Photo Diary | San Juan, Puerto Rico

Caribe Hilton Pool in Puerto Rico

Traveling to San Juan, Puerto Rico was the first trip that my boyfriend and I went on since the pandemic started. We went in November 2021—yes, this is a bit of a late blog post—and wanted to share recommendations for where we went.

Puerto Rico was a short and sweet getaway from being cooped up indoors for over 18 months. There’s a lot to see in the territory, but we kept it a relaxing trip, so there will be no recommendations for the southern, isolated parts of the island nor historic Old Town.

Although there have been significant weather events that have affected the region, Puerto Rico’s warm and radiant culture persists.

  1. Where to Stay
  2. Where to Eat and Drink in San Juan, Puerto Rico
    1. José Enrique
    2. Cocina Abierta
    3. Serafina’s
    4. Acapulco Tacqueria Mexicana
    5. Eter Rooftop & Lounge
Caribe Hilton Hotel Room Balcony

Where to Stay

Located by itself on a peninsula in between the Condado neighborhood and Old San Juan, the Caribe Hilton in San Juan, Puerto Rico offers a secluded, private resort feel compared to other hotels that are more centrally located. The resort attracts both couples and families, but rest assured that there’s enough space by the beach and the pool and a variety of activities to make everyone happy.

We spent most of our time sipping, snacking, and sunbathing by the beach.

The Caribe Hilton underwent extensive renovations and structural improvements after substantial damage from Hurricane Maria—the work shows well throughout the hotel’s exterior and interior spaces.

Fun fact: The Caribe Hilton was the first international Hilton location and is the birthplace of the piña colada.

Where to Eat and Drink in San Juan, Puerto Rico

We found restaurants off-premises for most meals and it was easy to order an Uber anywhere we went.

José Enrique

1021 Ashford Ave, San Juan, 00907, Puerto Rico

If there’s one restaurant that you must go to, it’s José Enrique—it’s recognized as one of top the restaurants in the country. As Condé Nast Traveler says, “if it weren’t for the hordes of people you might not be able to tell you’re at one of America’s best restaurants from the outside,” so make sure that you book a reservation in advance.

Cocina Abierta

58 Caribe St, San Juan, 00907, Puerto Rico

The tasting menu changes, but the creative dishes are a delicious introduction to Puerto Rican cuisine. If you drink, I would recommend taking the experience to the next level with the wine pairing.


1077 Ashford Avenue, San Juan, Puerto Rico 00907

For New Yorkers looking for something familiar, there is a Serafina restaurant located inside La Concha hotel.

Acapulco Tacqueria Mexicana

2021 C. Loíza, San Juan, Puerto Rico 00911

This hole-in-the-wall taco spot is off the beaten path and well worth the trip. We ended up ordering from this restaurant via Uber Eats a few days later for lunch.

Eter Rooftop & Lounge

752 Av. Manuel Fernández Juncos, San Juan, 00907, Puerto Rico

When you arrive in front of the building, you are in the middle of what seems to be a residential area—then you look up on the rooftop of the building and you will see the lights from the bar and restaurant. Watch the sunset over San Juan while you enjoy the fresh red snapper and one of the bar’s signature cocktails.

Cocina Abierta Puerto Rico
Eter Lounge Puerto Rico

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A Francophile based in coastal New England

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