San Juan is actually pretty big but if it’s your first time to the city, do yourself a favor and stay in Old San Juan. There’s a good amount of boutique hotels and a few chain hotels to choose from in many of the touristy areas. However, we prefer the Airbnb route because we like the feel of living like locals. There is an abundance of Airbnb apartments, so you can find them easily in Old San Juan and the neighboring areas, like Condado or Isla Verde for a range of prices, some even under $100 a night! We’ve stayed both in Condado and Old San Juan. Old San Juan is where you want to be to experience the culture, the architecture, historic landmarks as well as the local bars and restaurants.

Condado is a wonderful place to stay if you are looking for a more relaxing vacation. Here, you can relax on the beautiful beaches and stay at a resort or a hotel. Many more locals live in this area.

Truly a romantic city full of character and history! If you are looking for a true Old San Juan experience or maybe looking to save on cost, you will want to find a vacation rental.  You can find some nice rentals starting under $100 all the way up to $250/night.

A very popular beach destination for tourists with lots of shopping and food experiences.

During one of your days there, put your walking shoes on and spend a few hours walking around and throughout the forts that surround the city. Built in the 1500s, these forts were primarily used to keep out invading countries and pirates. Spend your first sunset walking the base at El Morro. The historic Spanish feel and the views are an unbeatable duo.

If you are with your family, it is also a popular place to fly kites.

If you’re into photography you cannot pass up the photo opportunities provided by Comunidad La Perla. Sitting beautifully just feet from the ocean and at the foot of El Morro (Fort), the creative spirit of the people that live there has really served as a treat for tourists and locals alike. La Perla is a gem regardless of it not being an upscale neighborhood.

It was put in the spotlight recently by the well-known music video for Despacito.

In case the name does not sell itself, let me tell you this is well worth a few hours of your day. Only a 5-10 minute ferry ride at $3 round trip, (plus a short taxi to the factory from the ferry port), you will find yourself entering the gates of Bacardi, which tastefully resembles the landscaping of a resort.

There are a few options of different tours to choose from. Each of them come with a welcome drink at the very least. You can go the less expensive route and just do the historic tour for $15, you can do a tasting tour for $50, or go all out and learn new bartending skills as you do a tasting tour for $60. All very worth the experience you choose.

It would be hard not to find yourself aimless walking around the streets of Old San Juan simply admiring the character of all the buildings. One street to make sure you get a look at is Calle Fortelaza. At the farthest west end of the street sits the Governors residence (or fortress as it is named). Right before the road ends is a net of kites that add even more unique personality to the already beautiful and historic scene.

This is a tucked away tourist hotspot. It is a perfect place for pictures! If you can get there at 7 am you will have it all to yourselves!

There are more gorgeous places to see than one can count but they all take some traveling to get to; both driving and hiking. Renting a car was swift, easy, and inexpensive to do from the Hertz at The Sheraton. I think it was $30 for the day plus the cost of gas. I would recommend leaving no later than 7 or 8 am so you can see more stops along the way.

Regions to see (in no particular order):

• Isabela, San Sebastián, Aguadilla, Utuado, El Yunque National Forest

La Madre          Cute modern Mexican restaurant with lots of flavored Margaritas and tasty food!

Cafeteria Mallorca          Very classic Puerto Rican experience. Similar to a diner in appearance with great tasting, real-deal Puerto Rican breakfast.

St. Germain Bistro & Cafe           Relaxing cafe for a refreshing drink. They have a great basil-lemonade and amazing tapas and panini’s. The ambiance reminded me of being in Spain.

Barrachina          Great Puerto Rican bites in a classy atmosphere! They’re popular so either book in advance or have a drink at the bar while you wait.

Punto de Vista Rooftop          Views! This place has some of the best views that we’ve seen at a restaurant. They are located at the top of Hotel Milano and serve the best Mofongo. Get there early.

El Picoteo          Perfect for a date night or day-time tapas. It’s mostly outside in a courtyard ambiance. A little pricier but definitely a treat.

The Mezzanine           Located on the second floor, above St. Germain Bistro & Cafe, this bar serves small plates at a low price and $4- $5 cocktails during happy hour with views of the beautiful streets of Old San Juan.

Al Fresco Rooftop Wine Bar          Located on the third/top floor above The Mezzanine, Al Fresco is a rooftop bar known for their views and great cocktails.

Barrachina          A MUST for their Piña Colada. I like Piña Colada’s but they’re generally not my favorite drink. I kid you not, this is the best tropical drink I have ever had. It might have to do with the fact that it was invented there in the 1950’s by one of their bartenders. Do yourself a favor and stop for one, or two! At $7 a pop, you can’t beat it.

La Factoria          This hotspot is one of our favorite top things to do in San Juan and is unique to any we’ve seen. Very Speakeasy feel with 5 adjoining rooms, 2 dance floors, and 4 bars. La Factoria is the third room back where locals come to Salsa and listen to live music. This is also where the dancing scene in the Despacito music video was filmed. It looks different with the low lighting and the DJ setup but it is indeed a fun and famous local hotspot.