Exploring the oldest protected rainforest, the soft coral reefs, and the all-night fêtes of the Caribbean's farthest reaches

By Bucky McMahon

Pete Seaward/Tony Stone Images

Pigeon Point, a Tobagonian megalopolis

True to his promise, we soon struck an old Carib hunting track that took us, with many serendipitous forkings, deep into the Forest Reserve, the oldest protected land in the Western Hemisphere, a living ark of species carried out to sea when Tobago broke away from the South American mainland at the end of the last Ice Age. The trail seemed both seldom traveled and well trodden, like a carpet path scuffed through the rooms of a long-abandoned home. We hiked up steep switchbacks between ancient samaan and banyan trees and clambered down gullies where razor grass spikes up high along the trail and mango and cashew trees form a fruitful canopy.

When you think of Trinidad and Tobago (or T-and-T, as the southernmost republic in the Caribbean is called for short), you probably think of a crowded melting pot of humanity, of steel-drum bands and human peacocks parading in a carnival bash that rivals Rio's. But that's Trinidad, really. Postage-stamp-size Tobago (26 miles long and seven miles wide) lies 21 miles to the north across a deep-water gulf. It's much less populous (about 50,000 Tobagonians compared to nearly two million Trinidadians) and in large part pristine. The island has its own party spirit, to be sure: "Liming," or hanging out with friends, and "wining," the voluptuous dancing that's the ultimate goal of every good lime, are the two slang terms every visitor learns. Tobago's nightlife—and most of its tourism—are concentrated in the developed western tip of the island around the Crown Point resorts and the nearby town of Scarborough.

Tourism, however, is beginning to take a stronger hold over tiny Tobago: Four new megaresorts are breaking ground in the west end, while the wilder east-end coastline is sporting a growing number of green, grassroots-style accommodations. These changes promise to restore to the island its precolonial title as the most coveted real estate in the West Indies—with tourist dollars supplanting sugarcane—but right now the renaissance is still in its infancy, and travel is open to interpretation as never before. You can invent your own roving itinerary, circumnavigating by jeep or bike or kayak, camping on the beach or overnighting in the host homes you'll find in most villages just by asking around. Or bed down in the small eco-lodges that are springing up in lush coastal locales with some of the most diverse diving in the Caribbean—from shallow coral gardens to high-speed drift diving—in addition to beguiling beaches, and easy forays into the rainforest. Just don't forget to mark your trail, or the strangler vines and primeval tree ferns might swallow you up and never spit you back out.

Caribbean Bays

David Sanger

Pigeon Point dive boat

Well, let 'em stay put. As far as you're concerned, it's open season on the rest of the island. Just follow the coast east: When you come to Castara Bay, you've found the best of Tobago, I think. Here tourism has established a light and graceful beachhead and the residents, nourished on fish stew, fried green bananas, and cod, routinely live to be 100. Or so the story goes. It's easy to believe. Castara Bay's beach is a perfect fingernail crescent of coarse yellow sand, bisected by the mouth of a mountain stream and half-shaded by trees through which flit flocks of wild blue parrots. The forest proper begins hard against a cricket ground, where a ten-minute walk on singletrack leads to a waterfall and a chilly pool. An ambitious hiker could continue up the steep 2,000-foot Main Ridge and clear on to the other side of Tobago without ever leaving the shade.

In the dry season (December to June) Castara Bay is superlatively clear, with a healthy coral reef beginning about 50 yards offshore. You can follow the rocky headland as far as mask and fins will take you, exploring caverns and deep stone pools flush with silversides, parrot fish, and the occasional solitary barracuda, while pelicans plunge in to pick up lunch right beside you.

Castara makes a pretty darn paradisiacal (and very affordable) base camp, ideally positioned in the middle of the north coast for excursions to any other part of Tobago. Keep an eye peeled just east of Castara for the old wooden sign marking Englishman's Bay, hidden from the paved road by deep bush. A venerable stand of bamboo some 60 feet tall shades the dirt track to the strand, which is exquisite and utterly undeveloped, except for Eula's refreshment stall (try the mango smoothie).

Just to the north, past pint-size Parlatuvier, the main coast road turns south to cut across the island, leaving behind a ragged paved spur perfect for rambling up the north coast. Above Bloody Bay, accessible only by hiking a near-vertical trail down to the mouth of the aptly named Dead Man River, this aggregate of potholes becomes a simple, brain-rattling dirt track. The next ten miles are true coastal wilderness; though a four-wheel-drive can tackle the "road," it deserves to be mountain-biked, or better yet hiked, to savor the view (from about 1,000 feet up) of the wind-tossed sea and rugged offshore rocks.

When you emerge from the backwoods you'll be in the easternmost point of civilization, Charlotteville, on Man O' War Bay. This is Tobago's main fishing town and a great place to charter a pirogue to fish for mahimahi and marlin or to scuba dive at those boulders, known as The Sisters, you spied way out to sea on the trip into town. The vigorous colliding of Caribbean and Atlantic currents attracts barracuda, dolphins, kingfish, and whale sharks to this end of Tobago. Man Friday Diving makes daily excursions to sites like London Bridge—a natural stone arch you can dive through—and the wave-washed seamounts around St. Giles Island. The outfitter also rents one- and two-person sea kayaks for exploring the deserted coast back toward Bloody Bay or on around the nearly uninhabited eastern point. A sandy path at the east end of town climbs among pink and yellow houses and then descends a hundred concrete steps to Pirate's Bay, the last idyllic beach on the edge of the Antilles. Next stop, the coast of Africa.