The Dominican Republic is a popular Caribbean destination for its coastal towns, beautiful beaches, and five-star beachside resorts. But Santo Domingo, the country’s capital founded in 1498, is the oldest colonial city in the Americas, and remains the epicenter of the Dominican Republic’s rich history and culture. Follow this guide to make the most of your weekend. (Note: this itinerary is best followed on a Saturday and Sunday, so if your trip is during other days of the week, find even more things to do here.)
Day 1: Morning
10 a.m.: Upon arriving in the city, make your way to the JW Marriott Hotel Santo Domingo to check in at the fifth-floor reception, or at least drop off your luggage until a room is ready. Once you’ve handed off your bags—keep a day pack with you, packed with a swimsuit, sunscreen, and sneakers for the next few hours—spend a few minutes relaxing before departing for the day. Have a seat in the lobby and admire the artwork on the walls, or step outside for panoramic views of Santo Domingo from the glass-bottomed terrace. If you look to your right, you’ll spot the hotel’s infinity pool overlooking the city’s skyline.
10:30 a.m. Grab your day pack, and head to Boca Chica, a white-sand beach that’s about an hour away. (Unless you rented a car, the easiest way to get there is by hailing an Uber.) Once there, you can spend your time relaxing or walking along the beach, shopping or sampling food from local vendors, or going for a swim through the multi-hued blue waters. Or before your trip, book a table at one of the seaside restaurants or beach clubs, like Neptuno’s, and enjoy the view and breeze with table-service lunch and drinks, and take a dip in the water from one of the ladders hanging over the docks.
Day 1: Afternoon
2:30 p.m. After a few hours at the beach, pack up your things, and head to Parque Nacional de los Tres Ojos (Three Eyes National Park). The park gets its name from three main underground caverns, each housing a magnificent blue lagoon. Historically, the caves were used as places of residence and ritual by the indigenous Taino people of the Hispaniola island. It only takes about 45 minutes to an hour to explore the park, as it’s fairly small; however, note that to reach the lagoons, you must ascend and descend several flights of stairs.
4 p.m. Wrap up your time at the park, and go back to the hotel (it’s a 30- to 40-minute drive) to check in and settle into your room. Once there, you have several options of things to do over the next few hours! If you still haven’t had enough time in the sun or water for the day, head out to the fifth floor for a dip in the hotel’s infinity pool overlooking the skyline. If you’re staying in an executive-level room, take advantage of the complimentary happy hour in the Executive Lounge on the 21st floor, where you can also take in the sweeping city views. If you want to leave the hotel for a bit, take the elevator to the ground floor of the building to access the attached Blue Mall Santo Domingo, a multi-story mall where you can shop for designer goods, local coffees and teas, artisan chocolate, and more; or hail a ride to Avenida Malecón a few miles away, a seaside boulevard that’s popular for sunset walks. Whenever you’re ready, head back to your room to freshen up for dinner.
Day 1: Evening
8 p.m. For dinner, make a reservation at Winston’s Grill & Patio, located on the fifth floor of the hotel. The menu comprises dishes from around the world, and the steak and lamb are popular choices. Sit inside the restaurant for an elegant ambiance, or in nice weather, ask for a table outside on the terrace. Afterward, head back to your room to relax, or continue to enjoy the nighttime views of the city with a drink at the nearby bar, Vertygo 101.
Day 2: Morning
10 a.m. The first item on today’s itinerary is a visit to the Dr. Rafael Ma. Moscoso National Botanical Garden. At more than 400 acres in size, this is the largest botanical garden in the Caribbean. You can explore at your own pace by walking through the many gardens and attractions (don’t miss the exhibit showcasing 300 types of orchids or the traditional Japanese garden), or if you’d prefer to stay off your feet to save your energy for the day ahead, you can take advantage of the trolley that will shuttle you around the grounds.
Day 2: Afternoon
12 p.m. The gardens merit a few hours of wandering, but once you’ve had your fill of all the beautiful flora, head straight for Santo Domingo’s Colonial Zone where you’ll spend the rest of the day.
1 p.m. First stop: lunch at El Patio Culinario, which is essentially a food truck park, but instead of trucks, it’s stationary booths. Order a variety of plates to share if you’re with a group, but save room for dessert, which you’ll get at your next stop.
2:30 p.m. Arrive at Kah-Kow Experience on Calle Las Damas. As soon as you walk in, you’ll likely get a whiff of chocolate wafting through the air—don’t worry, you’ll get to taste it soon enough. Chocolate is a major industry in the Dominican Republic, and this attraction offers a variety of tours that teach visitors about the cacao plant (how it’s harvested and where it grows), the history of chocolate, and the entire process of making chocolate from bean to bar. Watch a multimedia presentation to learn essential context for the rest of the visit; step into the tasting room to sample different types of chocolate (from white to dark) and learn what goes into each; and finally, craft your own chocolate bar in the glass-enclosed factory. (These can all be booked online in advance.) There’s also a soap lab onsite that allows you to make your own bar of soap using cacao butter combined with your preferred fragrance. At the end of your visit, walk through the gift shop to buy any other chocolate treats you might want for the rest of your trip.
5 p.m. Meet at Trikke República Dominicana for your next activity, a Trikke tour of the Colonial Zone, a UNESCO World Heritage Site. A trikke is a three-wheeled scooter, and this experience allows you to roam around the historic district while learning all about the city’s history and culture (via a headset) from your guide. You’ll ride past and stop at several major landmarks and historic sites in the area—such as the National Pantheon, Museum of the Royal Houses, and more, some of which date back to the 16th century—while your guide explains the significance and history of each. The evening tour is especially fun because lots of people are out enjoying the sunset and nightlife in the area, so you’ll also see glimpses of the local lifestyle.
Day 2: Evening
7 p.m. For dinner, make a reservation at Lulú Tasting Bar, a popular tapas-style restaurant also in the Colonial Zone. Request a table in the indoor courtyard, and choose a few dishes to split with the group—this place is best experienced by sharing and sampling many different items.
9 p.m. After your meal, go out to experience the nightlife! Several streets in the Colonial Zone (such as Calle Hostos or Calle Isabela Catolica) are lined with bars and nightclubs to grab a post-dinner drink. And if you're here on a weekend, making your second day a Sunday, you’re in luck because every Sunday night, you can go see free musical performances of merengue and jazz at the Ruins of the San Francisco Monastery from 6 to 10 p.m. When you’ve exhausted all your energy, make your way back to the hotel for a good night’s rest before departing the city in the morning.