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Roads are often pretty lousy but there's not much traffic outside Havana (we went west). Accommodations are limited, although we did meet a couple of young ladies from Seattle who were getting by on their own OK. Knowledge of Spanish would be a real asset since there's not a lot of English outside tourist spots. Finding food can be a challenge so eat when you find something. I hope you like beans since they'll be in every meal. Some chicken and pork, not much beef. The ladies from Seattle took old bikes that they had tuned up before they left and that they were leaving in Cuba. I've also sent several bikes to Cuba through someone in the Toronto area. He sends them down with tourists and they don't seem to have any problem getting bikes into the country. If you'd be prepared to take a bike and leave it, he'd have places you could drop it off or, if you're in Canada, he may have a bike somewhere across the country that needs to get to Cuba.
When I say roads are lousy, I mean it. I was clipping along some downhill section at about 45-50 km/hr and realized that there was going to be no road for about 6-8 feet about 20 feet in front on me. Good practice jumping. We also came across a spot where the road was gone but we were able to get through with bikes.
We had a lot of fun and might go back to ride east of Havana. Just realize that although Havana in 1958 was a lot like American cities of that time, there's been almost no new construction or infrastructure except for a half finished freeway that the Russians built. It's an interesting route. Hitch hikers at every overpass or exit and there's even horse drawn carts on the road in places.
Also, recently the couple who run the travelling two website did a trip to Cuba, I think with their little kids in a trailer behind them. Reading up a few months ago about it, it sounded like a fantastic place to tour. Sounds like accomodation is pretty easy to come by, as is food and water on the road. Lots of homestay/B&B-type accomodation with families.
Can't remember any mention of being able to hire a bike there. However, if you pack light (eg just a saddlebag of spare clothes and tools and snacks, staying in accomodation), and take your own road bike, its highly likely you'll be well under your airlines check in baggage limit and so I would just take my own bike. Fit some fatter rubber (28 or 32mm if possible) to smooth out the rougher roads, and pack a spare tyre, boot and tubes, especially if you run 700C, I doubt you'd find many replacements of that there.
I'm looking forward to the trip report
How many drivers does a buggy have?
So let's just say I'm drivin' this buggy...
and if you fix your attitude you can ride along with me.
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