Seabourn has opened bookings for its winter 2028–2029 Caribbean season, with 10 itineraries designed to make the most of the luxury line’s small-ship access to yacht harbours and less-visited island ports.
Operating aboard Seabourn Ovation and Seabourn Quest, the program features voyages ranging from seven to 12 days and visits 21 ports across 20 countries and island territories.
Ports including St Barts, Bequia and Little Bay in Montserrat feature in the program, alongside late departures from St Maarten, Antigua, Barbados, Aruba and Curaçao.
Seabourn Ovation will operate voyages between Bridgetown, Barbados, and Philipsburg, Sint Maarten, while Seabourn Quest will sail roundtrip from Miami.
Smaller ports take the spotlight

Seabourn President Mark Tamis said the itineraries had been developed to combine established Caribbean destinations with smaller ports.
“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,” Tamis said.
“Whether guests are joining us for a week or combining itineraries for a longer escape, they’ll experience the personalised service, extraordinary cuisine and immersive destination experiences that define Seabourn.”
The season will also include the line’s signature Caviar in the Surf experience at Carambola Beach in St Kitts, where Champagne, caviar and a beach barbecue are served by the onboard team.
Holiday sailings will feature New Year’s Day celebrations at Carambola Beach aboard both ships, while selected 10-day voyages include Christmas Eve at Carambola Beach followed by Christmas Day in Jost Van Dyke.
Seabourn Quest emerges from major refresh

Guests aboard Seabourn Quest will experience the ship following a recently completed drydock, described by Seabourn as one of the most comprehensive interior updates in its history.
The refurbishment encompasses suites, public spaces, dining venues and the spa, with refreshed accommodation, redesigned social areas and updated wellness facilities.
Onboard programming will complement the destination focus through regionally inspired dining and Seabourn Conversations, which brings guest speakers and subject-matter experts aboard for presentations and discussions.
UNESCO sites feature ashore

Shore experiences include visits to several United Nations Educational, Scientific and Cultural Organization (UNESCO) World Heritage-listed locations.
In Antigua, guests can explore Nelson’s Dockyard and continue to Shirley Heights, while a St Kitts excursion combines Brimstone Hill Fortress National Park with Romney Manor and Caribelle Batik.
Other options include sailing by catamaran to St Lucia’s Pitons, exploring Historic Bridgetown and its Garrison in Barbados, and discovering Willemstad’s Punda and Otrobanda districts in Curaçao.
Featured sailings include an eight-day Caribbean Yachting & Caviar in the Surf voyage departing 10 November 2028, a seven-day St Barts & Caribbean Yacht Harbors itinerary departing 16 December 2028, and longer 14- and 21-day Southern Caribbean voyages in early 2029.


