A 4 Day Puerto Rico Itinerary for First Time Visitors

You land in Puerto Rico, and the air feels warmer, softer. Palm trees sway. Music drifts from somewhere nearby. Suddenly, four days doesn’t feel like much time at all.

That’s usually when the question hits. What are the must-do experiences? What can you realistically see without running yourself ragged? My 4 day Puerto Rico itinerary answers that quickly.

I spent a full week in Puerto Rico during the spring. Some days were full. Others were slow and perfect. That balance shaped this itinerary.

This guide is designed for first-time U.S. visitors who want to experience Puerto Rico’s history, beaches, food, and natural beauty effortlessly. It focuses on what’s worth your time, what’s easy to skip, and how to enjoy four days.

What to Know Before Your Trip to Puerto Rico

Puerto Rico is a U.S. territory, which makes travel simple for U.S. citizens. No passport. No customs line.

San Juan’s Luis Muñoz Marín International Airport is the largest and busiest airport in the Caribbean, so finding flights from the continental United States is not difficult.

U.S. dollars are used everywhere. Cell service usually works the same way as at home.

Spring and summer are popular times to visit.

Expect warm days, cooling breezes near the water, and quick rain showers that rarely last long.

Lightweight clothing, comfortable walking shoes, and sunscreen are non-negotiable.

While renting a car is not necessary, especially for this 4 day Puerto Rico itinerary, you may want your own wheels for El Yunque and beach days.

Ride shares work well in San Juan.

Day 1: Old San Juan and the Heart of Puerto Rico

Start your first day in Old San Juan. It’s colorful, walkable, and full of history. After traveling, this area eases you into the island at a comfortable pace.

Breakfast in Old San Juan

Old San Juan feels alive early in the morning. I suggest starting with breakfast at Kaffe Haus.

I recommend trying the Mallorca Chicken Sandwich with tender chicken stacked on Mallorca bread, drizzled with garlic aioli, and dressed with crisp lettuce and ripe tomatoes.

And for a sweet finale, don’t miss the Chocolate Temptation. This heavenly coffee concoction of Nutella and hazelnut melds into something absolutely sinful, in a good way!

Stroll through Old San Juan

After breakfast, walk through Old San Juan for a delightful experience that takes you back in time.

Cobblestone streets shine after a quick rain. Blue doors and pastel walls pop against the sky. It’s one of the most photogenic places I’ve visited.

As you walk through the city, there are a few places that you simply can’t miss.

Begin at Castillo San Felipe del Morro, a 16th-century fortress that offers stunning ocean and city views. Walk the grounds slowly and imagine what life was like centuries ago. From there, stroll through the old city instead of rushing from place to place.

Lunch is a good time to try mofongo or a simple plate of arroz con gandules.

We stopped at Puerto Criollo near Plaza de Colon. The garlic chicken with a Puerto Rican dish called mamposteao is fabulous, as is the chicken stuffed avocado.

Order a mojito, and dine on a cobblestone patio surrounded by brightly colored umbrellas for a charming outdoor experience.

In the afternoon, browse local shops and small galleries. This is also a good time to stop by Calle de la Fortaleza, also known as the colorful umbrella street.

For a fun photo in front of the I love San Juan letters, visit Plaza Colón near the Castillo San Cristóbal or the location where most taxis and Ubers drop off visitors heading into Old San Juan.

As evening sets in, stay in Old San Juan for dinner. Sit outside. Take your time. The streets feel magical after dark, when the city truly shines.

Day 2: El Yunque Rainforest

Day two brings a complete change of scenery.

Head east toward El Yunque National Forest, the only tropical rainforest in the U.S. National Forest system.

You will want a guided tour to ensure forest reservations. Your guide will lead you to the best waterfalls, like the renowned La Mina. Arrange for a tour to pick you up at your hotel.

The drive is easy and scenic. Once inside the forest, the air feels cooler and fresher. Short trails, waterfalls, and lookout points make this visit approachable, even for casual hikers.

After the rainforest, return to San Juan in the early evening.

If you’re up for it, experience Puerto Rico’s nightlife at La Factoría, an unmissable spot showcased in the “Despacito” music video.

Day 3: Beach Time and Local Flavor

In Puerto Rico, there’s a saying, “Live Boricua.”

It’s all about celebrating the island’s rich traditions, lively music, and warm, welcoming spirit.

By day three, slowing down feels right.

Breakfast at Numero Uno Beach House

We began our morning lounging on giant beanbag chairs with beachfront dining at Numero Uno Beach House on the picturesque Ocean Park Beach.

These tables do come with a minimum purchase requirement and a time limit, but the delicious breakfast options and views are worth it.

Condado Beach and Isla Verde are two more beaches that are easy to reach and well-maintained. Bring a towel, sunscreen, and a book. That’s all you need.

Lunch can be simple. A sandwich shop or beachfront café works perfectly. Puerto Rican food shines even in casual settings.

Local Culture

In the afternoon, explore a different side of San Juan. I would use this afternoon to either visit Santurce to see street art and local neighborhoods or plan a trip to the Bacardi Rum Factory for a tour and tasting.

Santurce is filled with murals and graffiti, each telling a unique story and showcasing the local artists’ talent and creativity. This area reminds me of Toronto’s graffiti alley, with a very artistic vibe.

Puerto Rico is the rum capital of the world, so it only makes sense to visit a rum factory.

The Bacardi campus is massive, and I enjoyed learning about the process and, of course, tasting the product.

Puerto Rican Nightlife

As your unforgettable 4 days in Puerto Rico come to a close, there’s no better way to spend your last night than at Distrito T-Mobile.

This premier entertainment destination offers endless possibilities of things to do.

The open-air venue is similar to Fremont Street in Las Vegas and 4th Street Live in Louisville, Kentucky.

Enjoy the open-air bars and restaurants serving various and authentic Puerto Rican food as you celebrate the perfect end to your island vacation.

Day 4: Day Trip or Easy Morning Before Departure

Your final day depends on flight timing and energy level. Both options work well.

For an early flight, enjoy a slow morning with a delightful breakfast at Caficultura, another local Puerto Rican cafe. Take one last walk. Enjoy one more cup of coffee. Pick up local treats to take home.

With extra time, consider a short day trip. Friends of ours took a catamaran sail from Fajardo to Icacos Island. They raved about the water and the snorkeling.

Puerto Rico doesn’t demand a dramatic farewell. It leaves you relaxed, well-fed, and already thinking about a return visit.

Where to Stay for a 4 Day Puerto Rico Itinerary

San Juan is the best home base for first-time visitors. Old San Juan offers charm and history. Condado and Isla Verde provide resort-style comfort and beach access.

During my visit, I stayed at the Caribe Hilton, the DoubleTree by Hilton Hotel San Juan, and the Hampton Inn & Suites in Isla Verde.

Each had its own pros and cons, but I would stay at each again. Check out my post, “Where to Stay in Puerto Rico“, for all the details.