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.

When are you free? From to — only cruises that fit entirely inside your dates

My result then click any cruise row to open it

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

Trip tap one or more Round-trip One-way Repositioning

Length tap one or more 3–5 nights 6–8 nights 9–12 nights 13+ nights

Cruise level tap one or more Luxury Premium Contemporary River

+ pick specific cruise lines · 1 selected

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

Must visit a specific port clear

Sort

Reset

Filtering Virgin Voyages ×Visits Castries × Clear all

Showing 17 of 17 sailings

Virgin Voyages · Valiant LadyRound-trip

Caribbean Nov 7, 2026 from San Juan, Puerto Rico

San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · … · San Juan, Puerto Rico7 ports

San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Bridgetown, Barbados · Castries, St. Lucia · Fort-de-France, Martinique · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Maho Beach Swim with wild green sea turtles + two shipwrecks…Cosol Tours +2 more

View → ✉ Email

from $1,755

Book This Cruise@ Cruisebound

Virgin Voyages · Valiant LadyRound-trip

Caribbean Nov 14, 2026 from San Juan, Puerto Rico

San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · … · San Juan, Puerto Rico6 ports

San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · St. John's, Antigua · Castries, St. Lucia · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Norman Island Private Half-Day Island Adventure & Trunk Bay Beach Cosol Tours +1 more

View → ✉ Email

from $1,153

Book This Cruise@ Cruisebound

Virgin Voyages · Valiant LadyRound-trip

Caribbean Dec 12, 2026 from San Juan, Puerto Rico

San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · … · San Juan, Puerto Rico7 ports

San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Bridgetown, Barbados · Castries, St. Lucia · Fort-de-France, Martinique · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Maho Beach Swim with wild green sea turtles + two shipwrecks…Cosol Tours +2 more

View → ✉ Email

from $1,335

Book This Cruise@ Cruisebound

Virgin Voyages · Valiant LadyRound-trip

Caribbean Dec 26, 2026 from San Juan, Puerto Rico

San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · … · San Juan, Puerto Rico7 ports

San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Fort-de-France, Martinique · Bridgetown, Barbados · Castries, St. Lucia · St. John's, Antigua · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Maho Beach Mount Pelée & Saint-Pierre Swim with wild green sea turtles + two shipwrecks… +2 more

View → ✉ Email

from $2,039

Book This Cruise@ Cruisebound

Virgin Voyages · Valiant LadyRound-trip

Caribbean Jan 2, 2027 from San Juan, Puerto Rico

San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports

San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · Bridgetown, Barbados · Castries, St. Lucia · St. John's, Antigua · St. Maarten, Netherlands Antilles · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Norman Island Swim with wild green sea turtles + two shipwrecks…Cosol Tours +2 more

View → ✉ Email

from $1,213

Book This Cruise@ Cruisebound

Virgin Voyages · Valiant LadyRound-trip

Caribbean Jan 16, 2027 from San Juan, Puerto Rico

San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · … · San Juan, Puerto Rico7 ports

San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Bridgetown, Barbados · Castries, St. Lucia · Fort-de-France, Martinique · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Maho Beach Swim with wild green sea turtles + two shipwrecks…Cosol Tours +2 more

View → ✉ Email

from $1,271

Book This Cruise@ Cruisebound

Virgin Voyages · Valiant LadyRound-trip

Caribbean Jan 23, 2027 from San Juan, Puerto Rico

San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · … · San Juan, Puerto Rico6 ports

San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · Castries, St. Lucia · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Norman Island Mt. Liamuiga Volcano Crater Hike Private Half-Day Island Adventure & Trunk Bay Beach +1 more

View → ✉ Email

from $1,127

Book This Cruise@ Cruisebound

Virgin Voyages · Valiant LadyRound-trip

Caribbean Feb 20, 2027 from San Juan, Puerto Rico

San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports

San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · Castries, St. Lucia · Bridgetown, Barbados · Roseau, Dominica · St. Maarten, Netherlands Antilles · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Norman Island Cosol Tours Swim with wild green sea turtles + two shipwrecks… +2 more

View → ✉ Email

from $1,273

Book This Cruise@ Cruisebound

Virgin Voyages · Valiant LadyRound-trip

Caribbean Mar 6, 2027 from San Juan, Puerto Rico

San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · … · San Juan, Puerto Rico7 ports

San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Bridgetown, Barbados · Castries, St. Lucia · St. John's, Antigua · Road Town, Tortola, B.V.I. · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Maho Beach Swim with wild green sea turtles + two shipwrecks…Cosol Tours +2 more

View → ✉ Email

from $1,283

Book This Cruise@ Cruisebound

Virgin Voyages · Valiant LadyRound-trip

Caribbean Mar 13, 2027 from San Juan, Puerto Rico

San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · … · San Juan, Puerto Rico6 ports

San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · Castries, St. Lucia · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Norman Island Mt. Liamuiga Volcano Crater Hike Private Half-Day Island Adventure & Trunk Bay Beach +1 more

View → ✉ Email

from $1,187

Book This Cruise@ Cruisebound

Virgin Voyages · Scarlet LadyRound-trip

Caribbean Nov 12, 2027 from San Juan, Puerto Rico

San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · … · San Juan, Puerto Rico8 ports

San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Bridgetown, Barbados · Castries, St. Lucia · Roseau, Dominica · St. Maarten, Netherlands Antilles · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Norman Island Mt. Liamuiga Volcano Crater Hike Swim with wild green sea turtles + two shipwrecks… +3 more

View → ✉ Email

from $1,134

Book This Cruise@ Cruisebound

Virgin Voyages · Scarlet LadyRound-trip

Caribbean Nov 27, 2027 from San Juan, Puerto Rico

San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports

San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · Bridgetown, Barbados · Castries, St. Lucia · Roseau, Dominica · St. Maarten, Netherlands Antilles · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Norman Island Swim with wild green sea turtles + two shipwrecks…Cosol Tours +2 more

View → ✉ Email

from $932

Book This Cruise@ Cruisebound

Virgin Voyages · Scarlet LadyRound-trip

Caribbean Dec 11, 2027 from San Juan, Puerto Rico

San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · … · San Juan, Puerto Rico6 ports

San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · St. John's, Antigua · Castries, St. Lucia · Port of Oranjestad, Aruba, Caribbean · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Maho Beach Private Half-Day Island Adventure & Trunk Bay Beach Cosol Tours +1 more

View → ✉ Email

from $997

Book This Cruise@ Cruisebound

Virgin Voyages · Scarlet LadyRound-trip

Caribbean Jan 22, 2028 from San Juan, Puerto Rico

San Juan, Puerto Rico · Port of Oranjestad, Aruba, Caribbean · … · San Juan, Puerto Rico6 ports

San Juan, Puerto Rico · Port of Oranjestad, Aruba, Caribbean · Castries, St. Lucia · St. John's, Antigua · St. Maarten, Netherlands Antilles · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Aruba Cosol Tours Private Half-Day Island Adventure & Trunk Bay Beach +1 more

View → ✉ Email

from $973

Book This Cruise@ Cruisebound

Virgin Voyages · Scarlet LadyRound-trip

Caribbean Feb 12, 2028 from San Juan, Puerto Rico

San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports

San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Bridgetown, Barbados · Castries, St. Lucia · St. John's, Antigua · St. Maarten, Netherlands Antilles · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Private Catamaran Sail & Snorkel at Honeymoon Beac…Swim with wild green sea turtles + two shipwrecks…Cosol Tours +2 more

View → ✉ Email

from $1,057

Book This Cruise@ Cruisebound

Virgin Voyages · Scarlet LadyRound-trip

Caribbean Mar 18, 2028 from San Juan, Puerto Rico

San Juan, Puerto Rico · Port of Oranjestad, Aruba, Caribbean · … · San Juan, Puerto Rico6 ports

San Juan, Puerto Rico · Port of Oranjestad, Aruba, Caribbean · Castries, St. Lucia · St. John's, Antigua · St. Maarten, Netherlands Antilles · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Aruba Cosol Tours Private Half-Day Island Adventure & Trunk Bay Beach +1 more

View → ✉ Email

from $1,113

Book This Cruise@ Cruisebound

Virgin Voyages · Scarlet LadyRound-trip

Caribbean Apr 8, 2028 from San Juan, Puerto Rico

San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports

San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · Bridgetown, Barbados · Castries, St. Lucia · Roseau, Dominica · St. Maarten, Netherlands Antilles · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Norman Island Swim with wild green sea turtles + two shipwrecks…Cosol Tours +2 more

View → ✉ Email

from $1,118

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.

19 lines
aboard

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