I first visited Puerto Rico back in 2016. I spent a week hopping around the Caribbean island, splashing around on famous beaches, going zip lining in the jungle, and wandering through the streets of Old San Juan.
That trip was a lot of fun, and convinced me that Puerto Rico is a fantastic option for anyone looking to plan a Caribbean vacation. But that trip was also a busy one; it was in partnership with Discover Puerto Rico, and while I got to see a lot, it was all really rushed.
Ever since then, I've wanted to plan another trip to Puerto Rico.
Unfortunately, a lot of things got in the way – including a pair of devastating hurricanes in 2017. Returning to Puerto Rico had to be put on hold, but I always knew I'd be back.
Fast forward to the end of 2019, when my husband Elliot and I were talking about where we might want to travel in 2020. We decided we wanted to go somewhere warm early in the year, and quickly settled on the Caribbean.
After researching everything from small-ship cruises to fancy island resorts, I finally suggested Puerto Rico for an easy, relatively affordable option. It ended up being the last trip we would take pre-global pandemic, and I'm SO glad we got to go.
Planning a trip to Puerto Rico
Why plan a trip to Puerto Rico? Well, it's easy to reach from the US, and we got an excellent deal on flights. And since Puerto Rico is still a US territory, we didn't have to worry about remembering passports, exchanging money, or doing anything to our phone plans, either.
But, most importantly, after hurricanes and earthquakes and a multi-year dip in tourism, I knew Puerto Rico could really use our tourism dollars.
Once Elliot and I decided we'd be going to Puerto Rico, I knew I wanted to do this trip differently than my first one. While road tripping around Puerto Rico is a great way to explore different parts of the island, I decided we would focus our visit on just two locations: the capital city of San Juan, and the island of Vieques.
A lot of people visit San Juan every year – but that's because the city is a popular joining point for Caribbean cruises. I wanted more than just a whirlwind tour of San Juan, though, so staying for multiple days in/around the city seemed like the best option for us.
If you want to plan a warm-weather getaway in the Caribbean that doesn't require a rental car or a huge time commitment, here's a great 5-day itinerary for San Juan that you can feel free to steal!
Where to stay in San Juan
Before we get into the itinerary, let's talk about where to stay in San Juan. There are a couple different areas where tourists will stay, with the most popular being Old San Juan and the hotel strip in Condado.
1. Old San Juan
If you want to stay in the heart of the action, then you want to stay in Old San Juan. Hotels in this part of San Juan tend to be historic (and slightly more expensive), but the area is very safe, and you can walk to most of the major sites.
My hotel picks in Old San Juan are:
- Hotel El Convento – If it's historic you want, you can't go wrong with this boutique hotel housed in a former convent. The luxury hotel is right next to San Juan's Cathedral square. (Book a room here)
- The Decanter Hotel – This is where Elliot and I stayed on our visit together. The small boutique hotel is found in an historic building, and many of the rooms have beautiful terraces (see the photo above). There's also a great rooftop bar to enjoy at night. (Book a room here)
- CasaBlanca Hotel – This small hotel is in a great location, and comes complete with a rooftop terrace and local artwork throughout the property. (Book a room here)
This hip and trendy beach district is east of Old San Juan. It's known for fancy hotels and nightlife, along with its stretch of beach and ocean views.
My hotel picks in Condado are:
- Condado Ocean Club – The first new hotel to open in San Juan after the 2017 hurricanes, this hotel is the one Elliot and I chose for our 2020 trip. It sits right on the beach, with a small infinity pool that overlooks the ocean. The ocean view rooms here have incredible floor-to-ceiling windows, and the beachy vibe extends throughout the whole property. (This used to be called the Serafina Beach Hotel.) (Book a room here)
- Condado Vanderbilt Hotel – Usually ranked as one of the best hotels in Puerto Rico (and certainly in San Juan), this luxury hotel sits right on the beach and delivers a resort-like experience. (Book a room here)
- La Concha – The La Concha is a Renaissance property, and is one of the iconic hotels in Condado. The hotel was recently renovated, and has a modern design and great on-site dining options. (Book a room here)
- Caribe Hilton – I stayed at this property on my first trip to Puerto Rico, and especially loved the pool area. The Caribar here is regarded as the birthplace of the Piña Colada, and this is one of the more family-friendly hotels in Condado. (Book a room here)
Other neighborhoods you could consider include:
- Santurce – A more “local” neighborhood, filled with street art, galleries, and shops. It's a bit grittier, and you'll find more vacation rentals available here than hotels.
- Ocean Park and Carolina – These are more residential neighborhoods, but they are right on the beach.
If you're looking for affordable rental options with ocean views, here are a few:
- This 1-bedroom condo in Condado has unblocked ocean views, and access to a pool
- This beachy studio sits ocean-front and has a balcony
- This Ocean Park penthouse can sleep 8 and has its own private rooftop pool
For this itinerary, I actually recommend splitting your time between two hotels, one in Old San Juan and one in Condado. That way, you can be in close proximity to both the historical center and the beach for a couple nights.
How to spend 5 days in San Jaun
This itinerary covers 4 nights in San Juan, but Day 1 is a pretty full day – meaning if you aren't arriving in the morning, you might want to tack on an extra night and arrive one day before this itinerary starts – that's what Elliot and I did!
A caveat: I don't live in Puerto Rico; this itinerary is written 100% by a tourist, with other first-time visitors to San Juan in mind!
Day 1: Old San Juan
When most people think of San Juan, Puerto Rico, they think of the colorful old colonial buildings and the Spanish forts found in Old San Juan. And while San Juan is more than just its “Old” city center, this is undoubtedly the part of the city that you'll be most excited to see.
1. San Juan fortresses
Start out your morning with a visit to Castillo San Cristóbal, part of the San Juan National Historic Site. The historic site comprises two different fortresses, as well as old city walls and gates. I recommend starting with Castillo San Cristóbal on the northeast end of Old San Juan, because it's within easy walking distance from most hotels.
Castillo San Cristóbal is one of the fortresses built by the Spanish to defend Puerto Rico. Construction on this fortress began in the 1600s, and it was used all the way through WWII, when US troops used the sentry boxes and lookouts to scan the waters for German U-boats.
Entry to the historic site is just $10 per person, and there's a lot to see. You can visit former prison cells, stand in sentry boxes, and explore much of the 27 acres that the fortress covers.
You can also get some fantastic views over San Juan in all directions.
Pro tip: Get to Castillo San Cristóbal as close to opening time as you can; the cruise ship tour buses will start rolling in 1-2 hours after opening, so get there early if you want to have the site mostly to yourself.
2. Lunch and drinks
After thoroughly exploring the fortress, make your way back into Old San Juan for lunch and some exploration on foot. There are lots of great places to eat, whether you're looking for a sit-down meal, or something quick from a food stand.
For lunch with a view, head to La Vergüenza, not far from Castillo San Cristóbal. With a rooftop terrace and drink specials throughout the day, this spot is touristy but still good, and the ocean breezes are nice.
If you want to pair your lunch with a cup of Puerto Rican coffee instead, head to Cuatro Sombras, which is a trendy cafe in the heart of Old San Juan.
3. Historic walking tour
This evening, I recommend signing up for a walking tour around Old San Juan to really learn about the city's history. Even though Puerto Rico is technically “part” of the United States, the relationship is a tenuous one, and it feels like a completely different country.
And this makes sense, of course, thanks to its history. A walking tour of Old San Juan will cover a lot of that history – from Columbus' “discovery” of the island all the way through to the present day – and give you a taste of what makes the city so special.
A walking tour like this won't delve too deep into the complicated relationship Puerto Rico has with the United States (I invite you to read more about it on your own), but it's nevertheless a great introduction to the island, and especially to San Juan.
For dinner tonight, try El Jibarito or Cafe El Punto, which both serve up traditional Puerto Rican dishes. If you're up for drinks and dancing after dinner, check out La Factoría, a speakeasy-esque bar/club that is very famous, but also serves up good drinks (try the Lavender Mule!).
Where to stay in San Juan: Elliot and I stayed at the Decanter Hotel, which we really liked. Another top pick is the historic Hotel El Convento. Both are in Viejo San Juan/Old San Juan and within walking distance to a lot of attractions and restaurants.
Day 2: Eat and drink 'til you drop
Today you'll focus on two things that Puerto Rican culture revolves around: food and drink! Puerto Rico has an amazing food culture, produces delicious coffee, and distills some of the world's most well-known rum.
Start out your morning with a nice big breakfast; Elliot and I really liked the Waffle-era Tea Room and their sweet and savory (and massive!) waffles.
1. Tour the Bacardi factory
If you're interested in rum, then you won't want to skip a visit to Casa BACARDÍ, or the “Cathedral of Rum.” Even if you don't like drinking rum very much (guilty), touring Puerto Rico's Bacardi factory to learn about the company's history is pretty fascinating.
Casa BACARDÍ is located across the bay from Old San Juan in Cataño. You can get there by taxi or Uber, or you can save some money by taking a ferry across the bay. Ferries leave from Pier 2 in Old San Juan (sandwiched between the cruise ship docks) roughly every 15-30 minutes. Tickets cost only 50 cents per person (yes, really, $0.50!), and the ferry ride takes about 10 minutes.
Once you get to the Cataño pier on the other side of the bay, you can either catch a taxi or call an Uber for the short ride to the Bacardi factory. (There's a taxi stand just outside the ferry terminal, but it was empty when we visited; we called an Uber, and it only cost $5 to get to Bacardi.)
At Casa BACARDÍ, you can choose from a variety of tours. We opted for the Legacy Tour, which is a 45-minute tour that covers the history of Bacardi and their rum production process. This tour costs $30, and includes a free cocktail from the outdoor pavilion bar.
Other tour options include a 90-minute rum tasting tour ($75 + tax) where you get to taste a handful of rums; or a mixology class ($75), where you learn how to make three classic rum cocktails – including a mojito, of course! More info on current tours here.
Even though I don't really love rum, I really enjoyed the historical tour at Casa BACARDÍ. We learned all about the brand's history (did you know it was started in Cuba, and is still owned by the Bacardi family?), and how Bacardi has evolved in Puerto Rico. I especially loved learning how the factory has worked to reduce waste, and how it produces almost all of its own energy.
After the tour, head back to Old San Juan by car or ferry.
Pro tip: Not interested in Bacardi? You could also consider visiting the home of Ron del Barrilito, a small-batch rum made at the oldest distillery in Puerto Rico. Ron del Barrilito just recently opened up a visitor center in Bayamón called Hacienda Santa Ana, which is only about a 15-minute drive from Old San Juan.
2. Go on a food tour
I hope you're hungry by now, because the next thing on the agenda is a food tour! I love taking food tours when I travel; you learn so much about an area's history and culture through its food.
In San Juan, the go-to food tour company is Flavors of San Juan, and the tour I'd recommend for this afternoon is the classic Old San Juan Food Tour. This 3-hour small group tour is a great introduction to Puerto Rican food and drink. It mixes history and good eats – and a bit of walking to help you burn off some of those extra calories!
I won't give away everything included on this tour, but you'll visit at least 5 different locally-owned spots and taste everything from Puerto Rican coffee to pastries to chocolate. My favorite part of the tour was when we made our own mofongo!
The Old San Juan Food Tour is offered several times throughout the day. I recommend going with a late afternoon option (there's usually a 3 p.m. tour), which will fill you up enough that you won't have to go out for a separate dinner.
3. Sunset and sundowners
If you opt for the afternoon food tour, your tour will end before sunset, so you can either head to the old city walls past Paseo de la Princesa and La Fortaleza, or all the way out to San Juan's second fortress, Castillo San Felipe del Morro, to watch the sun go down.
Either before or after, consider stopping at Barrachina, a restaurant in Old San Juan that claims to be the birthplace of the Piña Colada. This is contested by the Caribe Hilton, which also claims to have invented the drink. Regardless, though, Barrachina does mix up a very tasty drink.
Day 3: Art and beaches
It's time to bid farewell to Old San Juan on Day 3 of your trip. While the old city is beautiful and fun, there's much more to San Juan than what's contained behind those fortress walls.
Today, I recommend exploring the Santurce neighborhood east of Old San Juan. This neighborhood is more residential and less touristy, but is still filled with restaurants and cafes – plus lots of colorful street art.
I also recommend switching hotels today so you can get a taste of the Condado neighborhood. Grab an Uber or taxi this morning and move your things over to your new hotel (I recommend the Condado Ocean Club); if you can't check into your room yet, leave your luggage while you head out to explore Santurce.
1. Get your art on
Start off your day in Santurce with a visit to the Museo de Arte de Puerto Rico*. This art museum showcases and celebrates Puerto Rican and Caribbean art spanning from the 17th century to the present, and is a must-visit for art lovers.
*Note: The museum building is currently only open Thursday-Sunday.
I'm not actually a huge fan of art museums, but the variety of styles represented in this museum (plus seeing so much work by Puerto Rican artists!) held my interest for a couple of hours. We made our way through all the galleries, and also took a walk through the museum's outdoor sculpture garden.
The best part is that tickets for this museum are just $6 per adult.
From the art museum, you can easily walk to other parts of Santurce, keeping your eye out for the colorful street art that the neighborhood is known for.
Often compared to Miami's Wynwood Arts District, Santurce has incredible murals to be found around every corner. Stroll up Calle Cerra or Calle Loíza for the greatest concentration of art – and artsy cafes. Read more about Santurce's street art here.
Grab lunch at one of the myriad cafes and restaurants along Calle Loíza – no matter what you're in the mood for, you'll find it here!
2. Hit the beach
A short walk north of Calle Loíza lies the Ocean Park beach (AKA Playa Último Trolley), a long public beach that's laid-back and not very touristy at all. This is a perfect spot to take a walk along the sand, or go in for a dip if you bring your swim gear.
You can also watch people trying out windsurfing, kiteboarding and other water sports, as this is a popular beach for all of those.
3. Experience La Placita
Head back to your Condado hotel to clean up and grab some dinner. You may just want to relax this evening, but if you're up for some excellent local atmosphere, head to La Placita de Santurce after dark.
During the day, this two-tiered market square is pretty quiet with a farmer's market and some restaurants. At night, though (and especially on weekend nights), it's where locals flock for street food, drinks, and live salsa music (and dancing) in the square.
Not all parts of Santurce are regarded as being safe after dark, but La Placita is an exception; the atmosphere on a weekend night is so vibrant. I recommend taking an Uber there/back from your hotel, and practicing basic safety precautions to keep yourself and your stuff safe. But this spot makes for a truly fun night out.
Where to stay in Condado: While there are lots of great hotel options in Condado (including some of the top-rated hotels in San Juan!), we ended up choosing the Condado Ocean Club (formerly the Serafina Beach Hotel). This hotel is newer, with light and airy rooms with a distinct beachy vibe. We especially loved the floor-to-ceiling window in our oceanview room, and the infinity pool right on the edge of the beach. (Read more reviews on TripAdvisor | Book a room here)
Day 4: Catamaran day trip
Don't party *too* hard at La Placita, though, because for your 4th day in San Juan, I actually recommend getting out of the city!
There are several day trip options (a couple more are suggested further below), but my top pick is to get out on the water. I've gone on a catamaran sailing trip on both of my visits to Puerto Rico, and those days have been some of my favorites!
Most day trips by boat actually leave from Fajardo, a city about an hour from San Juan. But several tour companies will offer hotel pick-up in San Juan for an extra fee.
Option 1: Catamaran trip to Culebra
On my first trip to Puerto Rico, I went on a day trip to Culebra island by catamaran. Culebra is a smaller island off the coast of the main island of Puerto Rico. It's not super touristy or commercialized, and is known for its beautiful beaches.
This day trip included a couple of snorkeling stops, lunch, drinks, and music on the boat, and a stop at Flamenco Beach on Culebra, often listed as one of the best beaches in the world.
A day trip to Culebra does require more time on a boat since the island is further away, though, so keep that in mind.
Option 2: Catamaran trip to Icacos
On my second trip to Puerto Rico, Elliot and I booked another catamaran trip. This time, we booked a day trip to the deserted island of Icacos.
There were two different options for this tour: to book onto a bigger boat (with a water slide!) with more people, or to book onto a smaller boat with fewer people. We went for the smaller boat option, and it ended up being perfect!
We didn't actually get to Icacos because of rough seas and bad weather on the day we sailed, but our captain still found us a nice beach and a separate spot for snorkeling. And the crew was fantastic, keeping the pina coladas and rum punch flowing, and cooking up a great BBQ lunch for us all.
Both of these days trips are full-day tours. You can expect to be picked up in San Juan before 8 a.m., and return around dinner time. I think this is a must-do in Puerto Rico, though, as the ocean around the island is so beautiful.
Pro tip: Don't forget your sun protection! While most catamarans offer up a bit of shade, you'll be out in the sun plenty. Sunglasses, a hat, UV-blocking clothing, and reef-safe sunscreen are all worth packing in your beach bag.
If you get back and are looking for a hearty dinner in Condado, I loved the meal we had at Condal (seafood paella and Spanish tapas – yum!), or you could book a table at one of the nearby fancy restaurants like 1919 Restaurant or Mario Pagán Restaurant.
Day 5: Pool/beach time
On your final day in San Juan, how about not doing much of anything? Spend the morning soaking up a last few hours of sun at the beach or your hotel's pool.
If you want to squeeze in one more water activity, pick up a rental paddleboard or kayak from VIP Adventures to explore the Condado Lagoon.
If you've had enough sun and sand, take a stroll through trendy Condado. Window shop (or actually shop) along Ashford Avenue.
Later today, it's time to either head home, or continue on to the next part of your Puerto Rico adventure. I would highly suggest spending a few days on Vieques next!
Other day tours from San Juan
Not super into snorkeling or boats? Or maybe want to skip the artsy day in Santurce? There are a couple other options for day trips you can take from San Juan, including trips to El Yunque rainforest, zip lining adventures, and more.
Other popular San Juan day trips include:
- El Yunque Off the Beaten Path Hiking Tour
- El Yunque Rainforest Off the Beaten Path and Bio Bay Kayaking Combo Tour
- Full-Day Zipline and Waterfall Rappelling Adventure Near San Juan
(But personally I would still stick to the catamaran trip!)
What to wear in San Juan
If you're curious about what to pack for your trip to San Juan, I have good news! Puerto Rico is a pretty casual place, and any of your typical tropical/beach attire should be just fine here.
Puerto Rico has a tropical climate year-round, so you'll always want to be prepared for warm and humid weather.
Some of my staples for a trip like this include:
- Light and airy clothing
- Comfortable shoes
- A packable sunhat like this one with built-in sun protection
- Sunglasses and some reef-safe sunscreen
- Swimsuit(s) and beach cover-ups
If you want to see some of my favorite picks for summer clothing, check out my summer travel must-haves here.
Many people will continue to visit San Juan for half a day or maybe a night before getting on a cruise. But I invite you to consider San Juan as a destination in its own right; there's so much to do, as you can see in this itinerary!
Whether you're into history or food or art or just chilling by the water, you can find it all in different parts of San Juan. Just writing this itinerary makes me want to plan another trip!
Who's ready to plan a trip to San Juan now? What would you be most excited about doing?
Pin it for later: