by Sarah Kuta
Last updated: 1:35 PM ET, Wed August 12, 2026
Bookings are now open for Seabourn’s winter 2028-2029 Caribbean season.
Offered aboard Seabourn Ovation and Seabourn Quest, the season runs from December 28, 2028, to March 29, 2029, It includes 10 unique itineraries ranging from seven to 12 days, visiting smaller ports such as St. Barts, Bequia and Little Bay (Montserrat).
The ships will visit 21 ports across 20 countries and island territories, featuring late departures in St. Maarten, Antigua, Barbados, Aruba and Curaçao, along with port-rich Southern Caribbean itineraries. Seabourn Ovation will sail between Bridgetown, Barbados and Philipsburg, Sint Maarten, while Seabourn Quest will offer round-trip voyages from Miami.
Guests will have an opportunity to enjoy Seabourn's popular “Caviar in the Surf” experience at Carambola Beach in St. Kitts, featuring Champagne, caviar and a beach barbecue served by Seabourn's onboard team.
Holiday sailings include New Year's Day celebrations at Carambola Beach aboard both Seabourn Ovation and Seabourn Quest, as well as Christmas Eve at Carambola Beach and Christmas Day in Jost Van Dyke on select 10-day voyages.
Travelers can also snejoy destination-inspired dining onboard the ships, as well as “Seabourn Conversations” featuring leading thinkers, cultural voices and subject-matter experts.
"The Caribbean remains one of our most sought-after regions, and we're delighted to return with a collection of thoughtfully designed voyages that showcase both iconic islands and lesser-known gems," says Mark Tamis, president of Seabourn. "Whether guests are joining us for a week or combining itineraries for a longer escape, they'll experience the personalized service, extraordinary cuisine and immersive destination experiences that define Seabourn.”
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