This Is the Caribbean’s Chillest Island

Perhaps you’ve heard of the Caribbean, the beach-filled, sunny, and resort-laden destination for cruise ships and tan-seeking vacationers? Maybe you’ve considered being one of those vacationers?

Here’s the upside: It’s easy and affordable to get there. And then the problem: Most popular spots within the Caribbean—like Turks and Caicos and Saint Thomas—are perpetually overrun by tourists (like you).

There is, luckily, an alternative to packing yourself into a Caribbean beach filled with hundreds of other sunscreen-soaked Americans. Let me introduce you to Tobago, the lesser-known sibling island to Trinidad. It’s the place you go when you want to sit on a quiet beach in the Caribbean and not be surrounded by yachts or spring breakers. From a lot of major cities, there’s a direct flight to Trinidad; from there, just hop on a quick 15-minute flight (very cheap and leaves every 30 minutes), and you’re in Tobago.

The island is intimate, the culture is chill, the locals are friendly, and it’s very easy to get around. Super developed, Tobago is not. Compared with its Caribbean cousins, the place is bare of malls and brand-name hotels. You’re coming to Tobago, instead, because you’re looking for unadulterated nature and a slow-going place to laze on the beach with friends.

And because it’s not yet a tourist town, the food caters to the locals—meaning you’re not getting watered-down resort fare. You’ll find spicey and chile-laden goat curry spots, as well as Italian food in tree houses, excellent takeout kebab, and freshly grilled seafood served beachside.

Tobago is so low-key that there are essentially no travel books available on the country. So here’s your beginner’s guide to the Caribbean gem.

Where to Stay

There are some hotels and resorts on the island, but most are still pretty rudimentary. Your best bet for comfy digs is to rent a condo or a house on HomeAway or VRBO, which will likely be both less expensive and more comfortable than the area hotels. Go for the properties right on the beach.

When to Go

Like most beach vacations, Tobago is best experienced in five days to a week. Lucky for those who have to endure chilly winters, the best time to visit is between January and March, when the weather there is temperate and not too humid.

What to Do

Spend a chill day at the beach
The beaches in Tobago are pristine—you can’t go wrong making a pit stop at whatever beaches you spot in your area. The most popular is Mount Irvine Beach, adjacent to a golf course and known for its excellent surfing. Englishman’s Bay is another good option, a crescent-shaped beach where you can spot leatherback turtles chilling on the sands. If you’re looking for hidden treasure, drive 45 minutes up to Castara, a tiny but stunning spot with gorgeous views of the forests below.

Visit Pigeon Point Heritage Park
This family-friendly enclave offers multiple activities in one spot—there are cute little shops, lots of great cafes for snacking, and a lifeguard-tended beach area, complete with a highly Instagrammable thatched-roof jetty.

Go around Buccoo Reef
Book a glass-bottom boat from Pigeon Point Heritage Park, and you can spend a day going around Buccoo Reef, a designated marine park containing hundreds of colorful species of fish and coral (Jacques Cousteau named it the third most spectacular reef in the world). There’s loads to see, so it’s the ideal spot to go snorkeling. Make sure your boat makes a stop at the surreal Nylon Pool, a one-meter deep enclave in the middle of the reef whose sheer waters and white sand prompted Britain’s Princess Margaret to name the pool after her nylon stockings.



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