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Things to do in Puerto Rico - Palomino Island

The Perfect Family Vacation in Puerto Rico

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Our family had a fantastic vacation in Puerto Rico last March. You would probably think that anybody surviving yet another brutal winter in the Windy City (our hometown) would love ANY warm weather destination, but the truth is that we are quite discerning when it comes to our family’s vacations. Not in terms of requiring luxury accommodations and VIP treatment, but in terms choosing a destination that will offer us diverse, fun and enriching experiences.

Puerto Rico definitely delivered on these criteria: we greatly enjoyed the island’s beautiful sandy beaches and warm tropical waters, but we also went on a several memorable adventures where we learned about Puerto Rico’s history and also gained an appreciation for how much this spirited island has to offer visitors.

If you are looking for a bit of an exotic spot, but also like the comforts of the familiar — often an important factor to families who travel with children — Puerto Rico is a great family vacation destination. Have I mentioned that it is also easy to get to from the central and eastern U.S. and great deals on airfares are not hard to come by? As much as our family loves to travel, I can’t believe we waited this long to visit!

Our Puerto Rico Itinerary

Our vacation in Puerto Rico was seven days long, which gave us an opportunity to experience several different regions, as the island is not particularly big. We spent the first few days near the capital of San Juan and then drove to Fajardo on the northeast side of the island for the remainder of our stay. On the day we were transitioning to the second resort, we spent a day at Puerto Rico’s famous rain forest El Yunque, because it is located en route, approximately half-way.

Depending on how many days you plan to stay on the island and your family’s preferences, you can, of course, choose to spend the entire time in one location. Alternatively, you can visit other parts of the island (such as Dorado or Isabela on the north side of the island or Ponce in the south) if you are staying for a longer period of time.

The Puerto Rico Resorts Where We Stayed

We spent the first three nights at Caribe Hilton, a wonderful family-friendly resort very close to both Old San Juan and the city’s contemporary area, Condado. In addition to the location, we loved the resort’s private lagoon and beach — the only one that is private on the island! We also enjoyed the fun activities for kids of all ages and their friendly and very helpful staff.

We spent the second part of our vacation at a Waldorf Astoria property in the Hilton Portfolio, El Conquistador. This resort, which extends across enormous grounds, is a little town in and of itself. This extensive property offers its guests a number of restaurants, coffee shops, ice cream parlors, stores, a casino, fitness center, beauty salon, and much more.

El Conquistador also has several pools, its own water park and boasts spectacular views of the ocean from the main pool area and many of the rooms. Our favorite part was access to their private island, El Palomino, which was postcard picture spectacular.

I highly recommend both properties.

Our Family’s Favorite Things to do in Puerto Rico

We truly enjoyed all our experiences in Puerto Rico, but these were our family’s five favorite Puerto Rico attractions:

1. Strolling though the old and picturesque streets of Old San Juan

There is so much history and beautiful architecture in Old San Juan. We started our tour at Plaza de Colon, then walked south to the city wall and followed it north to the fort, Castillo San Felipe del Morro.

A must-do: stop by one of the many street ice cream vendors for a refreshing, authentic and very tasty tropical treat. Try to schedule your visit for early in the morning or later in the afternoon/early evening as it can get very hot in the middle of the day.

2. Stepping back in history at Castillo San Felipe del Morro

This 16th century fort, which is one of Puerto Rico’s most famous and recognized landmarks, is incredible and well worth the visit even if you are not into history. There is so much to see and do, but you can adjust your self-guided tour depending on your family’s interests and ages of your children.

Things to do in Puerto Rico - Castello San Felipe del Morro

Entrance to the Castillo San Felipe del Morro.

3. Hiking in El Yunque rainforest

This lush tropical forest, the only one in the United States National Forest System, is less than an hour drive from Old San Juan! There is a myriad of choices to experience its splendor: from hiking one of its many trails, to taking a dip in one of its spectacular (and very cold!) waterfalls, to enjoying amazing views from the Yokahu Observation Tower. You can research recreation in El Yunque ahead of time, or simply stop by the Visitor Center when you arrive for a great overview of the park and advice from the Rangers on where to go and what to do.

Things to do in Puerto Rico - El Yunque rain forest

View of El Yunque rain forest as seen from the Yokahu Observation Tower.

4. Kayaking to the Bioluminescent Bay in Fajardo

Puerto Rico is famous for not one, but three bioluminescent bays, which are bodies of water containing millions or microorganisms called dynoflagellates that glow in the dark for a short time when disturbed. The adventure began with kayaking through a mangrove forest to an enclosed lagoon. Our journey in complete darkness with only flashlights to guide us to this rare phenomena was an unforgettable experience. We used Kayaking Puerto Rico and were very happy with our choice.

5. Day trip to the Palomino Island on the northeast side of Puerto Rico

This tiny private island is spectacular, but any other will do as well. There are well over 100 islands surrounding Puerto Rico! Two of the most popular ones are Culebra and Vieques, which are also the only two that are inhabited. We look forward to visiting them next time we are on the island.

Things to do in Puerto Rico - Palomino Island

Visiting the stunning Palomino Island was one of our favorite things to do in Puerto Rico.

Puerto Rico Restaurants

There are many excellent restaurants all over the island, but especially in San Juan and the Condado area. We loved sampling authentic Puerto Rican food at Jibarito in Old San Juan. You must try the signature dish of Puerto Rico, mofongo, made with mashed plantains and different add-ons like meats, vegetables and sauces. My favorite was mofongo de camarones en salsa criolla, made with shrimp and a delicious sauce. Outstanding!

Puerto Rico Restaurants - Mofongo and Jibarito

Mofongo, one of Puerto Rico’s signature dishes.

For a completely different, contemporary experience, head to Oceano in Condado. This restaurant has a spectacular location on the beach, a South Beach, Miami vibe (it transforms into a hopping dance club late in the evening), fantastic cocktails and the best red snapper ceviche I ever tasted. The rest of the menu is equally terrific.

For yet another different island experience, try Cuban food. We enjoyed a simple, but very tasty meal at Ropa Vieja, also located in Condado. Try ropa vieja, their signature dish, which the restaurant is named after, and of course, don’t forget those refreshing mojitos.

Tips for Visiting Puerto Rico

As mentioned, traveling to Puerto Rico is easy because it is a U.S. territory; however, there are a few things that are good to know to ensure your vacation runs smoothly.

  • For example, put some thought into timing of your vacation because the hurricane season in the Caribbean generally runs from June through October.
  • If you are planning on renting a car, don’t forget to bring a copy of your proof of insurance with you to avoid unnecessary delays.
  • On the day of your departure, make sure all your bags are scanned by the U.S. Agricultural Inspection at the airport prior to lining up for a check-in or you will need to go back and re-enter the line after you have completed the inspection. (Yes, I’m speaking from experience.)
  • For even more information, read my 10 Puerto Rico Travel Tips.

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A native of Slovenia, Vera moved to the U.S. 20+ years ago after meeting her American husband. Together with their two children they live on the North…

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