Weekend Getaway to San Juan

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A colorful street in Old San Juan
A colorful street in Old San Juan. Photo credit: Casey Clark

I recently traveled to San Juan, Puerto Rico, whose kind people, beautiful beaches and rich culture make it one of my top five travel destinations! Just a three hour flight from Florida, San Juan is a   perfect weekend getaway for bachelorette parties, honeymoons and vacations. For most travelers, three days is a great starting point when visiting Puerto Rico. Also, if you’re traveling from the United States, you don’t need to have a passport so that’s one less document you need to worry about during your travels — all the more reason to take a visit to this island.

Interested in a weekend getaway to San Juan? Here are my favorite hotels, restaurants and activities to help you plan your next trip to Puerto Rico.

Where to Stay in Puerto Rico

Three flags waving in the air on a colorful street in Old San Juan, Puerto Rico.
Flags on a street in Old San Juan. Photo Credit: Casey Clark

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Aire de Olive

Rooftop pool at Aire de Olive in Puerto Rico.
Rooftop pool at Aire de Olive in Puerto Rico. Photo credit: Casey Clark

There are a lot of hotels to choose from in Puerto Rico, however, you can’t go wrong with a beachfront luxury boutique property. Located in Isla Verde, the hotel is known for its attention to detail and sustainable practices. The rooms have wooden furnishings and earthy elements in them too. Be sure not to miss out on the hotel’s infinity pool and definitely make a reservation for KUMO, an on-site Asian fusion restaurant. I suggest spending an hour in the pool, freshening up for dinner and then going to KUMO – it’s a great way to end any night in Puerto Rico.

Caribe Hilton

Furniture in a hotel room at Hotel Caribe in Puerto Rico with a view of the beach.
View from a room at Caribe Hilton in San Juan, Puerto Rico. Photo Credit: Caribe Hilton

For those loyal Hilton Honors members, Caribe Hilton is an exquisite property in San Juan. This isn’t your standard hotel as it spans across nine acres and is located right along the beach. Choose from a standard room or suite for the duration of your stay and enjoy on-site amenities including an ocean-front pool and full-service spa.

Hotel Rumbao

Blue multi-story hotel in Old San Juan with flags and trees next to a Walgreens.
Exterior of Hotel Rumbao, a Tribute Portfolio Hotel in Old San Juan, Puerto Rico. Photo Credit: Hotel Rumbao, a Tribute Portfolio Hotel

If you plan on spending a lot of time in Old San Juan, then Hotel Rumbao, a Tribute Portfolio Hotel, is a great option. It’s located steps away from the district’s shopping, dining, and historic sites and is a pet-friendly property if you plan on bringing your furry friends to Puerto Rico. The hotel is equipped with an outdoor pool, on-site restaurant and fitness center so you have everything right at your fingertips for those days you just want to stay in and relax.

What to do in Puerto Rico

Green grass and a long castle made out of brick.
Castillo San Cristóbal in Old San Juan. Photo Credit: Casey Clark

LAU Pottery Studio

A private pottery class at LAU Pottery Studio.
A private pottery class at LAU Pottery Studio. Photo Credit: Casey Clark

I’ve always wanted to go to a ceramics studio and make my own pottery and that’s exactly what I did. I figured there’s no better time or place to try something new than while on vacation. I found LAU Pottery Studio on Instagram and she had rave reviews so I gave it a try. During the class, I made a heart-shaped pinch pot (so cute) and painted it myself. The studio itself was so cute and it was such a personal experience that I’d do it again in a heartbeat.

Walking tour of Old San Juan

Rocks lined up near a body of bright blue water.
View from the pathway near the San Juan Gate. Photo Credit: Casey Clark

You can’t go on a trip to Puerto Rico without visiting Old San Juan. While you can just walk around yourself, it’s even better to have a tour guide. Not only do they know all the best spots, but also have a wealth of knowledge about the history of the area and culture. I used Turismo Borincano when I was in Puerto Rico and I can’t recommend them enough. My tour guide, Gloria, was super nice, insightful and even took us to all of the picturesque spots so I could get my Insta-worthy photos.

Go on a cacao tour

Green plants and yellow cacao beans next to pots of soil.
Plants and cacao beans at Semila in Old San Juan. Photo Credit: Casey Clark

A more unique experience you’ll find in Puerto Rico is a cacao tour. As a chocolate lover, I was ecstatic to actually visit the place where cacao beans grow and chocolate is made. It’s a bit far out from Old San Juan and Isla Verde so it’s helpful to have a car, but it’s definitely worth the drive. On the two hour tour at Semila, you’ll be able to see how chocolate is made from start to finish. The experience ends by having a chocolate tasting session where you’ll be guided on how to eat chocolate the right way to really make it a full sensory experience.

Go to a beach

Luscious trees, white sand and a clear blue water beach.
Beach across the street from Aire de Olive in Puerto Rico. Photo Credit: Casey Clark

The best time to visit Puerto Rico is when the weather is nice and outside of hurricane season so you can go to the beach — that’s essentially any month between December and June. You can still visit during the traditional summer months, but you’ll want to check the weather a week or two from your planned trip time to make sure everything looks good to go.

There are plenty of beaches to choose from across the island but Condado Beach and Flamenco Beach are two popular picks for fluffy sand, calm waves and overall good vibes. Don’t forget to lather up on sunscreen before heading out too because the sun is strong in Puerto Rico.

Where to Eat in Puerto Rico

Signature rice dish from Verde Mesa.
Verde Mesa rice dish from one of the first farm to table restaurants in Old San Juan. Photo credit: Casey Clark

Verde Mesa

Red tomatoes and corn on a white dish.
Tomato dish at Verde Mesa in Old San Juan. Photo Credit: Casey Clark

Verde Mesa was my favorite restaurant I ate at during my trip to Puerto Rico. From the moment I stepped inside, it felt like I was instantly transported into someone’s home for mealtime. This restaurant is unique because it’s one of the first farm to table restaurants in Old San Juan and has a robust menu filled with locally sourced ingredients from farmers all across the island. If you make it over to Verde Mesa (which I strongly suggest you do), you must order the Verde Mesa Rice which is the restaurant’s signature dish.

Casilda Cocina Creativa

Chicken with cheese and green asparagus on a white plate.
Chicken breast stuffed with cassava and asparagus from Casilda Cocina Creativa. Photo Credit: Casey Clark

As a foodie, I think there’s really no better way to get a feel for a place than by trying the food. Casilda Cocina Creativa in Cataño is a more casual, laid-back spot with a diverse menu. On the menu, you’ll find everything from steak and lobster to risotto and gnocchi so whether you’re craving something more meaty or a savory pasta dish, you’ll find them both here. After your meal, don’t forget to head up to the rooftop for a drink and some exquisite views.

You’ll want to bring both cash and cards with you to Puerto Rico because some restaurants and attractions only take one form of payment. You may also find that signal is weak in some areas so cash will be the only accepted form of payment sometimes.

Cocina al Fondo

Vegetables and potatoes on a intricate dinner plate.
Vegetarian dish from Cocina al Fondo in San Juan. Photo Credit: Casey Clark

Another notable mention is Cocina al Fondo which is in San Juan and features a menu carefully curated by James Beard award-winning chef Natalia Vallejo. The menu features dishes with food sourced from local farmers and fisherman and each item has a unique twist for a flavor explosion in your mouth. Since I don’t eat meat often, I ordered the vegetarian dish which was mouthwatering good and left my heart and stomach full.

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Casey Clark is a writer from New York City who specializes in Disney and family travel. Casey splits her time between NYC and Orlando and goes to the Disney theme parks often. Casey has written for a handful of national publications including Parents, HuffPost, The Wall Street Journal, Brit + Co, and more.
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