Pineapple Cup – Miami to Montego Bay Yacht Race

Follow the thrilling Pineapple Cup yacht race from Miami to Montego Bay and its celebratory Jamaican finish.

The Pineapple Cup – Miami to Montego Bay Race is one of the world’s longest-established offshore yacht races, bringing accomplished sailors and competitive racing yachts together for an extraordinary ocean passage from Miami, Florida, to Montego Bay, Jamaica.

First held in 1961, this prestigious 811-nautical-mile race combines exceptional seamanship, international competition and a rich maritime tradition.

Held biennially, the Pineapple Cup concludes in the beautiful waters of Montego Bay, where participating crews are welcomed with Jamaican hospitality and a programme of celebrations at the Montego Bay Yacht Club.

What to Expect

An Iconic Offshore Sailing Challenge

The Pineapple Cup takes competitors on an exhilarating journey across the Caribbean’s northern waters.

Beginning in Miami, racing yachts cross the Gulf Stream, navigate the waters surrounding the Bahamas and sail past Cuba before entering the Windward Passage for the final approach to Jamaica.

The challenging course tests sailing skill, navigation, teamwork and endurance, attracting experienced crews from around the world.

A Spectacular Finish in Montego Bay

The race culminates off Jamaica’s beautiful northwest coast, where competing yachts cross the finish line near Montego Bay.

Arrival times vary depending on weather conditions and individual yacht performance, adding to the anticipation as crews complete their ocean crossing.

For sailing enthusiasts, the arrival of these impressive racing yachts offers an opportunity to experience an important international sporting event in Jamaica.

A Rich Maritime Heritage

Established more than six decades ago, the Pineapple Cup has earned a distinguished place in offshore sailing history.

Its list of past champions includes celebrated yachts and accomplished sailors, among them three-time winner Ted Turner.

The event continues to celebrate the traditions of competitive ocean racing while strengthening Jamaica’s connection to the international sailing community.

Jamaican Hospitality & Post-Race Celebrations

The Pineapple Cup experience continues after the yachts reach Montego Bay.

The Montego Bay Yacht Club traditionally hosts a programme of welcoming activities and social gatherings, bringing together competing crews, supporters and members of the sailing community.

Past celebrations have included Jamaica Night, featuring Jamaican hospitality and entertainment, followed by a prestigious awards ceremony honouring the race’s outstanding competitors.

A Caribbean Sailing Experience

Beyond the competition, the Pineapple Cup introduces international sailors and their supporters to Jamaica’s beautiful coastline, warm hospitality and vibrant culture.

For visitors interested in competitive sailing, the event offers a distinctive opportunity to experience Jamaica’s maritime heritage.

Race Information & Spectator Arrangements

The Pineapple Cup is a biennial offshore yacht race, traditionally held in odd-numbered years. Race dates, entry requirements and the programme of post-race activities are announced by the organisers for each edition.

Visitors wishing to follow the race or attend activities in Montego Bay should check the official programme, as yacht arrival times and access to individual social events may vary.

For race announcements, yacht tracking, entry information and event schedules, visit the Pineapple Cup – Montego Bay Race.

The official organiser confirms the race’s history, route and Montego Bay finish, along with its programme of Jamaican celebrations.