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If you plan to stay in San Juan only, you don’t need a rental car as the bus system is really good and cheap (75c a ride). However, if you want to explore the island (which you should if you have more than a couple of days!), renting a car is good value, especially for families. There is limited inter-town transportation so a car is the only way to get around. All the major rental companies such as Avis, Hertz, Budget etc operate on the island so take your pick! Some hotels offer free parking but most don’t so be prepared to pay for parking.
Out on the island travel parking is not a problem. The small bed and breakfasts like tressirenas.com in Rincon or rainforestinn.com in the El Yunque rainforest all have parking available for their guests. It is only the major resorts like the El Conquistador or Paradisus which charge for parking. If you want to visit Culebra or Vieques as part of your vacation rent a car from Avis or L&M car rentals as they will let you drop the car off at the their offices in Fajardo to take the ferry or fly on saving some money.
Please rent a car and see the island!
Having a car while staying in Puerto Rico gives you an unimaginable advantage. The fact that PR is only 100x35 miles makes it extremely easy to see almost the most of the island in one trip of about a week or two. There is so much to see and do out of San Juan that it is a shame to come here and only stay in the city. Coming here and not leaving San Juan isnt even grounds to say you came to Puerto Rico, because the real beauty is the secrets you will uncover out on the road through the mountains or finding a secluded crystal clear beach that you can be king or queen of for an entire day.
The road conditions in Puerto Rico range from poor to great. Most of the main highways are in great condition, while some of the lesser roads are in very poor condition. Side streets in major cities tend to be in fair condition. You will notice a great deal of cars on the side of the road with flat tires; this seems to be a problem in Puerto Rico! Make sure you know where your spare tire is, and how to put it on. If you don't speek Spanish well, you may have difficulty talking to your rental agency's Roadside Assistance representative. If you need a flat tired repaired, often times you will find tire changing/repair trucks on the side of the road - just look for an old truck and a pile of tires!
The signage on all roads and highways tends to be poor. Roads and highways will change names as you go, without notice. Street corners are poorly marked. One way streets are often not marked. Navigation can be very difficult at times - keep that in mind, and be prepared to be frustrated at times with getting from A to B.
You have probably heard that the drivers in Puerto Rico are crazy and that it isnt worth renting a car because it is too risky. The drivers here are aggresive, but you notice that things calm down as you get away from the city. San Juan, as New York or Boston, is a large city area with people in a hurry and driving badly. You just have to keep an eye out for yourself and the ones around you and you will be fine. You'll learn that Puerto Rican drivers aren't even slightly courteous; they are out for themselves only. They will cut you off, pull out in front of you, and stop in middle of the road for no reason. You have to keep your eyes peeled at all times. Sooner or later, you will find you are driving just a "crazy" as the ones around you!
Another thing to note: on the freeways, the rules are different than they are in The States. The lanes are different; on the mainland, the left lane is for passing and fast drivers only, while the slow traffic stays right. In Puerto Rico, the slow cars can be in any lane, and don't expect them to move if you drive up on them! Puerto Ricans only change lanes if they are passing someone, and when they are coming up on someone they expect that car to stay in it's present lane. So, rule of thumb, it doesn't matter what lane you drive in, just don't change lanes unless you are passing someone!
In Puerto Rico, most of the people work in the city. This is way the traffic from 6:45am-8:45am is heavy on all roads heading towards San Juan. From 12pm-1:30pm, traffic is heavy in the city area because people are on their lunch break. From 4:30pm-6pm, traffic is heavy in all roads leading out of the city. Any time not mentioned is typically slow and you wont have much to worry about.
There are plenty of toll stops when on the highways, particulary in between San Juan and Ponce. Make sure you have plenty of small bills and change with you when making a long drive. The tolls typically aren't expensive; the most expensive toll is the bridge to the Airport, $2.00, while the rest are from $0.35 to $1.50.
*** Remember, if driving at night, from 12:00am-5:00am you do not have to wait for the red light to turn green, you can treat it as a Stop sign.