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Escape from Boston to San Juan on a budget

If you're in the mood for a tropical 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 of interest, all worth visiting, including 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.

Whether you’re trying to depart as soon as you can or are looking to plan your travels around upcoming deals, take a look at these forthcoming flights between Boston and San Juan, which we pulled from travel site Skyscanner.

We've also included popular hotels, restaurants and attractions in San Juan to help inspire your next island excursion. (Prices and availability are current as of publication and subject to change.)

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Cheapest San Juan flights

The cheapest flights between Boston and San Juan are if you leave on Sept. 4 and return from Puerto Rico on Sept. 10. Spirit Airlines currently has tickets for $205, roundtrip.

There are also deals to be had in August. If you fly out of Boston on Aug. 31 and return from San Juan on Sept. 4, Spirit Airlines can get you there and back for $221, roundtrip.

Top San Juan hotels

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

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

Photo: Trip by Skyscanner

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

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, which has rooms for $261/night.

"Great location for family fun and a some adult fun as well. You can enjoy the pool or the beach," wrote visitor MrsGrant.

La Concha Resort: A Renaissance Hotel (1077 Ashford Ave.)

Photo: Trip by Skyscanner

A third option is La Concha Resort: A Renaissance Hotel. The 4.6-star hotel has rooms for $209/night.

Located in San Juan, this beachfront hotel is near attractions such as Condado Beach and the San Juan Bautista Cathedral.

Top picks for dining and drinking

If you're looking to snag a bite at one of San Juan's many quality eateries, here are a few popular culinary destinations from Skyscanner's listings that will help keep you satiated.

Santaella (219 Calle Canals)

Photo: Trip by Skyscanner

If you're looking for a local favorite, head to 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."

Kasalta (1966 Mc Leary)

Photo: Trip by Skyscanner

Another noteworthy dining destination is Kasalta, with 4.6 stars from 29 reviews.

"Great place for sandwiches, seafood, cheeses and pastries," wrote Hector. "Beverages include beer, wine and all kinds of refreshments, including great coffee. A local's favorite."

El Jibarito (280 Calle Sol)

Photo: Trip by Skyscanner

Also worth considering is 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."

Acapulco Taqueria Mexicana (2021 Calle Loíza)

Finally, there's Acapulco Taqueria Mexicana.

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

What to see and do in San Juan

San Juan is also brimming with sites to visit and explore. Here are two 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. "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

Finally, 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.


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.