48 Hours in San Juan, 2019’s No. 1 Hotspot

Nice beaches exist in Condado
San Juan bridge to fancy area known as Condado

Every year in January the New York Times publishes its list of 52 places to visit during the year. The number 1 place on the list for 2019 is Puerto Rico, so I headed that way to find out why.

After having been ravaged by Hurricane Maria in September 2017, and the subject of many news reports about the need for emergency money to rebuild, the capital city of San Juan and surroundings, at least, have rushed to get back to normal. Locals tell me that following the storm, you could not drive on any streets as the debris covered everything. Still today, if you look closely, you see broken street lights without bulbs, places on the sidewalk where large trees were ripped from their roots severely damaging surrounding concrete walkways, and roofs (even on multi-million dollar homes) that are still in need of repair. But, by and large, the electricity is on in the major tourist areas, and things look pretty good.

My conclusion: Puerto Rico is on the New York Times list because it is coming back stronger than it was, with many new and exciting restaurants blooming and nightlife booming. Reputedly the best restaurant in San Juan is Casita Miramar off Ponce de Leon. Trendy vegetarian restaurant Pure and Natural on Ponce de Leon, across from the Music Conservatory, is quite good and representative of the new creative offerings. Otherwise, most of the tourist attractions focus around golf on lush green fairways, beach-based fun, and typical tropical extreme activities, such as zip-lining.

You can do any water activity in Puerto Rico
Water sports abound in San Juan

I visited during the high winter season when temperatures are a very delightful 70-80 degrees Fahrenheit with very low likelihood of rain; and, yet, there were relatively few crowds, although the flights were full—given the limited competition. My goal was to go somewhere with warm weather in the winter, where I didn’t need a passport, and where I could arrive within about four hours—Puerto Rico is just about the only place that meets that bill.

Although Puerto Rico is part of the United States, it still feels foreign. In the places tourists and upper class Puerto Ricans visit, English is spoken, but the official language of the island is Spanish. The local courts are conducted in Spanish, for example. Of course, the federal courts are in English, and everyone speaks at least a bit of English. One overnight gas station attendant—the person who takes your money to turn on the pump—couldn’t speak English and kept referring to the price in “pesos” when he meant dollars, so speaking some Spanish is still helpful, but not necessary.

The city of San Juan feels very large. There are many smaller contiguous cities, so considering the metropolitan area as one big city, the population of the metropolitan area is around 2.6 million and growing. Because the island is rebuilding more upscale, finding typical rural Puerto Rican foods in the city was difficult. For example, I searched high and low for a sampling of mofongo, a plaintain or casaba (yucca) stuffed with your choice of fish or meat. I do not like to drive in unfamiliar places, but all the smart phone apps work to guide you. Although there are beaches everywhere, to find a really nice beach, you’ll really want to leave the urban area. Swimming is another issue: the Atlantic Ocean is cold, unlike the Caribbean.

If you have only 48 hours to visit Puerto Rico, here’s the itinerary I suggest:

Beautiful buildings abound in Old San Juan
Ships in port at Old San Juan

Start your first day with visiting Old San Juan. This is by far the top tourist destination in San Juan, with its brightly colored old buildings. Cruise ships dock here to disgorge their hordes of passengers for sightseeing on a shore stop. Try NOT to go when a cruise ship is in port. The ship’s passengers will clog the restaurants and streets to your detriment.

Old San Juan is the largest of the old towns in the Caribbean
Brightly colored buildings with elaborate balconies add charm to Old San Juan

Old San Juan is one of the largest old Spanish towns in the Caribbean. Because it is the area’s main attraction, it has been quick to rebuild following Hurricane Maria, but there are still houses along the Atlantic waterside that you can see were badly destroyed by the storm.

The cruise port is a good place to start your tour. There are Segway tours that can assist if you can’t walk, but the streets are so narrow that walking or Segways are about the best way to get around. There is also a free trolley that goes around the area, but it does not enter the narrow streets. Near the cruise ship dock is the main tourist office to pick up maps and other tourist information. You can spend days seeing everything in Old San Juan. I will suggest spending a half day and lunch or dinner there.

Only one gate leads into the Old San Juan city area
Gate leading from outside the walled Old San Juan into the interior

From the port you should walk outside the wall that surrounds the bay side of Old San Juan. The wall is massive, so you should be able to spot it. If not ask someone where it is. The street is called Princess Way. As you walk you will find many interesting sculptures along the path, as well as street vendors. Follow the wall until you reach the only remaining entrance to go through it. The entrance has a red wooden frame. From here you have a choice. If you want to hike, you can continue along the outside of the wall to the tip of Old San Juan, heading toward the garita (guard house) visible in the distance at the tip of the old fortress (Castillo San Felipe) that protected old city, or you can enter the inner city of Old San Juan.

The Old San Juan fort has many garitas like this
A garita in Old San Juan

I suggest you enter the gate and walk straight ahead. Within a few blocks past a shaded park, you will find the beautiful Cathedral where Ponce de Leon is buried, well worth a visit. As you leave the Cathedral, turn right. Up the hill you arrive at the oldest church in Puerto Rico. Beyond that is a totem pole, outside the art museum. From there take the stairs down to a view of Castillo San Felipe with El Morro (the large grassy area) in front of the fort. Walk to El Morro and the fort or turn right along the road that parallels the water. If you walk on that road, turn right when you reach Calle San Justo. Follow this road and you will end up where you started near the port. The road passes the main street of Old San Juan, Fortaleza. There are restaurants all over the area, but this street has some of the best. Marmalade (reservation suggested) is reputed to be the best of the Old San Juan restaurants.

The next recommended stops are across the bay. If there is time, do it today, or else leave it for tomorrow. Take the ferry from the port to Cataño (1/2 hour, 50 cents). Cataño is a typical Puerto Rican town, worth a visit poking around. From Cataño, take an Uber ($3-5) to the nearby Bacardi Rum Factory for a tour. You can see the two windmills of the factory from Old San Juan. Leave time to taste their products.

Before you leave San Juan, you’ll want to see the beach scene. If you have a car, I suggest getting out of the city to one of the many nice beaches around. I personally chose Dorado, about one hour from the city. But you need a car to get there easily. If you don’t have a car or don’t like to drive, the beach everyone seems to recommend in San Juan proper is Isla Verde, close to the airport.

So, one option is to spend the second day of your 48-hour trip at Isla Verde. There are many hotels along this beach. You’ll end up close to the airport for your trip home.

If you choose to go to Dorado, your experience will depend in large part on where you stay. I explored two options: the ever-popular Embassy Suites Hotel (a Hilton product), and the Ritz Carlton, a Marriott product. They are like night and day.

The Embassy Suites is in a gated development, and it offers a decidedly understated, low-key accommodation. A nightly “manager’s reception” is billed as a big deal, but it served only chips and salsa with a few raw vegetables. On some nights there is “live” lip-synched music…nothing special. The beaches in Puerto Rico have strong tides, so the hotels create a rock levy to break the waves. The beach area at the Embassy Suites is quite small, but quiet nonetheless as the action is at the pools surrounding a swim-up bar. Guests were a mixed bag with many locals, lots of tattoos, and, it seemed, they enjoyed free food. The hotel offers a free breakfast, but it wasn’t much to it…eggs to order, bacon, very basic cereals, limited cut fruit, simple breads, and pre-cooked pancakes. Except for the fact that the hotel is a drive away from the town of Dorado, I would rather eat out.

Barrier levy protects small Embassy Suites beach from strong tide
View of beach from Embassy Suites

The Ritz Carlton, on the other hand, had a much longer beach levied off, long enough to have a nice beach walk. Two of its restaurants are among the best in Dorado. The clientele appeared to be mainly rich Latins without the mixture of cultures at Embassy Suites. Located on a lush, manicured golf course, it appeared guests mainly come here to golf. I got into the gated complex with a reservation for lunch at its Encanto restaurant which was beach side and first class. My waitress explained that during Hurricane Maria sand filled the pool area. The hotel paid staff to clean up, rather than hire outside contractors, earning their lifetime loyalty and excellent service in return.

Hurricane damage no longer evident at Ritz Carlton Hotel
Lush gardens surround the Ritz Carlton at Dorado Beach

On your last day in San Juan there is one more must-do activity, a trip to El Yunque, located on the eastern side of the island about ½ hour from San Juan, is one of the few rain forests in the national park system,. Heavily damaged by Hurricane Maria, when I visited in February 2019, the visitor center was still closed as was the road to the highest elevations of the park. Hiking enthusiasts can still walk to the peak where precipitation is likely (after all, it is a rain forest). Alternatively, you can climb to the top of the brick Yokahu Tower, about 15 minutes up the mountain, for a view over the canopy to the ocean. Visitors flock to the park for some great birding.

Overlook El Yunque rain forrest from Yokahu Tower
Yokahu Tower in El Yunque

Nearby, on the road leading to the park, a private zip-line operator caters to adventure tourists.

This itinerary exposes you to the highlights of Puerto Rico around San Juan. There’s a lot more to explore away from the urban center.



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