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Explore the best of San Juan with cheap flights from Jacksonville

Photo: iStock
By Hoodline - Published on July 31, 2019.

Can't stop daydreaming about an island escape? Consider heading to San Juan, which was named the top destination on the New York Times' list of places to visit in 2019. Settled on the island's north shore facing the Atlantic Ocean, San Juan is Puerto Rico's capital and largest city — and has plenty to offer.

San Juan boasts many areas worth visiting, including 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's also the Paseo de la Princesa bayside promenade in Old San Juan, home to a number of imposing fortresses, as well as El Yunque National Forest, located within fairly close proximity of the city.

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

Hoodline offers data-driven analysis of local happenings and trends across cities. Links included in the articles may earn Hoodline a commission on clicks and transactions.

Cheapest San Juan flights

The cheapest flights between Jacksonville and San Juan are if you leave on Aug. 28 and return from Puerto Rico on Sept. 4. Spirit Airlines currently has tickets for $127, roundtrip.

There are also deals to be had in September. If you fly out of Jacksonville on Sept. 7 and return from San Juan on Sept. 10, Spirit Airlines can get you there and back for $132, roundtrip.

Top San Juan hotels

Regarding where to stay, here are some of San Juan’s top-rated hotels that we selected from Skyscanner's listings, based on price and customer satisfaction.

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

Photo: Trip by Skyscanner

For an all-around top recommendation, consider Hotel El Convento, which has a 4.9-star rating on Skyscanner.

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 Marriott San Juan Resort & Stellaris Casino, rated 4.7 stars.

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, which currently has a 4.8-star rating.

"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. 

Local restaurant picks

If you're looking for a quality spot to grab a bite, San Juan has plenty of excellent eateries to choose from. Here are a few suggestions from Skyscanner's listings to help you get started.

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)

Photo: Trip by Skyscanner

Another notable 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 [with] music and dancing in the streets on most weekend nights."

El Jibarito (280 Calle Sol)

Photo: Trip by Skyscanner

Finally, there's El Jibarito.

"San Juan dining at its best," wrote visitor Aaron. "The friendly atmosphere, the local feel and the celebration of Puerto Rico's history are just the visual appetizers for the culinary delight that is to come. ... And everything was fantastic."

Featured San Juan attractions

To round out your trip, San Juan offers plenty of popular attractions worth visiting. Here are some top recommendations, based on Skyscanner's descriptions and reviews.

Old San Juan (San Juan)

Photo: Trip by Skyscanner

First up is Old San Juan.

"Old San Juan was beautiful," wrote visitor Sofia. "So much history, and great restaurants! ... 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

Castillo San Felipe del Morro is another popular destination.

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

"El Morro was breathtaking!" wrote visitor Sofia. "It's located in Old San Juan. Make sure to wear comfortable walking shoes."

The Bacardi Rum Factory (Cataño)

Photo: Trip by Skyscanner

Lastly, spend some time at The Bacardi Rum Factory.

See how Bacardi is made and enjoy rum samples while taking a tour of the original Bacardi Rum Factory.

"This place is quite charming. ... They have a nice free tour of their plant, and then they even offer you a complimentary drink," wrote visitor Julio. "The view from Cataño Bay to Old San Juan is really astonishing, especially during sunset."


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.

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