Our best driving experience was along the Leeward Road (Caribbean side) from Charlotteville to Castara. The northernmost bit, from Charlotteville to L’Anse Fourmi, is officially unfinished, but only about a third of it is still unpaved. The rest is passable for any 4WD, though it’s probably smart to ask someone first if there’s been a lot of recent rain. For us, it was the most pleasant drive of the trip—no traffic, new pitch, and wider passes. We made numerous stops to admire the tiny roadside waterfalls (yes, waterfalls), unusual wildlife, and fantastic views where the ocean bled into the sky, creating a hazy blue infinity beyond the lush green bounds of the island. When passing through L’Anse Fourmi and past Bloody Bay, keep a close eye out to avoid the turn back to Roxborough, on the other (windward) side of the island through the forest preserve. You’ll want to keep hugging the coast and stay firmly to the right, making sure you’re headed toward Parlatuvier. It’s easy to take the wrong turn here, so don’t be afraid to stop and ask.
Once you’ve passed L’Anse Fourmi, you’ll drive through Parlatuvier, a small fishing village with a pretty beach. Head a little further south, keeping an eye out for the signs to Englishman’s Bay (if you’re going south, this will be a small right-hand turn). This, in my opinion, is the most beautiful beach on the island. After parking and walking through a tiny cluster of souvenir stands, past a small café, you’ll enter onto a sweeping expanse of golden sand, surrounded by swaying palms and rocky cliffs mottled with small cave-like inlets. The water is a deep turquoise, crystal-clear, with one small boat rocking gently offshore when we visited. The beach was utterly quiet, with no more than 10 or 20 other people all along its length. In the tiny entrance area, visible only from the stretch of beach directly in front of it, a few beach-chair-and-float-rental employees sat lazily under a covered patio, smoking a joint, and café staff sat fanning themselves in the quaint, open dining area. We stopped by on our last day and determined that we’d spend at least a few days here on a return trip, snorkeling or just relaxing in the beautiful surroundings.
Since Englishman’s Bay is such an easy place to settle into and never want to leave, you might want to first head all the way down to Castara, one of Tobago’s most charming fishing villages, a feast for the eyes whose buildings spill down a hillside to a lovely beach at Castara Bay. There are numerous accommodation options here, mostly in the form of small inns and self-catering apartments, and you couldn’t find a prettier, more serene setting. Restaurants serving up local fare make this a perfect stop for lunch. As we didn’t spend much time in Castara, read about it at (you guessed it) My Tobago. Check out restaurant options here.
If you’re looking for the Caribbean beaches you’ve seen in magazines and guidebooks, this is the side of the island to explore. It’s quieter, slower-paced, and so chock-full of amazing scenery, it turns the usually nerve-rattling task of driving on Tobago into a whole new sensory experience.