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The Caribbean’s Best Streets

Sure, the Caribbean has great beaches. But it’s so much more than that. And that’s nowhere more apparent than on the many boulevards, avenues and streets in the Caribbean, where you can spend entire days just hopping from restaurant to restaurant, historic nook to historic nook and local bar to local bar. The Caribbean has some spectacular streets, and we’ve put together a list of our favourites here. What are your favourite streets in the Caribbean? Let us know in the comments section.

Calle Fortaleza — San Juan, Puerto Rico

It gets its name from the oldest governor’s residence in the Western Hemisphere, and this beautiful street is full of shopping, eating and drinking. It doesn’t get much more beautiful than Old San Juan.

Western Main Road — Port of Spain, Trinidad

This is a rather long road, but we’re specifically talking about the stretch that heads through the neighbourhood of St James, dubbed the “City That Never Sleeps.” From roti to rum, that’s 100 percent accurate.

St Lawrence Gap — Barbados

If it’s happening in Barbados, it’s happening here. The St Lawrence Gap is one of the more raucous streets in the Caribbean, and there’s a party atmosphere almost any time of day (along with one of the region’s few 24-hour bars).

Bay Street — Nassau, Bahamas

One of the more famous streets in the region, this is well known by cruise ship visitors and travelers alike. It’s also one of the best places for duty-free shopping around.

Kaya Grandi — Kralendijk, Bonaire

It may not be very long, but it’s not short on charm. The main thoroughfare of Bonaire’s tiny capital is full of terrific restaurants, cafes and shops.

Rue du Commerce — Jacmel, Haiti

Jacmel is the cultural and artistic capital of Haiti, and the historic Rue du Commerce is the place to take in the art, the culture and the soul of one of the most passion-filled cities in the Caribbean. (Make sure to stop at the famous Hotel Florita, above).

The Hip Strip — Montego Bay

Home to the hustle and bustle of Montego Bay, the Hip Strip, also known as Gloucester Avenue, is the most exciting stretch in Jamaica’s major tourism hub.

Calle de las Damas — Dominican Republic

This was the first street in the New World, and among the crown jewels of the beautiful Zona Colonial of Santo Domingo in the Dominican Republic. You’re surrounded by history on all sides.

Rue Jean Calot — Terre de Haut, Guadeloupe Islands

You won’t realize you’re in the Caribbean on this street in one of the most picturesque villages in the entire region. It’s full of delightful restaurants, tiny bars and quiet cafes, with nearly everything in plain view of the sea.

Ashford Avenue — San Juan, Puerto Rico

The Condado neighbourhood of San Juan is perhaps the Caribbean’s capital of chic — and it’s also full of some of the region’s best dining. You can spend a whole day on just a few blocks.

Rue de la Republique — Fort de France, Martinique

Fort de France, Martinique is among the most interesting, cosmopolitan cities in the Caribbean, and the Rue de la Republique pedestrian street is the perfect place to explore the sights, sounds and scents of Martinique’s capital. (Photo: David Giral)

Route 5, Cabarete — Dominican Republic

The Dominican Republic’s bohemian enclave has all the beach bars, cafes and attractions you can handle on its main drag.

Main Street— St Thomas, US Virgin Islands

Charlotte Amalie is ground zero for shopping in the USVI.  And Main Street and parallel Back Street have hundreds of shops with some of the best deals on duty free jewelry and liquor anywhere in the world.

Queen Emma Floating Bridge — Curacao

Ok, it’s more of a bridge than a street. Built for feet, The Queen Emma floating bridge, also known as the swinging lady, would qualify alone as a terrific place for a stroll.  It connects the Punda and Otrobanda districts of Willemstad with great shopping, restaurants and charming, fascinating places to explore.

Malecon — Havana, Cuba

The most famous stretch of land in Cuba, the Malecon draws visitors from around the world for a stroll sandwiched between colonial Old Havana and the water.

Waterfront Drive — Tortola, British Virgin Islands

The British Virgin Islands isn’t big, but that doesn’t mean you can’t take long, fascinating walks around their main thoroughfares. Our favourite is Waterfront Drive (above: photo by BVITB).

LG Smith Boulevard, Aruba

Aruba’s most popular thoroughfare is all about shopping — with duty-free shops, boutiques and more in the heart of Oranejstad. Of course, you can’t go wrong on Aruba’s Main Street, either.

Front Street — Philipsburg, St Maarten

Front Street is one of the Caribbean’s shopping Meccas, just a few steps from the beach. You’ll never get tired of strolling, window shopping (and, naturally, actual shopping) on this popular thoroughfare.

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