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Escape from Portland to San Juan on a budget

If you're looking to escape to the tropics, head to San Juan, Puerto Rico, the destination with the top spot on the New York Times' list of places to visit in 2019. The island's capital and largest city faces the Atlantic Ocean, and it has plenty to offer. Plan to visit both the Isla Verde resort strip, known for its bars, nightclubs and casinos and Old San Juan, which features colorful Spanish colonial buildings, cobble-stoned streets and 16th-century landmarks. There is also the Paseo de la Princesa bayside promenade, a number of imposing fortresses and the close proximity to El Yunque National Forest, all of which are worth visiting.

Thankfully, there are plenty of relatively inexpensive flights between Portland and San Juan. We pulled from travel site Skyscanner to provide you with a short list of flights and hotels handpicked with the trendy adventurer in mind. (Prices and availability are current as of publication and subject to change.)

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Cheapest San Juan flights

Currently, the cheapest flights between Portland and San Juan are if you leave on Oct. 1 and return from Puerto Rico on Oct. 5. Delta currently has roundtrip, nonstop tickets for $279.

There are also deals to be had in August. If you fly out of Portland on Aug. 30 and return from San Juan on Sept. 3, Frontier Airlines can get you there and back for $345 roundtrip.

Top San Juan hotels

To plan your accommodations, here are some of San Juan's top-rated hotels, that we selected from Skyscanner's listings based on price and customer satisfaction.

The Hotel El Convento (100 Cristo St. Old, San Juan)

Photo: Trip by Skyscanner

If you're looking to splurge on top quality, consider The Hotel El Convento. The hotel has a 4.9-star rating on Skyscanner, and rooms are currently available for $280.

Nestled in the historical district of Old San Juan, this boutique hotel offers convenient access to several noteworthy attractions, including the San Juan Bautista Cathedral, Puerta de San Juan and La Fortaleza Palacio de Santa Catalina.

The Marriott San Juan Resort & Stellaris Casino (1309 Ashford Ave.)

Photo: Trip by Skyscanner

There's also the 4.7-star rated The Marriott San Juan Resort & Stellaris Casino. Rooms are currently set at $261/night.

This beachfront resort is close to Plaza del Mercado and Condado Beach, as well as the Puerto Rico Convention Center.

The Condado Plaza Hilton (999 Ashford Ave.)

A third option is The Condado Plaza Hilton. The 4.8-star hotel has rooms for $188/night.

"Great place to stay. The hotel is big with tons of restaurants and things to do right in the plaza. The pool area is large and it's right on the beach," wrote visitor Maddie. 

Top picks for dining and drinking

Don't miss San Juan's food scene, with plenty of popular spots to get your fill of local cuisine. Here are a few of the top-rated eateries from Skyscanner's listings.

Santaella (219 Calle Canals)

Photo: Trip by Skyscanner

One of San Juan's most popular restaurants is Santaella, which has an average of five stars out of 10 reviews on Skyscanner.

"Santaella celebrates the roots of the island's comida criolla, and incorporates techniques, flavors and fusions from around the world into its food," wrote www.puertorico-rentals.com. "Santaella will elevate and redefine your Puerto Rican dining experience."

Acapulco Taqueria Mexicana (2021 Calle Loíza)

Another popular dining destination is Acapulco Taqueria Mexicana, with five stars from six reviews.

"Started out with [the] fried cheese and it was delicious," wrote reviewer Dani. "The tacos are to die for, especially la cochinita."

Jose Enrique (176 Calle Duffaut)

Photo: Trip by Skyscanner

Also worth considering is Jose Enrique.

"Awesome local food," wrote Jasey. "Lots of other restaurants in the area and music and dancing in the streets on most weekend nights."

Featured local attractions

San Juan is also full of sites to visit and explore. Here are a couple of popular attractions to round out your trip, again from Skyscanner's listings.

Old San Juan 

Photo: Trip by Skyscanner

First up is Old San Juan.

"Old San Juan was beautiful," wrote visitor Sofia. "Spent the whole day there with my family. We loved it! So much history and great restaurants. There's a lot to do here. I highly recommend coming here if you're interested in learning history, local food, museums and much more!"

Castillo San Felipe del Morro (501 Calle Norzagaray)

Photo: Trip by Skyscanner

Then, there's Castillo San Felipe del Morro.

Constructed in 1540, this six-story fort hides a warren of prison cells, barracks and hallways and was attacked on many occasions by both English and Dutch forces. It is listed in the National Historic Register.


This story was created automatically using flight, hotel, and local attractions data, then reviewed by an editor. Click here for more about what we're doing. Got thoughts? Go here to share your feedback.