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.

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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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Filtering Princess ×From Miami, Florida × Clear all
Showing 21 of 21 sailings
Princess · Regal PrincessRound-trip
Mexico 15 nights Nov 20 – Dec 5, 2027 from Miami, Florida
Miami, Florida · Belize City, Belize · … · Miami, Florida11 ports
Miami, Florida · Belize City, Belize · Roatan, Honduras · Cozumel, Mexico · Celebration Key, Bahamas · Miami, Florida · Amber Cove, Dominican Republic · San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Tortola, B.V.I. · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Great Blue Hole Flightseeing & Lighthouse Reef Sno…Hold a Sloth at Daniel Johnson's Monkey & Sloth Ha…El Cielo + Palancar + Columbia 3-Stop Snorkel +5 more
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from $1,418
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Princess · Regal PrincessRound-trip
Bahamas 15 nights Nov 27 – Dec 12, 2027 from Miami, Florida
Miami, Florida · Amber Cove, Dominican Republic · … · Miami, Florida10 ports
Miami, Florida · Amber Cove, Dominican Republic · San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Tortola, B.V.I. · Miami, Florida · Princess Cays, Bahamas · St. Thomas, U.S. Virgin Islands · St. Maarten, Netherlands Antilles · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…27 Charcos of DamajaguaWalk El Morro & Old San Juan's City WallsMaho Beach +3 more
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from $1,513
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Princess · Regal PrincessRound-trip
Bahamas 14 nights Dec 5 – Dec 19, 2027 from Miami, Florida
Miami, Florida · Princess Cays, Bahamas · … · Miami, Florida10 ports
Miami, Florida · Princess Cays, Bahamas · St. Thomas, U.S. Virgin Islands · St. Maarten, Netherlands Antilles · Miami, Florida · Belize City, Belize · Roatan, Honduras · Cozumel, Mexico · Celebration Key, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Bungalow DayPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Maho Beach +4 more
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from $1,438
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Princess · Regal PrincessRound-trip
Mexico 7 nights Dec 12 – Dec 19, 2027 from Miami, Florida
Miami, Florida · Belize City, Belize · … · Miami, Florida6 ports
Miami, Florida · Belize City, Belize · Roatan, Honduras · Cozumel, Mexico · Celebration Key, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Great Blue Hole Flightseeing & Lighthouse Reef Sno…Hold a Sloth at Daniel Johnson's Monkey & Sloth Ha…El Cielo + Palancar + Columbia 3-Stop Snorkel +1 more
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from $799
Book This Cruise@ Cruisebound
Princess · Regal PrincessRound-trip
Caribbean 14 nights Dec 19 – Jan 2, 2028 from Miami, Florida
Miami, Florida · Amber Cove, Dominican Republic · … · Miami, Florida10 ports
Miami, Florida · Amber Cove, Dominican Republic · San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Tortola, B.V.I. · Miami, Florida · Celebration Key, Bahamas · Amber Cove, Dominican Republic · Grand Turk, Turks and Caicos · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…27 Charcos of DamajaguaWalk El Morro & Old San Juan's City WallsMaho Beach +3 more
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from $2,293
Book This Cruise@ Cruisebound
Princess · Regal PrincessRound-trip
Mexico 13 nights Dec 27 – Jan 9, 2028 from Miami, Florida
Miami, Florida · Celebration Key, Bahamas · … · Miami, Florida10 ports
Miami, Florida · Celebration Key, Bahamas · Amber Cove, Dominican Republic · Grand Turk, Turks and Caicos · Miami, Florida · Belize City, Belize · Roatan, Honduras · Cozumel, Mexico · Celebration Key, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Kayak the Lucayan Caves & Gold Rock Beach with the…27 Charcos of DamajaguaGibbs Cay Private Stingray Swim & Reef Snorkel +3 more
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from $1,701
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Princess · Regal PrincessRound-trip
Caribbean 14 nights Jan 2 – Jan 16, 2028 from Miami, Florida
Miami, Florida · Belize City, Belize · … · Miami, Florida10 ports
Miami, Florida · Belize City, Belize · Roatan, Honduras · Cozumel, Mexico · Celebration Key, Bahamas · Miami, Florida · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico · Amber Cove, Dominican Republic · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Great Blue Hole Flightseeing & Lighthouse Reef Sno…Hold a Sloth at Daniel Johnson's Monkey & Sloth Ha…El Cielo + Palancar + Columbia 3-Stop Snorkel +4 more
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from $1,263
Book This Cruise@ Cruisebound
Princess · Regal PrincessRound-trip
Caribbean 7 nights Jan 9 – Jan 16, 2028 from Miami, Florida
Miami, Florida · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico · Amber Cove, Dominican Republic · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Mt. Liamuiga Volcano Crater HikeWalk El Morro & Old San Juan's City Walls27 Charcos of Damajagua
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from $639
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Princess · Regal PrincessRound-trip
Caribbean 7 nights Jan 16 – Jan 23, 2028 from Miami, Florida
Miami, Florida · Princess Cays, Bahamas · St. Thomas, U.S. Virgin Islands · St. Maarten, Netherlands Antilles · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Bungalow DayPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Maho Beach
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from $829
Book This Cruise@ Cruisebound
Princess · Regal PrincessRound-trip
Caribbean 7 nights Jan 23 – Jan 30, 2028 from Miami, Florida
Miami, Florida · Belize City, Belize · … · Miami, Florida6 ports
Miami, Florida · Belize City, Belize · Roatan, Honduras · Cozumel, Mexico · Celebration Key, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Great Blue Hole Flightseeing & Lighthouse Reef Sno…Hold a Sloth at Daniel Johnson's Monkey & Sloth Ha…El Cielo + Palancar + Columbia 3-Stop Snorkel +1 more
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from $734
Book This Cruise@ Cruisebound
Princess · Regal PrincessRound-trip
Caribbean 7 nights Jan 30 – Feb 6, 2028 from Miami, Florida
Miami, Florida · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico · Amber Cove, Dominican Republic · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Mt. Liamuiga Volcano Crater HikeWalk El Morro & Old San Juan's City Walls27 Charcos of Damajagua
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from $829
Book This Cruise@ Cruisebound
Princess · Regal PrincessRound-trip
Bahamas 14 nights Feb 6 – Feb 20, 2028 from Miami, Florida
Miami, Florida · Princess Cays, Bahamas · … · Miami, Florida10 ports
Miami, Florida · Princess Cays, Bahamas · St. Thomas, U.S. Virgin Islands · St. Maarten, Netherlands Antilles · Miami, Florida · Belize City, Belize · Roatan, Honduras · Cozumel, Mexico · Celebration Key, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Bungalow DayPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Maho Beach +4 more
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from $1,431
Book This Cruise@ Cruisebound
Princess · Regal PrincessRound-trip
Mexico 14 nights Feb 13 – Feb 27, 2028 from Miami, Florida
Miami, Florida · Belize City, Belize · … · Miami, Florida11 ports
Miami, Florida · Belize City, Belize · Roatan, Honduras · Cozumel, Mexico · Celebration Key, Bahamas · Miami, Florida · Amber Cove, Dominican Republic · San Juan, Puerto Rico · Grand Turk, Turks and Caicos · Celebration Key, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Great Blue Hole Flightseeing & Lighthouse Reef Sno…Hold a Sloth at Daniel Johnson's Monkey & Sloth Ha…El Cielo + Palancar + Columbia 3-Stop Snorkel +4 more
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from $1,548
Book This Cruise@ Cruisebound
Princess · Regal PrincessRound-trip
Bahamas 14 nights Feb 20 – Mar 5, 2028 from Miami, Florida
Miami, Florida · Amber Cove, Dominican Republic · … · Miami, Florida10 ports
Miami, Florida · Amber Cove, Dominican Republic · San Juan, Puerto Rico · Grand Turk, Turks and Caicos · Celebration Key, Bahamas · Miami, Florida · Princess Cays, Bahamas · St. Thomas, U.S. Virgin Islands · St. Maarten, Netherlands Antilles · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…27 Charcos of DamajaguaWalk El Morro & Old San Juan's City WallsGibbs Cay Private Stingray Swim & Reef Snorkel +4 more
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from $1,508
Book This Cruise@ Cruisebound
Princess · Regal PrincessRound-trip
Caribbean 7 nights Feb 27 – Mar 5, 2028 from Miami, Florida
Miami, Florida · Princess Cays, Bahamas · St. Thomas, U.S. Virgin Islands · St. Maarten, Netherlands Antilles · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Bungalow DayPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Maho Beach
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from $769
Book This Cruise@ Cruisebound
Princess · Regal PrincessRound-trip
Caribbean 14 nights Mar 5 – Mar 19, 2028 from Miami, Florida
Miami, Florida · Celebration Key, Bahamas · … · Miami, Florida11 ports
Miami, Florida · Celebration Key, Bahamas · Falmouth, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Cozumel, Mexico · Miami, Florida · Celebration Key, Bahamas · Amber Cove, Dominican Republic · San Juan, Puerto Rico · Grand Turk, Turks and Caicos · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Kayak the Lucayan Caves & Gold Rock Beach with the…Blue Hole & Secret FallsStingray City Sandbar +4 more
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from $1,526
Book This Cruise@ Cruisebound
Princess · Regal PrincessRound-trip
Caribbean 7 nights Mar 12 – Mar 19, 2028 from Miami, Florida
Miami, Florida · Celebration Key, Bahamas · … · Miami, Florida6 ports
Miami, Florida · Celebration Key, Bahamas · Amber Cove, Dominican Republic · San Juan, Puerto Rico · Grand Turk, Turks and Caicos · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Kayak the Lucayan Caves & Gold Rock Beach with the…27 Charcos of DamajaguaWalk El Morro & Old San Juan's City Walls +1 more
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from $781
Book This Cruise@ Cruisebound
Princess · Regal PrincessRound-trip
Bahamas 7 nights Mar 19 – Mar 26, 2028 from Miami, Florida
Miami, Florida · Princess Cays, Bahamas · St. Thomas, U.S. Virgin Islands · St. Maarten, Netherlands Antilles · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Bungalow DayPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Maho Beach
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from $899
Book This Cruise@ Cruisebound
Princess · Regal PrincessRound-trip
Mexico 7 nights Mar 26 – Apr 2, 2028 from Miami, Florida
Miami, Florida · Belize City, Belize · … · Miami, Florida6 ports
Miami, Florida · Belize City, Belize · Roatan, Honduras · Cozumel, Mexico · Celebration Key, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Great Blue Hole Flightseeing & Lighthouse Reef Sno…Hold a Sloth at Daniel Johnson's Monkey & Sloth Ha…El Cielo + Palancar + Columbia 3-Stop Snorkel +1 more
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from $1,149
Book This Cruise@ Cruisebound
Princess · Regal PrincessRound-trip
Caribbean 7 nights Apr 2 – Apr 9, 2028 from Miami, Florida
Miami, Florida · Celebration Key, Bahamas · … · Miami, Florida6 ports
Miami, Florida · Celebration Key, Bahamas · Amber Cove, Dominican Republic · San Juan, Puerto Rico · Grand Turk, Turks and Caicos · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Kayak the Lucayan Caves & Gold Rock Beach with the…27 Charcos of DamajaguaWalk El Morro & Old San Juan's City Walls +1 more
View →
from $804
Book This Cruise@ Cruisebound
Princess · Regal PrincessRound-trip
Bahamas 7 nights Apr 9 – Apr 16, 2028 from Miami, Florida
Miami, Florida · Princess Cays, Bahamas · St. Thomas, U.S. Virgin Islands · St. Maarten, Netherlands Antilles · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Bungalow DayPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Maho Beach
View →
from $909
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