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Cycle Across All 14 Parishes of Jamaica |8 Days|387.59 Miles|14,034ft Elevation|April 29-May 6, 2027

What Makes this Tour Special

✔ Ride across Jamaica's all 14 parishes
✔ Police escort for rider safety
✔ SAG support vehicle
✔ Travel nurse and on-call medical support
✔ Jamaican meals during the ride
✔ Experienced ride leaders and mechanical assistance
✔ Luggage transport between hotels
✔ Hydration and refreshment stops along the route






 




The Ultimate Caribbean Cycling Adventure

Reserve Your Spot Below

Make a Deposit Today

Secure your spot on the DJBB Cycling Tour today—make your deposit of $350 usd now and get ready to ride, connect, challenge yourself and experience Jamaica's 14 parishes like never before.

Secure Your Spot

Ride Only

8 Days Ultimate Experience - 387.59 miles/14,034ft elevation (Ride Only)

Montego Bay - Negril - Mandeville - Kingston- Port Antonio - Montego Bay (DOES NOT INCLUDE EXCURSION) - Price for one cyclist $1,285 usd

Ride + Accommodation Package - 1 Cyclist

8 Days/7 Nights - Ride Plus Accommodation (One Cyclist)

Montego Bay/Negril/Mandeville/Kingston/Port Antonio/Montego Bay

(INCLUDES ACCOMMODATION ON MAY 5TH) - $2,530 usd

Ride + Double Accommodation Package

8 Days/7 Nights - Ride Plus Accommodation (Two Cyclist)

Montego Bay/Negril/Mandeville/Kingston/Port Antonio/Montego Bay

(INCLUDES ACCOMMODATION ON MAY 5TH) -  $3,600 usd

The Caribbean's Ultimate Cycling Challenge

Book by the Day Ride+Accommodation

Day 1 The Starter - 44.69 Miles/1,119ft (Ride +accommodation for 1 Cyclist)

Day 2 The Spur Tree Hill Challenge - 82.74 Miles/4,370ft (Ride Plus accommodation for 1 Cyclist)

Day 2 The Spur Tree Hill Challenge - 82.74 Miles/4,370ft (Ride Plus accommodation for 1 Cyclist)

Montego Bay - Negril $382 usd

Day 2 The Spur Tree Hill Challenge - 82.74 Miles/4,370ft (Ride Plus accommodation for 1 Cyclist)

Day 2 The Spur Tree Hill Challenge - 82.74 Miles/4,370ft (Ride Plus accommodation for 1 Cyclist)

Day 2 The Spur Tree Hill Challenge - 82.74 Miles/4,370ft (Ride Plus accommodation for 1 Cyclist)

Negril - Mandeville $343 usd

Day 3 The Cruise - 60.18 Miles/1 263ft (Ride Plus accommodation for 1 Cyclist)

Day 2 The Spur Tree Hill Challenge - 82.74 Miles/4,370ft (Ride Plus accommodation for 1 Cyclist)

Day 4 Rolling Coast - 75.56 Miles/3,001ft (Ride Plus accommodation for 1 Cyclist)

Mandeville - Kingston $344 usd

Day 4 Rolling Coast - 75.56 Miles/3,001ft (Ride Plus accommodation for 1 Cyclist)

Day 4 Rolling Coast - 75.56 Miles/3,001ft (Ride Plus accommodation for 1 Cyclist)

Day 4 Rolling Coast - 75.56 Miles/3,001ft (Ride Plus accommodation for 1 Cyclist)

Kingston - Port Antonio $353 usd

Day 5 Cultural Explosion + Accommodation-

Day 4 Rolling Coast - 75.56 Miles/3,001ft (Ride Plus accommodation for 1 Cyclist)

Day 6 The Century + - 124.42 Miles/4,281ft (Ride Plus accommodation for 1 Cyclist)

Portland $386 usd

Day 6 The Century + - 124.42 Miles/4,281ft (Ride Plus accommodation for 1 Cyclist)

Day 4 Rolling Coast - 75.56 Miles/3,001ft (Ride Plus accommodation for 1 Cyclist)

Day 6 The Century + - 124.42 Miles/4,281ft (Ride Plus accommodation for 1 Cyclist)

Port Antonio - Montego Bay $382 usd

Cycle Group Special

Cycle Group/Club of 15 Cyclists Special Package

 

Exclusive Group Perk:

Book 15 full tour + accommodations for your club, and you’ll receive: 

  •  2 FREE full tour admissions
     
  •  1 FREE double occupancy room
     

That’s added value — perfect for club leaders, giveaways, or extra guests! Reserve your spots now!
Space is limited, and the road is calling. For booking and further inquiries, contact us today and let’s get your club rolling into the ultimate experience.

Payment Plan Options

Shop Ride Wear (DJBB 2026 Jersey)

DJBB 2026 Jersey

Our DJBB 2026 Jersey is now available. $110 usd. Asian fit, order one size up. Please indicate in the notes when ordering your size and name to be printed on the back. Jersey orders are closed for our 2026 Tour. 

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Frequently Asked Questions

Please reach us at discoverjamaicabybike@gmail.com if you cannot find an answer to your question.

No. You can do any one or multiple days you want to. We think that most participants will want to choose the 6 days tour to ride through all 14 parishes and finish the full challenge. If you are unable to, however, each day is a challenge itself an allows you to see the best spots in Jamaica on a bike


The ride will have police escorts, to ensure that we have uninterrupted passage. Also we will have health personnel accompanying the ride, as well as support vehicles and a mechanic


Yes. We will have Tours available for family and friends who are not riding and they can be transported from start to end destinations if desired. You can also have your friends and family stay in the your favourite Jamaican destination until you have finished the ride and then rejoin them to complete your vacation


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