Visit the Ciudad Colonial, the oldest permanent European settlement in the Americas and a UNESCO World Heritage Site, in the country's capital of Santo Domingo. Founded by the Spanish in 1498, the colonial city was designed to follow a grid pattern. This would serve as the model for virtually every city planner in the Americas.
Source: UNESCO
While you're there, check out the Fortaleza Ozama, a 16-century fortress built at the entrance to Santo Domingo and overlooking the Ozama River. It's the oldest formal European military building in the Americas.
Keep in mind that many of these structures were built using the labor of indigenous Taino people, hundreds of thousands of whom were enslaved by the Spanish and forced into horrific conditions. Just a fraction of them survived, so in 1501, the monarchs gave the colonists permission to kidnap and enslave Africans and bring them to the island.
At the fort's center is this castle, which served a number of purposes — including as a military jail and later as a detention center for political dissidents under former Dominican Republic President Rafael Trujillo, who was assassinated in 1961.
Source: "Dominican Republic (Other Places Travel Guide)," 2012
Afterwards, take a stroll through the cobblestone streets of Calle Damas (named "the street of the ladies" after the Spanish royalty who once walked there) and the shaded, tree-lined El Conde.
Don't forget to stop inside the Museo de las Casas Reales, or the museum of the royal houses, for a fascinating look inside what it was like to live in the city as a member of Spanish royalty.
If you have time, take a cab or a bus to check out the surrounding area as well. Here's a view from an apartment in the Evaristo Morales neighborhood, which is about a 25-minute drive from the colonial zone.
Don't forget the food! Dig into a plate of grilled pulpo, or octopus. It's typically fried or grilled and seasoned. I ordered some at a fancy food truck in the Evaristo Morales neighborhood, and it came with grilled potatoes. Delicious.
The city even has vegetarian options, such as this all-veg Taiwanese spot called Para Te. We got steamed dumplings and chilled noodles with "chicken" (soy) meat. Fresh juices or "batidas" are also omnipresent in the DR, and they're usually cheaper than soda. A carrot-orange blend was one of my favorites.
After you see Santo Domingo, drive to the Bahia de las Aguilas, or "the bay of the eagles," to relax on one of the most pristine beaches in the world.
On the way, stop in Barahona at the Casa Bonita hotel for an unforgettable view. The hotel's infinity pool almost seems to run right into the Caribbean Sea in this photo.
The hotel's rooms were way out of my budget, but its small, relatively uncrowded restaurant is open to the public. I recommend stopping by for breakfast.
Take in the view as you continue the drive. Stop at a number of gorgeous lookout points along the way, like this remarkable spot by the side of the road in San Rafael.
At some of them, you'll find restaurants and small beaches too. At this one, you can literally eat lunch while cooling your toes in the crystal clear water.
If you don't have time for the 7-hour drive to Bahia de Las Aguilas, try a weekend trip in Las Terrenas, a much more doable 2.5-hour drive from Santo Domingo. Local buses, or "guaguas," depart from the city's bus depot on Fridays at around 6 p.m.
In Las Terrenas, you can also see gorgeous beaches with the crystal-clear turquoise water characteristic of the Caribbean.
Check out the protected Los Haitises National Park, which is accessible only by boat. You'll need to get a licensed tour guide to take you, but it's not to be missed.
Source: Fodor's
Inside the park, you'll see caves that were formed over thousands of years via water erosion and which were once inhabited by indigenous peoples.
Source: Fodor's
Since the park was founded in 1976, the government has added bridges and other structures to allow visitors to access the caves.
Source: Fodor's