Santo Domingo, Dominican Republic

The extensive Zona Colonial, a UNESCO World Heritage site, offers countless Spanish-colonial buildings—interesting prospects for both investment and lifestyle—plus, it hasn’t yet become populated with expats like many of the typical colonial city options.

From real estate to the general cost of living, it can be hard to believe you’re in the Caribbean when here. Prices across the board are more Latin American. You could live well in the DR on your monthly Social Security check alone.

There certainly is no lack of entertainment in Santo Domingo, particularly in the Piantini district, which has several good malls, theaters, and fantastic restaurants. For the best sight-seeing, the Colonial Zone is not to be missed. 

Visiting Parque Colon is something residents never tire of, and you’ll find several galleries and small museums throughout the city.

If you’re looking for upscale activities, Santo Domingo is home to the National Symphony Orchestra of the Dominican Republic (Orquesta Sinfónica Nacional), which hosts many events throughout the year.

The two largest shopping malls in the Dominican Republic are located in Santo Domingo: Blue Mall and Agora Mall.

Not to be missed is a meal at Pat’e Palo. The eatery was established in 1505 by a retired one-legged, one-eyed pirate and is located across a courtyard from the Columbus family home… it’s a truly unique Dominican experience.

You should also take a jaunt to the Columbus Lighthouse, a fascinating structure said to contain the remains of Columbus. 

The famous explorer was a voyager even in death; his remains were moved from Spain, to Santo Domingo, to Cuba, and before finally coming back to rest in Spain.