San Juan, Puerto Rico Travel Guide

Puerto Rico has had its fair share of bad PR (no pun intended) in the past couple of years. Between the one-two punch of Hurricane Irma and Hurricane Maria and then the recent earthquakes, I’ve encountered a lot of questions regarding Puerto Rico’s readiness for visitors and capability for hospitality. I drove around the entire island, literally from tip to tip, and the while there is still visible damage from the hurricanes, it’s not going to affect your trip. The earthquakes, while they are still active, are near Guanica which is in the south west portion of the island and does not have a heavy tourist presence. Let me be the umpteenth person to tell you - Puerto Rico is ready for you!

San Juan is the capital of Puerto Rico, the most populous city, and has something for everyone. The old, walled city filled with brightly painted Spanish Colonial architecture is aptly named Old San Juan and you can spend a day walking its cobblestone streets and exploring historic fortresses. Condado is a beachside strip of high rises housing luxury hotels, restaurants, clubs, and shopping. Santurce is a large area filled with smaller neighborhoods, each with their own vibes, but is considered a more local feel and an up-and-coming area.

I spent a large majority of my time in San Juan exploring the Santurce neighborhoods. I stayed in Ocean Park, a beautiful gated community of beautiful homes with a semi-private beach where you can watch windsurfers glide through the air. I wandered down Calle Loiza and Calle Cerra checking out street art, murals, and little shops. I bar hopped on Calle Canals near La Placita where all of the locals gather on the weekends. Exploring areas outside of the typical tourist spots is how I like to spend most of my time so if you’re ready to walk outside of the walled city of Old San Juan (you really should) then read on.

Stay:

Old San Juan - The beautiful walled city where most of the tourist spots will be. Personally I think it’s great to visit this area, but I would be more apt to stay outside of it, especially if you’ll be going to the beach often as beach accessibility is limited here.

Condado - This area reminds me of Miami. Tall buildings, luxury hotels, restaurants, and shops. Stay here if you don’t want the fuss of walking very far or exploring much. Everything is at your fingertips here - beach included.

Santurce - A local experience and no-frills neighborhood. Tons of restaurants and bars and streets to wander. Ocean Park is the nicest area in Santurce and the following spots are in/close by:

The Dreamcatcher - This is a boutique hotel inside the gated community of Ocean Park and seems made up of a few different buildings with beautiful courtyards entwining them. Every room is unique and has its own special touches. There are great common areas, yoga on the beach, a beautiful restaurant, beach supplies, and a general feeling of calm and serenity here. It’s in an incredibly walkable area, a block to the beach and a few blocks from Calle Loiza to hit any kind of food you might be looking for. They’re very vegetarian and vegan friendly and offer an incredibly detailed map of other spots in Santurce, including highlighting the ones that are veggie friendly.

Tropical Guest House - This is a small, modern, boutique hotel a block from the beach right outside of Ocean Park. The rooms are big and the bathrooms are even bigger. They offer a welcome drink at the lovely bar and restaurant and ridiculously good cookies too. They have beach supplies available and they’re in walking distances to a ton of great restaurants and bars.

Eat:

Caficultura - Breakfast, brunch, and coffee all day.

La Penultima - Casual spot with elevated bar bites such as a fried chicken sandwich, cauliflower wings, pork belly bao, and disco fries. Picnic tables outside and good drinks.

Kasalta - This spot is like a Puerto Rican deli. One counter has sandwiches and hot soups and another counter does pastries and coffee. All of the locals get soup, and the Sancocho doesn’t disappoint. It’s like a Puerto Rican version of Dinty Moore Beet Stew. The cuban is a classic choice.

Lote 23 - A food truck area (gastronomic park) with a few great vendors. Everyone talks about the guy slinging pork.

Cocina Abierta - A cool, small spot for a great meal that is globally influenced with great wine pairings.

Cafe Regina - Very small cafe with outdoor seating. Fabulous toasts and brunch bites with coffee, juice, and tea. One of my favorites.

Vianda - Beautiful, well regarded restaurant with big open windows looking a few blocks from La Placita. Pro tip: you can get half portions of the appetizers so you can try more dishes.

Marmalade - Upscale, tasting menu restaurant which I heard many refer to as the best restaurant in San Juan. 

Jose Enrique - San Juan’s most celebrated and well known chef. An upscale spot for Puerto Rican cuisine.

Santaella - Upscale, elegant Puerto Rican food in a trendy spot with good cocktails near La Placita.

Sabrina - A pretty spot on Calle Loiza that has a good brunch and occasional live music.

Spiga - An unassuming cafe with great food and bread in Old San Juan.

Bottega - Wine bar with tapas on Calle Loiza.

Pinky’s Bar - Bustling cafe for breakfast and brunch on Calle Loiza.

Juaja - Arepas and Peruvian inspired food in a small, semi-outdoor food truck spot on Calle Loiza.

Cafe TinTan - Newer spot for cafe bites and brunch on Calle Loiza.

Drink:

La Factoria - One of the World’s 50 Best Bars. There are a few different rooms (I think 5) with a different menu in each. Of course you can get a normal cocktail, wine, or beer here but that kind of defeats the fun. Lots of tourists but the bartenders are still welcoming, thoughtful, and like to make custom creations.

El Batey - Classic dive bar with writing all over the walls and ceiling. Dimly lit and serving cheap drinks like all good dive bars must.

La Penultima - A little divey, a little bit hipster, cool spot with an outdoor patio. Great cocktails and bar bites. The carbonated negroni piqued my interest.

La Coctelera - More of a cool cocktail bar on Calle Loiza with lots of homemade ingredients but they have a menu full of interesting food as well.

El Tap - A hybrid brewery/bar with a bunch of Puerto Rico and beyond beers and even some housemade sangrias.

La Taberna Lupulo - A cool tap room with a ton of local beers and small bites.

Jungle Bird - A tiki bar serving Caribbean drinks and fare with low lounge seats, pink neon, and palm aesthetic. Fun spot to grab a drink if you’re in La Placita.

La Placita - this is an area, not a bar. It’s the spot where all of the locals gather on Thursday-Saturday nights to get together and go out. There are many bars around this area to hop into.

Hacienda San Pedro - A coffee shop in Santurce that sources its beans from their close by farm.

Do:

Castillo San Felipe del Morro - This old citadel was built between the 16th and 18th centuries as a fortress to protect the city from attacks. Walking around the grounds both inside and outside of the walls is impressive. Inside the walls gives you incredible ocean views and an intimate look at the architecture of the building. The grounds outside are a great spot to lounge on the grass, watch the sun set, and fly a kite. A ticket to the Castillo San Felipe del Morro will also get you access to Castillo San Cristobal if you’re a history buff.

La Placita Bar Hopping - During the day it’s a bustling market. At night, especially on Thursday, Friday, and Saturday it’s the epicenter of nightlife in San Juan. This is the spot where the locals gather to go out to the bars, listen to music, and get lively.

Go to the beach - San Juan is bordered by the Atlantic Ocean and you should absolutely take advantage of the nice weather and access to the beach while you’re here. Many hotels and AirBnbs offer beach towels or other beach accessories. The wind around San Juan can be really strong so you’ll often see a lot of windsurfers and little sail boats whipping around in the ocean while you lounge. 

El Yunque National Forest - This is the only tropical rainforest in the US National Parks System. It’s about 45 minutes from San Juan and there are many tours you can get that will take you out there. Renting a car and making this drive yourself is also incredibly easy. There are beautiful waterfalls to see and many are very easily accessible from the road. Some of the trails are still closed since the Hurricanes, so if you’re looking to hike make sure to check openings before you go. There’s a very busy strip of bars on the beach on the way to/from El Yunque so make sure to stop and enjoy if you have a designated driver.

Santurce Art Tour - You don’t need to book a guided tour to do this, although you can if you like the structure and having a guide. Simply find your way to Calle Cerra and walk along it and you will see tons of murals and street art. The movement began with an art festival called Santurce es Ley (Santurce is Law) and has grown exponentially since then. Tons of young professionals start coming out to the bars in this area after work for happy hour.

Art Museums - If you like to look at art in the confines of art conditioning then there are a few art museums in San Juan such as the Contemporary Art Museum, Museo de Arte de Puerto Rico, Museum of Art and History, and MADMi.

Casa Bacardi - You can take a ferry from Old San Juan to the Bacardi Factory and there are quite a few different types of tours to experience for the rum lovers among us.

Shop:

Ole - You can customize your own Panama hat here. They’re pretty affordable as far as custom hats go.

El Galpon - A slightly more expensive hat store but with a ton of variety.

Concalma - Unique, handmade fabric bags in all types of styles, colors, and patterns.

Pure Soul - Flowy, linen clothes for those hot PR days.

Marisel Herbal Bath and Body - An all natural, handmade skincare and beauty store with great soaps, body scrubs, and even natural bug repellent and sunscreen.

Cigar House - A great stop for cigar lovers to hang out, have a smoke or drink and check out their gigantic humidor.

Gemileo - More smudge sticks and incense than I’ve seen anywhere else.

Tres Palmas - A trendy surf shop with a few locations.

Vintage - Vice Versa and ElectroShock Vintage both have a great selection of clothing. Vice Versa has the largest amount of vintage luxury shoes I’ve ever seen.

Calle Loiza - Walking along Calle Loiza you will see a ton of boutique shops to pop into.

The Look:

City cool but trying to literally stay cool. Loose, breathable, and light. Super bright and tropical is okay, but you will likely stand out a little as locals aren’t dressed like they live at the beach. All of the coastal essentials - suits, sandals, sunnies, and sunscreen required.