Photo of two touring bikes parked by a beach bar in a tropical-looking location.

No Stupid Questions: How To Plan Cycle Tours In Unusual Places (Like Jamaica)?

A reader writes:

I am a new subscriber to your mailing list as I hope to get into travelling by bike. I was wondering if you have any insights about biking in Jamaica?

While being there I will able to do both short and very long rides. So my questions are: Is it safe? Is Jamaica friendly to cyclists? I have a gravel bike and wondering what kind of wheels I may need in that country. Any route suggestions?

Anything that you can provide I will greatly appreciate it.

This is an interesting question for a couple of reasons.

First, for a personal reason: for years I’ve been dreaming of an unorthodox cycle tour of the Caribbean involving bikes and boats, first blogging about the idea back in January 2014 – and now, here you are, planning something very similar!

Second, for the more broadly relevant reason that it could be rephrased thus:

‘I was wondering if you have any insights about biking in Unusual Country X? Is it safe and friendly to cyclists? I have a bike and am wondering if it’s suitable. Any route suggestions?’

So let’s see if a universal answer can also help you with your questions about cycle touring in Jamaica…

For anyone planning on cycle touring in any specific part of the world – whether a country, region, state, or any other named and recognisable area – I first suggest looking at (CGOAB).

The site was launched at the turn of the millennium to host the founder’s own cycle touring journals, and, as websites tended to do back then, grew from there. A quarter-century later, it is the largest and longest-lived repository of cycle touring journals on the internet. It’s run by a hobbyist, funded purely by donations, and contributed to by people with no interest in becoming “influencers” or getting famous or making money. In other words, it’s about the most objective place to read subjective cycle touring journals that you could hope for.

In your case, I filtered the CGOAB journals by location to Jamaica and indeed found a total of three trip reports, posted between 2013–2019.

On closer inspection, the first was incorrectly categorised and actually took place somewhere else, and the second involved a single 16-mile ride to and from a cruise ship… leaving one bona fide cycle touring trip report from Jamaica.

The point here is that wherever on Earth you can imagine going cycle touring, it’s almost certain that someone else will have beaten you to it, written about it, and posted the story on CGOAB.

It is a literal goldmine of stories illuminating what to expect, often answering whatever more detailed questions you might have in the process.

Sometimes, however, information can be scant, incomplete, or out of date, or you might on rare occasions find a location on which nothing has been posted at all. In this case, rather than seeing a reason why you can’t or shouldn’t go cycle touring there, instead try thinking of yourself as a pioneer, and part of your goal being to come home with something new to share.

Information on routes and road conditions does seem thin on the ground for Jamaica. So why not shift gears into route design mode? There’s a wealth of route planning and navigation platforms available, of which my personal favourites are (not yet covering Jamaica unfortunately), komoot, and RideWithGPS. Ignore Google Maps’s cycling directions; use the StreetView functionality to inspect road conditions and thus decide what kind of touring bike will be appropriate.

(I maintain an up-to-date list of indispensable cycle touring apps, covering route planning and a whole lot more.)

Incidentally, my advice is to do as much of this kind of research as you need to feel confident enough to pack your bike and go. Planning is important, but too much can in fact be damaging to the spirit of adventure. Remember the three easy steps!

Regarding safety, you should always check the travel advice issued by the government of your home country for a given destination, as this will affect the details of any travel insurance you might need (Jamaica will require a policy covering the U.S. and the Caribbean, for example), and what kind of support you can expect from your home embassy or consulate if things go wrong.

Beyond that, more of my thoughts on safety and security when cycle touring can be found here and here.

Hope this helps!