The warmer months are getting close and you can’t stop daydreaming about lying on a beautiful beach on a Caribbean island, sipping from a coconut in your favorite bathing suit. But, how do you exactly plan a trip? Here’s where this Puerto Rico 5-day itinerary comes to the rescue!

After so many times planning my own trips as a part-time nomad and passion for exploring the hidden gems in every location, I know that the perfectly crafted itinerary should be well-balanced with a variety of different activities and spots that go beyond the tourist traps.

From touring the picturesque alleys and historic forts of Old San Juan, and dancing at the buzzing bars of Placita de Santurce to swimming under the cascading waterfalls in El Yunque and paddleboarding on the crystalline waters of Condado Lagoon, you’ll have a little bit of everything San Juan has to offer.

The Only Puerto Rico 5-Day Itinerary You’ll Ever Need

Here’s a whole trip planned for you to save you hours of research. After reading this, you’ll want to pack your suitcases right away!

Best Time To Visit San Juan

The best time to visit San Juan, Puerto Rico, will ultimately depend on your preferences. Each season has its own charm and advantages. However, for this particular itinerary, the period between mid-April and June is the most suitable. The weather is warm and pleasant but not overwhelmingly humid compared to the summer months. So, you’ll be able to enjoy outdoor activities and explore as much as you want with unbearing heat.

How many days do you need in Puerto Rico?

San Juan is not just beaches and bars. There’s actually so much to see and do around the island! If you want a relaxed trip, taking your time to explore even beyond Old San Juan and the touristy areas, 5 days will be ideal to see everything.

However, for those seeking more of a short getaway, a 3-day itinerary will be the best choice and just the right amount of time to cross all the hotspots from your bucket list.

Day 1: Get the Feel of Old San Juan

Upon your arrival, the first thing in your Puerto Rico 5-day itinerary should be exploring Old San Juan’s cobblestone streets with colorful, colonial buildings, imposing fortresses, and cultural landmarks. After a delicious lunch break, your adventure continues on the San Juan Bay for a snorkeling class. To finish the day, you can either take a food tour sampling the best dishes and drinks around the island or just chill in one of the best bars in town.

Morning

Start the day by taking a walking tour to help you get oriented and learn about the history and culture of the place. You’ll visit iconic sites in the historical district and even invaluable hidden gems that only an experienced local guide can show you.

Book your Old San Juan Walking Tour.

If you still have time before lunch, you should check out at least one of these absolute must-visit locations in town to capture the essence and history of Old San Juan:

• La Fortaleza
• Castillo San Felipe del Morro
• Castillo San Cristóbal

La Fortaleza

Now serving as the official Governor’s residence, this National historic site was originally built as a defense fortress, carrying great historical and political significance. The mansion has undergone extensive preservation and restoration efforts to preserve its authenticity. Visitors can wander the mansion’s elegant interior as well as the courtyards and lush gardens.

La Fortaleza offers 30-minute guided tours Monday through Friday from 8:15 am to 3:30 pm. 

Castillo San Felipe del Morro

Also known as “El Morro”, this fortress has witnessed numerous battles and sieges throughout history, becoming one of Puerto Rico’s most iconic landmarks and a UNESCO World Heritage Site. Besides being an architectural marvel, the elevated structure offers breathtaking panoramic views of the coastline, the ocean, and the surrounding landscape.

Here’s a walking tour to add to your that includes El Morro among other historic locations as a nice addition to your Puerto Rico 5-day itinerary.

Castillo San Cristóbal

Like El Morro, Castillo San Cristóbal is a significant colonial fortification, and it played a key role in the Spanish-American war defending the land from foreign attacks. Visitors can tour its expansive grounds, explore its underground tunnels, and climb its ramparts for stunning sights of Old San Juan’s town and coastline.

You can visit El Morro and Castillo San Cristóbal seven days a week from 9:30 a.m. to 4:30 p.m. The admission fee is $10 for adults, and free for children under 15 years old — The best part? With the purchase of your ticket, you get access to both fortresses.

Afternoon

After spending all morning walking and exploring, you’re probably going to be hungry and in need of a break from the heat. Here’s my top pick of restaurants to have a taste of traditional Puerto Rican food:

• Marmalade – top rated on TripAdvisor for its fine dishes with upscale, five-course menus and a wide selection of wines.
• La Taberna Lupulo – for a more relaxed atmosphere to enjoy craft beer and a classic menu including wings, fish tacos, beer fries, and more.
• Cafe El Punto – a local favorite for a cozy atmosphere and a varied menu with appetizers, full meals, coffee, smoothies, and so much more.

Once you’ve got your energy back, it’s time to get your swimsuit and sunscreen and go for a short walk to Escambron Beach. This is a public, small beach, but it’s very clean, with crystal clear, calm water and nice views of the old forts. 

As you get to Escambron get ready to take a Guided Snorkel Tour – one of the many fantastic water activities in San Juan. You’ll get to dip into the shallow areas and admire the captivating coral reefs and marine life.

Tip: a great advantage of Escambron is that it has bathrooms and showers so you can wash the sand off and change into dry clothes before heading back to your hotel.

Evening

When it comes to nightlife in Old San Juan there are plenty of options to enjoy the evening and finish the first day of this Puerto Rico 5-day itinerary the best way. For dinner, I suggest going to Princesa; an open-air restaurant that feels like dining in the middle of a rainforest, surrounded by tropical plants under the starry sky and live music to complete the enchanting ambiance of the place.

If you have some extra time –and if you’re not too tired–, you should definitely go for a food tour or bar crawl in town. Here are some tour options:

• Flavors of San Juan Food Tour
• Savor the Sunset: Old San Juan Walk and Food Tour
• Craft Cocktail Tour in San Juan 

Where to Stay in Old San Juan

• Budget ($) — Acacia Boutique Hotel
• Best Value ($$) — Condado Palm Inn
• Luxe ($$$) — Cervantes Hotel
• Unique ($-$$$) — El Colonial

Day 2: Laid-Back Day in Condado

Wake up early for a day full of exciting activities in the beachfront neighborhood of Condado. Spend the morning strolling one of Condado’s best-known avenues for upscale shopping and entertainment venues, followed by a visit to Puerto Rico’s Art Museum. In the afternoon, put on some comfortable shoes to give your best in a Salsa dancing class. Once the sun sets, get ready for a luminous kayak tour in Condado’s Lagoon.

Morning

Take a morning stroll along Ashford Avenue, the fancy area of Condado where you’ll find boutique shops, bars, nightclubs, and entertainment venues. As you spend a couple of hours window shopping, you might find some nice souvenirs to take back home.

Head to Condado Beach and rent a paddleboard for a couple of hours to explore the calm waters and hopefully spot sea turtles and manatees. You can also take an introduction class if you’re new to paddleboarding.

Afternoon

By midday, enjoy a delicious meal at the beachfront restaurant Ola Ocean Front & Bistro, with marvelous views of the ocean. There’s also 1919 Restaurant, where you’ll experience world-class dining with creative seafood dishes. Or if you’re looking for a trendy, instagrammable vibe, the top-rated Luisa won’t disappoint you.

Make sure to eat well because you’re gonna need the energy for the next activity in your Puerto Rico 5-day itinerary. Show off your moves at this outdoor Salsa dance workshop designed to fit all skill levels, even complete beginners. Whether you’re with friends or your partner, you’re sure to have lots of fun dancing to the rhythm of the lively music.

Evening

Spend the rest of the day touring the grounds of Casa Bacardi, the world-renowned distillery where the famous rum is crafted. Get interesting insights into the history of the business and how it evolved over time. Not to mention you get to sample a variety of high-quality rum and even get access to its on-site restaurant – just in time for dinner.

Check out the tours of Casa Bacardí:

• Rum Tasting Tour at Casa BarcadÍ
• Legacy Tour at Casa BarcadÍ

Before calling it a night, don’t miss this LED Night Kayak Excursion. You’ll be paddling your way across Condado Lagoon on a clear bottom kayak with LED lights, which you’ll turn on once the sun goes down, creating a unique atmosphere as you enjoy the magical views of San Juan buildings light up the dark sky.

Where to Stay in Condado

• Budget ($) — Coral Princess Hotel
• Best Value ($$) — Olive Boutique Hotel
• Luxe ($$$) — Condado Vanderbilt Hotel
• Unique ($-$$$) — La Concha Renaissance San Juan Resort

---

Clueless about where to stay in San Juan? Check out my full guide to San Juan neighborhoods!

Traveling alone for the first time? Here are 8 ways to stop the anxiety.

Loving San Juan so far? You’ll love these popular festivals in Puerto Rico even more!

---

Day 3: Celebrating Art & Culture in Santurce

No Puerto Rico 5-day itinerary would be complete without venturing into the vibrant neighborhood of Santurce. Known for its artsy vibe, Santurce offers an eclectic blend of art, culture, and history. On your third day, you’ll be exploring the neighborhood’s colorful murals and art museums, and enjoying an evening of thrilling entertainment.

Furthermore, you’ll be taking breaks between activities to grab a meal at some of the best eateries in the area.

Morning

Start the day by taking a drive to Santurce –a 10-minute drive from Old San Juan– and stroll the colorful streets as you admire and take photos of the creative murals along Calle Loiza, Calle Cerra, and Avenida Juan Ponce de León. 

While you’re in the area, take a short walk to Museo de Arte de Puerto Rico. This art museum features gorgeous art galleries, sculpture gardens, and engaging exhibitions with artworks from the 16th century to the present, focusing on both local and international artists.

If you prefer visiting many places in less time, take this walking tour that includes Puerto Rico’s art museum as well as other artistic and historic sites around San Juan.

Afternoon

If you feel in need of a break from all that walking, grab lunch at Lote 23. This is an open-air food court with food trucks selling a variety of food, ranging from local cuisine to international dishes. You can grab a sit outdoors and enjoy the chilling vibes and friendly atmosphere.

If you’re looking for something more up-scale, try the top-rated Santaella for a menu with traditional Puerto Rican dishes that are as delightful as the sophisticated ambiance.

For your next activity, you’ll be venturing into Santurce’s art scene with this Santurce Urban Art Tour. You’ll be walking around the streets of Santurce, exploring the murals and street art as your guide provides you with valuable insights into the history of the neighborhood and its local artists.

Next, you’ll be visiting the art studio of a local artist from Loiza, where you’ll see and learn from his creative process, focused on Afro-Puerto Rican culture and traditions.

Finally, your tour ends at Luquillo Beach, where you’ll be treated to a sip-and-paint experience to show off your own creativity.

Evening

As a must-visit in your Puerto Rico 5-day itinerary, head to La Placita de Santurce to see this small farmer’s market and the surrounding area transform into one of Puerto Rico’s nightlife hotspots after 6 pm. The streets are filled with party lovers, food vendors, live music, and even salsa dancing.

Getting hungry? Stop by San Juan Smokehouse, one of the many bars and restaurants you can find there. Enjoy tacos, barbeque, empanadillas, and drinks while you relax at one of the tables outside – this way, you can still be part of the lively scene on the street.

However, don’t take too long at the bar so you can catch a show or live concert at Centro de Bellas Artes Luis A. Ferre. This is a beautiful, fine arts venue that features theater, dance, and music events. You can see everything from local, independent productions to international shows.

Check out upcoming events and tickets.

After the show, you’re going to want to go right back to your hotel and have a really good night’s sleep – you need to be prepared for your next big adventure the next day!

Where to Stay Near Santurce

• Budget ($) — Casa Santurce
• Best Value ($$) — The Wave Hotel
• Luxe ($$$) — Coral Princess Hotel
• Unique ($-$$$) — San Juan Marriott Resort & Stellaris Casino

Day 4: Off-the-Beaten-Path Treasures

Day 4 is all about exploring – from hidden beaches and natural wonders to the best spots to enjoy nightlife in San Juan. Have a delightful experience as you swim in the lagoon caves of  Charco Azul Canyon and sunbathe as you lie on the dusty, white sand of Vega Baja Beach.

Later in the evening –and after taking a power nap–, you’ll head to Old San Juan for a fun night hopping from bar to bar, tasting delicious cocktails, and befriending other partygoers.

Morning

Your day starts early with this lagoon and beach cave combo tour that will take you on a day trip outside of town. You’ll visit several spots on the outskirts of San Juan. These places are often overlooked by travelers due to tourist traps or not having their own vehicles. But this tour includes private transportation during the whole trip.

Your first stop will be at La Poza de las Mujeres, a breathtaking cave and beach where you can find pink coral rocks and beautiful fish – if you want to, you can request snorkeling gear to explore this paradisiac location even further.

Next, you’ll visit Charco Azul Canyon. Here you’ll see a mix of mesmerizing caves, rivers, and waterfalls to take as many photos as you want.

Afternoon

Before continuing with the tour, you and your group will stop by a local restaurant for a lunch break. You’ll also get wise suggestions on what Puerto Rican dishes to order from your local guide.

Your last stop is a local beach called Vega Baja. Here, you’ll be able to enjoy this huge, uncrowded beach with calm, crystalline waters and natural pools to swim and relax under the Caribbean sun.

Depending on your physical condition, you can take advantage of the rock formations by climbing your way up to the top and enjoying the spectacular views of the giant waves breaking on the rocks.

Your guide will be with you at all moments watching your back, and at the end of the tour, they will safely return you to your accommodation.

Similar tours in Puerto Rico:

• Arenales Caves and River Adventure
• Camuy Cave and Waterfall Adventure

Evening

When you come back to the hotel after a long day, you’re probably going to sleep the rest of the afternoon. This is great because you’re close to the end of your Puerto Rico 5-day itinerary and you have to go party at least once!

My first recommendation is to try this Old San Juan Bar Crawl so you get to know the best spots in town for music, dancing, and cocktails – including free drinks and complimentary dinner at the end of the tour! This is a great experience if you’re traveling with friends or even on your own since you’ll share the tour with a big group of lively people you can get to know and have fun with.

If you prefer a more relaxed night and just enjoy a few drinks with good music, my second suggestion is to go to La Factoria. From the outside, it might look like an old building, but inside there’s a bustling speakeasy-style bar where all the crowds go to enjoy top-notch cocktails, a dancing floor, and live DJs, creating a vibrant atmosphere unlike anywhere else in Old San Juan.

Day 5: Day Trip to El Yunque & Saying Goodbye to PR

This is your last day on the island, but you still have one more gem to see – El Yunque National Rainforest; home to an incredible diversity of tropical, lush vegetation and animal species. Here, you’ll be able to do a variety of recreational activities such as exploring hiking trails, going horseback riding, swimming or kayaking among manatees, visiting observation towers, and more.

Later in the afternoon, you’ll relax by the nearby Luquillo Beach before going on an exciting boat ride to celebrate your last day on the island with views of the sunset and complimentary drinks.

Morning

You’ll want to get an early start to arrive at El Yunque National Rainforest as soon as they’re open at 7:30 am. This way you can have a more quiet and enjoyable experience before the crowds start showing up by midday.

Tip: bring good hiking boots and a rain jacket since sporadic showers are common in the area.

If you’ve never visited El Yunque before, your first stop should be  El Portal Visitor Center is a great place to start. Here, you’ll find displays and film screenings about the forest’s wildlife and endangered species. The Center also has a nice café and restrooms for visitors. This is great if you want to take a break and keep exploring after lunch.

Key spots to visit in El Yunque:

• Yokahú Observation Tower
• La Coca Falls & La Mina Falls
• Angelito Trail
• El Yunque Peak

There’s so much to see and do here that you could easily spend the whole day enjoying the tranquility of the forest and jaw-dropping views in every direction. This is why I suggest going on a guided tour in El Yunque so you can make the most of your visit. This includes several short hikes leading to breathtaking waterfalls where you can swim, rope swing, and free dive. At another stop, you can enjoy a natural rock slide and cliff jumping into the river. Everything while learning the history of the rainforest’s ecosystem from your guide. Your tour ends with lunch at a local small family-owned restaurant with delicious home-style dishes.

I can’t recommend a tour of El Yunque enough – you don’t want to miss this National treasure.

Other tours in El Yunque Rainforest:

• El Yunque Rainforest: Waterslides, Waterfalls, and Rope Swing
• El Yunque: Half-Day Hidden Rainforest Waterpark Tour 
• El Yunque National Forest and Luquillo Beach Tour

Afternoon

After El Yunque, take a short drive to the stunning, crescent-shaped Luquillo Beach. Here, you can relax on the warm sand and take a fresh dip in the water for the rest of the afternoon. You’ll surely come across several kiosks and food vendors where you can grab a bite and a fresh piña colada.

Before sunset, go back to the hotel and put on your best attire for the evening.

Evening

Since this is the last evening of this Puerto Rico 5-day itinerary, you have to celebrate it the right way! A great way to say goodbye to Puerto Rico is to take a San Juan Catamaran Sunset Sail. The catamaran cruise admits groups of up to six passengers to provide an intimate and relaxing experience as you sail the Caribbean Sea. Whether you’re with friends or a romantic partner, you’ll have the perfect setting. 

Furthermore, you’ll be able to take in the breathtaking views of San Juan Bay, as well as the town’s historic landmarks like the San Juan Gate and El Morro Fort.

During the cruise, enjoy complimentary drinks of your choice, including wine, beer, rum, and soft drinks. Although dinner is not included in the tour, passengers are allowed to bring their own snacks aboard.

So, step out on the deck and make a toast for this incredible trip and many more to come!

Other sailing tours in San Juan:

• San Juan Historical Bay Sunset Sailing Tour
• Icacos Deserted Island Catamaran & Picnic Cruise from Fajardo
• Culebra Day Trip by Catamaran from Fajardo 

Where to Stay Near El Yunque

• Budget ($) — Luquillo Sunrise Beach Inn
• Best Value ($$) — Casa Coral
• Luxe ($$$) — Casa Alternavida
• Unique ($-$$$) — El Conquistador Resort

Other Tours You Might Like

Want to fit as much as you can into your Puerto Rico 5-day itinerary? Or maybe you decided to stay a few days more! Whatever the case, I’ve got you covered. Here are more exciting activities in San Juan to complete your trip:

• Off-road UTV Tour: Explore Puerto Rico Minutes from San Juan
• Luquillo Beach Horse Ride from Carabalí Rainforest Adventure Park
• Jet Ski Tour through San Juan Bay
• Bioluminescent Bay Kayak Adventure from San Juan

Last Thoughts

If you made it to the end of this itinerary, you’re probably super excited about your upcoming trip! Feel free to make little tweaks to suit your preferences – and if you want to add extra days, even better! 

Visiting Puerto Rico is an absolute joy for history, nature, and food lovers. With such beautiful places, rich history, and delightful cuisine, I’m sure that this trip will provide you with new knowledge, experiences, and unique memories that will stay with you long after you come back.

Safe travels and have a great time!

XO,

Anna