BEST TIME TO TRAVEL: Mid April – June. This falls perfectly in between peak season and Puerto Rico’s rainy season.

WHERE TO STAY: I recommend staying in Isla Verde. It is a bit out of the way, but you will be spending most of your time on the beach, so you want to be right on the water. This area is less popular than Condado, but this means the beach will be less crowded. We ended up renting a car for whenever we wanted to drive into Condado, and there was virtually no traffic, so Isla Verde is your best option for staying somewhere BEAUTIFUL and pretty centrally located. We stayed here and I really enjoyed it!

day 1.

After checking into your hotel, head right to the beach to spend the day relaxing. I also recommend picking up some rum and snacks at the grocery store at some point during Thursday so that you don’t have to worry about leaving the beach for lunch. Once you are properly sunburnt and ready for dinner, check out El Jibarito. This is an AWESOME local spot for authentic Puerto Rican food. It is popular with locals, so plan for about a half-hour wait on most nights. Afterwards, grab a drink just five minutes away at Los 3 Cuernos. It has lively music, friendly bartenders, and a KILLER rum punch. Make sure to try the chichaito! Then, finish your night at La Factoría. The bar has such a cool vibe and the cocktails are unreal. Definitely don’t miss this popular spot.

day 2.

Feel free to spend the morning on the beach again to soak up some sun. If you want to try a different beach than Isla Verde, Condado Beach is the most popular beach in San Juan. Either buy lunch on the beach, or pack your own. Then, spend the rest of the day exploring Old San Juan. I recommend stopping by Ole Curiosidades. It is a cute, but expensive hat shop in San Juan. If you want a nice gift for yourself or someone else, you can design your own Panama hat here. Otherwise, I would still recommend popping in, if you have time, to see the store itself. For an afternoon lunch and treat, pop into Barrachina, where the Piña Colada allegedly was created. It’s fairly affordable, and the mofongo here is one of my favorites that I had on the trip. Less than five minutes away, you will also find the Puerto Rican Flag Door. It’s a cliché spot to get a picture, but there are a lot of murals around this area to see as well.

Afterwards, catch your transportation to Fajardo for the Bioluminescent Bay tour. This is a MUST-DO while you are in Puerto Rico as there are only five places in the world to see this wonder. Most tour companies will arrange for you to take a personal kayak through the bay, and since you will be going when it is pitch black outside, the water will be glowing all around you.

day 3.

Start your morning out with breakfast at Caficultura. It is a nice coffee shop in one of the main plazas, so it is a perfect spot to grab brunch and people watch. Then, head to Castillo San Cristobal and Castillo San Felipe del Morro, just around the corner. Both forts have BEAUTIFUL views of the ocean. Also, if you are walking around on a Saturday or Sunday here, you will likely see a bunch of kites flying in the air, making for a really INCREDIBLE photo opportunity. Pack a lunch, and plan to have a picnic in the expansive grass area here overlooking the ocean. For more strolling, walk along Paseo la Princesa. If you want a break before dinner, definitely use the afternoon to have a siesta on the beach. You will want your energy to go out in Santurce later.

To kick off your evening, grab dinner at Triana Tapas. I highly recommended spot if you want typical Puerto Rican food and the opportunity to see some flamenco. It is a more expensive option, but worth the value for the entertainment. I recommend ordering the paella. After dinner, if you want to go out and experience the Puerto Rican nightlife, head to Condado to La Placita de Santurce. It is a market during the day, but turns into a big block party at night. This is the go-to place that tourists and locals come together to dance and have a good time.

day 4.

For your last morning in San Juan, pop over to Kasalta for a cheap but delicious breakfast. It is technically a popular San Juan “diner,” but there are so many selections that you’ll likely be overwhelmed with options. If you’re lucky, grab a seat at the table that President Obama selected when he visited (clearly distinguished with a gold plaque). Then, spend the rest of your day relaxing on the beach before it is time to head back home.