Three-Day Towns: San Juan, Puerto Rico

When you land in Puerto Rico, it’s hard to remember you’re still in the USA. The immediate island/vacation vibe you get makes it hard to believe people are actually coming here for business.

The first thing that hits you about the people in Puerto Rico is that everyone who lives here loves it and wants to recruit you—either to live or run a business here.

Which, by the way, is not altogether a bad idea. It has the benefits of the US mainland, without the taxes (a small percentage of state taxes, but the kicker is no federal taxes). It’s perennially tropical, surrounded by water, and the people are incredibly warm and hospitable.

It’s a perfect long weekend, or three-day “town” (even though it’s more than one town). If you’re lucky enough to come for business, extend your trip a few days.

walking into San Juan

First, a truncated, loosely narrated history lesson:

Juan Ponce de León, of the Fountain of Youth fame, created the original settlement in 1508 in Caparra. Then came the Spanish colonists in 1521. The US Navy arrived in 1898 with a bunch of ships, creating the first hostile encounter. The US trashed the city, then decided Puerto Rico should be ours as a future tax haven for east coasters, retired and otherwise, and Spain finally gave in.

That’s the gist of it.

Puerto Rico has a collection of great places to stay. Almost everyone gravitates to the beaches, but if you just stay on the beach, you miss out on the great culture and incredible people that make up Puerto Rico.

First, there’s the city of San Juan. The city is like a peninsula connected to the rest of the island by bridges and roads that look like spaghetti. The peninsula includes old San Juan as the highlight, but there are also several big-dog chain hotels, condos, restaurants (mostly chain), and shopping within a short walk.

placita neighborhood

San Juan is really an equal mix of the historic and the touristy (thanks to the multitudes of cruise ships—it’s the second-busiest cruise-ship port behind Miami). The architecture is great, and the Castillo San Cristóbal and its walls (from the 1600s) dominates the city. The old city streets hold a collection of tourist shops and restaurants, with a few gems hidden throughout. If you love history and the old city, you can’t beat a stay at Hotel El Convento. It’s a great stop even for a night or two (which you can combine with a night or two on a beach). The streets are narrow and cobblestoned, and the buildings have Spanish colonial influences from the 16th and 17th centuries. And, of course, it’s best at night, when the cruise ships leave.

If you move off the peninsula a little further east, there are a few neighborhoods with options for hotels including Isla Grande, Condado, Miramar, and Ocean Park.

Condado combines an opportunity to stay on the beach and walk into the old city, as well as walk some of the other neighborhoods, like Santurce (and the cool little enclave of Placita) and Miramar, and check out the incredible local restaurants that make San Juan unique. The best hotel and best location is the Vanderbilt, but it’s decidedly overpriced, even with its grand historic lobby. (It’s next door to the giant Renaissance hotel with a shared beach.) There is small luxury hotel, O:live, a stone’s throw away on the lagoon (not the ocean), that’s also a bit unique and gives a much more intimate experience.

If you move a little further away from town, you can stay on the water a bit closer to the airport (Ritz Carlton, InterContinental). It’s still only maybe a 15-minute drive into the city, but not a walk, and there are definitely no neighborhoods. These hotels are destinations for a beach vacation, and you’ll miss the great parts of the city.

tilework walking in San Juan

If you are really a “want to get away” beach-going “flipper” who likes to get your towel on your chair early in the morning, the other option is the Bahia Beach area at eastern end of the island. The big dog there is the St. Regis, and it’s also close to big Wyndham and Gran Melia resorts. It’s lovely if you’re into that kind of thing… Golf, snorkeling, sun, beach. (We thought of it as a beach-like prison full of people walking back and forth, as if possessed.)

Off the very eastern edge of the island is Vieques Island, where a lot of US mainlanders have chosen to live 180 days. There are a few hotels there, and the dominant one is the W Hotel. The people who live there love it, but also have to ferry back and forth for the day-to- day basics.

If you really want seclusion, head to the far western side facing the Dominican Republic to a completely secluded hotel called the Horned Dorset.

bar at jose santaella
red snapper at jose enrique

Of course, we recommend Condado and Old San Juan, and the great options for walking and restaurants that come with them. In Old San Juan, there are a few finds that range from traditional, like Café Manolin and El Jibarito, to a bit more unique and eclectic, such as Mesa Verde. There is a not-half-bad pizza and small-plate place masquerading as a dark, dank bar called Pirilo Pizza Rustica. Don’t miss swinging by the Casa Cortés Chocolate Bar for a hot or cold chocolate, or an ice-cream chocolate.

In the neighborhoods, there are a lot of great chefs and restaurants including José Enrique and Santaella (from chef José Santaella), both renowned chefs with great menus. La Jaquita Baya in Miramar is another incredible local find, with the coolest little outdoor bar, where you can mingle with those recruiting locals, the relocated mainlanders, and a few tourists who’ve stumbled into the right place. The thing about all these restaurants is that they’re not big into signage (with the exception of Santaella), so you have to be cool enough to know where you’re going.

cocina abierta entrance
cocina abierta
lote 23
lote 23 3

 A few others worth noting are Cocina Abierta and Soda in Miramar. It’s definitely worth a walk to Lote 23, a fairly new area created in the spirit of a permanent food-truck court, with amazing food and drink choices and picnic tables. It’s surrounded by businesspeople coming down for lunch (while we were sipping our frozen tequila drinks).

Everyone will send you to Wilson Street (in Loíza) for a collection of hipster local restaurants, clubs, and shops in about a mile stretch, with a few weird chains thrown in. It’s definitely more interesting at night, if you’re cool enough for that kind of thing.

All in all, a great combination of weather, water, beach, and food. Christopher Columbus swung by here on his second trip in 1493. He should have stayed.

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