If we had the freedom to do so, we’d move to Puerto Rico tomorrow. The people we’ve met there are warm and inviting, the food is out of this world, and the culture and architecture are both incredibly vibrant. But with so much to do and see, planning even one week in Puerto Rico can be daunting. So, from two lovers of Puerto Rican culture, food, history, and beaches, here’s our ideal Puerto Rico itinerary, recommendations on where to stay, and ideas about what to do.
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Table of Contents
Where to stay in Puerto Rico on your first trip
- Old San Juan
- Pros: it’s the hub of activity on the north side of the island, has the most plentiful cultural sites and tour pickups, and is incredibly charming and photogenic. This is where we choose to stay when we visit.
- Cons: None that we can think of!
- Condado
- Pros: views from all the high-rise hotels, a sweet little beach, lots of shopping with a modern feel
- Cons: a little too far from OSJ to really enjoy all the city has to offer, requires a car or ride-share to do much outside of the area, made pretty much for tourists
- Isla Verde/Carolina
- Pros: less touristy, can be very close to the beach, lots of nearby water sports, close to Panadería España
- Cons: also a little too far from OSJ to really enjoy all the city has to offer (about 20 minutes by car), a fair amount of visible poverty, requires a car or ride-share to do much outside of the area. We’ve stayed here in the past, but have found we prefer OSJ.
- Santurce
- Pros: truly non-touristy view of daily life, beautiful street art everywhere you look, lots of cool/up-and-coming restaurants and shops
- Cons: also a little too far from OSJ to really enjoy all the old city has to offer (about 20 minutes by car), a large amount of visible poverty, requires a car or ride-share to do much outside of the area
Things to do in San Juan, Puerto Rico
- Take food tours
- Regardless of destination, we can’t stress this enough. Food is such an integral part of any culture that it’s impossible to fully get to know that culture without also getting acquainted with its local menus. In Puerto Rico, you can taste your way through the island’s Afro-Caribbean roots, Spanish influences, and come to understand how all of these things have melted together to make a vibrant, robust culture.
- Walk around!
- OSJ is incredibly charming, and honestly, just walking around Old San Juan is one of our favorite things to do in Puerto Rico. While poverty is certainly visible in some places more than others, the buildings are largely old, with brightly-painted, Spanish-style facades. Shops that range from local pharmacies to upscale designer stores sprinkle the city. And you can get a great feel for what restaurants you may want to try just from walking past and getting both a whiff and a view of the typical clientele. There’s just so much to do walking around OSJ! Just be sure to wear comfy shoes – the hills may not be San Francisco-level, but they’re still no joke.
- Get out of San Juan
- Go hiking or exploring in El Yunque rainforest, snorkeling off the coast of Culebra, or kayaking in Bio Bay. The opportunities are endless!
- Try AirBNB experiences
- On our last trip to San Juan, we made all of our activity reservations (with the exception of our food tour) through AirBNB. We cared for injured manatees in Bayamon, took a walking tour of Santurce’s famous murals, spent an evening listening to traditional music with a local musician, and even indulged in a morning photo shoot with a local photographer. The opportunities are endless and intensely valuable, as they give you an even deeper look into daily life for locals.
- Tour historic sites in Old San Juan
- Perhaps best-known is El Morro, the most imposing of the walled city’s Spanish forts. You can also walk through the Castillo San Cristobal and the San Juan Bautista cathedral, among others.
- Go to the beach!
- San Juan is within easy distance of about 5 beaches, each with different selling points, so you have absolutely no excuse NOT to enjoy any or all of them.
- Try Puerto Rican coffee, a REAL pina colada, and other local dishes
- Mofongo, sangria, flan, mallorca bread with ham and cheese, and coffee from the island all require the attention of your taste buds. You may get these experiences from food tours, but make sure you try them in a few different spots, as different restaurants and cafes can have different takes on traditional dishes.
- Explore artisan shops
- Visiting places like Ole Hat Shop, and various other spots that sell local art work and wares, is a wonderful way to support the economy and help Puerto Rico continue to recover from all the hardships the island has recently faced. Plus, you’ll leave with incredible, one of a kind souvenirs!
- Visit La Perla
- This barrio may not be affluent, but it’s one of the most vibrant and colorful neighborhoods in Old San Juan. Sitting just a short walk from El Castillo, the art and music have played a large part in influencing current Puerto Rican culture, and it’s 100% worth experiencing. Please note that locals did recommend not visiting after dark, and not being flashy with any sort of valuables even during the day.
Our 7 day Puerto Rico itinerary, based in Old San Juan
Day 1: Flights and check-in; enjoy dinner and a real pina colada at T’Tuan
The amazing thing about Puerto Rico, particularly if you live on the East Coast of the US, is that flights are typically inexpensive and fairly short (we’re talking less than 6 hours, often including layover). Once you arrive on the island, order an Uber from the airport and enjoy the quick ride into Old San Juan. If you arrive before check-in and have chosen to stay at a hotel like La Terraza de San Juan, you’ll find most quite willing to either hold your luggage or attempt to offer early check-in. Once your bags get sorted, feel free to wander around and get to know the vibe of the city. For the most part, as long as you aren’t super flashy with your giant DSLR camera and other valuables, you’re more than safe walking the streets of this charming, historic city.
Finally, when dinner rolls around, head down near Paseo de la Princesa for dinner at T’Tuan, our favorite restaurant in the city. They mix pina coladas by the original recipe, as well as the predecessor to the pina colada, the monchito. Pro tip: order the monchito!! And while you can’t go wrong with their menu, the fish tacos are absolutely out of this world. If the weather is nice, sit outside on the pedestrian street and watch the sunset with your dinner.
If you still have space, walk just down the street to Señor Paleta and enjoy one of San Juan’s best desserts: fresh popsicles and ice cream, made with local ingredients. The line gets long, but it’s SO worth it!!
Day 2: Get a custom Panama hat, and relax on the best beaches near San Juan
Unless you spend a ton of time in sunny, hot, humid weather, it’s impossible to describe just how profound the impact of a good hat can be. Thankfully, Ole Hat Shop is easy to get to from almost anywhere in Old San Juan, and is run by a family of milliners specializing in straw Panama hats. When you step inside, it feels like stepping back into the early 20th century – the shop is all dark wood and stacks upon stacks of hats in all different sizes, styles, and colors.
The first time we visited in 2016, the original owner of the shop helped us find a hat for me, customized the fit, and helped me pick a brim. He was an outgoing, jovial guy who loved to chat. The last time we visited, his daughter and a few other folks had taken over the store, and we were helped by a very nice, younger man, who showed every bit as much professionalism, expertise, and willingness to engage customers as his predecessor. We both purchased surprisingly affordable custom hats and went through the process of fitting and brim-color picking, and have never been happier with a purchase.
With a brand new Panama hat on your head, it only makes sense to head to the beach – which is precisely what we did. Happily, staying in Old San Juan means you’re within walking or easy Uber distance of the best beaches near San Juan. We walked 15 minutes from our hotel to Playa Peña and spent a relaxing several hours on this quiet beach, basking in the clear, warm water and enjoying sunbathing with the locals. You can also take your new hat and your bathing suit over to Escambron Beach (which did require an Uber), spend awhile settled on the white sand with local families, and then take another Uber over to Panaderia Espana, home of our favorite ham and cheese mallorca sandwich in Puerto Rico.
Finally, once you get back into the city, this is probably a great day to end with a dinner and drinks at a casual local bar like El Lupolo, followed by a leisurely stroll home.
Day 3: Go hiking in El Yunque rainforest; get dinner at El Jiberito
On our first trip to Puerto Rico, we spent a full day hiking through El Yunque – up river beds, under waterfalls, the whole shebang – and then zip-lined back down the mountains to meet our ride home. One of the best parts of the excursion was having local chicken, beans/rice, and flan thanks to the family who owned the company. Seriously, you’ve never had flan until you’ve had island flan. Mmmmm.
That said, plenty of reputable local companies offer rainforest experiences, along with activities like rappelling, cave exploration, four-wheeling/ATV tours, and more. You can also visit coffee plantations located in the mountains, or go waterfall hunting. The options are truly endless, and your only real limit is just how intense you want your day to be.
Once you get back to OSJ, if you haven’t had your fill of local, traditional food, head over to El Jiberito on Calle Sol for a downhome Puerto Rican dinner experience. Outfitted to look like an open air restaurant inside, this place is bustling, loud, and definitely not fancy. But the food, while basic, is absolutely packed with flavor. The best part is, you can walk over there right after your shower from your day, and no one will think twice.
Day 4: Take a food tour of Old San Juan
We’ve realized that we tend to travel and plan from meal to meal, which can add a little stress when we’re in an unfamiliar place. One of the best parts about food tours is that you don’t have to worry about meals for an entire day. Typically, they start early enough that you can skip breakfast, and end late enough that you’re tired and definitely out of stomach space for dinner. We’ve taken tours with Flavors of Old San Juan and, more recently, with Spoonfood Tours. Both are walking tours chock full of the city’s history and anecdotes, and include several stops at local restaurants, bars (if you’re 21!), and shops to partake in the tasty part of that history.
Our tour with Spoonfood included 5-7 stops, and we never ended up feeling TOO full because we had the opportunity to walk and settle our mini-meals in between stops. Need more options? See more San Juan food tours here, and San Juan walking tours here.
Day 5: Snorkel Culebra and enjoy Flamenco Beach; get dinner at Hecho en Casa
You’ve already explored the city and the rainforest – now it’s time to hop out to one of the island’s islands. After a drive, a ferry ride, and another drive, arrive on Culebra at your guide company’s home base. If they’re like to provider we used, they’ll outfit everyone with snorkel gear and safety lessons, and take their intrepid adventure-seekers snorkeling with green turtles, kayaking on the ocean, and snorkeling a reef. The rest of the afternoon is spent lounging on Flamenco Beach, consistently ranked one of the most beautiful white sand beaches in the world. There are tons of other tours out there, as well. It’s hard to go wrong!
When we did this, we arrived back in Old San Juan just in time for dinner, and were more than ready to eat. After your long day, we recommend hitting Hecho En Casa for their unique white wine and garlic mofongo and a couple of piña coladas – you won’t regret it.
Day 6: Get breakfast at Chocobar, tour El Morro, then explore the local music scene
We found the best breakfast in Old San Juan at Chocobar Cortes. Their mallorca sandwiches, waffles, pancakes, egg dishes, and coffees steeped with cacao beans were all a delight for the taste buds, while the colorful, historically-significant decor provided plenty for the eyes to explore. Chocobar is the restaurant arm of locally-owned Cortes chocolate, which you can buy in the restaurant, as well as taste in many of their sauces and other sweet AND savory dishes. Don’t miss this place!!
After you’ve had your fill, head over to the Castillo San Felipe del Morro – better known locally as El Morro. This medieval fortress constitutes one of the most well-known historic sites in Puerto Rico. Here, you can not only walk the battlements to see canons and lovely sea views, you can also tour internal rooms open to the public that include exhibits around the way occupants would have dressed, the weapons they would’ve known or carried, what life was like in the Middle Ages in Puerto Rico, and also a history of many of the battles that took place near the island. Neither of us is much of a history buff, but the fort is beautiful and, since PR is one of the oldest walled cities in the New World, a huge part of the area’s history.
If you happen to have the time or motivation, you can also tour the Castillo San Cristobal, which neighbors the La Perla barrio and is the largest Spanish fort in the New World. You can spend hours here, wandering or taking a tour of the grounds. You can easily get tickets for both forts pretty inexpensively, and can spend the day taking in the area’s Spanish history.
Finally, give an AirBNB experience a try with Andres, a local musician who knows the music scene like the back of his hand and will show and teach all about the types of music that have most heavily influenced the island’s culture. Expect live bomba and plena music, with tasty food and LOTS of Medalla beer. Basically, you’ll walk away – like we did – feeling like you’ve just enjoyed an incredible night out with friends.
Day 7: Breakfast/coffee, depart
Finally, it’s time to head out. We enjoyed another meal at Chocobar before we left, but this is a great time to pick your favorite morning meal from your trip to revisit. If you’ve got awhile before your flight, you can also go hang out at one of the city’s coffee shops to deliciously kill time. Then, call an Uber to the airport and you’re all set to go.
Common questions for your first trip to Puerto Rico
Do US residents need a passport or visa?
Nope! Though it’s not a state, Puerto Rico is a part of the United States and as such, US citizens don’t need any sort of special documentation or passports to travel to the island. Just make sure you have your government ID with you – same as you would for any flight within the United States – and you should be all good.
Do Puerto Ricans speak English? Or should I speak Spanish in Puerto Rico?
We’d be lying if we said Spanish wasn’t the language most folks are comfortable with in PR, and learning a bit could only help. That said, we’ve never encountered anyone on the island who doesn’t speak lovely English. Even if you’re not bilingual, you’ll be able to converse easily with the vast majority of tour guides, restaurant and hotel staff, and anyone else you may meet if you speak English.
Do I need any vaccinations?
According to the CDC website, you should make sure you’re up to date on all of your routine vaccines before you go (duh), and should also consider Hepatitis A and typhoid vaccines. While food and water in San Juan should be just fine to consume, when you get into more rural areas you may find water more likely to be contaminated in a way that US water supplies usually aren’t. Better safe than sorry.
Should I stay in a resort?
We don’t think so! In fact, Puerto Rico isn’t an especially resort-specific place, like other Caribbean islands or places in Mexico might be. We’ve been more than happy with AirBNBs and hotels during our stays, because they tend to be far more convenient, still very comfortable, and offer a much better glimpse into what Puerto Rican life is actually like.
Is everything okay after the 2017 hurricanes? How about the 2019-2020 earthquakes?
For the most part, yes. There are plenty of trees still standing, and most buildings and structures in Old San Juan look none the worse for wear. That said, we actually experienced a blackout IN Old San Juan one evening that completely handicapped a couple of restaurants. We also heard from other guests and locals that some of the suburbs, like Santurce, are still experience rolling blackouts because the infrastructure that was already tenuous before the hurricanes was never able to be fully repaired. And as you get further out to the south and east of the island, you’re likely to find these issues even more frequently. This is especially true in the wake of the earthquakes.
That said, the way to help isn’t to stay home or choose another destination. Indeed, the way to help the Puerto Rican economy continue to recover is to make sure you visit and spend your tourist dollars with independent businesses and local service providers. Help nourish the economy (for your own enjoyment, of course 😉 ) and you’ll help the country recover faster.
Did we miss anything? Do you have a favorite one week in Puerto Rico itinerary? How about things to do in Puerto Rico, or places to stay? We’d love to hear them!
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