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? — 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
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
Must visit a specific port clear
Reset
Filtering Visits Little Bay × Clear all
Showing 36 of 42 sailings
Seabourn · Seabourn VentureOne-way
Caribbean 8 nights Oct 5 – Oct 13, 2026 from Halifax, Nova Scotia to Bridgetown, Barbados
Halifax, Nova Scotia · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Little Bay, Montserrat, Leeward Islands · Rodney Bay, St. Lucia · Bridgetown, Barbados
★ Bucket-list Peggy's Cove & LunenburgMt. Liamuiga Volcano Crater HikeSoufrière Hills Volcano Exclusion Zone Helicopter…Full-Day Private Catamaran Sail to Soufrière & the… +1 more
View →
from $3,569
Book This Cruise@ Cruisebound
Silversea · Silver ShadowRound-trip
Caribbean 11 nights Nov 7 – Nov 18, 2026 from Miami, Florida
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida8 ports
Miami, Florida · San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Little Bay, Montserrat, Leeward Islands · Jost Van Dyke, British Virgin Islands · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsTrunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. Barts +3 more
View →
from $7,150
Book This Cruise@ Cruisebound
Silversea · Silver ShadowRound-trip
Caribbean 12 nights Nov 18 – Nov 30, 2026 from Miami, Florida
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida9 ports
Miami, Florida · San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Gustavia, St. Barts · Codrington, Barbuda · Little Bay, Montserrat, Leeward Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Jost Van Dyke, British Virgin Islands · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsTrunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. Barts +4 more
View →
from $8,550
Book This Cruise@ Cruisebound
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 WallsPrivate Island HoppingMt. Liamuiga Volcano Crater Hike +6 more
View →
from $5,599
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationRound-trip
Caribbean 14 nights Nov 28 – Dec 12, 2026 from Bridgetown, Barbados
Bridgetown, Barbados · Rodney Bay, St. Lucia · … · Bridgetown, Barbados13 ports
Bridgetown, Barbados · Rodney Bay, St. Lucia · Little Bay, Montserrat, Leeward Islands · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Virgin Gorda, British Virgin Islands · 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
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Full-Day Private Catamaran Sail to Soufrière & the…Soufrière Hills Volcano Exclusion Zone Helicopter…Private Half-Day Island Adventure & Trunk Bay Beach +7 more
View →
from $6,479
Book This Cruise@ Cruisebound
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 +6 more
View →
from $7,054
Book This Cruise@ Cruisebound
Silversea · Silver ShadowOne-way
Caribbean 10 nights Dec 10 – Dec 20, 2026 from Miami, Florida to San Juan, Puerto Rico
Miami, Florida · Cruz Bay, St. John, U.S. Virgin Islands · … · San Juan, Puerto Rico9 ports
Miami, Florida · Cruz Bay, St. John, U.S. Virgin Islands · Philipsburg, St. Maarten · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Iles des Saintes, Guadeloupe · Fort-de-France, Martinique · Little Bay, Montserrat, Leeward Islands · Jost Van Dyke, British Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Trunk Bay Underwater Snorkel Trail & VI National P…Random Wind 'Paradise Day Sail'Mt. Liamuiga Volcano Crater Hike +5 more
View →
from $3,850
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationOne-way
Caribbean 7 nights Dec 19 – Dec 26, 2026 from Bridgetown, Barbados to Philipsburg, St. Maarten
Bridgetown, Barbados · Castries, St. Lucia · … · Philipsburg, St. Maarten7 ports
Bridgetown, Barbados · Castries, St. Lucia · Little Bay, Montserrat, Leeward Islands · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Great Harbor, Peter Island, BVI · Philipsburg, St. Maarten
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursSoufrière Hills Volcano Exclusion Zone Helicopter…Private Half-Day Island Adventure & Trunk Bay Beach +3 more
View →
from $3,759
Book This Cruise@ Cruisebound
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 WallsPrivate Island HoppingMt. Liamuiga Volcano Crater Hike +8 more
View →
from $8,799
Book This Cruise@ Cruisebound
Silversea · Silver ShadowRound-trip
Caribbean 7 nights Dec 20 – Dec 27, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Jost Van Dyke, British Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Jost Van Dyke, British Virgin Islands · Little Bay, Montserrat, Leeward Islands · Castries, St. Lucia · Fort-de-France, Martinique · Sopers Hole · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran CharterSoufrière Hills Volcano Exclusion Zone Helicopter…Cosol Tours +2 more
View →
from $5,950
Book This Cruise@ Cruisebound
Silversea · Silver ShadowRound-trip
Caribbean 7 nights Jan 3 – Jan 10, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · … · San Juan, Puerto Rico8 ports
San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Gustavia, St. Barts · Codrington, Barbuda · Little Bay, Montserrat, Leeward Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Jost Van Dyke, British Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsTrunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. BartsBarbuda's Pink Sand Beach at Dawn, Private & Empty +3 more
View →
from $6,150
Book This Cruise@ Cruisebound
Explora Journeys · EXPLORA IOne-way
Caribbean 7 nights Jan 4, 2027 from San Juan, Puerto Rico to Miami, Florida
San Juan, Puerto Rico · Philipsburg, St. Maarten · … · Miami, Florida12 ports
San Juan, Puerto Rico · Philipsburg, St. Maarten · St. John's, Antigua · Little Bay, Montserrat, Leeward Islands · Road Town, Tortola, B.V.I. · Miami, Florida · Puerto Plata, Dominican Republic · Nydri, Nisos Lefkada, Greece · San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Virgin Gorda, British Virgin Islands · Miami, Florida
★ Bucket-list Walk El Morro & Old San Juan's City WallsRandom Wind 'Paradise Day Sail'Private Half-Day Island Adventure & Trunk Bay BeachSoufrière Hills Volcano Exclusion Zone Helicopter… +6 more
View →
from $8,995
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationOne-way
Caribbean 7 nights Jan 9 – Jan 16, 2027 from Bridgetown, Barbados to Philipsburg, St. Maarten
Bridgetown, Barbados · Castries, St. Lucia · … · Philipsburg, St. Maarten7 ports
Bridgetown, Barbados · Castries, St. Lucia · Little Bay, Montserrat, Leeward Islands · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Great Harbor, Peter Island, BVI · Philipsburg, St. Maarten
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursSoufrière Hills Volcano Exclusion Zone Helicopter…Private Half-Day Island Adventure & Trunk Bay Beach +3 more
View →
from $3,759
Book This Cruise@ Cruisebound
Silversea · Silver ShadowOne-way
Caribbean 10 nights Jan 10 – Jan 20, 2027 from San Juan, Puerto Rico to Bridgetown, Barbados
San Juan, Puerto Rico · Jost Van Dyke, British Virgin Islands · … · Bridgetown, Barbados11 ports
San Juan, Puerto Rico · Jost Van Dyke, British Virgin Islands · Gustavia, St. Barts · Codrington, Barbuda · Little Bay, Montserrat, Leeward Islands · Iles des Saintes, Guadeloupe · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Trois Ilets · Castries, St. Lucia · St. Georges, Grenada, West Indies · Bridgetown, Barbados
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran CharterPrivate Open-Top Mini Moke Island Tour of St. BartsBarbuda's Pink Sand Beach at Dawn, Private & Empty +7 more
View →
from $4,650
Book This Cruise@ Cruisebound
Silversea · Silver ShadowOne-way
Caribbean 10 nights Jan 20 – Jan 30, 2027 from Bridgetown, Barbados to San Juan, Puerto Rico
Bridgetown, Barbados · Bequia, Grenadines · … · San Juan, Puerto Rico11 ports
Bridgetown, Barbados · Bequia, Grenadines · Castries, St. Lucia · Trois Ilets · Roseau, Dominica · Iles des Saintes, Guadeloupe · Little Bay, Montserrat, Leeward Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Cruz Bay, St. John, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Tobago Cays & Mystique Full-Day Private SailCosol ToursLa Savane des Esclaves +7 more
View →
from $7,150
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationOne-way
Caribbean 7 nights Jan 23 – Jan 30, 2027 from Bridgetown, Barbados to Philipsburg, St. Maarten
Bridgetown, Barbados · Castries, St. Lucia · … · Philipsburg, St. Maarten7 ports
Bridgetown, Barbados · Castries, St. Lucia · Little Bay, Montserrat, Leeward Islands · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Great Harbor, Peter Island, BVI · Philipsburg, St. Maarten
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursSoufrière Hills Volcano Exclusion Zone Helicopter…Private Half-Day Island Adventure & Trunk Bay Beach +3 more
View →
from $5,184
Book This Cruise@ Cruisebound
Silversea · Silver ShadowRound-trip
Caribbean 7 nights Jan 30 – Feb 6, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · … · San Juan, Puerto Rico8 ports
San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Little Bay, Montserrat, Leeward Islands · Codrington, Barbuda · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Jost Van Dyke, British Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsTrunk Bay Underwater Snorkel Trail & VI National P…Soufrière Hills Volcano Exclusion Zone Helicopter…Barbuda's Pink Sand Beach at Dawn, Private & Empty +3 more
View →
from $6,150
Book This Cruise@ Cruisebound
Silversea · Silver ShadowOne-way
Caribbean 10 nights Feb 6 – Feb 16, 2027 from San Juan, Puerto Rico to Bridgetown, Barbados
San Juan, Puerto Rico · Jost Van Dyke, British Virgin Islands · … · Bridgetown, Barbados11 ports
San Juan, Puerto Rico · Jost Van Dyke, British Virgin Islands · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Little Bay, Montserrat, Leeward Islands · Iles des Saintes, Guadeloupe · Roseau, Dominica · Trois Ilets · Castries, St. Lucia · St. Georges, Grenada, West Indies · Bridgetown, Barbados
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran CharterPrivate Open-Top Mini Moke Island Tour of St. BartsMt. Liamuiga Volcano Crater Hike +7 more
View →
from $5,750
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationRound-trip
Caribbean 14 nights Feb 13 – Feb 27, 2027 from Bridgetown, Barbados
Bridgetown, Barbados · Castries, St. Lucia · … · Bridgetown, Barbados13 ports
Bridgetown, Barbados · Castries, St. Lucia · Little Bay, Montserrat, Leeward Islands · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Great Harbor, Peter Island, BVI · 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
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursSoufrière Hills Volcano Exclusion Zone Helicopter…Private Half-Day Island Adventure & Trunk Bay Beach +7 more
View →
from $9,051
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationRound-trip
Caribbean 14 nights Feb 20 – Mar 6, 2027 from Philipsburg, St. Maarten
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · … · Philipsburg, St. Maarten13 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 · Castries, St. Lucia · Little Bay, Montserrat, Leeward Islands · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Great Harbor, Peter Island, BVI · Philipsburg, St. Maarten
★ Bucket-list Random Wind 'Paradise Day Sail'The Baths of Virgin GordaMt. Liamuiga Volcano Crater HikeLa Savane des Esclaves +7 more
View →
from $8,414
Book This Cruise@ Cruisebound
Silversea · Silver ShadowRound-trip
Caribbean 7 nights Feb 26 – Mar 5, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · … · San Juan, Puerto Rico8 ports
San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Codrington, Barbuda · Little Bay, Montserrat, Leeward Islands · Jost Van Dyke, British Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsTrunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. BartsMt. Liamuiga Volcano Crater Hike +3 more
View →
from $5,450
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationRound-trip
Caribbean 14 nights Feb 27 – Mar 13, 2027 from Bridgetown, Barbados
Bridgetown, Barbados · Castries, St. Lucia · … · Bridgetown, Barbados13 ports
Bridgetown, Barbados · Castries, St. Lucia · Little Bay, Montserrat, Leeward Islands · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Great Harbor, Peter Island, BVI · 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
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursSoufrière Hills Volcano Exclusion Zone Helicopter…Private Half-Day Island Adventure & Trunk Bay Beach +7 more
View →
from $8,244
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationRound-trip
Caribbean 14 nights Mar 13 – Mar 27, 2027 from Bridgetown, Barbados
Bridgetown, Barbados · Castries, St. Lucia · … · Bridgetown, Barbados13 ports
Bridgetown, Barbados · Castries, St. Lucia · Little Bay, Montserrat, Leeward Islands · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Great Harbor, Peter Island, BVI · 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
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursSoufrière Hills Volcano Exclusion Zone Helicopter…Private Half-Day Island Adventure & Trunk Bay Beach +7 more
View →
from $8,924
Book This Cruise@ Cruisebound
Explora Journeys · EXPLORA IIIRound-trip
Caribbean 7 nights Mar 29, 2027 from Miami, Florida
Miami, Florida · Saint John/cruz Bay · … · Miami, Florida11 ports
Miami, Florida · Saint John/cruz Bay · St. John's, Antigua · Terre-de-haut, Guadeloupe · Road Town, Tortola, B.V.I. · San Juan, Puerto Rico · Gustavia, St. Barts · Little Bay, Montserrat, Leeward Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Key West, Florida · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Half-Day Island Adventure & Trunk Bay BeachPrivate Catamaran Sail & SnorkelNorman Island +5 more
View →
from $9,450
Book This Cruise@ Cruisebound
Explora Journeys · EXPLORA IIIOne-way
Caribbean 17 nights Apr 5, 2027 from San Juan, Puerto Rico to Miami, Florida
San Juan, Puerto Rico · Gustavia, St. Barts · … · Miami, Florida6 ports
San Juan, Puerto Rico · Gustavia, St. Barts · Little Bay, Montserrat, Leeward Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Key West, Florida · Miami, Florida
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Open-Top Mini Moke Island Tour of St. BartsSoufrière Hills Volcano Exclusion Zone Helicopter…Mt. Liamuiga Volcano Crater Hike +2 more
View →
from $4,760
Book This Cruise@ Cruisebound
Seabourn · Seabourn VentureOne-way
Caribbean 24 nights Oct 1 – Oct 25, 2027 from Halifax, Nova Scotia to Rio de Janeiro, Brazil
Halifax, Nova Scotia · Port of Basseterre, St. Kitts, St. Kitts and Nevis · … · Rio de Janeiro, Brazil13 ports
Halifax, Nova Scotia · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Little Bay, Montserrat, Leeward Islands · Rodney Bay, St. Lucia · Bridgetown, Barbados · Port of Spain, Trinidad · Devils Island, French Guiana · Fortaleza, Brazil · Natal(Rio Grande do Norte), Brazil · Bahia de Salvador, Brazil · Buzios, Brazil · Paraty, Brazil · Rio de Janeiro, Brazil
★ Bucket-list Peggy's Cove & LunenburgMt. Liamuiga Volcano Crater HikeSoufrière Hills Volcano Exclusion Zone Helicopter…Full-Day Private Catamaran Sail to Soufrière & the… +9 more
View →
from $11,814
Book This Cruise@ Cruisebound
Seabourn · Seabourn QuestRound-trip
Caribbean 10 nights Nov 13 – Nov 23, 2027 from Miami, Florida
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida7 ports
Miami, Florida · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Little Bay, Montserrat, Leeward Islands · Gustavia, St. Barts · 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 HikeSoufrière Hills Volcano Exclusion Zone Helicopter… +2 more
View →
from $4,504
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 WallsPrivate Open-Top Mini Moke Island Tour of St. BartsSoufrière Hills Volcano Exclusion Zone Helicopter… +3 more
View →
from $4,504
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationOne-way
Caribbean 7 nights Nov 27 – Dec 4, 2027 from Bridgetown, Barbados to Philipsburg, St. Maarten
Bridgetown, Barbados · Castries, St. Lucia · … · Philipsburg, St. Maarten7 ports
Bridgetown, Barbados · Castries, St. Lucia · Little Bay, Montserrat, Leeward Islands · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Great Harbor, Peter Island, BVI · Philipsburg, St. Maarten
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursSoufrière Hills Volcano Exclusion Zone Helicopter…Private Half-Day Island Adventure & Trunk Bay Beach +3 more
View →
from $3,994
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…Trunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. BartsMt. Liamuiga Volcano Crater Hike +6 more
View →
from $5,949
Book This Cruise@ Cruisebound
Seabourn · Seabourn QuestRound-trip
Caribbean 10 nights Dec 18 – Dec 28, 2027 from Miami, Florida
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida7 ports
Miami, Florida · San Juan, Puerto Rico · Road Bay, Anguilla · Little Bay, Montserrat, Leeward Islands · 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 WallsPrivate Island HoppingSoufrière Hills Volcano Exclusion Zone Helicopter… +2 more
View →
from $5,184
Book This Cruise@ Cruisebound
Seabourn · Seabourn QuestRound-trip
Caribbean 10 nights Dec 28 – Jan 7, 2028 from Miami, Florida
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida7 ports
Miami, Florida · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Little Bay, Montserrat, Leeward Islands · Gustavia, St. Barts · 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 HikeSoufrière Hills Volcano Exclusion Zone Helicopter… +2 more
View →
from $5,184
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationOne-way
Caribbean 14 nights Jan 8 – Jan 22, 2028 from Bridgetown, Barbados to Philipsburg, St. Maarten
Bridgetown, Barbados · Rodney Bay, St. Lucia · … · Philipsburg, St. Maarten12 ports
Bridgetown, Barbados · Rodney Bay, St. Lucia · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Kralendijk, Bonaire, Dutch Antilles · Bridgetown, Barbados · Castries, St. Lucia · Little Bay, Montserrat, Leeward Islands · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Great Harbor, Peter Island, BVI · Philipsburg, St. Maarten
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Full-Day Private Catamaran Sail to Soufrière & the…Private Full-Day Curaçao Island Tour with Local Ex…Aruba +7 more
View →
from $7,309
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationOne-way
Caribbean 7 nights Jan 15 – Jan 22, 2028 from Bridgetown, Barbados to Philipsburg, St. Maarten
Bridgetown, Barbados · Castries, St. Lucia · … · Philipsburg, St. Maarten7 ports
Bridgetown, Barbados · Castries, St. Lucia · Little Bay, Montserrat, Leeward Islands · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Great Harbor, Peter Island, BVI · Philipsburg, St. Maarten
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursSoufrière Hills Volcano Exclusion Zone Helicopter…Private Half-Day Island Adventure & Trunk Bay Beach +3 more
View →
from $3,994
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationRound-trip
Caribbean 14 nights Jan 29 – Feb 12, 2028 from Bridgetown, Barbados
Bridgetown, Barbados · Castries, St. Lucia · … · Bridgetown, Barbados13 ports
Bridgetown, Barbados · Castries, St. Lucia · Little Bay, Montserrat, Leeward Islands · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Great Harbor, Peter Island, BVI · 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
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursSoufrière Hills Volcano Exclusion Zone Helicopter…Private Half-Day Island Adventure & Trunk Bay Beach +7 more
View →
from $8,329
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationRound-trip
Caribbean 14 nights Feb 5 – Feb 19, 2028 from Philipsburg, St. Maarten
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · … · Philipsburg, St. Maarten13 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 · Castries, St. Lucia · Little Bay, Montserrat, Leeward Islands · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Great Harbor, Peter Island, BVI · Philipsburg, St. Maarten
★ Bucket-list Random Wind 'Paradise Day Sail'The Baths of Virgin GordaMt. Liamuiga Volcano Crater HikeLa Savane des Esclaves +7 more
View →
from $7,989
Book This Cruise@ Cruisebound
Load more 6 more

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.

23 lines
aboard
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