The Everygirl’s Long Weekend Guide to Puerto Rico

I’ve been jonesing for the perfect ~beachy vibes~ vacation for eons now — think the shift of sand underfoot, the vibrant backdrop of colorful Spanish architecture, a piña colada conveniently in hand. And after only a four-hour flight and 10-minute uber ride, I was poolside in San Juan, Puerto Rico sipping a much-needed cocktail. BLISS.

Puerto Rico is a relatively small island in the northeast Caribbean and it is a U.S. territory which means — if you’re coming from the U.S. — you won’t need your passport (score). You’ll also be able to use your cell phone (without additional fees) and your cash (the US dollar is the currency of Puerto Rico). And one more thing to thing to add to your list of pros: there is an abundance of inexpensive direct flights from many U.S. cities.

Most tourists chose to stay in either Condado (a resort area along the beach) or Old San Juan, which are about 10 minutes apart. If you’re looking for a true beach vacay — i.e., lounging lazily by the water — then Condado is your best option. Bon voyage! 


Puerto Rico is still feeling the effects of Hurricane Maria, which hit the island in 2017. If you’d like to donate to the relief efforts, you can find more information here


See My Puerto Rico Itinerary Here!




Where to Stay


Serafina Beach Hotel

A boutique beachfront hideout inspired by the owners’ travels to Italian beach clubs. Serafina is San Juan’s newest hotel and is located in Condado (which is only 10 minutes from the airport and a 10-minute uber ride to Old San Juan). Splurge on a room with an ocean view and enjoy the clean, modern design inspired by the colors of the sea. And plan on spending your afternoons sipping piña coladas while watching the waves crash on the rocky beach from the envy-inducing infinity pool overlooking the Atlantic.


Condado Vanderbilt Hotel

A large, luxurious hotel in Condado with exquisite ocean views, two pools, and four incredible restaurants. For opulent rooms and highly personalized service, stay at The Condado Vanderbilt.



Hotel El Convento

A historic hotel located in the heart of Old San Juan. If Spanish tile, mahogany beams, and Juliet balconies are your thing, then this is the spot for you. Step outside and you’ll find yourself wandering the colorful, cobblestone streets that San Juan is known for. And don’t worry, there’s a rooftop plunge pool for cooling off during those warm Puerto Rican afternoons.



Where to Eat


Cuatro Sombras

A local micro-roaster and coffeehouse located in Old San Juan with a rustic interior and cozy courtyard.


El Jibarito

An unassuming, inexpensive, local restaurant where you must know what to order. And what to order is the sweet fried plantain (thank me later) and creole chicken. I promise you won’t regret it.


La Factoría

If you want to party with the locals, then this is the bar for you. Or walk through the swinging doors located behind the bar for a quiet, cozy drink in the hidden speakeasy wine bar.



Señor Paleta

Artisanal popsicles sold near the port in Old San Juan. I have not stopped craving the strawberry-mango popsicle (vegan-friendly!) since leaving. I promise not to judge when you lose count of how many popsicles you’ve had.


Patio del Níspero

Rest your feet after hours of wandering Old San Juan in Hotel El Convento’s restaurant. You’ll feel like you’ve stepped back in time while eating beneath the shade of the hotel’s century-old Níspero fruit tree.


Lote 23

Another spot highly recommended by many locals. Enjoy a diverse menu from a collection of food carts — including a vintage airstream. I heard several people rave about the fried mac n’ cheese. Enjoy your lunch with locals at shaded picnic tables.


Ola Ocean Front Bistro

One of the four mouth-watering restaurants located at the Condado Vanderbilt Hotel. Sit ocean-front and enjoy brunch, lunch, or dinner. These fresh, flavorful dishes are 100% worth the splurge (if you’re there for lunch, order the quinoa power bowl).



Serafina Restaurant

Dine al fresco beneath the string lights and meandering ivy at this locally owned Italian restaurant. Order the brick oven pizza and snap your perfect #foodie gram between slices — every corner of Serafina is winning at the aesthetic game.


1919 Restaurant

If you’re looking for a fine-dining experience with ocean views, then make a dinner reservation at Condado Vanderbilt Hotel’s highly reviewed 1919 restaurant. But be prepared for an unforgettable island creation from the Michelin-star rated chef.


Ropa Vieja Grill

A delightful fusion of Cuban and Puerto Rican cuisine located in Condado. The entrees are large, thus perfect for sharing.



Where to Explore


Get lost in Old San Juan

Put away the map and simply wander down the colorfully-lined cobblestone streets. Keep an eye out for one of the gorgeous murals and color block walls. Note: Old San Juan is small enough that you can easily get around on foot. But start exploring as early in the day as possible to avoid crowds (still allowing yourself several hours to see the city).


La Placita

Join locals for an evening of salsa dancing in the square.



San Juan Beaches

Playita del Condado and Playa Ocean Park are wonderful beaches to lay down your towel and go for a swim. Take note: Playita del Condado is the perfect spot for a sunset swim.


Laguna del Condado

If you want to get out on the water, rent a kayak or paddleboard on the Lagoon.



Castillo San Cristóbal  &  Castillo San Felipe del Morro

History buffs unite. Old San Juan was once surrounded by three miles of stone walls and two forts, both of which you can explore to your heart’s content. Note to the neutral lovers: there’s a gorgeous all-white arched corridor In Castillo San Felipe del Morro if you’re looking for the perfect gram.



Day Trip

Once you’ve explored San Juan, take a day to chase waterfalls in The El Yunque Forest, discover hidden coves on the southwest corner of the island, or swim in the crystal clear waters of a Spanish Virgin Island.


Source: Skyscanner


El Yunque National Forest

About 45 minutes from San Juan you’ll find the entrance to Puerto Rico’s national rainforest — a refuge the locals take great pride in. Rent a car (or hire a tour guide) and chase waterfalls on the 29,000 acres. Just between you and me: for a quiet swim, head to the hidden and less known Rio Espiritu Santo. You’ll likely have this waterfall all to yourself.


Island Hop

Visit one (or several of the Spanish Virgin Islands). There are plenty to choose from: Culebra, Vieques, Icacos Island, Palomino Island, or Palominito Island! If you prefer to go to an island and stay several hours you can hire a water taxi for $20-$40 to take you to: Icacos Island, Palomino Island, or Palominito Island. Or if you prefer to visit several islands you can join a catamaran tour for $80-120 (this option usually includes lunch, snorkeling, and a lot of music). If your budget allows, you can even charter your own sailboat.



Extra Tips


  • Don’t drive a car around Old San Juan. The streets are narrow and parking is scarce. Support the local economy by Ubering. The only time you may need a car is if you chose to drive outside of San Juan (heads up: the road signs aren’t always visible, so allow for a little extra time in case you miss a turn).
  • Unless you’re renting a car, you will need to take a taxi from the airport to your hotel. There is a taxi stand as soon as you exit baggage claim. They will give you a flat rate based on which hotel you are heading to so you don’t have to worry about being swindled.



  • During the summer, it is hot and humid. Plan on exploring Old San Juan early in the morning and/or in the evening. This way you avoid the heat as well as the majority of tourists (cruise ships begin arriving at 9 am). Spend your afternoons cooling off with a poolside cocktail.
  • Taxes are high. Be prepared for an additional 10.5% on your dinner bills due to sales taxes.
  • January — June is supposedly the best time to visit San Juan (go after mid-April to avoid the winter crowds).



Puerto Rico is still feeling the effects of Hurricane Maria, which hit the island in 2017. If you’d like to donate to the relief efforts, you can find more information here

  • Many Puerto Ricans have been saying the best way to contribute to hurricane relief efforts is to directly spend money at their local establishments and put money back into their economy so they can rebuild themselves. Puerto Rico based aid groups are probably great to donate to, but institutions like Red Cross are notorious for pocketing donated funds.

  • Jaclyn Taylor

    FYI there is a strong taxi union in Puerto Rico, and they’re very against Uber. Uber isn’t allowed to drive to or from the airport, and there are certain blocks and locations which have “no Uber” zones. When I went, we got yelled at by a taxi driver for waiting for our Uber on the wrong street corner. You might want to consider sticking to taxis for simplicity!

  • I have family that lives in Puerto Rico (specifically from Rio Grande and El Yunque, you can actually see our home from el portal del yunque) and the whole island is still struggling from last year. I would encourage looking up bed and breakfasts outside of San Juan, the city has been recovered but once you go to the center of the island and more rural areas they desperately need more support. I also would not use an Uber in san juan, there’s taxis and there are free hop on and hop off trolleys that go to el morro and all the tourist spots. Speaking of el morro and the forts, those walls are beautiful but they’re not meant to be stood or sat on, even for the perfect instagram photo. So much more of the fort was open when I was a child and now parts are being closed off because people don’t respect the site. Look into kiosks and the markets on the side of the roads, they have the best food and fruit. I appreciate you listing a spot to donate but disappointed to see American Red Cross listed on the page, they did little to help during the hurricane. I hope people do start returning to the island, thanks for writing about my second home.

  • My husband and I love PR-such an easy trip from Chicago. P.S. we are so obsessed with El Jibarito. I have no idea how they make their hot sauce but it is the best EVER. I asked the server if I could buy a bottle to take home as a souvenir, he told me to come back 2 days later around noon and we did just that! The things I will do for food, haaha. It lasted us 5 months and the year after we returned for more. Thankfully the same server was there and remembered us and provided us with another bottle-we totally lucked out. We’ve got to get back down there soon and reload! P.S. You’re pics are lovely!