We had been up since 4am, spent five hours on airplanes, and lugged heavy bags full of snorkel equipment through two airports, so the 15-mile drive from our car rental agency to our hotel seemed like a piece of cake. Not so. As soon as we pulled out onto the main road from the Crown Point area, it became clear that driving on Tobago is a harrowing experience, with vaguely followed traffic laws and winding, narrow roads. Local drivers tear around each other within inches of oncoming traffic; in town, they stop in the middle of the road to run to the roadside stands, and locals meander across the street through spaces that hardly look wide enough to accommodate a small motorcycle. If you’re an American, you’ll have to get used to driving on the left-hand side of the road on top of all that. But if you can take a deep breath and take the plunge, it’s worth it for the extra flexibility (easy for me to say, however, since I’m unable to drive a standard and therefore left the driving up to my mom).
There are several reliable car rental agencies near the airport, from the recognizable Thrifty to locally run agencies. We followed the advice of My Tobago and rented from Sheppy’s. Colin "Sheppy" Shepherd is a full-time policeman on Tobago who also runs a car rental business, and he was nothing but friendly and helpful every time we spoke with him, before and during our trip (he responds quickly to email too). His rentals offer great value for money—we rented a standard-transmission soft-top Suzuki Samurai for US$265 for the week, and that included additional taxes, insurance fees, and a cell phone rental. Sheppy picked us up at the airport, we had no trouble with the car all week, and returning it was a quick and easy process. I would absolutely recommend renting a car through him and will rent with him again when we return to Tobago.
Directions can be vague on the island, and maps are not very detailed, so be sure to ask someone to explain directions (a hotel staff member, store employee, or your car rental representative—Sheppy gave us really helpful directions to a number of places we asked about). They’re sure to include more landmarks than street names, so designating someone in the car to navigate is a must. Otherwise, you’ve got to just throw caution to the wind and get on the road. The Windward Road in particular is quite a journey, especially without power steering—it’s less than 30 miles from Crown Point, at the south tip of the island, to Charlotteville at the north, but plan for the drive to take 1.5 to 2 hours, as it’s all steep inclines and blind curves. Break it up by stopping at the many beautiful beaches along the way—Barbados Bay, King’s Bay, and Tyrrel’s Bay, among others—all accessible by parking and walking from the road.
Unless you’re feeling really confident on the road, try not to drive after dark. Roads are not wonderfully lit, and adding poor visibility to the list of driving hazards might be a little too much for the hapless tourist not used to the roads. If you do need to go anywhere after dark, hire a taxi, or, for short distances, get out and walk.
See my "Driving The Leeward Road" entry for an account of the most beautiful drive on the island.