Read my original nature poems right here!

Read my original nature poems right here!

Where to Stay in San Juan: Old San Juan vs Condado

Visiting San Juan, Puerto Rico should be on every beach-lover, foodie, and history-lover’s travel bucket list. It’s a domestic flight for U.S. travelers and is ringed with beaches, brimming with good food, and is over 500 years old, founded by Juan Ponce de León in the early 1500s.

San Juan is the gateway to all Puerto Rico has to offer (like all these things). Whether San Juan is just a stop along your Puerto Rico itinerary or you’ll spend days in the city, you want to stay closest to the best things San Juan has to offer.

All those things are in Old San Juan. Sorry, Condado lovers. The blue cobblestone streets, diverse architecture, cathedrals and crypts, and world-famous gelato easily beat the concrete and cars in Condado. These great pictures of Puerto Rico don’t feature any from Condado…

Condado is hardly walkable, the concrete runs right up to the water in some parts, and it’s busy with cars.

It’s a suffocated and overdeveloped strip of land that must have been beautiful before the hotels and casinos moved in.

In short, stay in Old San Juan, not Condado, when you visit Puerto Rico.

Old San Juan vs Condado

It all comes down to character. Maybe you don’t like character. Perhaps charm, beauty, and originality aren’t important to you when traveling. Maybe you want one hotel, the same pool each morning and bar each night, and the same reserved strip of sand for resort guests. If you’ll never step outside your resort, I can’t promise you’ll enjoy Old San Juan much more than Condado. Those casinos, resorts, and condom shop (yes, Condado is home to “Condom World” 🤢) need your business, anyway.

But I don’t want you to have a dull vacation. I want you to cover yourself in newness, walk around colorful places, and come back a better person. Staying in Condado doesn’t get the job done.

Let’s compare some specifics…

1. Photogenic: Old San Juan vs Condado

Unless your dream Caribbean photoshoot is a concrete wall or Condom World, you’ll need to walk over to Old San Juan. So why not just stay there instead?

I get it, not everybody is an Instagram snob. I don’t think I am much of one either, though I do like sharing vacation photos (right here). We spent three days in Old San Juan and took tons of photos of architecture and historical sites. Spending an over an hour in touristy Condado, we took zero. Now don’t get me wrong, Old San Juan is touristy, too. It’s just a better kind of touristy. Yes, that means more expensive. But it’s also clean and stylish with so much to see and do.

Old San Juan has Instagram-worthy settings around every corner. Condado is an overdeveloped concrete beach town.

For views and scenery, stay for a few days in Old San Juan.

The streets of Old San Juan are lined with colorful, preserved buildings with various styles of European architecture. Check out more amazing pictures from our 2 weeks in Puerto Rico right here!

2. Food and Drink

Here’s the perfect vacation dinner: you wake up from an afternoon nap (the morning was spent at breakfast and then exploring cathedrals, but my! how hot the afternoons are. Good thing your Airbnb has good air conditioning.), slip into a fresh change of clothes, and step onto the cobblestone streets. There are no cars, just a few people, and you see the closest restaurant (just ahead, on the corner) is filling up.

No worries, there are ten others within a five minute walk you haven’t tried yet. Plus, you want to stop for gelato at San Juan’s world famous Anita La Mamma del Gelato (Apple Maps | Google Maps) before sitting down for dinner. Why not? You’re on vacation!

Dinner is Puerto Rican food in a small, charming restaurant. Or maybe it’s Italian in the hard-to-get-into Pirilo (Apple Maps | Google Maps). Then again, if you grab something quick, you can walk along the old blue streets and people-watch while you eat.

In a few hours you might be hungry again: walk south toward the cruise ship docks. There’s a bit more life down there, at night. There are some larger chain restaurants, casual eateries, and plenty of stops for a piña colada.

This is a glimpse of your evening in Old San Juan. We haven’t even mentioned the art galleries and shops, street food, and strolling beneath the massive city walls.

In Condado, you won’t be walking on blue cobblestone streets, poking in and out of shops and restaurants and bars. You’ll be dodging cars, so close to the sea but hardly able to hear it. Old San Juan is curiosity and charm; Condado feels cheap and over commercialized.

3. History

Old San Juan is the historical epicenter of Puerto Rico. Sure, there are indigenous archaeological sites that are older, an art museum in Ponce with priceless paintings, and old sugar cane plantations to explore. But when you’re walking around Old San Juan (hopefully with Andy on this tour), you are immersed in European colonial history.

You might see the tomb of Juan Ponce de León, descend into a crypt, drink a piña colada where it was invented, or look over the sea from a WWII bunker. There are Spanish forts, ornate cathedrals, cisterns and cobblestones and cannons.

Lots of these things (and more!) are on my Old San Juan scavenger hunt.

Condado, stacked with hotels and restaurants, is urbanized. There’s no preserved architecture from the 1500-1800s to ogle at, no crumbling cathedrals to donate to, and no fortified walls from colonial times. Isn’t that a little dull?

4. Beaches: Condado beats Old San Juan

Alright, Condado wins if you’re going to sit on the beach your whole trip and won’t be leaving San Juan. If you’re anchored to San Juan and won’t be seeing the beaches of Vieques, Rincon, or Cabo Rojo, you may be better off not lodging in Old San Juan.


Well, Old San Juan was built as a fortress, with defensive walls looming right over the sea. So it’s not got much in the way of beaches. In fact, if you’re staying in Old San Juan and need to get to the beach, you’ll likely be taking an Uber across the bridge to Condado or Isla Verde.

In this case, you could stay in the true beach towns 10-30 minutes outside Old San Juan and take a day trip to explore the old city. But I’d bet, as you wander around Old San Juan, you’ll begin planning your next trip to Puerto Rico–and daydreaming about waking up in that historical district.

Old San Juan views from Castillo San Cristóbal (first) and Catedral de San Juan Bautista (second).

5. Experiences in Old San Juan vs Condado

A favorite method of mine for planning a vacation or trip is going to Airbnb’s Experiences page and checking out what areas have the most (and most fun) experiences. Old San Juan wins this one (check out your options here). In OSJ you can book snorkel trips, food tours, history & architecture tours, and professional photoshoots.

If you’re looking for experiences that go above and beyond laying on the beach, stay in Old San Juan.

It’s Your Vacation

At the end of the day, where to stay in San Juan depends on the kind of vacation you’re looking for. If you want something more historic, photogenic, and cultural, Old San Juan will exceed your expectations. However, if you want to hang out in at a casino resort and lounge on the beach during your trip, check out Condado (and even neighboring Isla Verde). These towns have a much more American beach town vibe (that’s not a compliment) while Old San Juan is a cultural treat.

To each his or her own, as they say.

If you do visit San Juan and stay in Condado, make sure to take a trip or two into the old city, just a few minutes down the road. Visit a fort, walk the blue cobblestones, and “ooo” and “ahh” at the architecture. Buen provecho!

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George Callahan is the creator of Pine Tree Poet. He is an author of fantasy stories and an adventure poet. He prefers mountains and pine trees to most other things, and usually takes his dog Cowboy along for the ride.

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