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
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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 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
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Filtering Seabourn ×Visits Port Elizabeth ×6–8 nights × Clear all
Showing 11 of 11 sailings
Seabourn · Seabourn OvationOne-way
Caribbean 8 nights Nov 20 – Nov 28, 2026 from Miami, Florida to Bridgetown, Barbados
Miami, Florida · San Juan, Puerto Rico · … · Bridgetown, Barbados7 ports
Miami, Florida · San Juan, Puerto Rico · Great Harbor, Peter Island, BVI · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Roseau, Dominica · Port Elizabeth, Saint Vincent · Bridgetown, Barbados
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsMt. Liamuiga Volcano Crater HikeBoiling Lake Hike +2 more
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from $4,098
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationOne-way
Caribbean 7 nights Dec 26 – Jan 2, 2027 from Philipsburg, St. Maarten to Bridgetown, Barbados
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · … · Bridgetown, Barbados7 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
★ Bucket-list Random Wind 'Paradise Day Sail'The Baths of Virgin GordaMt. Liamuiga Volcano Crater HikeLa Savane des Esclaves +3 more
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from $5,998
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationOne-way
Caribbean 7 nights Jan 16 – Jan 23, 2027 from Philipsburg, St. Maarten to Bridgetown, Barbados
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · … · Bridgetown, Barbados7 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
★ Bucket-list Random Wind 'Paradise Day Sail'The Baths of Virgin GordaMt. Liamuiga Volcano Crater HikeLa Savane des Esclaves +3 more
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from $5,798
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationOne-way
Caribbean 7 nights Jan 30 – Feb 6, 2027 from Philipsburg, St. Maarten to Bridgetown, Barbados
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · … · Bridgetown, Barbados7 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
★ Bucket-list Random Wind 'Paradise Day Sail'The Baths of Virgin GordaMt. Liamuiga Volcano Crater HikeLa Savane des Esclaves +3 more
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from $4,798
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationOne-way
Caribbean 7 nights Feb 20 – Feb 27, 2027 from Philipsburg, St. Maarten to Bridgetown, Barbados
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · … · Bridgetown, Barbados7 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
★ Bucket-list Random Wind 'Paradise Day Sail'The Baths of Virgin GordaMt. Liamuiga Volcano Crater HikeLa Savane des Esclaves +3 more
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from $5,998
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationOne-way
Caribbean 7 nights Mar 6 – Mar 13, 2027 from Philipsburg, St. Maarten to Bridgetown, Barbados
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · … · Bridgetown, Barbados7 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
★ Bucket-list Random Wind 'Paradise Day Sail'The Baths of Virgin GordaMt. Liamuiga Volcano Crater HikeLa Savane des Esclaves +3 more
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from $4,798
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationOne-way
Caribbean 7 nights Mar 20 – Mar 27, 2027 from Philipsburg, St. Maarten to Bridgetown, Barbados
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · … · Bridgetown, Barbados7 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
★ Bucket-list Random Wind 'Paradise Day Sail'The Baths of Virgin GordaMt. Liamuiga Volcano Crater HikeLa Savane des Esclaves +3 more
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from $5,998
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationOne-way
Caribbean 7 nights Dec 4 – Dec 11, 2027 from Philipsburg, St. Maarten to Bridgetown, Barbados
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · … · Bridgetown, Barbados7 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
★ Bucket-list Random Wind 'Paradise Day Sail'The Baths of Virgin GordaMt. Liamuiga Volcano Crater HikeLa Savane des Esclaves +3 more
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from $4,298
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationOne-way
Caribbean 7 nights Jan 22 – Jan 29, 2028 from Philipsburg, St. Maarten to Bridgetown, Barbados
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · … · Bridgetown, Barbados7 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
★ Bucket-list Random Wind 'Paradise Day Sail'The Baths of Virgin GordaMt. Liamuiga Volcano Crater HikeLa Savane des Esclaves +3 more
View →
from $4,798
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationOne-way
Caribbean 7 nights Feb 19 – Feb 26, 2028 from Philipsburg, St. Maarten to Bridgetown, Barbados
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · … · Bridgetown, Barbados7 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
★ Bucket-list Random Wind 'Paradise Day Sail'The Baths of Virgin GordaMt. Liamuiga Volcano Crater HikeLa Savane des Esclaves +3 more
View →
from $4,998
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationOne-way
Caribbean 7 nights Mar 18 – Mar 25, 2028 from Philipsburg, St. Maarten to Bridgetown, Barbados
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · … · Bridgetown, Barbados7 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
★ Bucket-list Random Wind 'Paradise Day Sail'The Baths of Virgin GordaMt. Liamuiga Volcano Crater HikeLa Savane des Esclaves +3 more
View →
from $4,998
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