Puerto Rico, The Local Way

Best bet is to fly into San Juan, since the airport is just minutes from where you’ll want to kick off your trip.

If you land early in the day, start with a visit to a panadería—local bakeries are a beloved part of Puerto Rican culture. Two great options nearby are Panadería España and Panadería Las Canarias, both known for their excellent sandwiches.

From there, head to Isla Verde for some beach time before freshening up for the evening.

Evening in Old San Juan

Old San Juan is the perfect place to spend your first night, with colorful streets, historic charm, and a wide range of dining options. Favorites include Restaurante Raíces, Verde Mesa, and Santaella (just a short ride away in Condado).

Cap off the night with Puerto Rico’s vibrant nightlife: La Factoría, El Cafetín, and Monostereo are all on the same street, making it easy to hop between spots and see where the night takes you.

If you haven’t already, today’s the perfect time to rent a car. Having your own wheels in Puerto Rico makes it much easier to explore beyond San Juan, and to tote your beach essentials without relying on rideshares.

Relax & eat at Luquillo Beach

Just a 30-minute drive east, you’ll find Luquillo Beach, a favorite among locals and visitors alike.

It’s not just the sand and water that draw people in—the famous kioskos (food stalls) line the area, serving up Puerto Rican classics like pastelillos (meat-filled turnovers), bacalaitos (crispy cod fritters), and pinchos (grilled meat skewers).

Be sure to bring cash, and note that there’s a small fee to park.

Evening in Calle Cerra

After soaking up the sun, make your way back toward San Juan to explore Calle Cerra, an emerging neighborhood full of street art, local shops, and buzzing nightlife.

For cocktails, you’ll want to check out Identidad Cocktail Bar, named a 2025 James Beard Award winner for Best New Bar.

Another standout is La Disquera, a Japanese-inspired cultural hub with a creative vibe and plenty of history.

Days three is all about adventure in the water—weather permitting, of course.

Option one: Beach

One option is to go beach-hopping: start with the farthest spots and work your way back toward San Juan for an easy return.

A great lineup is:

• La Poza de Las Mujeres (a natural swimming pool surrounded by rocks)

• Mar Chiquita Beach (a stunning crescent-shaped cove)

• Playa Vega Baja (a lively local favorite)

Spend as much or as little time at each as you like. It’s a build-your-own kind of day.

Option two: Rainforest

Suppose you’d prefer a different type of natural escape, head to El Yunque National Rainforest, just under an hour from San Juan. Here, you’ll find lush trails, waterfalls, and natural pools perfect for a refreshing dip.

Whether you’re up for a longer hike or want to frolic in the fresh water, there’s a path for every energy level.

Evening

To wrap up the day, I recommend dinner at La Casita Blanca for authentic Puerto Rican comfort food (open until 9 pm on Fridays and Saturdays) or YOKO for a more modern vibe.