San Juan, Puerto Rico

San Juan is the capital city of Puerto Rico founded in 1521 on the islands northern coast. It is the main point of arrival by sea and air, and serves as the modern day hub of Boricua culture. Join us as we visit the island in February including Old San Juan, Condado and El Yunque National Forest.

The north coast of Puerto Rico faces the Atlantic Ocean and has dangerous rip currents at most beaches. The Southern coast faces the Caribbean and is relatively calm. Choosing where to stay can be a difficult decision, especially for first-time visitors. If you want the city and the beach without compromise there are a handful of hotels with protected beaches like Caribe Hilton, but nothing is cheap.

Viejo or Old San Juan feels European due to it's history, design and preservation. Waves of cruise ship day-trippers can swamp the cobblestone streets, but with careful planning and reservations you can avoid the bulk of the swarm and side-step the traps.

The Caribe Hilton is a vacation machine. The Garden Wing offers tiled floors and is the best option to avoid the scent of wet carpet. On-site food isn't very good, but the tropical drinks can be tasty if you get the right bartender. The main reason to stay is the central location between Old San Juan and Condado with a large pool complex and protected beach. Many tours offer Caribe Hilton as a standard pickup/drop-off point. The Piña Colada is said to have been invented here in 1954 and flows from the battery of buzzing blenders at $14 per cup.

Just outside the city in the northeast of the island is El Yunque National Forest - the only tropical rainforest within the United States national forest system. Booking a tour that matches your energy level is a great way to avoid driving rental cars on tight twisting roads and parking issues. Pick an early tour that aims to beat the crowds at popular spots.

Swimming in the beautiful rivers was a highlight for us. As natives of New England we are normalized to swimming in cool or cold water, but we were surpsied to see our family as the only individuals who swam. Your mileage may vary depending on the time of year you visit.

The view from Yokahu Tower in El Yunque is breathtaking!

We were told that Iguanas are invasive and got their foothold in Puerto Rico as abandoned pets that outgrew their owners. Hunting them is a popular past time for locals, although no one recommended eating them.

We ate at our share of tourist traps, but also enjoyed some truly great spots. El Vino Crudo is a small-plates bar that we challenged with our 7-member extended family for an early dinner. A short menu of Italian dishes that included many fresh vegetables. Even though Puerto Rico has a climate that supports year-round agriculture they import roughly 85% of their fresh produce. This makes a meal flush with fresh fruit and veg a luxurious experience. The focaccia was gone in seconds, and the hand-cut pasta al limone was exceptional.

The popsicle culture in Puerto Rico is strong, which makes sense given the tropical climate. A famous homemade treat is the Limber - a popsicle frozen in a disposable cup that you gently squeeze to raise the treat out of the cup for consumption. On the other end of the spectrum is Señor Paleta which makes artisanal frozen treats. They offer simple frozen pops on a stick made from fruit purees as well as elaborate pops with layers of flavor and texture. Grab something from the location in Old San Juan and walk to the Bastion de las Palmas for a view of the harbor.

Mario Pagan is a famous Puerto Rican chef and restaurateur whose flagship location is in the busy Condado neighborhood of San Juan. The focus is contemporary Puerto Rican cuisine with no shortage of modern takes on classics like alcapurrias (stuffed fritters), bacalaito (cod fritters) and habichuelas guisadas (stewed beans) with crispy rice. A highly recommended dining experience where Puerto Rican flavors can be explored at an elevated level - not to be missed!

Dos Lobos Empanada bar opened in late 2025 and has a location in the heart of Old San Juan serving nothing but Empanadas and drinks. These savory pastries have a thin shell and are baked Argentinian style for a lighter alternative to the fried empanadas common in Puerto Rico. The Carne empanada features ground beef cooked with soffrito and was our favorite. We ordered about a dozen for the three of us along with tasty dipping sauces. Cold sodas and craft cocktails made for a perfect lunch. They have a second location in Condado.

No trip for us would be complete without a cooking lesson and we were fortunate enough to learn from a local in her backyard kitchen studio. We started by preparing fresh achiote oil, mincing culantro and aji dulce peppers, onions and garlic to make a Puerto Rican sofrito. With a small pinch of cumin this flavor mixture serves as the foundation for a large number of Puerto Rican dishes like Arroz Con Gandules or pigeon peas with rice. We learned about life in Puerto Rico as we spent the afternoon cooking and the evening sharing a meal with our host.

On this adventure we traveled with additional family which always makes for a unique experience as plans are shared and expectations around experience are tempered with those of our companions. We overlapped for most of our time on the island, but also had the opportunity for individual family events.

For U.S. Citizens, Puerto Rico is a simple domestic flight and just 4 hours from New England. It is amazing that over such a short distance the climate and weather can be so different. A universal thumbs-up experience from our family to yours.