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Renting a car and driving in Cuba is not as difficult as some comments may lead you to believe.
The road from Santiago de Cuba to La Gran Piedra is safe as long as you drive with caution as you would on most Cuban roads.
There are adequate highway signs while travelling between major cities, e.g. from Santiago de Cuba to Baracoa.
There are certainly difficulties in driving in Cuba but with planning and common sense you can handle them.
The first hurdle to get over is that you can not use a GPS in Cuba and you will need to use both map reading skills and develop the knack to locate highway and street signs. However, Smartphone GPS does work in Cuba (April 2015).
While many of the guide books have city maps they usually do not show the one-way streets and these are numerous in Cuban cities. The guide books assume you are a pedestrian. The one way streets make sense given the narrowness of the streets designed not for cars and trucks but for horse carts. When planning your routes inside cities knowing ahead of time the one-way streets will reduce frustration and make your experience less stressful.
Knowing these things in advance allows you to use strategies to make it all workable.
Recommendations on maps:
1) download the app CityMaps2Go by UlmanPro. The maps are highly readable on an iPad. Once you have the app download the entire set of maps for Cuba. You can zoom in right down to street level which makes this very useful. These maps show the one-way streets. When you are in Cuba and you want to reorient yourself you can open up the app and zoom into your present location and then figure out how to get from where you are to where you want to be. This is also very useful when you are walking around.
2) some will remember in the old days you used to get trip maps from your motor association with a strip map for each segment of the trip. You can create these yourself by using an online map and then by whatever means copying an onscreen segment and either printing it or copying it into a document file, e.g. use PrintScreen or equivalent. An online map suggestion is www.OpenStreetMap.org. You can search for a city in Cuba and zoom in or out as need be to navigate to another location. These maps show one-way streets. I used it to provide segment maps for each section of a trip starting with my location inside a city until arriving at a new location in a different city, e.g. From a Casa in Santa Clara to a Casa in Santiago de Cuba. This can be a lot of work but you quickly get the hang of the the process and it becomes routine. You can print out each day of travel and put them in a binder. When you get to Cuba with your printed out map sets you will quickly understand the value of the work you have done.
3) when you get to Cuba you will want to find an Infotur office and buy a copy of the Guia de Carreteras de Cuba which costs $7 (7 CUC). The is a map book with a ring binding which has both highway maps and city maps. It shows all the small towns and helps you gauge progress as you travel. It also shows the distances between locations on the maps so you can gauge how far it is to the next identifiable town or city. You won't find it outside of Cuba and so buy it when you arrive. There are usually Infotur offices at airports as well as in the larger cities.
4) Infotur offices in larger cities usually have a free city map of the particular city which is useful to have primarily for walking around and locating things you want to visit. The staff are usually very knowledgeable about local things to see and the operating hours, costs, etc.
5) street signs in Cuba tend to be on the side of buildings and these may not be readable as some are not maintained, have been painted over, or vandalized. Usually they are not readable from a car unless you stop and look. Even in walking the signs can be difficult as they are usually only visible in the vehicular direction of travel on one-way streets.
6) you will likely get lost a few times. Use the Guia and iPad maps to figure out where you are and where you need to go. You need to allow time in your travel estimates for getting lost as well as for the other noted occurrences which all act to slow you down.
7) Smartphone GPS works in Cuba, usually locking on to at least 15 satellites. Returned (April 2015) from a 30 day trip driving solo around western and central Cuba. Used the brilliant free android satnav app OSMAnd, together with the downloaded OpenStreet map of Cuba, on android phone to navigate over 2,200km, both in car, walking around the countryside and the streets of Havana. Prepare the map by locating and saving all planned destinations and points of interest, adding more during the trip. The app gives both visual and verbal directions, warnings, including lane changes, one-way streets, speed limits and cameras. Take a dashboard clip and in-car charger.
Recommendations about rental cars:
1) the roads in Cuba are well noted for their potholes. While in driving you will miss most of these, you will still hit some. When you examine your rental car take a very good look at the tires and make sure they are in good condition. In addition, have them show you the spare tire and ensure that the jack, wrench, etc are all there.
2) you may not want the newest and shiniest rental car. Given the road conditions you will end up with many bumps and scrapes. A car with a history already of bumps and scrapes means you are more likely to get your deposit back. Ensure when you examine your rental car they note all such bumps and scrapes.
3) rental cars require you to use especial gasoline (high octane). Note well that this is not available at all gas stations. For example, there is one in Baracoa but not another one until Guantanamo. This is not obvious as the various maps show gas stations but not whether they have especial or not. Knowing the travel you have ahead of you it is best to fill up when you can. If you ask at the gas stations which do not have especial they can direct you to a station that does.
4) a quirk of car rentals in Cuba is that it is based on you returning the car empty. Of course you don't do this but that's how it works. You do not get a refund for any gas left in the tank. When you pick up the car they will charge you for the gas that is in the tank. The tank may or may not be full.
5) it is advisable to arrange secure parking for your vehicle at each location where you are staying. A watcher or a garage can be arranged for about 2 or 3 CUC per day. You should not assume that a Casa Particular can arrange parking. You should check the descriptions closely and ask about parking before booking.
Recommendations about driving:
1) for a whole host of reasons travelling in Cuba takes longer than in more developed areas. You should not expect, for example, to achieve 80 kmph on a posted 80 kmph highway. Most roads are congested with slower moving traffic primarily bicycles, horse carts, and small motorcycles. Most roads are two lane and passing slower moving traffic is an art form you will perfect out of necessity. As well, there are numerous no passing sections on curves and in built up areas. My experience is that you effectively achieve about 65 kmph on an 80 kmph posted highway.
2) in addition to potholes you need to be wary of numerous farm animals wandering onto the road. This ranges from goats to pigs to horses to cattle and to oxen.
3) most Cuban roads have trees along both sides of the road and part of the road will be in shade depending on the time of day. This makes discerning potholes difficult and you will need to slow down and exercise caution.
4) road markings may be non-existent or well faded especially lane markers in cities. You will need to have a good sense of where you are on the road to approximate where you should be as if there were markings.
5) the roads are heavily policed and speeding is not advised. They tend to be on motorcycles hidden off on the side of the road (usually on the shady side of the road). In many places there is not a sign indicating the change in speed limit and so you need to recognize when you enter a town and drop to the expected speed. You can usually take the hint when you see the town name sign and conversely when you see the exiting the town sign.
6) Many cities in Cuba have ring roads which allow you to bypass the city. Usually on the main highway just outside the city there will be a traffic circle which connects to the ring road. They call the ring roads Circunvalacion and look for this on the maps. It is easy to miss these when driving and then you’re on your way through the city. You should plan your route to find the bypass for that city and save time.
7) Given the road hazards already described, you should not consider driving at night. We usually planned our travel early in the day and before the afternoon heat so we arrived and were still able to enjoy exploring our destination of the day.
8) Roadside puncture: a couple or family may await your passing car to create a puncture. VERY soon they will arrive to offer assistance. Perseverance and friendliness win the day. Even if they cannot steal the luggage, now safely locked inside the car, one member can puncture the spare tyre while you are distracted so that now the only course of action is to accept a lift with both tyres to a garage for an inflated repair or replacement bill. One such family: 2 men, 3 women and a child operate 4km north of Moron (yes Moron !) which is on the tourist route from Cayo Coco back to Havana. Another recently reported site was close to Santa Clara. Sit in the locked car and sound the horn till they go away. Take their vehicle registration number. Photographing the family and their car ‘helping’ during the process may well deter them from going through with the scam and at the very least, widespread publicity with the photos could be helpful.
Some will wonder why drive anyway.
We’ve done the Viazul bus approach in the past but we wanted the flexibility a car gives you. You also get to see the real Cuba rather than just through a bus window assuming you’re not snoozing or reading on the bus. In my experience you will also get from city to city faster than the bus which seem to make frequent stops. As well, exiting a bus station can in Cuba can be like running the gauntlet to escape the hustlers.