Morning: Arrival and Old San Juan walking tour

Arrival and coffee—Welcome to San Juan! After landing at the San Juan Luis Muñoz Marín International (SJU) Airport, you’re going to want to caffeinate yourself before starting your adventure. Sip some of Puerto Rico’s world-renowned coffee in Old San Juan—but locals recommend saving room for a cafe con leche at Finca Cialitos. 

Walking tour— Old San Juan is tiny (only 7-square blocks) but is absolutely jam-packed with gorgeous architecture, amazing history, and really cool things to do—many of which are totally free.

Paseo de La Princesa—Don’t forget to head down to Paseo de La Princesa and stroll below San Juan’s massive city walls, two iconic San Juan attractions. Locals say if you’re looking for things to do San Juan on a weekend, check out the food and crafts tents that line Paseo de La Princesa (and maybe grab an empanada or some guava candies).

Afternoon: Castillo San Felipe del Morro

Lunch—If you’re getting a little hungry after your morning adventure, refuel at one of Old San Juan’s amazing Puerto Rican restaurants. This can be a touristy part of town, so use local advice to avoid tourist traps. Our local trip planners tell us that Cafe Manolin is a great stop for Puerto Rican-style fare. 

El Castillo San Felipe del Morro—Next, make your way westward towards one of San Juan’s most famous attractions, El Castillo San Felipe del Morro. This iconic fort is historic and photogenic. 

• The fort grounds—Make sure to stroll through (or just kick back on) the huge green field that surrounds the castle’s 500-year-old walls. You’ll pass the colonial cemetery, and see people hanging out flying kites and eating ice cream. 
• Guided tour—Our local trip planners suggest taking the English-language tour at del Morro to get the full scoop about this important landmark. Just ask your trip planner to add a tour like this to your customized itinerary. 

Downtime—Go home and chill for a second before heading back out for the night. Staying in Old San Juan will make things easier (it’s by far one of the best places to stay), but the entire city of San Juan is easily and cheaply accessible via Uber.

You can get personalized recommendations for where to stay from our locals. No matter your budget, you'll have tons of choices of boutique hotels and hostels. 

Evening: Dinner and nightlife in Old San Juan

Dinner—Using local advice is a great way to find hidden gems—and avoid tourist traps. Our local trip planners in Puerto Rico tell us that many restaurants in Old San Juan are "aimed at tourists" but that there are "diamonds in the rough."

Punto de Vista Rooftop Restaurant, for example, comes locally recommended—and has an incredible rooftop view. 

Nightlife—When you’re done with dinner, go bar-hopping through Old San Juan! Don't wander blindly—have one of our locals recommend their favorite cocktails spots. Locals say that other things to do in San Juan at night include going night-kayaking or taking a romantic stroll around Paseo de la Princesa.

Morning: Explore Miramar and Condado

Breakfast—Rise and shine! Now that you’ve conquered Old San Juan, it’s time to see some other parts of the city. Grab breakfast somewhere in Miramar—Caldera Café is a local favorite, but you can always ask for personalized recommendations closer to where you’re staying.

Miramar—Stroll along the Laguna del Condado to see local life in action, and feel free to dip your feet in the water at Jaimie Benítez Park. Miramar is a lovely place to stroll. And if you're looking for a snack, locals tell us that Miramar Food Truck Park is a great place to start. 

Condado—Head east through Condado to see Puerto Rico’s original tourist attractions. The Miami-esque Condado strip had its heyday in the ‘60s and ‘70s, but it’s still the most fashionable area of the city. It’s also packed with hotels and upscale shopping, so if you’re looking to buy some nice gifts, this is a good option.

Afternoon: Beach time at Isla Verde

Lunch at the beach—Grab some lunch in Condado, or head straight out to Isla Verde. Just on the other side of the airport, this upscale stretch is home to some of the best beaches in Puerto Rico. Depending on which Isla Verde beach you choose, you’ll be able to rent chairs and umbrellas, buy snacks, and even piña coladas!

Fun in the sun—Whether you want to drink, sunbathe, eat, swim, surf, or even snorkel (the beaches are packed with things to do), you can make it happen if you know where to go. When you’re done at the beach, Uber home for a shower and a rest—you’re going to need it.

Evening: Party at La Placita

Santurce—Once you’ve freshened up, head into San Juan’s hipster central, the neighborhood of Santurce, for a night out.

Calle Cerra—Make your first stop in the trendy area of Santurce, Calle Cerra, to see the neighborhood’s famous murals. This area of Santurce is probably the best place to stay in San Juan if you’re a hipster at heart—or if you just love cheap beer.

La Placita de Santurce—Walk over to La Placita de Santurce for the rest of the evening. La Placita is a massive plaza of restaurants, bars, and kiosks. The entire area is packed with locals every evening, and the partying goes on until late at night. Grab dinner, bar-hop, and don’t be afraid to dance!

Our local trip planners can give recs tailored to your travel style. (Plus, they'll help you steer clear of the more mediocre La Placita bars.)

Morning: Check out La Perla & San Cristobal

Traditional breakfast—Even though it was probably a late night (Santurce, baby!) you should get up early. On the way down to La Perla (off the northern end of Old San Juan), grab a traditional Puerto Rican breakfast. Start your day with some local advice—our trip planners tell us that  El Panadero Artesanal is an excellent spot for freshly baked bread and pastries. 

La Perla—Take the winding road into La Perla. Colorful, rustic, and interesting, it’s actually perched on the outside of the Old City Wall. You'll likely recognize La Perla, as it was the setting for the Despacito music video. 

La Perla is a place in Old San Juan where you still see the devastating effects of Hurricane Maria. It’s now safe to visit, but it’ll give you a feel for what Puerto Rico went through in 2017. 

Castillo San Cristobal—After you leave La Perla, head up to the nearby Castillo San Cristobal, del Morro’s sister fort. Locals tell us that visiting San Cristobal is one of the best things to do in Puerto Rico for history buffs, as it’s super intricate, bigger than del Morro, and less crowded. 

Afternoon: Head out to Piñones

Piñones—Head out to Piñones with an empty stomach—our local trip planners tell us that this Puerto Rican vacation spot is known for its food. Just on the other side of Isla Verde and past the SJU Airport, Piñones is a long stretch of gorgeous beach packed with restaurants, roadside stands, and kiosks (aka chinchorros) that sell beer, piña coladas, and most importantly, Puerto Rico’s beloved fried snacks.

Tropical afternoon—Visit Piñones in the mid-to-late afternoon. That way, you can eat and drink on the boardwalk, catch some live music, maybe have a swim, and head out before it gets dark. Puerto Rico is safe in general, but locals tell us that Piñones can get a bit sketchy at night.

Evening: Have classy drinks in Condado. 

Spend the evening in Condado: Condado’s beachfront hotels and resorts have some of the nicest restaurants in town. Have dinner and drinks overlooking the ocean (definitely use local recs to find a spot—our trip planners are full of suggestions), and get home early. You have a big day tomorrow!

Morning: Drive to El Yunque

Rent a car—You’ll want to get an early start; if you haven’t already rented a car, this is the time to do it. Local travel planners recommend renting a car from the SJU Airport for $10-$14 a day—Puerto Rico travel prices tend to be super low. 

Road trip—Grab some breakfast and hit the road—you’re heading to the United States' only tropical rainforest and hands down one of the best places to visit in Puerto Rico! The drive to El Yunque is surprisingly short, only 45 minutes to an hour.

Afternoon: Hike through the rainforest

El Yunque—Lots of companies that do Puerto Rico tours offer exploration packages and hiking trips through El Yunque. These are a great option if you want something all-inclusive, but they’re often expensive and last all day.

For more personalized recommendations, ask your local trip planner for how to best explore El Yunque. Whatever you do, keep an eye out for endangered Puerto Rican parrots (bright green and red) and adorable coqui tree frogs.

Evening: Mosey around Fajardo

Mini road trip—The drive east from El Yunque to Fajardo is even shorter than from San Juan to El Yunque—locals tell us the drive takes just 30-45 minutes.

Fajardo—Fajardo is an adorable town on the eastern shore of Puerto Rico. Grab a room at a hotel, Airbnb, or parador (a locally-owned inn), and start exploring! Locals note that the town is famous for its 19th-century Spanish lighthouse, its bioluminescent bay (one of the three in Puerto Rico), and its excellent seafood. Fajardo also has some great places to swim and snorkel.

Morning: La Ruta de Lechon (aka The Pork Highway)

La Ruta de Lechon—Oh yes, you read that correctly. From Fajardo, you’re going to want to make your way to Highway 184 near the town of Guavate. This stretch of road is known as The Pork Highway, and it’s one of the most incredible off-the-beaten-path attractions in Puerto Rico.

Road-side restaurants—This three-mile stretch of highway is covered in roadside restaurants that specialize in whole roast pig, or lechon. Many of the restaurants are open-air, with the road on one side, and the jungle on the other. You can also find cheap drinks, live music, and dancing at most spots throughout the day.

Afternoon: El Charco Azul Swimming Hole

El Charco Azul—A 15–minute drive south down Highway 184 (a gorgeous jungle road through the mountains), you’ll arrive at a gorgeous hidden gem: El Charco Azul. 

This freshwater swimming hole is a 10-minute walk through the jungle and a local secret; only a few people have even mentioned its existence on TripAdvisor Puerto Rico, and they love it as much as we do. If you're looking to get off the beaten path, work with one of our trip planners to discover sites that most tourists miss. 

Hop in the car—After your swim, make the 1.5-hour drive down to Ponce, Puerto Rico’s “Jewel of the South”.

Evening: See the town of Ponce by night

Ponce—Ponce is Puerto Rico’s second-largest city and full of stuff to see and do—so you’ll want to shower up and take a rest before you head back out for the evening. 

La Guancha—Once you’re ready to boogie, head straight down to the most happening place in Ponce—La Guancha Boardwalk. La Guancha is to Ponce what La Placita is to San Juan. So enjoy bites and drinks from the boardwalk's kiosks, and definitely keep an eye out for Ponce's famous pelicans. 

Morning: Walking tour of Ponce

Old Ponce—Spend your morning walking around Ponce’s old town. Its Art Nouveau architecture is second to none in the Americas (seriously, it’s internationally recognized), and there are tons of incredible buildings to see.

Self-led walking tour—See Ponce like a local—have your trip planner make you a custom walking map as they did for San Juan; that way, you’ll also have some great local recs for breakfast. Whatever you do, don’t miss Parque de Bombas or Serralles Castle—they’re two of Ponce’s most iconic landmarks.

Afternoon: Late lunch and Hacienda Buena Vista

Lunch—Ponce has some great lunch spots. One of our local trip planners suggested El Barril de la Mulata for classic Puerto Rican fare. 

Hacienda Buena Vista—After lunch, head to into the mountains above Ponce to Hacienda Buena Vista. On this restored and fully functional coffee plantation, you’ll get to experience the history of coffee cultivation in Puerto Rico first-hand. Plus, consuming delicious coffee really helps Puerto Rico's economy. 

Evening: El Observatorio de Arecibo

Arecibo coastline—Sadly, it’s time to say goodbye to Ponce…but hello to Arecibo! Only a 1.5-hour drive away, Arecibo is perched on Puerto Rico’s northern shore. Locals tell us it's a great place to see some natural wonders and take one final swim.

El Observatorio de Arecibo—Before getting into town, stop by the Arecibo Observatory. This massive telescope is operated by NASA scientists 24 hours a day, and its size alone makes it worth a look. You can also stop into the visitor center, but our local trip planners note that it's only open until 3 PM Wednesday through Sunday.

You may recognize the observatory. It was the scene of the climactic battle in the James Bond film/video game “GoldenEye”. 

Downtown Arecibo—After your jaunt to the observatory, head into Arecibo proper for the night. Have some dinner and get to bed early—you’re going to want to be well-rested for your last day on the island!

Morning: Arecibo walk and Journey to Cueva del Indio

Breakfast in Arecibo—Arecibo is a great town, and locals recommend spending a couple of hours exploring. If you're looking to jump-start your day, our local trip planners in Puerto Rico recommend grabbing a coffee from Delicias Café.

Cueva del Indio—Arecibo is also close to some incredible sites. Locals highly recommend checking out Cueva del Indio, a seaside cave where you can see petroglyphs (rock carvings) made by Puerto Rico’s pre-Columbian Taino people centuries before the arrival of Europeans. Just keep in mind that accessing the cave is difficult—there's no longer a ladder, so you'll have to lower yourself in. Be careful!

Afternoon: Cueva Ventana and swimming at the Arecibo Lighthouse

Cueva Ventana—Locals tell us that a trip to “The Cave Window” (pictured above) is an absolute Puerto Rico must-do. This cave provides a gorgeous view over the Arecibo Valley. 

Back to the Arecibo coastline—Since the drive from Cueva del Indio to Cueva Ventana is pretty short (about 25 minutes), you’ll easily be able to loop back into town for a final swim. Use local advice to find hidden gems—our trip planners tell us that next to the Arecibo Lighthouse, you can find a secluded ocean cove called “The Bishop’s Well.” With a view of the old Spanish lighthouse, you couldn’t ask for a better place to take a final dip.

Evening: Departure

By now, it’ll be time for the drive back to San Juan and the airport. But worry not, my friend—you’ll be coming back to Puerto Rico again. It is called the Isle of Enchantment for a reason, after all.