3 Days in Puerto Rico: Itinerary & Places to Eat!

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Since my friend was waiting on her visa and couldn’t leave the U.S, we wanted to go somewhere a bit different without leaving the country. An obvious choice for a long weekend was Puerto Rico – a Caribbean island that also happens to be an unincorporated U.S territory.

At 3.5 hours flight time, the journey from New York to San Juan is fairly short and you don’t have to take your passport since it’s a domestic flight. A U.S driver’s license will do. We stayed 3 nights in San Juan and rented a car for 24 hours so we could explore a bit more of the island.

Since the island is fairly big it’s impossible to cover everything there is to do in Puerto Rico in 3 days, so we stuck to the north and east coast. I really enjoyed my time in PR and fully intend to go back another time to explore other parts of the island.

If you plan to spend 3 days in Puerto Rico, here’s my suggested itinerary.

Where to Stay On Your 3 Days in Puerto Rico


First a little note on where to stay. We stayed in an Airbnb, specifically this one. It has a pool and an incredible ocean view. It’s also centrally located in Condado so you’re just a few steps from all the restaurants and bars, as well as the beach.

If you don’t stay at an Airbnb, there are a few hotels in San Juan area I’d recommend.


O:LV Hotel – This is without a doubt one of the nicest boutique Design Hotels I’ve ever seen. Situated in Condado, the OL:V has a trendy rooftop with incredible views of the lagoon, which you can visit whether you’re staying at there or not. This isn’t just your typical hotel – the interiors are to die for, with brass, marble and velvet accents a-plenty.

La Concha Renaissance – If you’re looking for a larger resort, La Concha Renaissance boats an infinity pool overlooking Condado Beach, several restaurants, a fitness center and a 24 hour casino. Rooms also have floor-to-ceiling windows and balconies with ocean views.

Old Town:

Villa Herencia Hotel – I you’d prefer to stay in San Juan Old Town, this boutique hotel has old world charm, funky interiors, local art work and a relaxing roof terrace. It’s also located just a short walk from Museum of the Americas and Santa Catalina Palace.

How to Get Around Puerto Rico

For your 3 days in Puerto Rico I’d suggest getting a car so you can explore the island. You can find rental car deals using Kayak or Rentalcars.com. Don’t forget to bring your U.S driver’s license with you in order to rent the car. If you plan to stick around San Juan and Condado, then you can easily get around by Uber, which is fairly inexpensive.

Day 1 – Relax in Condado

View of Condado, San JuanView of Condado, San Juan

Flying can be exhausting so plan to have a relaxing day the first day of your Puerto Rico itinerary. Once you land at San Juan Airport (SJU), either order an Uber or pick up your rental car and make your way to your accommodation.

San Juan is basically split into two parts. There’s the old town, which is full of colorful buildings and bars, then there’s the newer part, Condado, which is by the beach. I’d suggest staying in Condado so you can easily walk to the beach. You can then Uber to Old San Juan in the evenings.

Relax on Condado Beach

Condado beach puerto ricoCondado beach puerto rico

Once you’ve checked in an unpacked your stuff, head on over to San Juan’s main beach area, Condado, which is lined with hotels such as the Marriott and La Concha Renaissance. I didn’t find the beach to be as beautiful as some others we visited on the island but it has a lively atmosphere and it’s great as city beaches go. Spend the afternoon soaking up the sun and sip on a piña colada or two.

Lunch at Jose Enrique

Jose Enrique San Juan restaurantJose Enrique San Juan restaurant

If you’re feeling a bit peckish you can walk along Ashford Ave, which has plenty of restaurants offering everything from Puerto Rican food to sushi.

One great restaurant I’d recommend is Jose Enrique, which serves really good Puerto Rican food with a modern twist. The restaurant’s interior is bright and airy, with simple wooden tables and mirrors adorning the walls.

Dishes are designed for sharing and are made with ingredients from local producers. The menu changes daily but you can expect everything to be super fresh and delicious. I particularly enjoyed the tuna crudo and pork belly with shishito peppers.

Sunset Drinks at ARYA Rooftop

OLV Hotel RooftopOLV Hotel Rooftop

For sunset you can head on over to ARYA rooftop at the O:LV hotel, which hands down is one of the most luxurious, hippest hotels I’ve ever seen. If you have the cash to stay there, then do it!

The rooftop has a beautiful pool/fountain and views of the Condado lagoon, so once sunset comes it’s a perfect spot for photos. Treat yourself to some cocktails and appetizers while you listen to their DJ play.

La Placita de Santurce

If you still have some energy left in you, head over to La Placita de Santurce which is a bustling market area that comes alive after 6pm. Locals flock there to have food, cocktails and dance salsa – it’s super fun!

La Placita has been around for 100 years and started as a two-tiered marketplace where people could buy fresh produces such as fruit, vegetables and meat. Today it still functions as a marketplace during the day but it transforms into a vibrant local hangout at night. It’s particularly lively Thursday through Sunday, so make sure you visit on one of these days.

Day 2 – El Yunque Rainforest and Bio Bay

For the second day of your Puerto Rico itinerary you’re going to drive out to El Yunque Rainforest and visit the town of Fajardo, which is on the east coast of the island. You’ll need a car for this part, as it’s too far to Uber from San Juan.

Breakfast at Cafe Regina

For an Instagram-worthy (and healthy) breakfast, visit Cafe Regina in Condado/Ocean Park, which is located one block from the beach. This neighborhood cafe serves quality coffee and healthy menu items made with ingredients from local producers. You must, must, must get their avocado toast with black garlic, it’s so good!

Another must-try from the menu is the Cashew Milk Iced Latte, which is made with cashew milk, two shots of espresso, organic maple syrup, and cinnamon.

Cafe Regina is open daily from 8am to 4pm.

Address: 58 Calle Taft, San Juan, PR 00911.

El Yunque Rainforest

El Yunque RainforestEl Yunque Rainforest

If you haven’t already, pick up a rental car and drive to El Yunque rainforest, which is a tropical rainforest in the northeastern part of Puerto Rico. To enter the rainforest we needed to book online from a choice of morning or afternoon slots. We chose the morning slot so we could beat the crowds and enjoy the rest of our day doing other things.

You’ll enter El Yunque Rainforest at the visitor’s center and then drive up steep, windy roads stopping at various lookout points along the way. If you get car sick at all (I definitely do) don’t go on an empty stomach and make sure you get out of the car for fresh air. The parking areas are super small so I can’t imagine how busy it would get if we had gone later in the day.

If you’re up for some exercise you can hike one of the trails, or if you’d rather do something more leisurely, you can take some photos and stop at one of the waterfalls for a swim.

Luquillo Beach

Luquillo Beach Puerto ricoLuquillo Beach Puerto rico

After visiting El Yunque it’s time to relax, so drive over to Luquillo Beach, which is roughly 20 minutes away. This tranquil bay is great for swimming and there’s a small kiosk there that serves the best Pina Coladas.

Fajardo and Bio Bay

fried fish in Fajardo Puerto Rico fried fish in Fajardo Puerto Rico

From Luquillo, finish your day in Fajardo with a bioluminescent bay tour. We were feeling peckish before the tour, so we stopped for some fried fish and arepas at Pescaderia Don Candi, which is a tiny local spot on the water with a bar next door.

The Bio Bay kayaking tour with Kayaking Puerto Rico was seriously one of the highlights of our trip. We kayaked in almost complete darkness and it was so relaxing under the stars that I wished I could stay longer.

If you want to see bioluminescence then it’s best to go close to a new moon when the sky is as dark as possible, but if the moon is out then they give you a tarp to put over your head so you can create shade and see the sparkle. It really is magical, and looks like you’re holding glitter in your hand.

Day 3 – Pinones and San Juan’s Old Town

Pinones Puerto RicoPinones Puerto Rico

On your final day in Puerto Rico, head to Pinones, which is an area close to San Juan airport that has beautiful, palm tree-lined beaches. Start at Ocean Lab Brewing Company, a brewery that serves beers brewed on the beach in Puerto Rico! Personally I love a good IPA in the sun and their yellowfin tuna poke bowl is really fresh.

tuna poke at ocean lab brewing company Puerto Ricotuna poke at ocean lab brewing company Puerto Rico

After Ocean Lab, grab some cocktails on the beach at Drift Beach Bar, which is slightly further along the coast. Their restaurant/bar Hook’d is right on the beach with oceanfront seating and a relaxing chill area. They have some great drinks specials, such as Mojito Wendesdays, 2 for 1 Thursdays and Wine Fridays – you get the idea!

beach at drift beach bar Puerto Ricobeach at drift beach bar Puerto Rico

Old San Juan

In the evening, head back to San Juan to explore the city’s Old Town, which boasts cobbled streets and colorful buildings, plus a citadel called Castillo San Felipe del Morro, which was built between 1539 and 1790.

Puerto Rico is home of the Pina Colada although from what I read online, people can’t decide on where it was invented. Some people say the Caribe Hilton Hotel and some say it was invented by a bartender at Barrachina.

We visited Barrachina to try their Pina Colada and I’m sad to say, it was not good. It tasted to me like it had come out of a machine and I was a tad disappointed. I’m guessing that since they get so many tourists coming through they perhaps rush or even have them pre-prepared.

To me a Pina Colada should be creamy and made with love (me and my friend love making them at home!), and this was just not like that, but you can find plenty of great Pina Coladas on the island!

San Juan Old TownSan Juan Old Town Barrachina San JuanBarrachina San Juan

San Juan has lots of cocktail bars and restaurants – our favorite bar being La Factoria, which was super busy. It looks quite small when you first walk in but there’s actually a much larger area for dancing through the back.

A Final Word…

I really enjoyed my time on the island and it’s definitely worth renting a car so you can get out of San Juan and see the less touristy areas. This Puerto There are all sorts of places to visit in Puerto Rico, such as Rincon, Vieques and the island of Culebra, so I’ll definitely be making a trip back at some point to see more. A long weekend in Puerto Rico is just enough to get a little taster but there are so many things to do.


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