Visiting San Juan, Puerto Rico for the first time? Soak up the sun in one of the oldest cities in the Americas.

San Juan: you have my attention. This is a vibrant Caribbean city filled with old world charm and modern excitements. Located on the northeastern coast of the island of Puerto Rico, it’s the perfect tropical getaway for sun-seekers, beach bums, and foodies alike! Picture yourself strolling down cobblestone streets flanked by colorful, colonial buildings with the sounds of reggaeton and rattling cocktail shakers wafting through the air.

Founded in 1521, San Juan is one of the oldest cities in the Americas. Its rich history is beautifully preserved in the iconic forts of El Morro and San Cristóbal, standing guard over the Atlantic Ocean. These stone sentinels have witnessed pirate attacks, colonial battles, and countless sunsets, and now, beckon the likes of six million tourists a year into their storied walls. But San Juan isn’t just focused on the past; it’s a city that pulses with life, from bustling bars, a vibrant art scene, and golden beaches. Grab a piña colada (did you know it was invented here?), sink your toes into the warm sand of San Juan’s many beaches, and let the laid-back island vibes wash over you. ¡Bienvenidos a San Juan – your top five adventure starts now!

San Juan Flags

Did you know the Puerto Rican flag was created in 1895, by the Puerto Rican section of the Cuban Revolutionary Party, which advocated independence for Puerto Rico and Cuba from Spanish rule.

What to do in San Juan Puerto Rico instagrammable streets

Find this famous mural at El Callejon de la Puerta Bandera (Flag Door Alley)

Tips for San Juan Travel

➔ Puerto Rico is a US territory and US citizens do not need a passport to visit.
➔ When arriving at SJU airport, there is a designated Uber pickup located by the JetBlue Domestic Arrival Area (Terminal A).
➔  Uber is an extremely affordable way to get around in the city but pay Latin American wages. They are widely available in the metro area and will take you to any place on the island. But MAKE SURE TO PRE-ARRANGE TRANSPORTATION BACK. Do not get stranded.
➔ Taxis are fixed rate and pay local wages.
➔ Some of the northern beaches such as Condado, Ocean Park, and Mar Chiquita are notoriously more rough and dangerous than beaches in the northeast area of the city. And not all beaches have active lifeguards on duty so swim at your own risk.
➔ Puerto Rico is in the tropics and experiences a hurricane season from June to October. Please be mindful about traveling to Puerto Rico and take weather advisories seriously.
➔ Remember Puerto Rico is an island and imports a number of ingredients so expect equal to, if not greater, prices for your meals. For example, a sushi roll cost us $22 USD. Restaurants that serve local fare are typically cheaper.


Top Five Things to Do in San Juan, Puerto Rico on The Next Somewhere

1. Snap photos around Old San Juan

Every corner tells a story in Viejo (Old) San Juan, the capital’s historic heart. The rainbow-hued colonial buildings that trim the cobblestone streets date as far back as the 16th century. Around every turn, you’ll find photogenic street art and hear salsa music spilling out of buzzing bars. There are pockets that feel touristy, but you can also find locally-made gems at many boutiques and restaurants primarily serving one-of-a-kind Boricua food like El Jibarito. Find more places to eat here!

Viejo San Juan is also home to the San Juan National Historic Site, with landmarks like the impressive El Morro and San Cristóbal fortresses that have stood guard for 500 years. The fortifications are actually the oldest European constructions in the Americas.

Here are some places to snap photos for instagram:

✚ Cross street of Calle Imperial and Calle de la Virtud – El Callejon de la Puerta Bandera (Flag Door Alley)
✚ Calle De San Jose – La Puerta de La Bandera (Puerto Rico’s black and white Resistance flag)
✚ San Jose Cruise Port –  ¡Boricua! Sign

Calle Fortaleza (Umbrella Street) where the colorful umbrellas have been taken down and its now reported to be blocked off at times.

Resistance Flag Graffiti in Viejo San Juan

La Puerta de La Bandera featuring the black and white Resistance flag was redesigned overnight as a political activity

Best places to take photos Old San Juan Antiguo 26

I will never say no to a bright yellow facade especially when it belongs to my favorite bar in the city, Antigo 26

Viejo San Juan where to take photos

Calle de la Virtud is the best backdrop for colorful photos in San Juan

2. Dance the Night Away in La Placita

La Plaza del Mercado de Santurce, simply known as “La Placita,” transforms from a sleepy marketplace in the daytime, to the city’s hottest dance spot come nightfall. Whether you’re in the mood for live salsa, reggaeton, or some electronic beats, La Placita has you covered. The area operates like a huge open-air bar with awesome people watching until the wee hours of the dawn. La Placita is also one of the few places in the city proper where you can experience a more local way of drinking known at places called chinchorros. Here are some fail-safe venues for a great night out:

✚ JungleBird
✚ Club Vibra
✚ Santurce Cafe
✚ Mijani The Club
✚ Aguardiente
✚  Garabatos

Hours: La Placita is open Thursday – Sunday, from 10 am to 5 am (bars are required to stop serving around 2 am)
Pro-tip: Use a rideshare or taxi although rideshares get harder to come by as it gets later into the night.

▶️ Check out my mini guide to San Juan!

3. Indulge in first-class Puerto Rican Food and Cocktails

In addition to local favorites like mofongo, arroz con gandules, and pasteles, you can also experience award-winning farm-to-table dining and fusion feasts. I learned that sushi is all the craze in San Juan and recommend you try any one of the Puerto Rico sushi rolls at Kisoro Sushi Bar. Of all the places I ate, I’m STILL thinking about Cocina Al Fondo, opened by James Beard winner Chef Natalia Vallejo that celebrates Puerto Rico’s culinary heritage and spotlights the seasonality of the island’s vegetables. Order their alcapurria (frittered plantains) with tuna sashimi. From hole-in-the-wall canteens to fancier dining options, there were no misses for every meal. My friend Kay put together this Best Restaurants in Puerto Rico list that I will happily endorse as I was present for most of the meals!

And did you know that Puerto Rico is the rum capital of the world? You’ll find rum-based cocktails a plenty, the most important being the piña colada, which was created right in San Juan! While the Caribe Hilton Hotel and Barrachina both claim to be the official birthplace of the piña colada, Antiguo 26 in Old San Juan is my favorite spot for piña coladas. Here, you can try a Monchito 2020, a clarified version of the classic that pays homage to its creator, Ramon “Monchito” Marrero. See more places to drink here.

Where to eat in San Juan Puerto Rico Cocina al Fondo

One of the best meals I’ve ever eaten in my life at Cocina al Fondo

Creative cocktails in San Juan Puerto Rico What to Drink

The Monchito 2020 is a clarified version of the Piña Colada at Antiguo 26

4. Splash around Waterfalls in El Yunque National Forest

A trip to El Yunque National Forest is a must when it comes to your Puerto Rico itinerary. While the forest isn’t technically within city limits, El Yunque is only an hour away from San Juan with a number of hotels operating daily tours to El Yunque. This is the only tropical rainforest in the U.S. National Forest System and home to over 240 species of trees and countless exotic plants and animals.  For over 200 years, El Yunque sheltered the indigenous Taíno. Today, it’s known for moderate hikes on jungle trails to hidden waterfalls, rock waterslides, and natural pool swims. Don’t forget to listen for the coquí frogs serenading you from the treetops. With its enchanting beauty and vibrant ecosystem, El Yunque offers an adventurous retreat into nature.

Important: Park reservations are NOT required as of August 2023.
Other Excursions: Zipline through, and over, the El Yunque treeline –OR– take in panoramic views from the Yokahú Tower.

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5. Chill at some of the Best Beaches in the Caribbean

You can’t say you’ve been to San Juan without visiting one of its many beaches. Start with Isla Verde Beach in Carolina (right outside San Juan), the city’s most popular urban beach with its golden sands and close proximity to SJU airport. Isla Verde is made up of three beaches: Alambique Beach, featuring turquoise waters and large palm trees; Pine Grove, popular among the surfers for larger swells; and Carolina Beach, a family-friendly swimming spot with active lifeguards.

Condado Beach, known for its upscale feel, breezier shores, and nearby luxury hotels, makes it a popular spot for sunbathers and couples. The surf can be pretty dangerous so be advised before swimming.

Nearer to Viejo San Juan is El Escambrón, a proud Blue Flag beach, meaning it upholds the highest standards when it comes to environmental safety. Grab a snorkel for a closer inspection of its many coral reefs and rolling waves. For a more laid-back atmosphere, head to Ocean Park Beach, frequented mostly by locals who take leisurely strolls up and down the long stretch of sand. Each beach in San Juan is a slice of paradise, promising sun, sea, and relaxation.

Best Beaches in San Juan Puerto Rico Ocean Park Beach

Catch the sunrise at Ocean Park Beach and see some locals enjoying the beach

Activities and Shopping in San Juan

▪️ DIY Street Art Tour: Head to the Santurce neighborhood to check out the incredible street art along Calle Cerra.
▪️ Culinary Walking Tours with Spoon Experience: Sample a variety of Puerto Rican dishes to learn more about the island’s Taíno, Spanish, and African roots, all while directly supporting small owned businesses. Book here.
▪️ Distillery tour at Casa Bacardí. Uncover the secrets of rum or take a mixology master classes too. Book here.
▪️ ATV Excursion: Hop on ATVs at Hacienda Campo Rico across 2,200 acres of land with views of mountains and mangroves. Book here.
▪️ Loiza African Heritage Tour: Visit nearby Loiza to dive deeper into the Island’s African and Taino cultures. Visit local artist Samuel Lind’s studio and Artesenias Castor Ayala to see vejigantes, masks carved from coconut shells and watch a Bomba dance performance. Book here.

Mal Caribe graffiti Calle Cerra

My favorite mural on Calle Cerra adorns the Mal Caribe building

Murals in Calle Cerra

Every year in May, there’s a street art festival called ‘Santurce es Ley’

Family friendly fun in San Juan Puerto Rico

The impressive LED lights of Distrito TMobile

▪️ Water activities in Laguna del Condado: If you love doing water-based activities, try your best at paddleboarding and more-out-of-the-box LED night kayaking and glass bottom morning kayaking.
▪️ Distrito T-Mobile: Family-friendly entertainment hub with ziplining, movie theaters, eateries, and an LED-screen covered plaza.
▪️ Handmade Avarcas & Espadrilles: Design custom espadrilles that can be shipped internationally in Viejo San Juan.
▪️ Santurce Pop: Local design market with a number of talented vendors that is especially bustling from Thursday to Sunday.
▪️ Cultura Bicicleta Coop: Experience guided bike tours of Puerto Rico or rent your own bike to travel at your own pace in the city.

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Where to Eat in San Juan

▪️ Princesa Cocina y Cultura: Old San Juan’s first gastrobar with dreamy outdoors-turned-indoors dining spaec featuring classic Puerto Rican dishes from the mid 1800s-1900s.
▪️ La Pradera: Hole-in-the-wall frequented by locals serving unfussy plates of flavor-packed Carribean food like Ropa Vieja and Bistec Encebollado con Tostones.
▪️ La Casita Blanca: House-style setting for traditional and well-flavored Puerto Rican dishes with constant queues and generous on-the-house starters.
▪️ Pinky’s Calle Loiza: Extensive breakfast menu eaten outdoors with the most accommodating waitstaff in Ocean Park.
▪️ Berlingeri Cocina Artesenal: Beloved vegetarian paradise with a wide number of vegan options and macrobiotic-esque food. Try some local kombuchas from Karibe Kombucha.
▪️ El Jibarito: Longstanding cafeteria-style eatery serving up the famous jibarito plantain sandwich, using fried plantain slices in lieu of bread.
▪️ Cayo Caribe: Seafood restaurant chain featuring fresh catches and memorable meat paellas.
▪️ Chocobar Cortes: Chocolate-themed restaurant with chocolate-themed beverages and eats, and even a full cocktail menu.

Princesa Gastrobar

Princesa Cocina y Cultura also serves amazing craft cocktails that I got to enjoy with friends who are also bloggers, Michele of Adventures Abound and Kay of The Awkward Traveller

Where to eat in San Juan Puerto Rico Princesa

The lamb piñon (cheesy plantain casserole) with mashed yucca puree lives in my head rent free. Order it at Princesa Cocina y Cultura.

Where To Drink in San Juan

▪️ La Factoría: Voted the best bar in the Caribbean, is filled with secret passages to six different bars, all with their own ambiance, and bartenders will whip up cocktails based on your preferences.
▪️ Antiguo 26: Moody, rustic bar with sharp and personable bartenders whipping up luxurious cocktails and tasty tapas plates.
▪️ El Batey: Rough-around-the-edges dive bar, which only adds to its air of cool given its the oldest bar in the city.
▪️ Los 3 Cuernos: Dive bar wallpapered in dollar bills peddling cheap shots but get the chichaito shot made with anise and rum, the bar’s specialty drink.
▪️ El Cafetin: Chill bartenders with drink promos like $5 mojitos and ice cold beers and bar food to feast on while you play board games.
▪️ Barrachina: Another location claiming piña colada origins but also a favorite on the tourist circuit for Puerto Rican specialty dishes and western options.

Antiguo 26 Best Cocktails in San Juan

Sit right at the bar for some awesome mixology at Antiguo 26

Los 3 Cuernos Best Dive Bars in San Juan

Can’t get enough of the specialty shots at Los 3 Cuernos

Where To Stay in San Juan


Boutique serviced apartments featuring a unique blend of contemporary aesthetics and bohemian finishes. The thoughtfully laid out apartment provides a comfortable living room, cozy bedrooms, and a fully equipped kitchen, and definitely caters to travelers seeking a home-like atmosphere. This property is located in the quieter Ocean Park neighborhood (15 minutes from Old San Juan). There’s a lot of natural light in this space and separate ACs in every room as well as smart storage options for every guest. I also loved the lasercut map of the neighborhood detailing favorite local spots like cafes and restaurants, which is front and center in the kitchen. We used this as our homebase for a travel blogging conference away from the conference ongoings just to see more local neighborhoods like Ocean Park.

The DW brand also owns Dreamcatcher Hotel, San Juan’s only vegetarian boutique hotel.

BOUTIQUE |  Full apartment begins at $300 per night for four people.

DW Tropicalia Map in Kitchen

Basically a mini travel guide right at our fingertips

DW Tropicalia Serviced Apt in San JuanGroup Travel in San Juan Puerto Rico


The Caribe Hilton Hotel is a luxury establishment in San Juan, ideal for both leisure and business travelers. The hotel features bright and serene rooms and suites with modern amenities such as high-speed Wi-Fi, flat-screen TVs, and plush bedding. Guests can enjoy a range of facilities, including three outdoor pools, its own secluded private beach, a well-equipped fitness center, multiple dining options serving local and international cuisine, and versatile event spaces for meetings and celebrations. And the hotel also is most famously known as the birthplace of the birthplace of the Piña Colada. Order one right in the main atrium at Caribar which offers gorgeous ocean views.

LUXURY | Rooms begin at $380 per night.

Map of all San Juan, Puerto Rico Locations

Have you ever been to San Juan? What would make it on your top five list? Comment below!

Filipina-American Millette Stambaugh is a thirty-something former expat who has traded her nomadic ways for Philadelphia living. Corporate worker by day, content creator by night, Millette specializes in visual storytelling and joyful journeys and wants to help others find their "next somewheres." Follow her escapades on Instagram, Youtube, and Tiktok @thenextsomewhere.


  • Kay

    June 26, 2024

    Have you ever gotten homesickness…but for a memory? That is what this post has given me. Thank you for giving such a beautiful overview of some of what Puerto Rico has to offer, but also for helping me slip back into such wonderful (and also beautiful!) memories of my time. Already anticipating our next memory-making trip!

  • Karen

    June 26, 2024

    We were just in San Juan recently and I wish I would’ve had this list. I’m not much of a city visitor so this would’ve been really helpful, especially since we had our young adult daughter who likes to see all the cool places in a city. These are some amazing ideas.

  • June 26, 2024

    Puerto Rico is on my bucket list. I can’t wait to visit this part of the world and to see the many places you recommend. Thanks for sharing.

  • June 27, 2024

    I’ve never been in Puerto Rico, but I’d love to visit! San Juan looks like a place with such a unique atmosphere, as it combines the colonial history with modern-entertaining vibe. With your helpful tips it will be easier to plan my first trip to San Juan! Thanks for sharing!

  • Natalie

    June 28, 2024

    I’ve never been but always wanted to go! Great guide!

  • June 28, 2024

    I’d love to visit San Juan! You know when you get a feel of a city through it’s vibe – yea, I can definitely get its vibe through this and I’m so excited to visit one day. The food at cocina al fonda looks delish. I am a rum drinker through and through so I’ve been 100% convinced to visit…
    Mom’s talked about visiting and I think she’ll actually enjoy it very much! Saving this for a little girls trip!


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