5 Best Restaurants in Old San Juan, San Juan

As you might guess from the name, the music is as much of a draw as the food at Carli's. The genial owner and host, Carli Muñoz, toured for a number of years with the Beach Boys (note the gold album on the wall) and plays nightly with his jazz trio, often accompanied by singers and musicians who happen to drop in. Inside the skyline-dominating Banco Popular building, this intimate supper-club bistro has elegant tables scattered around the room and a bar made of black Italian granite. Have a seat indoors or on the outdoor out on the patio, and dine on such fusion specialties as pumpkin and shrimp risotto, filet mignon with wild mushroom sauce, or blackened ahi tuna with Cajun spices.

Casita de Rones is the headquarters for all things rum with a restaurant, two bars, and the flagship store for Rums of Puerto Rico inside. Its bright pink exterior is hard to miss, and ocean views serve as a serene backdrop to your meal. There is a full menu with items like Italian longaniza sliders with spiced rum jam and grilled skirt steak with a rum chimichurri sauce. Try a variety of rum based drinks here, like a rum flight or a 1950 Hand Shake Colada, paying homage to the original version of the piña colada.

This lively restaurant is known for its waitresses in all-white campesina (peasant) dresses. It is a nostalgic portrayal of country life in Puerto Rico. Guests who may have seen it featured on various TV shows are willing to wait more than an hour for a table. Serving local comida criolla, signature dishes are the giant deep-fried kan kan pork chop, and mofongo with churrasco (marinated skirt steak). The garlic shrimp mofongo, served country-style in a pilón (pestle), is quite tasty. Drinks, including fruity frappés, come in tin mugs.

Tucked away on the second floor of the historic El Convento Hotel, Santísmo is a dreamy and romantic dining destination. A stone oven is used to cook many of the dishes, including the catch of the day.  All dining is alfresco on two terraces overlooking the hotel's striking arches. It's a great spot for a date night.