If a traveler has their heart set on seeing an island’s iconic sights, and time is limited, there’s nothing better than joining an organized tour that has a set itinerary and a strict timetable. A traveler with more time on their hands might have a different agenda. Could be they want to see the sights, but also have the option to explore a side street, chat with a stranger, or stop at a roadside stand – in other words, to let real life and serendipity seep into their travels. These self-guided tours could be either walking tours or self-drive adventures, depending on how closely sights are clustered together, and if the island is driver-friendly.
Discovering the Colonial Zone Santo Domingo
Santo Domingo, the capital of the Dominican Republic, is often referred to as the Oldest City in the Americas. Nowhere is this more evident than the city’s Colonial Zone, which is studded with architectural treasures from the 15th and 16th centuries. It’s a compact area, easily explored by foot. Pick up a map and tick off the major sites, such as Columbus Palace, Ozama Fort, and the Casa del Cordon, the former residence of Christopher Columbus. Take a break and sit on one of the benches in front of the Nuestra Senora Santa Maria de la Encarnación, the first cathedral in the New World, built in 1508. This is a great vantage spot to people-watch. It also places a traveler in prime position to change focus and stroll down Calle El Conde, the city’s major shopping district, also studded with restaurants and outdoor cafes.
Walking in Willemstad
Curacao’s Dutch heritage is on display in Willemstad, the island’s capital. The city dates back to 1634, and there are a variety of historic structures, such as Fort Amsterdam and the Fort Church museum. A must-see is The Mikve Israel-Emanuel Synagogue, the oldest synagogue in the western hemisphere, famous for its sand floor. Take time to wander along the “floating market” selling colorful displays of fish, fruits and vegetables. It’s called the floating market because the produce has been brought by small boats making the 40-mile journey north from Venezuela. Walking across the 552-feet pontoon Queen Emma Bridge (also known as the “Swinging Old Lady”) brings a traveler to the Otrabanda side of the city, where they can look back to view Curacao’s iconic sight – a cityscape of pastel-colored 18th century colonial houses.
Touring Old San Juan, Puerto Rico
There’s a lot of history packed into the seven square blocks of Old San Juan, founded by Ponce de León back in 1509. There are scores of historic buildings – including Casa Blanca, the former home of Ponce de Leon. But the Big Kahuna is definitely El Morro, an expansive fort offering superb sea views from its walls. Mixed in with the Spanish colonial history are trendy shops, restaurants, and cafes, offering a pleasant respite from sightseeing. Old San Juan’s narrow cobblestone streets can be steep, so wearing comfortable shoes is a must.
Self-Drive Puerto Rico
Puerto Rico makes a great first self-drive Caribbean adventure. Driving is on the right, like the mainland U.S; the main highways are excellently maintained; and signage is bilingual. Having a vehicle of one’s own allows for really getting out and seeing the island, including the surf scene in Rincon; the sights of Ponce, Puerto Rico’s other historic city; the exhilarating beauty of El Yunque Rainforest (yes, you can drive through the rainforest); and the array of beachside kiosks in Luquillo, selling all manner of seafood. One tip: if possible, pick up the rental car at the airport, instead of San Juan’s city center, where the traffic is much more challenging.
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Taking a Spin in Saint Lucia
Saint Lucia is one of the most beautiful and romantic islands in the Caribbean. Couples especially will want to rent their own vehicle and set off to explore. Roads are winding, and the speed limit is most often a leisurely 30 mph. The scenery of Saint Lucia is the main player, and the coastal road that circles the island offers one amazing sea view after another. Main stops on any itinerary should include the drive in volcano in Soufriere; the soaring peaks of the volcanic twin Pitons, which can be viewed in the fishing town of Soufriere; and the lookout point at Marigot Bay. If driving on the left is a new experience, practice a bit on a quiet road before setting off.
Rolling Through Antigua
Antigua is rich in English heritage and is easily explored by car. Bypass the capital and harbor city of St. John’s and head out to the countryside. Here a traveler will find roads leading to historic sugar mills dating back to the 17th century (Betty’s Hope windmill is a standout). Make a stop at the Devil’s Bridge, a blowhole shooting plumes of salt spray into the air; catch the sea views from historic Fort Barrington; and plan the drive so the last stop is at sunset, at the 500-foot vantage point of Shirley Heights, and wait for the green flash as the sun dips into the sea. If it’s a Sunday drive you’ll be in luck, since Shirley Heights throws the island’s biggest party every Sunday, with island barbecue and live reggae and steel band music.
Looking for more off-the-beaten-path attractions in the Caribbean? You’ve never seen tours like these!
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