Old San Juan is a seriously adorable part of Puerto Rico. Some people will try and tell you it’s boring, but honestly it’s the best place to start. Old San Juan has the most colorful and pretty streets! It’s the perfect introduction to Puerto Rico.
Arrive the evening before and settle in. You’ll want to take a taxi that is able to drive into Old San Juan on this day (there are driving restrictions because it is a historical area!) so it’s best to take a taxi from the airport. It will most likely cost about $20 – $30 depending on the location of the hotel, traffic, and number of people.
Stay in Old San Juan this night at one of the boutique hotels within walking distance of all the restaurants and bars. I’d recommend Hotel Plaza Del Armas for it’s awesome location and pretty courtyard.
Make sure you find a flamingo show happening too in the evening on your first night or second! There are tons of restaurants that offer dinner and a show that make for a special experience. You’ll need to make a reservation in advance so make sure you look up where you want to go. It’s worth a reservation to check out one of these awesome shows.
Wake up the next day and spend your whole day in San Juan and create your own pace! I’ve created my own walking tour below with the things I’d recommend seeing/loved when I was there. It’s very walkable and easy to get around. Make sure you make lots of stops for street vendors serving ice cream and yummy snacks!
Start your walk with a visit to Castillo San Cristóbal
San Cristóbal is the largest and best-preserved Spanish military fortification in the Americas. It was built to protect San Juan residents from land attacks from the east side and covers almost 27 acres of land. Walk through an S-shape tunnel, enter a dungeon, and take a picture inside a sentry box. There’s an amazing panoramic view on the third floor that is just beautiful. It’s less-visited which means it’s even more worth your time.
From here, keep walking until you get to El Morro and Castillo San Felipe Del Morro. Keep on a lookout for the cutest spots with the Puerto Rican flag as you walk! This area is a really popular spot in Old San Juan. You’ll find a historic cemetery, large plazas, and lots of kites. El Morro is one of the first military defenses in the Americas, it brings you back in time and has an amazing view of the entrance to the San Juan bay.
Cruise ships entering or leaving port are almost at the same height as the 6 level fort and it actually took over 250 years to build! It’s got amazing views, lots of iguanas, and fun history.
There is a set of stairs and a walkway that leads around the outside of the fort along the coast from the inside of the fort. This is a great way to walk around the outside of the fort or you can walk above the walls as well for a great view. The walk takes about 20 minutes either way and you will see the San Juan gate which is the only original gate into the city that is left.
Stop for a picture here and keep walking until you get to Paseo de Princessa. You’ll know your there because you’ll see a large fountains and steps.
The Paseo de Princessa starts with a large fountain and a promenade that is really pretty to walk. From there, you can start to walk the streets of San Juan and take in the colorful scenery! Famous streets include Calle del Sol and Calle San Sebastian.
Some notable stops include the cathedral, awesome murals like the San Juan flag, tons of shopping, and the perfect spot for a pina colada. Puerto Rico is the home of the pina colada and two different spots claim to have the original. Make sure you check them out!
This evening, you can go pick up your car in Carolina by the airport or stay another night in San Juan if you have the budget! There are also lots of affordable AirBnBs in and around San Juan. Many are in Carolina and Condado right by the beach which could be a great way to spend the evening!
Day 2: San Juan to Aguadilla to Rincon
Old San Juan to Carolina 15 minutes
On day two, it’s time to get out of the old city! There are some incredible and secluded beaches in Puerto Rico that are just amazing. Time to get to some of those perfect spots on your Puerto Rico road trip.
Pick up a rental car from near the airport for just $12 a day, then head out west. As I mentioned, the traffic can be pretty bad around typical rush hour times. Leave after (or before if you want to get up early) rush hour by making a stop in Carolina for some great breakfast! There’s a whole strip of really cute restaurants that are all local.
There’s tons of cool street art and a super relaxed feel. Once you’ve grabbed some food head out on an hour-long drive to Cueva Ventana.
Carolina to Cueva Ventana 1 hour
Type Cueva Ventana into your GPS
Cueva Ventana is a section of 5 caves that you can only go to on a guided tour. It’s just about an hour from San Juan and really pretty easy to find. I was there over the weekend and walking up to get a ticket was easy. You can walk right up and buy a ticket. There is a large parking lot behind where there is space to park. Bring cash and buy some refreshing juice and stop for gas at the gas station right next door.
For $20 you are taken on a guided hike through the rainforest and two of the 5 caves for some awesome views and history. You’ll see amazing views, bats, shy plants, petroglyphs, and more. The whole experience takes about 2 hours and happens every half hour so it’s not difficult to find a time.
Cueva Ventana to Aguadilla 1 1/2 hours
Type Surfer Beach into your GPS
From here, drive another hour to Aguadilla to check out some awesome beaches. If you’ve got more time, the town of Aguadilla is really cute and I’ve heard it’s worth a stop! I only had time to check out some of the beaches – Surfer Beach and Survival Beach. I’m so glad I made this stop to an amazing local beach spot.
These two beaches are surfer beaches but offer awesome views. The large waves almost knocked my rental car keys into lost oblivion but I was able to rescue them thankfully. They are also a little off the beaten path which I loved. Getting there was easy because you can drive all the way to the beach where there is a large parking lot. Once parked, walk toward the trail and away from the road to get to Survival Beach.
When I was there I was almost alone on the beach except for a few surfers. This led to amazing views along the water. I found tons of turtle tracks and was able to walk from Surfer Beach to Survival Beach during low tide. If you visit during high tide then you’ll have to hike through the forest. There is a trail so you’re still able to make it there! The only issue is the mosquitos. Be prepared with bug spray so you don’t get bit!
Aguadilla to Rincon 30 minutes
Type Villa Cofresi (your hotel) into your GPS
After this beach stop, head to Rincon in time for sunset! I chose to stay at Villa Cofresi. This hotel is known for its perfect sunset view and private beach. I couldn’t recommend this hotel enough. You can read my full review here.
Day 3: Rincon, Cabo Rojo, and Fijardo
This is the most driving you’ll do in a day on this three-day Puerto Rico road trip. It’s going to be across the island and total about 6 hours. I chose to do it this way because the east side of the island is still recovering from the hurricane. When I was driving through, there were many spots that were still closed and the main city on the east side is still rebuilding and so it made sense to visit what I could in one day. Each drive is pretty easy though and there was no traffic. It’s also broken up with some amazing stops.
Morning in Rincon
Morning in Type Steps Beach or GastroPark Rincon into your GPS
Rincon is another spot known for its surfing, but while I was there, the water was pretty calm and tons of people were swimming. I chose to relax on the beach and by the pool at my hotel. However, there are a lot of beaches that are good for snorkeling that you can get to easily, most famously Steps Beach.
From the beach, I headed to Gastropark Rincon. This cute area is full of awesome food trucks with choices for drinks and food. I chose to eat at Plantanas which served every dish with plantains. So good! They are open late here too so if you’re staying in Rincon, it’s the perfect spot late at night.
Note: if you decide to do a longer road trip, I’d recommend an extra day in Rincon. Stay longer and take a surf lesson, visit the lighthouse for sunset, and enjoy walking around town!
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