Pineapple Cup Montego Bay Race

View on map
Sports & AdventureMontego Bay
DatesDates TBACheck locally before booking
DurationAnnualEstimate from available data
Crowd-Public scale varies
Best forCompetition, enduranceRunning only 36 stagings since 1961 shows
LanguageLocal language; English access variesCurrency: JMD
CategorySports & AdventureFestival type
The story

Pineapple Cup Montego Bay Race in Montego Bay

An offshore ocean race that has run since 1961, covering 811 nautical miles from Miami through the Bahamas and the Windward Passage to a finish off Montego Bay, making it the longest-running race of its kind between the US and the Caribbean. Organized with the Montego Bay Yacht Club and Storm Trysail Club, it runs periodically rather than strictly annually and races ORC, PHRF, multihull and double-handed classes.

Sailors have raced this course since 1961, when the Pineapple Cup began as one of the earliest offshore ocean races linking the United States to the Caribbean, and it remains the longest-running race of its kind between the two coasts.
Your trip starts here
What is special

The part that makes it specific.

01

The place changes

Running only 36 stagings since 1961 shows this is a periodic rather than annual race, with editions occasionally postponed, as happened with the planned 2025 running

02

The mystery stays covered

Its course structure, a tactical Bahamas passage followed by a roughly 240-mile downwind sleigh ride through the Windward Passage, gives sailors two distinct tactical phases within one race, a combination competitors say tests both patience and pure downwind boat speed over several demanding days at sea

Traditions & symbols

The language of the festival.

What moves first

Living ritual

The race's Windward Passage downwind finish

Water and renewal

Living ritual

following the tactical Bahamas island-chain leg

The sacred route

Living ritual

is the course's signature stretch

The local code

Living ritual

and finishing crews are traditionally welcomed at the Montego Bay Yacht Club after their multi-day Caribbean crossing

Before you go

Essential information

When to go

Dates TBA

Getting around

For Pineapple Cup Montego Bay Race, plan transport around the exact Montego Bay venue, route or gathering point rather than the city name alone.

What to wear

Yacht club casual for shoreside finish events; competitors require full offshore sailing gear appropriate to a multi-day ocean passage.

Safety

Keep valuables light, follow local instructions, and watch how residents use the space before joining in.

Where to stay

For Pineapple Cup Montego Bay Race, stay near the part of Montego Bay you will actually use, with reliable return transport.

Tickets/cost

Check official or local sources for ticketed areas, paid stands, and same-year access rules.

Language/currency

JMD

Family friendly

unknown

Interactive map18.47 N, 77.92 WOpen in Google Maps

Montego Bay, St. James, Jamaica

Nearest airportMBJ — Sangster
TransportFor Pineapple Cup Montego Bay Race, plan transport around the exact Montego Bay venue, route or gathering point rather than the city name alone.
Stay areaFor Pineapple Cup Montego Bay Race, stay near the part of Montego Bay you will actually use, with reliable return transport.

Your Trip Starts Here

External travel services to turn the plan into a trip — each opens in a new tab.

How to get thereRoutes, times and prices to Montego Bay via local transport.Search routesFind a place to stayStays near Montego Bay, close enough for the event-day route.Browse staysFind flightsCompare fares into the nearest practical airport for festival season.Compare faresFestival gearYacht club casual for shoreside finish events; competitors require full offshore sailing gear appropriate to a multi-day ocean passage.Shop the kitCheck visa requirementsSee whether you need a visa for Jamaica and apply online.Check entry rulesTravel insuranceCover for trip hiccups, gear and health on the road.Get covered

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FAQ

Quick answers.

When is Pineapple Cup Montego Bay Race?

Pineapple Cup Montego Bay Race is listed for Multiple months. Always re-check the official or local source close to travel.

Where does Pineapple Cup Montego Bay Race take place?

The festival is listed in Montego Bay, Jamaica. The map coordinate is a planning reference, not a guarantee of a ticket gate or exact venue.

How long should I plan for?

Annual is the listed festival span. Add time for arrival, local transport, queues, and any route changes during the event.

Is a source linked?

Official source linked. Eventisimus separates source confidence from travel suggestions, so check final details before booking.

Where exactly is it?

Montego Bay, St. James, Jamaica

Is it family friendly?

unknown

Sources and editorial review

About this guide

This guide is independently written by Eventisimus using publicly available information, official event and organiser sources where available, local tourism references, and additional editorial research. Eventisimus is not the official organiser of this festival and is not affiliated with it unless explicitly stated.

Festival dates, schedules, ticket conditions, access rules, and local arrangements can change. We aim to present useful and accurate information, but travelers should confirm important details with the official event source before booking transport, accommodation, or tickets.

Found something inaccurate or outdated? Email hello@eventisimus.com with the festival page link and the correction.

Official URLpineapplecup.com
Organizer accessAre you the organizer? Claim this listing →
SourceSource link available
Listed datesDates TBA
Source statusOfficial source linked
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