The tour runs from Thursday 29 April to the following week in 2027, opening with an arrival and welcome day in Montego Bay. All flight arrivals and departures should be at Montego Bay Airport, since the tour starts there and ends in Kingston.

Day 1 is the starter: out of Montego Bay's beaches and through countryside to Negril, 44.69 miles with 1,100 ft of climbing. Day 2 is the hard one, leaving Negril and climbing through the hills on the Spur Tree Hill Challenge to Mandeville. Day 3 is a cruise from the Mandeville highlands on winding roads to Kingston. Day 4 follows the rolling coast from Kingston up Jamaica's eastern side, through mountains and coastal views.

What separates this from a resort-based cycling week is the logistics. Routes are police escorted, a SAG vehicle shadows the group, luggage is moved between hotels, and a travel nurse is on the tour. Food stops are Jamaican rather than generic ride fuel.

The operator also takes special requests: for small group tours they will adjust an itinerary around your interests, and .

What's included

- Eight days of supported riding across Jamaica - Police-escorted routes - SAG vehicle support - Luggage transport between hotels - Travel nurse on tour - Hotel accommodation along the route - Jamaican food stops

What's not included

- Flights to and from Montego Bay Airport - Travel insurance - Bicycle hire (not stated as included) - Meals not listed in the tour package - Personal expenses