 8 nights Oct 16 – Oct 24, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · St. Croix, U.S. Virgin Islands · … · Port Canaveral, Florida6 ports
Port Canaveral, Florida · St. Croix, U.S. Virgin Islands · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico · Perfect Day at CocoCay · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexBuck Island ReefPrivate Full-Day Boat CharterWalk El Morro & Old San Juan's City Walls +1 more
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from $596
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Royal Caribbean · Harmony of the SeasRound-trip
Bahamas 7 nights Oct 17 – Oct 24, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Perfect Day at CocoCay · Nassau, Bahamas · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexPrivate Full-Day Boat CharterDaredevil's PeakSwim With the Wild Exuma Pigs
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from $740
Book This Cruise@ Cruisebound
Royal Caribbean · Star of the SeasRound-trip
Caribbean 7 nights Oct 18 – Oct 25, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Perfect Day at CocoCay · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexDaredevil's PeakPrivate Full-Day Boat CharterMt. Liamuiga Volcano Crater Hike
View →
from $720
Book This Cruise@ Cruisebound
Royal Caribbean · Icon of the SeasRound-trip
Bahamas 7 nights Oct 24 – Oct 31, 2026 from Miami, Florida
Miami, Florida · Philipsburg, St. Maarten · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Perfect Day at CocoCay · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Random Wind 'Paradise Day Sail'Private Full-Day Boat CharterDaredevil's Peak
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from $1,216
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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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Holland America · ZuiderdamRound-trip
Bahamas 21 nights Oct 31 – Nov 21, 2026 from Miami, Florida
Miami, Florida · Philipsburg, St. Maarten · … · Miami, Florida15 ports
Miami, Florida · Philipsburg, St. Maarten · St. John's, Antigua · Fort-de-France, Martinique · Roseau, Dominica · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Half Moon Cay (Little San Salvador Island), Bahamas · Miami, Florida · Kralendijk, Bonaire, Dutch Antilles · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Cabo Rojo, Dominican Republic · Half Moon Cay (Little San Salvador Island), Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Random Wind 'Paradise Day Sail'Private Half-Day Island Adventure & Trunk Bay BeachMount Pelée & Saint-Pierre +7 more
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from $1,679
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MSC Cruises · MSC PoesiaRound-trip
Caribbean 21 nights Nov 1 – Nov 22, 2026 from Miami, Florida
Miami, Florida · Ocho Rios, Jamaica · … · Miami, Florida15 ports
Miami, Florida · Ocho Rios, Jamaica · Cartagena, Colombia · Colon, Panama · Puerto Limon, Costa Rica · Roatan, Honduras · Belize City, Belize · Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Charlestown, Nevis, St. Kitts and Nevis · Philipsburg, St. Maarten · St. John's, Antigua · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…The Roman Theatre of Cartagena with the Rafael Mon…Panama Canal Full TransitHold a Sloth at Daniel Johnson's Monkey & Sloth Ha… +6 more
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from $2,225
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Royal Caribbean · Star of the SeasRound-trip
Caribbean 7 nights Nov 1 – Nov 8, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Perfect Day at CocoCay · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexDaredevil's PeakPrivate Full-Day Boat CharterRandom Wind 'Paradise Day Sail'
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from $1,166
Book This Cruise@ Cruisebound
Royal Caribbean · Icon of the SeasRound-trip
Bahamas 7 nights Nov 7 – Nov 14, 2026 from Miami, Florida
Miami, Florida · Philipsburg, St. Maarten · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Perfect Day at CocoCay · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Random Wind 'Paradise Day Sail'Private Full-Day Boat CharterDaredevil's Peak
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from $1,147
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Celebrity · Celebrity XcelRound-trip
Caribbean 7 nights Nov 8 – Nov 15, 2026 from Miami, Florida
Miami, Florida · 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…Random Wind 'Paradise Day Sail'Private Full-Day Boat CharterThe full 27 jumps at the Damajagua Waterfalls
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from $907
Book This Cruise@ Cruisebound
Royal Caribbean · Allure of the SeasRound-trip
Caribbean 7 nights Nov 8 – Nov 15, 2026 from Miami, Florida
Miami, Florida · Perfect Day at CocoCay · San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Daredevil's PeakWalk El Morro & Old San Juan's City WallsPrivate Full-Day Boat Charter
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from $772
Book This Cruise@ Cruisebound
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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