The Ultimate Itinerary Puerto Rico

Planning a trip to Puerto Rico? Here is an ideal itinerary with tips on where to stay, where to eat, and where to explore. My family of four recently traveled to Puerto Rico and had the best time discovering the city, exploring the jungle, and relaxing on the beach! It was a great vacation with enough variety of activities to satisfy both the adults and kids!! Below is a layout of our itinerary with some extra details on the things we did and the things we look forward to doing on our next visit.

Puerto Rico is an island situated in the Caribbean Sea, East of the Dominican Republic. It is home to a little over 3.2 million people and is about 100 miles long. Its capital city, San Juan, can be reached on an approximately 2.5 hour flight from Miami. Many of the flights from the States requires a layover at one of the major airports in Florida.

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Traveling to Puerto Rico

If you are coming from the States, there are lots of flights offered through most major airlines. However, when flying more domestic flights under 8 hours, my family’s favorite airline is Southwest Airlines. Their flights are typically affordable and comparable in price to flights offered by other major airlines. They offer free checked-bags, family boarding, and flexible flight modifications, making them a great choice for families. However, if you are flying internationally, Travel Up is a great site to search the best deals! On our trip, we flew from Phoenix to San Juan with a layover in Tampa. The total trip was about 7 hours.

While visiting Puerto Rico, I would highly recommend renting a car to get around the island. We stayed in multiple cities and hotels around the island and there are so many cool attractions and destinations to visit, renting a car is the easiest and most practical way to get around. When booking a rental, we always check the Costco rental program, and booked through them for this particular trip. Many times they offer great deals on rental cars. We also consider flight+car packages, which has saved us on many of our trips.

6 Day, 7 Night Itinerary

Here is a short breakdown of our itinerary:

Day 1: Travel Day, checked into hotel close to downtown San Juan

Day 2: Explored Old San Juan and kayaked the bioluminescent bay in Fajardo

Day 3: Hiked El Yunque with natural waterslides

Day 4: Moved westward and explored town of Isabela and Aguadilla

Day 5: Beach day and snorkeling in Isabela

Day 6: Back to San Juan

Day 7: Travel Day back home

This blog will review places to stay, where to eat, and things to do. This is not an exhaustive list but will include places we stayed, ate, and drank. Puerto Rico is a beautiful place with so much to offer that I have also included some recommendations that we would have loved to have seen but ran out of time.

Read my blog Tips for First Time and Seasoned Travelers Alike for tips on planning, booking, and traveling.

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Day 1: Travel Day

With a 4am wake up call, our family was up and out the door, bright and early, to catch our flight from Phoenix Arizona to San Juan Puerto Rico. It was a long day with a 4 hour delayed layover in Tampa Florida. This was unexpected but whenever you are traveling you have to expect the unexpected and roll with whatever the day may throw at you. When these events occur, I try to stay as calm as possible and repeat to myself “we will get there when we get there”. If I become stressed about a delayed flight or long lines, I find that it makes things so much worse than just going with the flow. It’s not easy, but after many years of travel, it is truly the mindset I try to adopt.

When we finally landed, we headed to the rental car center to pick up the rental. A great feature of the San Juan airport is that the rental center is connected to the airport and there is no need to take a shuttle! We made our way to our hotel, Aloft San Juan, which is situated in the heart of Distrito T-Mobile. This is a really cool venue that has space for concerts, DJs, and tons of restaurants to choose from. The night we got in, there was a live band playing great latin music followed by a DJ. We sat out on the patio of Lupe Reyes listening to the music while eating tacos. It was a great start to the trip!

Aloft San Juan is a very accommodating hotel with modern rustic features. It is quaint but provided all the amenities we needed including a small snack store. It is located close to both downtown San Juan and Old San Juan. It also provides a free shuttle to and from Old San Juan.

Day 2: Old San Juan

The next day we allowed ourselves a little time to sleep in to help with adjusting to the time difference. Puerto Rico is on Atlantic Standard Time so it is one hour ahead of Eastern Standard Time and for us west-coasters, 4 hours ahead. We then headed out to Old San Juan, Puerto Rico’s historic town with brightly colored houses lining cobbled streets and shady plazas. We were dropped off by the shuttle and explored the town by foot. Our first stop was breakfast! We quickly learned that a cruise ship had recently docked and all of the hot spots for breakfast had lines out the door! ChocoBar Cortes was our number one spot but the line was out the door and around the corner. This sweet little shop received great reviews on Yelp! for its variety of baked goods and breakfast dishes, but we were starving and couldn’t wait to find out for ourselves. The other place recommended was Cafeteria Mallorca, but unfortunately, this place had closed permanently. As we wandered the town, desperate to find food at this point, we stumbled upon an empanada shop that sold freshly made empanadas and juices. The name escapes me, but it was a just a little to-go stand around the corner from ChocoBar Cortes. We got the chicken and beef empanadas and they did not disappoint! They were juicy and flavorful, leaving a great first impression for this island. We then stopped by the local Starbucks to get our morning joe, but again it was quite busy due to the cruise ship in port.

While walking about the town, we ventured up to Calle de Fortaleza to see the beautiful umbrellas hanging over the streets below. There was some construction and there were very few umbrellas, but definitely something I would recommend checking out once the construction is complete! We then made our way up to the Museo de Old San Juan, passing many colorful houses and great Instragram spots along the way. Although we did not go into the museum, across the street from it is a great cliff view of the ocean. There are a couple of fortresses in Old San Juan worth seeing, Castillo San Felipe del Morro and Castillo San Cristobal. However, they are quite the hike from the middle of Old San Juan. We made our way back down to Barrachina, which is the proclaimed home of the original pina colada! This place is very popular and you DO need reservations. We were able to get in for a late lunch, having the fried red snapper, mofongo, and of course, the Pina Colada!

One thing we learned as our trip went on is that the food in Puerto Rico was a little underwhelming and not what we expected. Although we had a few good meals, much of the local food is fried and somewhat bland. My husband and I are big foodies and love to try the local fair when traveling. Puerto Rico is known for mofongo, which is smashed up plantains covered in different toppings of meat and gravy. It is our understanding that everyone makes their own version of mofongo and just because you do not like one mofongo does not mean you do not like mofongo- you have to keep trying! But, we did keep trying and did not find one that we enjoyed to the extent of the locals. However, we were happy we tried it and expanded our palates.

Later in the day we headed out to Fajardo where we kayaked two miles in a mangrove to reach Laguna Grande. Here we were able to watch the sunset and then later experience the bioluminescent organisms that light up the water like fireflies in the sky on warm summer nights. This was such a cool experience and could not recommend this enough! We booked through Travelocity. You have experienced guides to assist you through the mangrove and teach you about the bioluminescent organisms. We went during a new moon so the night conditions were perfect for this activity; however, if you going during another time of the moon cycle, do not worry, the guides provide you with tarps to cover your kayak so you can see the organisms no matter.

Much of my research I did prior to our trip suggested going to the island of Vieques for the bioluminescent bays, but when I tried to book a trip to the island all of the hotels were either already booked or required a two night stay, which we did not have room in the schedule to do. Although I am sure Vieques is worth the extra booking and planning, we were very pleased with our bioluminescent experience from the main island.

Day 3: El Yunque

On our third day, we woke bright and early and met our tour guide to take us to El Yunque, the only rainforest in the United States. We prefer to get guides or join excursions to experience these types of adventures, as it does tend to lessen the stress of finding your locations and many times enhances what you see and learn along the way. However, we encountered many people who were exploring on their own and seemed to be doing fine. On our tour of the rainforest, we had two short hikes to two different natural waterslides, a waterfall, and a swimming hole. Our guide recommended we wear socks, making it easier to climb the wet rocks. This was my kids’ favorite part of the whole trip! I have pictures below but they do not do it justice. This was a great experience and would highly recommend this. We booked this excursion through our Chase Rewards, but Travelocity also offers many options for this tour. Our tour then took us to a local food plaza where we were able to try some local fair and hang by the beach. We ended our day back in the city with a great burger at The Place off of Avenida Ashford in downtown San Juan. This place had great food and a great atmosphere! A definite recommendation!

Day 4: Isabela and Aguadilla

After two adventurous days, we headed westward to the very small mountain town of Isabela for a couple of days to decompress. Isabela is a very small rural town settled among the beachside mountains. There are very few restaurants and shops, but we chose to stay in Isabela for the beautiful Villa Montana Resort. This is a quiet yet picturesque resort where you have your own bungalow villa just steps away from the sand. The beach is practically a private beach with only residents of the resort occupying it. The crystal clear blue water and golden sand truly is breathtaking. The resort has two pools and a high end restaurant for guests to enjoy. The restaurant was super yummy and we ended up eating most of our meals there while staying in Isabela. Villa Montana also provides snorkeling gear and beachcruisers for free. My only complaint is that we did not stay here longer.

Before arriving at the resort, we seeked out some Instagram-worthy stops. We made it to Cara del Indio for some cool pictures with the oversized rock carving. We wish we had made it to the Guajataca Tunnel. This tunnel is a little out of the way but seems like it would be worth the time. We continued on to Aguadilla, which is a little bigger beach town just west of Isabela. Aguadilla has restaurants and shops along its malecon or boardwalk. It is a fun place to explore the colorful streets and views. We continued on further to Crash Boat Beach, which is a public beach with platforms the locals jump off. This beach is a great way to experience the local vibes with music and street carts selling food.

Another 20 minutes further west you run into Rincon. This is a cute surfer town that is even bigger than Aguadilla. We did not make it to Rincon, but all of my research said it is definitely a place to see when you visit the island. Whether it is having a sunset cocktail at The Beach House or taking a surf lesson at Sandy Beach, this surfer town is a Puerto Rican icon.

Day 5: Isabela

We continued our relaxation at Villa Montana Beach Resort, enjoying early mornings with a cup of tea on the beachside loungers and cool evenings on the patio of our villa. The kids enjoyed playing in the waves and rolling in the sand before moving to the pools. We did adventure off property to Shacks Beach, which is just a short five minute walk East of the resort. Here there are lots of rocks and coral where you can see sea urchins and other fun sea creatures. This is supposed to be a great place for snorkeling; however, during the time we went (March) the waves were quite strong and was not ideal for snorkeling. It is my understanding that at other times during the year there are better conditions with calmer waves.

Day 6: Back to San Juan

As our trip was coming to a close, we headed back to downtown San Juan. We stayed at AC Hotel San Juan in Condado, which is a newly renovated hotel with a rooftop pool and bar. The accommodations are very well done and quite modern. They have a great lounge area next to the lobby with a small snack bar where you can order food and drinks. This hotel does seem to cater more towards kid-free adults and businessmen and women. During our stay, we did not see a single other family with kids. We did enjoy our time at the pool, but we seemed to be a little out of place compared to the other patrons.

In the afternoon, we explored Condado Beach and Avenida Ashford. Avenida Ashford is one of the main streets of downtown San Juan with restaurants and shops for a little over a mile. We chose to eat dinner at Tacos & Tequila located at the Condado Vanderbilt Hotel. This is a luxury hotel situated right along Condado Beach. Not only were their tacos mouthwatering but the view was unbelievable. We then treated ourselves to a little Ben & Jerry Ice Cream. It was a great way to end our trip on this gorgeous island.

Day 7: Travel back home

And with that we have reached the end of our trip. Our flight itinerary back home very much mimicked our itinerary to get here with long layovers, but we are happy to say we made it safe and sound.

Although this blog doesn’t even scratch the surface of things to do and see in Puerto Rico, I hope you found some helpful information, along with some inspiration for your planning or your dreams.

Comment below about your favorite experiences on the island or ask questions you may have for planning your next adventure.

with love and dreams,

Jessica