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.

Vieques Travel Guide

Vieques is the vibrant green of all of the plants, the bright pink of the flowers, the sparse street art, the colored buildings, and the constant fear of the wild horses running in front of my Jeep as I roll through single lane roads on my way to the next beach or snorkel spot. I pick up the bones from sea urchins on the shoreline and listen to the trance of the palms blowing in the wind. The beaches are completely different from one to the next and finding your favorite is a serious endeavor. I start every morning with yoga and sound baths at La Finca Victoria and end every night in awe of the amount of stars in the sky. Vieques is beautiful, but it must be acknowledged that it’s an island borne out of hardship.

Vieques is going through it’s second rebirth - once after the Navy left and now rebuilding after Hurricane Maria. The US Navy used each end of Vieques as training grounds for bombing, shooting, and disposing of waste until 2003 after the island fought back to regain control of their land. Not only is some of the island still closed to the public because of the risk of live munitions, there is even a report 27% higher risk of cancer for Viequenese than those in mainland Puerto Rico, assumedly from the high amount of contaminants that they were exposed to. As with the rest of Puerto Rico, Vieques was devastated during Hurricane Maria and driving around you can still see the effects of the storm on infrastructure 2 years later. After the storm every leaf on the island was blown away but now even the 400 year old Cieba tree is back to blooming. They’re still without a hospital or medical facility since Maria and after the unfortunate death of a teen complaining of flu-like symptoms they’re garnering more public outrage in their fight for healthcare on the island. All of this just proves the resilience of the island, and it’s people, and it’s impossible not to be taken aback by their strength and appreciate all of it even more.

The people, fauna, and spirits of the island are thriving despite the struggle and I feel lucky to bear witness to it when I’m there. It’s wild and beautiful and a place where the growth and energy around you is infectious. Vieques should be both a pitstop on a Puerto Rican trip and a destination unto itself.

Getting There and Around

Flying: Flights from San Juan to Vieques are about 25-30 mins long in a 10 seater plane and cost around $80-140 depending on the season and the airport. You can depart from either the San Juan International Airport or Isla Grande Regional Airport. While SJU is convenient if you’re arriving or departing and trying to align connections, I would actually recommend flying out of Isla Grande as it’s closer to the center of the city, little to no hassle or check-in time, and about 2x cheaper. AirLink Vieques and Seaborne are the two main airlines that fly this route and are codeshare partners. You can also fly from Ceiba to Vieques which is about $40 one way and a 10 min flight but that would only make sense if you were already out and about in Puerto Rico with a car.

Ferry: There is a ferry service from the town of Ceiba to Vieques that runs a few times a day. The ride is about 45 mins and costs only $2. Getting a ticket and getting onto the ferry during the high season (Nov-March) is reportedly difficult and the advice I’ve heard is to book a ticket in advance. If you’re unable to get a ticket in advance make sure you’re at the ferry terminal early. The ferry is large and I didn’t experience any issues with either of my passages but I’ve heard many others have had more volatile rides depending on waves, storms, and swells. If you’re driving to Ceiba there is a parking lot available for parking your car as it’s HIGHLY unrecommended to downright prohibited to attempt to take a vehicle with you as that would expose you to the extremely frustrating and unpredictable cargo ferry situation. Stick with the passenger ferry and either leave your car in the lot (about $12 a day) or take a taxi to Ceiba.

While on the Vieques: I strongly believe you will want a form of transportation to fully enjoy the island. Taxis are fairly easy to obtain from about 8am-10pm but you will need to call ahead or wait for them and they typically cost at least $15 for a ride. If you’re planning to stay put or stay in town you can get away without transportation but I prefer full autonomy and the ability to see everything. There are 3 options to get around Vieques. You can rent a scooter, a golf cart, or a car. A scooter is fun and quick, but you can’t carry bags and you may not feel entirely confident, especially on some of the pot-hole ridden beach roads. A golf cart is fun, slow, and leisurely, but you might regret this choice when you see cars zipping around you and out of sight. I also regretted this during errant rainstorms that seem to pop up. A car is my recommended mode of transportation and most places offer Jeeps. The Jeeps are about $90 a day, but you’ll have music, AC, and speed on your side. It is highly recommended and essentially required to book your mode of transportation well in advance as there is extremely limited inventory to go around.

Stay

La Finca Victoria - This property is incredible. Stunning architecture surrounded by small, edible gardens, and beautifully curated spaces. The property was devastated in Hurricane Maria (like many things) and was taken over by Sylvia DeMarco, a designer and hotelier from the mainland who runs a beautiful property (The Dreamcatcher) in San Juan. Her team has rebuilt La Finca Victoria into an oasis in the middle of this beautiful island. They’ve gotten the rooms up and running and are now expanding out the kitchen and dining area and are adding on a wellness center which will host their daily 7am yoga classes and Ayurvedic treatments. They grow much of the food on-site, which they serve at their vegan breakfasts and the for-purchase snacks which you can pair with well stocked kombucha, beer, and wine. Local coffee, hot tea, and infused water is offered all day long. Each room has a diffuser with homemade oils for day and night. And most importantly, every room has an outdoor shower! La Finca is a bit secluded and right in the middle of the island so it’s highly recommended to have your own transportation. 

Hix Island House - This compound of buildings is located off the same road and technically next to La Finca Victoria. The architecture is both modern and wabi-sabi and an interesting juxtaposition in the middle of the jungle. I love the open-air feeling of the rooms. The pool and lounge area look incredibly inviting.

El Blok - El Blok is a brutalist building at the entrance of Esperanza that you can’t miss. It’s part hotel, part restaurant, part bar. This is a great spot to stay if you want to be in town and close to the beach. The rooms are on the smaller side but they’re well stocked with Aesop products. There is a rooftop lounge with a plunge pool that is guest access only besides Sunday afternoons.

Malecon Beach House - This is a small, pretty boutique hotel in Esperanza.

There are quite a few other small hotels and AirBnbs to choose from too.

Eat

Tin Box - Recently reopened after the hurricane. They host a reggae night on Mondays. They have an interesting menu of BBQ and sushi and everything I ate there was really good. Happy hour from 4-6 with $2 tacos!

El Quenepo (Esperanza) - I would say this is the fanciest restaurant on the island, but I also went in yoga pants, so I’m not sure that is saying much. The food was okay. I think I went on an off night as they’re pretty popular and have a good menu to choose from. Friends really enjoyed it there.

Bananas or Duffy’s (Esperanza) - Both very casual restaurants with a wide menu and good happy hours.

El Callejero (Esperanza) - This is a small food truck on the corner of 996 and 997. It’s run by a couple, he’s a local and they met in Miami. They have been open for a few months serving crazy good tacos, quesadillas, and elotes. 

Food trucks (Esperanza) - On the corner of 996 and 997 there are a smattering of food trucks that pop up. There is a meat focused one, two taco trucks, and a truck with skewers and pastelillos and a seating area. The pastelillos from the big truck with the seating area are crazy good.

Rincon del Sabor - An outdoor area with a food truck. You can pick from a lot of grilled or fried meats or seafood and quite a few sides. The salmon with monfongo or trifongo is SO GOOD. Literally my favorite salmon ever.

Coqui Fire Cafe (Isabel) - A small restaurant in Isabell with a good menu. Get the cuban taco. They have a ton of homemade hot sauces to try and will pick out a few for you based on your preferences.

Rising Roost (Isabel) - A cute cafe with breakfast and brunch and great coffee and juices.

Isla Nena Cafe (Airport) - Yes, the cafe at the airport. Absolutely no-frills but if you’re on the north side of the island and hungry or waiting for a flight this a good spot to grab some quesadillas or a burger. This is also a Green Packers “Lil Backers” bar so if you’re a cheesehead you should stop by for that alone.

Drink

El Blok - They have both a nice bar on the ground floor and a beautiful rooftop bar that is open on Sunday afternoons for the public.

Crab Island Distillery - Off the beaten path past Mosquito Pier. It’s only a minute or so off the main road but it’s a brand new distillery making rum and doing tastings.

Duffy’s - outdoor bar, chill, locals, dog friendly

Banana’s - outdoor bar, chill, extensive drink list

El Sombrero Viejo - wine and liquor store attached

Rising Roost - juices, tea, coffee

Do

Snorkeling (or SCUBA diving) - Mosquito Pier is the easiest spot to explore as you just jump right in and follow the pier and see everything from colorful fish to huge urchins to the occasional sea turtle or ray. About ¾ of the way down the pier there are steps where you can park and easily enter/exit the water. There is usually a scuba flag flying here. Punta Arenas is another good place to go snorkeling. There is a ledge reef that starts about 20 yards from the water line and extends for quite a while. There is really beautiful coral here but I didn’t see nearly as many fish as I did off Mosquito Pier.

Bioluminescent Bay - Vieques has the brightest bioluminescent bay in the world. The dinoflagellate in the water glow when they are agitated by our hands, oars, or kayaks. They briefly emit a bright blue light which is magical to see. On a clear night they mirror the stars in the sky. You can go on a tour in a glass bottom kayak for $50 and it’s a really special experience.

Punta de Tierra/Cayo de Tierra - you can walk to a small island in the south next to Esperanza. There is a loop trail that goes around the island and there is some really incredible beachcombing. Get there in between Sun Bay and Esperanza on a road tagged “Quebrada La Mina” on Google Maps. You can watch people surf the waves in between the islands, about 300 yards off shore.

Puerto Ferro Lighthouse - There is a dilapidated lighthouse, or at least what remains of it, in the Wildlife Refuge. While the lighthouse is really nothing to see the views from this spot are expansive and beautiful and there are some trails that veer off from this area.

Gallery Oro - A small gallery of local and Puerto Rican artists, right next to the entrance to Playa Negra.

Beach Hop - Absolutely the best thing to do while on the island. These are all named beaches but there are plenty of spots just to pull over and have a space for yourself:

• Playa Negra: Black Sand beach. You will have to walk about 10-15 mins along a dried up river bed to reach this beach, which is black in spots because of the volcanic sediment. It’s beautiful and the surf is usually big.

• Playa Grande: A big expanse of beach with big surf, rocky sand, and no one in sight.

• Playa Caracas - A popular beach spot with more people than you will see on others. Pretty calm waves and white sand.

• Playa la Chiva - A semi-circle of beaches with about 15 pull off points, each with their own picnic table and hut. A good place to post up and have a picnic. The water is usually pretty calm and there can be some snorkeling here depending on conditions.

• Pata Prieta: You will need to walk through a short trail to the beautiful beach.

• Playa Sun Bay: This it the large, “public” beach. There are bathrooms on site and wild horses are a common sight. You will see a lot of people here and the waves are moderate.

• El Gallito: Aka Gringo Beach, close to the airport. Very small and very chill.

• Playa Bladin: On the left hand side of Mosquito Pier this is an incredibly calm area with shallow water and good shell picking.

• Punta Arenas: A small beach with great snorkeling.

Bring

Stainless steel straws 

Koozies - It’s hot. You want your beer to stay cold.

Bug spray - The bugs can be bothersome, usually after rain. I mean, there is even a place called Mosquito Bay!!

Snorkel gear - There are so many spots to jump in and explore on your own. It’ll be advantageous to have your own mask and snorkel if you’re adventurous.

Sunscreen - Reef friendly please!

The Look

Casual, relaxed, beachy. You’ll stick out in heels, heavy makeup, or being super put-together. Guys in collared shirts and polo shirts stick out too. Casual dresses and sandals for dinner. Snapbacks and tshirts for men. Workout gear for excursions. Beach coverups for the beach and lunch runs. Think surf style.

Shop The Look here: