Living the Boricua Way: A 5-Day Graduation Trip to Puerto Rico

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Advisor - Julie Winston
Curated By

Julie Winston

  • Puerto Rico

  • City Travel

  • Family Travel

  • Arts & Culture

  • Greatest Hits

Advisor - Living the Boricua Way: A 5-Day Graduation Trip to Puerto Rico
Curator’s statement

A different country with no passport needed? Say less! Puerto Rico was a special graduation trip for my daughter, and it gave summer destination travel vibes without the hassle of dealing with customs. Old San Juan and its vibrant, colorful streets did not disappoint—and the options for food, entertainment, and nature excursions made for such an enjoyable trip.

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Day 1: Touchdown in Puerto Rico

Factoria - Top 50 bars in the US

That fabulous feeling of leaving the plane and not having to wait in a customs line. Welcome to Puerto Rico!

Rental cars are not recommended if you’re staying solely in Old San Juan due to limited parking, but sometimes they will be needed if visiting other parts of the island. They’re very affordable and can be rented for around $20-$30 a day, and some hotels contract with the parking garages for an extremely reasonable daily rate.

Once checked in to your hotel, Old San Juan has an abundance of restaurant choices. After dinner, head to La Factoria. This is one of the top 50 bars in America and is filled with laid-back vibes and salsa music. There are seven different bars, and each one has a different ambiance.

Day 2: Chasing waterfalls and a day at the beach

Waterfall at El Yunque Rainforest

Early morning wake-up call! San Juan is a port stop for the cruise lines, and El Yunque Rainforest is a popular excursion. Getting an early start is recommended for the 45-minute drive to the east side of the island to beat the crowds.

Once you make your way into El Yunque, you can follow the road up to Yokahu Tower and observation point where you can take in beautiful sites of the rainforest nestled in the clouds. Drive just beyond that, and you will see parking for a short hike to a waterfall. Pro tip: There’s an even better waterfall if you don’t mind the off-the-trail hiking. Your early start will pay off when you see the lines of people waiting to get to the waterfalls.

If you get hungry, stop at the El Yunque Rainforest Cafe for some empanadas.

After the rainforest, Luquillo Beach is on the way back to San Juan. For a small fee, you can have an umbrella and chairs set up for you to enjoy for as long as you want. Right down the road from the beach are the Luquillo kiosks where you can find a variety of different delicious foods and drinks.

After you’ve had a chance to freshen up from the waterfall and beach, head to the Condado area. There’s an Italian restaurant called Tavola that handmakes their pasta. Ask to go to their secret bar, and you’ll be escorted through a secret door to an intimate speakeasy with vibrant glow-in-the-dark art.

Day 3: VIP treatment and late-night adventures

Luquillo Beach

Visit the Blanca Fragrance Factory, where you can create and name your own perfume. You’ll have someone assigned to just your party and guide you through customizing your own scent. Once finished, your formula is saved, so if you run out, you can order again. Best part—every time you use the perfume, you’ll think about your trip!

For lunch, walk right down the street to Barrachina, which is where the pina colada was created. Consider trying mofongo, a popular Puerto Rican dish, and of course, a pina colada!

If you’re in the mood to check out the nightlife, take a short Uber ride to La Placita de Santurce to find a cultural hub of food, live music, bars, and clubs.

Day 4: Exploring Old San Juan

Beautiful artisan shops

Visit the stunning Cathedral of San Juan Bautista. This is the second-oldest church in the Americas, holding the tomb of Juan Ponce de Leon and the mummified remains of Saint Pius.

After you’ve taken in the beauty of the cathedral, cool off with some gelato at Anita Gelato. From there, you can feed pigeons at the pigeon park and get lost in all the artisan shops.

Day 5: San Cristobal Castle and check-out

Inside Castillo San Cristobal

For a mix of history and coastal views, visit Castillo San Cristobal. Considered the largest fortress built in the Americas, it showcases beautiful architecture and the history of its importance, protecting the city of San Juan. It opens at 9 am, and I recommend getting an early start to beat the cruise crowds.

If time permits after visiting San Cristobal, try 787 Coffee for a coquito with rum-infused coffee beans to get a smokey, cinnamon, and rich dark chocolate flavor. It comes in a pouch and gives an adult capri sun feel.

The time has come to leave this beautiful city. When leaving Puerto Rico for the US mainland, you’ll need to have your luggage scanned by USDA inspectors before dropping them off at the airline counter. You’ll receive a sticker saying your luggage has been inspected. This sticker is required for all checked luggage.

Need to know

Additional days and eateries:

If you have extra time and weather permits, try a bioluminescent excursion. The water glows at night due to the presence of microscopic organisms, and Puerto Rico is home to three different bays. December to April is the best time to try this due to it being the dry season with clearer skies.

Bebo’s BBQ—close to the airport and right next door to a rental car location, this open-air restaurant is popular for its delicious food. Highly recommend as a first or last stop in San Juan.

Advisor - Julie Winston

Travel Advisor

Julie Winston

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For more information and insider recommendations, visit our Puerto Rico page.