Cycle Jamaica -Montego Bay

Jamaica Reggae Ride

Jamaica RR Logo.png

5 day, 4 nts all-inclusive cycling vacation
Includes: 4 nights accommodation in all inclusive resort  including all meals and drinks, airport transfers, 3 fully supported rides, finishers medal &more! FREE Covid test for your return trip.


Our rides  are designed with the perfect combination of riding time and resort relax time!

The Jamaica Reggae Ride is an all inclusive cycling  vacation  which  includes 4 nights stay at an all inclusive resort based in  Montego Bay, and 3 organized rides. There is time in the afternoons to meet up with fellow cyclists, spouses and friends to explore the island's many  attractions, relax at the spa and to enjoy the facilities  of  your all inclusive resort.

We cater to ALL pace levels. If you are an elite cyclist, be prepared to be challenged by the island's top champions and if you are a newbie or intermediate cyclist, know that we make it fun for everyone and there is full service support at all times along the way. This is a concierge service tour with pros as tour leaders. 


Our stops are well planned so as to ensure everyone experiences the real Jamaica: we will have a rest stop at a local fruit stall. Enjoy coconut water straight from the  nut: the best rehydration ever!  Enjoy local roasted yams - as we pedal through "Usain country"! The Jamaican people are warm and genuinely friendly.  You'll get to meet them up close and in their real world!

For our Ride in August only the shorter route is offered, due to heat.  For our April  and November rides have two  ride distances each  day. Please note that when  we have two routes, the shorter ride group returns with  a sag and guides and not  with the police.


So come on, let's ride!
Let us show you why Jamaica is truly the "heartbeat" of the Caribbean


Package inclusions:
•    Experienced English-speaking guide(s)

.    Round trip airport transportation for host hotels
•    Pre-tour orientation meeting

.    Private farewell dinner 

     Private award ceremony

      Finisher's and Repeaters Medals
•    All inclusive hotel accommodations in host hotel booked
•    3 days fully supported cycling as per itinerary
•    Sag vehicles 

     Police escorted
•    All entrance fees to include events and activities
•    All in-country ground transportation
•    Clean drinking water available at all times

      Access to Wix App - with Forum and communication with organizer 

      and other participants

Not Included: 
•    Round-trip airfare
•    Staff gratuities
•    Personal expenses such as souvenirs, gifts, additional drinks/entertainment, and incidentals

     Travel Health Insurance - compulsory


Rates are per person based on two persons sharing in a room, for the 4 night package.

Rates increase each month. Please go to the booking  link to view the prices.


If you are traveling alone, you can get a room  for yourself but  you would need to add the single supplment  under optional  extras. 

Because rates increase each month, we suggest you make your $399 deposit and lock in the early rate with easy monthly payments thereafter. If you wait, the prices increase and there also can  be no more availability.

Rates increase every month.  Pay $399 deposit to lock in the early rate and then further payments are made monthly installments.  The payment plans are flexible. Go to our booking link for rates and payment options.


Cyclists:  2 route options are provided each  day - one short and one long, except for our July ride where only the shorter route is offered. Each route has at least two pace level groups.  Sag vehicles are provided for ALL  groups. Maps below are approximations and are subject to change depending local conditions.  This is a fun event, pleaen't get too geeky!

DAY 1 - Thursday -ARRIVAL- Montego Bay airport MBJ

We highly recommend to arrive on the earliest flight you can get into MBJ airport so that you have time to relax and enjoy the hotel facilities and get your bike set up.   We also  highly recommend you book the arrival services of Club Mobay for so many reasons: you are met right off the plane and join the fast track  through  immigration and customs and then have a comfortable place to relax and have a snack and drink before heading off to your hotel as you await everyone to clear through. Its important to book it early because it often gets sold out early.

   4:30-5:15pm   Meeting by the lobby,  Holiday Inn 

   5:45-6:30pm   Meeting at the stage, Riu Montego  Bay 

   7:00pm             Dinner and evening at leisure in  your hotels

Overnight Host Hotel: Riu Montego  Bay

DAY 2 - Friday - Welcome Ride -Ironshore- Rose Hall-Falmouth

Travel through the residential areas of Montego Bay and the old  historic town of Falmouth.  There are scenic views of the Caribbean with smooth gently undulating, roads.  We make a stop at a Rastafarian home to get an in depth view of the culture and lifestyle of this unique religion.

  • 07:00-07:30 - Breakfast

  • 07:30-08:00 - Group Photos and then Ride out ( August ride is 05:30-08:00am)

  • 11:30am - Return to hotel

  • Lunch at leisure in the hotel

  • 4:00-5:30pm - Optional Cycling - One hour training with 3 time Olympian Coach Peter Aldridge and his team on a closed course/or rollers - skills training.  Book under optional  extras. In July: rollers only.

  • Dinner and evening at leisure to enjoy the hotel

  • 6:00pm  Optional tour: Luminous Lagoon

  • Overnight Host Hotels:  Riu Montego  Bay

DISTANCE AND ROUTE OPTIONS: Welcome Ride (Subject to change. Use this only as a current guideline)

Cycling Option 1- Full route - 42 miles/1079 FT  

Cycling Option 2-Short route - 28 miles/707FT  (only this  option for the August  ride)



DAY 3- Montego Bay - Carey Park

KOM Strava Challenge Day: 51 miles/1514f

Today sees us heading along the northcoast of the island, along perfectly paved roads, with a few  climbs along the way for fun!  Today is a serious challenge with some hills to climb including the KOM/QOM Strava challenge of Spring  Hill. We always regroup at the top - so pace yourself and do it in your own time!

We turn around at "Yammis" a local vendor famous for roasted yams. Since Usain Bolt is from this parish and its claimed that it's these yams that made him so fast,  we'll be sure to try some and fuel up for the return ride home. 

  • 06:30-07:00 - Breakfast

  • 07:00-07:30 - Photos and then Ride out ( in August the ride out time is 05:30am)

  • 1:30pm       - Return to  resort for lunch

  • 6:30pm         Farewell dinner with award ceremony

Overnight Host Hotel:  Riu Montego  Bay

DISTANCE AND ROUTE OPTIONS: Sunday  (the routes may change. Use this as a guideline only)


Cycling Option 1- Full route - 50.6 miles/1514 ft - Spring Hill KOM Strava Challenge  

Cycling Option 2-Short route - 38  miles/745ft  



DAY 4-Sunday - Montego Bay - Sandy Bay 

scenic ride with a few rollers, along the northcoast of the island. We stop to enjoy fresh coconut water straight from  the nut- it's the  best natural  hydration and it's so delicious. Not like from the box!

  • 06:30-07:00 - Breakfast

  • 07:00-07:30 - Photos and then Ride out ( August ride out is 05:30am and we aim  to be back by 8am)

  • 11:30am - Return to hotel

  • Lunch at leisure in the resort

  • 13:00- 17:30  Optional Sightseeing tour Tour: Dunns River Waterfalls

  • Dinner and evening at leisure to enjoy the hotel

  • Overnight Host Hotels:  Riu Montego  Bay


Cycling Option 1- Full route -  41miles/15ft48

Cycling Option 2-Short route - 25.6 miles/695ft (only this route  offered in August)




Transport from  Host Hotels to Montego Bay airport


Every effort will be made to adhere to the planned route. Any unforeseen adjustments will be noted on our website in advance of the event , noted on the route guides, or explained by our Discover Jamaica Ride Tour Leaders and Road Master during our rides. There are no refunds or compensations for any route changes, whatsoever.