Driving in the cuban countryside is not for those with weak hearts. Cuban roads are pot holed, road markings are limited at best. Detailed road maps are next to non existent and not nececessarily up to date when available.
As for renting a car, it would be best to do a fly and drive package. There are some available. It would be cheaper to do it ahead of time.

We've driven in some pretty hairy situations, the worst being remote mountain regions of Portugal: no guard rails, barely wide enough for two, badly broken pavement where it exists, tailgating delivery trucks while you wait to pass a donkey-cart with oncoming traffic screaming by so close you think you will lose your mirror, and lots of potholes. So faintness of heart is not an issue.

Suggested rental agencies from Canada?

I have rented a car and driven in Cuba and although it is not difficult, you need to be sharp and aware of exactly what you are doing. Also good if you can drive a standard shift.

The best rentals I found are from.

Havanautos
Central de Reservas: 23-9833 or 24-0647
Asistencia tecnica: 24-8176/77
Email: lamas@cimex.com.cu
www.havanautos.cubaweb.cu

I walked in and rented in Havana after my arrival.

As to maps, ask Havanauto for the Guia de Carreteras, a supurb 23 page map book given to people who rent from them. It has great road maps of Cuba. The country is divided into 23 sections and each double page is for a single section. There are also city maps at the back. This book is FREE when you rent from Havanautos. Do NOT let them tell you there is an extra charge for this. It's included. But you can't blame them for trying

Also carefully note ALL scratches and small dents and dings on the car. You WILL end up paying for them when you return the car if they are not noted on the rental contract BEFORE you accept the car. Check the spare tire, jack, and wiper blades as well. They will check when you return the car. Just basic common sense and being a cautious consumer.

The main central highway (A1) or (A4) in Pinar del Rio province, is quite good and is a 4 lane divided highway. But beware it is also used by any vehicle, from horse drawn carts to bicycles. From Pinar del Rio to Sancti Spiritus it is quite good, but east of Sancti Spiritus it begins to be less well kept. Note that this report is as of my last drive in January 2000.

BE VERY AWARE OF THE FOLLOWING taken directly from The Consular Affairs Bureau of the Department of Foreign Affairs and International Trade, Government of Canada website.
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http://www.voyage.gc.ca/destinations/menu_e.htm
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Road travel can be hazardous. Bicycles, pedestrians, and horse-drawn carts use the middle of the road and do not readily give way to oncoming vehicles. Drive defensively at all times. Night driving is not recommended as few roads or city streets are lighted. Vehicles, bicycles, carts, etc, rarely have proper lighting. Many vehicles are old and poorly maintained. Inoperable vehicles are often left on the road until repaired. The Autopista Central (national highway), which runs the length of the island, is generally in good condition. Other roads are generally poor.

Car rental insurance differs from that in Canada. If you are in any way at fault in an accident, rental agencies will nullify coverage and Immigration officials will prevent you from leaving the island until damages are paid. Under Cuban law, those involved can be detained until the case is resolved in the courts. Depending on the severity of the accident, resolution can take from five months to a year.

An International Driving Permit (IDP) is required. The IDP is a special licence that allows travellers with a valid Canadian driver's licence to drive in over 160 countries without a specific test. The Canadian Automobile Association (CAA) is the sole issuer of the IDP in Canada. Contact your local CAA office to pick up an application or have one mailed to you; you can also download the application from the CAA Web site (CAA). An IDP is valid for one year from the date of issue.

That it as far as I know. Gas (as of October 2001) is around 75¢ US. per litre in Havana and is a bit higher in the countryside. You CAN get black market (market negro) gas at around 50¢ per litre, but beware of what you are risking if you take this source. I personally don't think it worth the few cents savings.

mis dos centavos
Steve