Seabourn has opened bookings for its winter 2028-29 Caribbean season, with 10 itineraries aboard Seabourn Ovation and Seabourn Quest sailing between Dec. 28, 2028, and March 29, 2029.
The 7- to 12-day voyages are designed around Seabourn’s small-ship experience, with calls at Caribbean ports and yacht harbors that are less accessible to larger cruise ships. Highlights include St. Barts, Bequia and Little Bay in Montserrat, along with extended stays and late departures in destinations including St. Maarten, Antigua, Barbados, Aruba and Curacao.
Caribbean Sailings Showcase Smaller Ports
The season will cover 21 ports across 20 countries and island territories. Seabourn Ovation will sail between Bridgetown, Barbados, and Philipsburg, Sint Maarten, while Seabourn Quest will offer roundtrip voyages from Miami.
Onboard, guests can expect destination-inspired dining featuring regional flavors and seasonal ingredients, as well as Seabourn Conversations programming with cultural experts and other guest speakers.
The season will also showcase Seabourn Quest following a recent drydock that brought updates to suites, public spaces, dining venues and the spa, with refreshed accommodations and reimagined social and wellness spaces.
Highlights of Seabourn‘s Caribbean season include shore experiences that showcase the region’s natural beauty, cultures and rich history, including visits to UNESCO World Heritage
Sites such as:
Antigua | Explore Scenic Antigua – Discover Antigua with a visit to Nelson’s Dockyard, the world’s only remaining Georgian naval dockyard, before continuing to Shirley Heights for panoramic views over English Harbour.
St. Kitts | Brimstone Hill Fortress & Caribelle Batik – Visit Brimstone Hill Fortress National Park, one of the Caribbean’s finest examples of 17th- and 18th-century military architecture, followed by stops at Romney Manor and Caribelle Batik.
Saint Lucia | Catamaran Cruise to the Pitons – Sail along the coast of St. Lucia to the iconic Pitons, the island’s twin volcanic peaks. Then visit the charming town of Soufrière and its famous Sulphur Springs.
For more information, visit seabourn.com.







