Every Caribbean island has its own personality, despite sharing features like pristine sugar-sand beaches, magically translucent azure waters and gently swaying palm trees, but Trinidad and Tobago makes for a superior standout destination that goes beyond the rest. Positioned just off the South American mainland, this twin-island republic has all the ingredients to be expected of a luxury holiday, as well as some incredible natural features that build an itinerary with a graceful and relaxing pace, ensuring a memorable Caribbean getaway unlike any other.

Driven by an emerging industrial center, Trinidad is the larger and busier island with cultural activities and historical landmarks found in abundance, as well as the nation’s best restaurants and nightspots. On the other hand, Tobago is an undiscovered paradise that’s packed to the brim with rainforests, savannahs, waterfalls, reefs and undeveloped beaches that give way to an abundance of unforgettable outdoor adventures. Our Trinidad and Tobago destination guide will lay out the rich rewards of the islands, which effortlessly blend urban and rural Caribbean culture.

The Villas at Stonehaven

Where to Stay

Tucked away within the serene nature of Tobago, the Villas at Stonehaven are the island’s hidden paradise. The gated hilltop property is set upon nearly 14 acres and offers spectacular sweeping views over Stonehaven Bay and the lush tropical landscape. The hotel has 14 exquisite stand-alone villas, each equipped with their own shaded verandahs, plunge pools, hot tubs, sundecks and al fresco dining spaces. Decked out in a beautiful French colonial style, the villas are positioned within their own tropical oasis to ensure maximum privacy and seclusion for an undisturbed stay, perfect for a secluded romantic getaway or intimate family vacation.

While tranquility is certainly a big theme around here, the property is also adjacent to a 260-acre protected forested bird sanctuary and within walking distance to the pristine white-sand beaches. It’s also a short drive away from nearby tennis courts, two 18-hole championship golf courses and downtown Crown Point, the focal point of the island’s dining, shopping and nightlife scene.

Our Trinidad and Tobago Destination Guide also includes a Luxury Hotel Guide with an expanded list of accommodation across the islands.


Where to Dine

Hidden within the Ellerslie Plaza in Port of Spain, Aioli is on a mission to bring European food culture to Trinidad and Tobago. The relaxing atmosphere is apparent from the moment you step inside, where you can choose between the inviting lounge with décor that will blow you away or the covered outdoor patio for a tranquil dining oasis.

Chef Johnny Aboud leads the way with his inventive local cuisine that incorporates the flavors of the Mediterranean with entrees like the Butter Poached Salmon Fillet served with shaved artichokes and spinach, or the Roasted Lamb Chops with couscous, roasted eggplant and heirloom vegetables. The sophisticated menu is accompanied by a vast selection of international wines, expertly selected pairings and luscious dessert offerings.

Our Trinidad and Tobago Destination Guide includes a comprehensive Restaurant Guide for a full list of gastronomic treats across the islands.

Trinidad and Tobago

What to Do

No trip to Trinidad and Tobago would be complete without a visit to Port of Spain. The atmospheric capital is full of vibrant life with its bustling markets and shady squares, whereas the outlying Woodbrook district hosts some of the country’s top restaurants, bars and nightclubs. The city kicks it up a notch during the electrifying Carnival, which is easily one of the wildest celebrations across the Caribbean and attracts thousands of visitors each year for its high-energy parties and vivid cultural events.

On the other end of the spectrum, Tobago is a tropical paradise that’s filled with adventurous outdoor experiences, including birdwatching, turtle watching, first-class diving, waterfall swimming and kayaking. Tucked between the lush rainforest and eternally blue waters of the Caribbean, Englishman’s Bay is the crescent-shaped stretch of coastline that will exceed all your beachside needs. In addition to great swimming and snorkeling, the virtually untouched beach is a nesting ground for leatherback turtles and a popular mooring area for yachts.

Elsewhere, you’ll also want to check out Fort King George, a beautifully-preserved fort that dates back to the 18th century and retains its original colonial grandeur. Explore the rows of cannons that once guarded the coastline before exploring the museum that features Amerindian artifacts, recovered military relics, artillery shells and colonial-era documents.

What to Pack

The white-sand beaches and idyllic blue waters of Trinidad and Tobago certainly live up to the Caribbean expectations, while lively island hangouts and a plethora of outdoor activities place an emphasis on day-to-night outfits. Between oceanside dining and long walks on the beach, this Onia Vacation Linen Shirt offers a lightweight and breathable material, as well as short sleeves, to stay cool, even on the warmest of days.

If sneakers aren’t your thing but you don’t want to go overboard on fancy footwear here, these Want Les Essentiels Heras Leather Espadrilles evoke an affable European style this side of the pond. Blending canvas with leather marrying comfort with versatility. If you’re a lively soul or down for a tranquil dinner, seersucker pants for an island getaway on Turks and Caicos are both a practical and sophisticated option.