Read my original nature poems right here!

Read my original nature poems right here!

Your Puerto Rico Itinerary: 7 Days, 5 Days, or 4 Days

Before we figure out your Puerto Rico itinerary, we should talk about who these 7, 5, and 4 day itineraries are for. When we travel, we don’t take advantage of all inclusive resorts, which are popular and abundant in Puerto Rico. If you’re looking for a luxurious resort, with all your needs just the ring of a bell away, here’s some good info for you.

But I am not that kinda guy, pal.

We prefer exploring the places we visit and jumping from town to town. Puerto Rico has tons of diversity in landscape, history, food, and adventures. You’ll want to visit beaches and El Yunque, tour Spanish forts and old cathedrals, eat mofongo and taste local rum, and snorkel with sea turtles. There’s a lot to see and do.

So if you like dirt and sweat and salt water and long days on your feet…here are the best itineraries for spending 7 days, 5 days, and 4 days in Puerto Rico…

How many days to spend in Puerto Rico

How many days should you spend in Puerto Rico?

That’s a tough question.

What if I asked you how many days you want to spend in paradise? You might say “Forever!”

Fair enough.

If you’re the type who likes rainforests, beaches, art, food, and hiking you could spend a month in Puerto Rico and not get bored. Or, if you’ve got a long weekend free, you could pop into San Juan for a few days and come back with tropical memories, a nice tan, and some pictures with sea turtles.

Puerto Rico won’t limit you. It’s small enough to drive across the island in a few hours, but large enough and diverse enough to spend a day or two in every town you pass through. There are art galleries, surfing lessons, mountains, hidden beaches, and more! We spent two weeks hopping around Puerto Rico, and we’re already excited to go back.

Here’s how you can decide how many days to spend in Puerto Rico: pick some of my favorite things to do and start outlining your perfect trip. Beautiful places and experiences always dictate how long I’ll spend on a trip, and where that trip will take me.

My recommendation? If you can swing it, spend at least 5 days in Puerto Rico.

4 Days in Puerto Rico Itinerary

Let’s start with 4 days in Puerto Rico. Some might say this isn’t long enough to enjoy everything Puerto Rico has to offer, but 4 days in the Caribbean beats 4 days sitting at home, or driving a few hours to the same old beach. Plus, there’s so much to see in Puerto Rico, and four days is a good, inexpensive, bite-size trip to check it out. The flights from the U.S. are domestic and pretty quick, so you won’t waste a lot of time just traveling. If you’ve got a long weekend and want to sit on a Caribbean beach, head to Puerto Rico for four days.

In this 4 day itinerary, I make Old San Juan the home base. That doesn’t mean you can’t venture out with a tour group to go snorkeling or visit El Yunque, but it puts you in the heart of the food, history, culture, and architecture that all make Puerto Rico special. Plus, it’s only a short drive from the airport and you won’t need to rent a car at all. In short, if you’re limited on time, stay in Old San Juan.

Stained glass windows in Catedral de San Juan Bautista (first) and the colorful, preserved streets of Old San Juan (second). Check out my favorite pictures of Puerto Rico, too!

Day 1: Arrive in San Juan

Try to land in San Juan early in the day to make the most of your time. Do this by booking an early flight, not yelling for the plane to fly faster. For a place to stay, make sure it’s in Old San Juan. Old San Juan is more expensive than the casino and high-rise hotel areas stretching east along the Atlantic, but there is very little desirable or beautiful about these other areas. I compared Old San Juan to Condado right here, check it out before you book your trip. I’d only recommend staying in the crown jewel of beauty, architecture, and history: Old San Juan.

Uber or taxi your way to your lodging in Old San Juan (I recommend staying on beautiful Calle Del Sol). For the rest of the day (unless you’re very eager to hit the beach), walk around this amazing little city, enjoy some good food and drinks, and check out some of the famous spots on my Old San Juan scavenger hunt.

Write down a few places in Old San Juan you can’t miss, and start with those.

Day 2: Hit the Beach

You’re in Puerto Rico, so you’d better spend some time lounging on the beach. On Day 2, take a long walk or an Uber to El Escambrón Beach (Apple Maps | Google Maps). Spend all day on the golden sand of the Atlantic ocean before heading back to Old San Juan to refuel, probably hitting Anita La Mamma del Gelato after lunch or dinner.

On your second night, find some more iconic locations from the scavenger hunt, exploring shops and restaurants and you walk about.

Day 3: Freestyle

This is your vacation, not mine. So on Day 3 you can hit the beach again, take some tours (this Airbnb page will help), or simply enjoy Old San Juan (I’m all about wandering around new places). A tour may go down to El Yunque, take you snorkeling with sea turtles, or show off authentic food around the city. Don’t be afraid to get out of your comfort zone; many of these tour guides are experts at showing off the best, unseen sides of their tropical home.

Day 4: Head Home

There are some good coffeeshops and bakeries in Old San Juan (and probably a Starbucks if you need it). Start your morning with one last walkabout, taking in the sights and sounds, perhaps planning your next trip to Puerto Rico. It’s an easy Uber ride from Old San Juan to the airport.

How are you feeling? Do you want to come back and see more of Puerto Rico?

I’ll bet you do after 4 days. Well, keep reading for some itineraries that could expand your trip.

El Yunque, the lush rainforest just an hour south of San Juan did not disappoint.

5 Days in Puerto Rico Itinerary

Let’s add a day to your itinerary. Now, with 5 days in Puerto Rico, I think we can get out of Old San Juan a bit more. Still, though, I’m using it as a home base and skipping the rental car. Uber is easy to use in Puerto Rico (especially around San Juan), and I lean on it heavy to avoid paying for a rental. When your trip is 5 days or shorter, stay in Old San Juan and use it as your home base. I’m all about maximizing my time to see and do the most (at a relaxed, enjoyable pace), and keeping your roots in Old San Juan is the perfect method to do so.

Day 1: Arrive in San Juan

Even with 5 days of vacation, book an early flight to reach San Juan early in the day. Again, stay in Old San Juan so you can experience the history and beauty of the preserved colonial city.

After grabbing your luggage Uber to your hotel or Airbnb in Old San Juan. For the rest of the day (unless you’re very eager to hit the beach), walk around this amazing little city, enjoy some good food and drinks, and check out some of the famous spots on my Old San Juan scavenger hunt.

Write down a few places in Old San Juan you don’t want to miss, and start with those.

For history lovers like me, the Spanish forts (Castillo San Cristobal and Castillo San Felipe del Morro) are must-see items in OSJ.

Day 2: Hit the Beach

Just like the 4 day itinerary above, I’m heading to the beach on Day 2. You’re on a tropical vacation, after all. Head to El Escambrón Beach (Apple Maps | Google Maps) via Uber, and hang in the Puerto Rican sun all day. I’ve got a list of things to bring to Puerto Rico, including some beach essentials.

Visiting popular beaches like El Escambrón, I recommend getting there early. You’ll want the best pick of spots to set up your beach day.

When you’ve had enough of the salt and sun, head to back to your lodging. After a shower (and maybe a nap), head out for piña coladas and dinner. Perhaps check out Barrachina (Apple Maps | Google Maps), the home of the original piña colada.

Day 3: Best Kept Secrets Tour

This tour in Old San Juan is perfect for anyone interested in history, architecture, and the on-going work to keep Old San Juan preserved and beautiful. It’s only a couple hours and winds through the pretty streets of the colorful city, with Andy pointing out details and points of interest invisible to the casual passerby. We went into a crypt, atop a hotel for views all around, and learned why Catedral San Juan Bautista is falling apart. Andy is a knowledgeable and eager host, happy to discuss anything Old San Juan. He works to restore old cisterns beneath the city and has ambitions to make OSJ totally free of cars. An amazing guy and tour. I don’t get paid for recommending this tour, it was just that good.

Because the Best Kept Secrets Tour is only a couple hours, there’s time left to play. After lunch you might snorkel with sea turtles, take an evening bar crawl, or learn how to dance salsa. There are plenty of personalized experiences to explore right here on Airbnb. Again, I don’t get paid for these recommendations. This is just one of my favorite ways to plan a trip.

Day 4: You Pick, Rainforest or Beach

For your final full day in Puerto Rico, I’d head to the beach (maybe back to El Escambrón for something close by) or take a rainforest tour. El Yunque is in the U.S. National Park System, one of the few rainforests on American soil.

Because you’re only in Puerto Rico for 5 days, I recommend using a local tour to experience El Yunque. We spent three whole days near the rainforest, and it held some of our favorite experiences in all Puerto Rico. Check out this highly rated tour to see what’s in store if you decide to visit the rainforest.

Day 5: Homeward Bound

On the last of your 5 days in Puerto Rico, have a slow day wandering around Old San Juan. Grab coffee if that’s your thing. Take a few pictures. Pack your bags and make your way back to the airport.

The beach below Puerto Ferro Lighthouse on Vieques (first) and the Vieques Ferry from above (second). Vieques was a favorite part of visiting Puerto Rico, for me.

7 Days in Puerto Rico Itinerary

Alright, even though we’re only adding two days, we’re going to get a lot out of them. Moving up to 7 days in Puerto Rico, I’m starting the trip by visiting Vieques.

Vieques is a laid back island off the east coast of Puerto Rico that has remote beaches, beach bars, and wild horses. You either have to fly or take a ferry to get there. I prefer flying; it’s an easy layover in San Juan. I recommend starting your trip in Vieques before flying back to San Juan.

Your trip cost for a whole week in Puerto Rico should range from $2,500-$4,000, depending on what you spend on lodging, transportation, and food. You could absolutely save money by not visiting Vieques, but it’s worth the added expense. Check out our 2 week Puerto Rico trip cost right here.

Day 1: Fly to Vieques

You can buy your plane ticket to Vieques at the same time you purchase your regular plane tickets. When you arrive in San Juan, you’ll just head to a part of the terminal where the Vieques Air Link operates little Cessna planes. We had an easy and great experience with their team, even with some rain delays. Flying in a little plane over the Caribbean Sea was a special experience.

To get the most out of Vieques, check out my guide to visiting Vieques. You’ll want to rent a Jeep from Vieques Car Rental (10/10 experience with them) upon arrival.

Settle into your Airbnb in Esperanza (we stayed in a guesthouse above Duffy’s–Flamboyan Guesthouse) before wandering out to Esperanza Beach (Apple Maps | Google Maps). Then head back to town for a vegan burger and drink at Duffy’s (Apple Maps | Google Maps).

Esperanza itself is good for a couple hours of wandering. There’s a pretty boardwalk, restaurants, and a large beach a stones throw away.

Day 2: Explore the Remote Beaches of Vieques

Get in your Jeep (you’ll need a 4×4 for this part of the trip) and head into the Vieques National Wildlife Refuge, just a short drive from Esperanza. Enter the park right here: Apple Maps | Google Maps

There’s only one road to follow in the park and every so often you’ll pass a beach (or a road leading to a beach) on your right side. Popular beaches like Playuela, Caracas, and La Plata (amongst others) are on this remote part of the island. Just remember, as you drive into the park, the ocean is on your right side. Follow the roads leading to it and check out the various beaches until you find one you could spend all day at.

We settled at Playa Caracas (Apple Maps | Google Maps) and stayed in the sun and calm water for hours. These are the beaches you see in the pictures. You might feel like you’re in Pirates of the Caribbean.

Day 3: Breakfast, Snorkeling, Back to San Juan

We snorkeled on Vieques with a guide. He showed us sea turtles, pointed out an octopus and stingray, and took us to his friend’s house for fresh mangos. If you’ve got time, go snorkeling on Vieques. Read about our experience here.

Before we snorkeled with sea turtles, we enjoyed a nice vegan breakfast burrito at Café del Mar, just across from the salty Caribbean sea. Very tasty!

Finally, board another puddle jumper back to San Juan. Vieques Car Rental was kind enough to shuttle us to and from the airport, so transportation was easy.

Day 4: Explore Old San Juan

Even with snorkeling, you should be able to make it back to San Juan before it’s too late for dinner. On Day 4, I’m Ubering from the airport to my Airbnb in Old San Juan. After a shower and fresh change of clothes, go wander the streets of Old San Juan, stopping when you find a place to eat. Seriously, just wander. Take it all in. OSJ is quite different than Vieques, and you’ll be glad for a change of scenery. The city is incredibly walkable and old, a treasure trove for history and architecture fans.

Get some sleep and get your walking shoes ready for Day 5.

Day 5: Old San Juan Tours

This tour in Old San Juan is perfect for anyone interested in history, architecture, and the on-going work to keep Old San Juan preserved and beautiful. It’s only a couple hours and winds through the pretty streets of the colorful city, with Andy pointing out details and points of interest invisible to the casual passerby. I don’t get paid for recommending this tour, but I recommend reading some of the thousands of positive reviews to see if it’s for you.

That tour is only a couple hours, so there’s time left to explore. After lunch you might snorkel with sea turtles, take a culinary tour of the city, or head out on your own Old San Juan scavenger hunt. There are plenty of personalized experiences to explore right here on Airbnb. Browsing these experiences is one of my favorite ways to plan a trip to somewhere new.

Day 6: Freestyle

I like to treat the final days of long trips casually. So on your second last day in Puerto Rico, I’d simply wander. Maybe you end up at a Spanish fort, or a cathedral, or sipping on a tropical drink at a popular bar. Pop into an art gallery or museum, take some photos, and relax. Spending too much time and energy running around getting things done is a popular way to finish a vacation, but let’s take a few deep breaths and enjoy the quiet corners, moments, and sensations of beautiful Old San Juan.

Deep breath in, deep breath out. Look at the sea. Touch an old fortress wall. Smile at a stray cat. Sip a glass of wine.

Day 7: Goodbye, Puerto Rico

A week anywhere special goes quick. In fact, the faster it goes by, the more special you know it is.

If your flight isn’t right in the morning, take your day slow. Ask for a late checkout and go get coffee, or a donut, or a breakfast sandwich. Just step out your door and see where your wanderings lead. Just don’t zone out and forget to return to the airport for your flight.

Floating at Playa Buye (first) and the cliffs of Cabo Rojo (second). If you have time to make it to Puerto Rico’s west coast, do it!

Bonus: 2 Week Puerto Rico Itinerary

When we travel, we like to take our time. We take pictures, we try lots of food (too much, sometimes), and we spend lots of time on our feet. I’m always ducking into cathedrals and writing poems, and my wife loves art galleries and gardens. So we don’t hustle this way and that (usually).

When we were planning our Puerto Rico trip, I knew I wanted at least 2 weeks. The island is small enough to drive across in a few hours and there’s tons to see and do. We’d also never been somewhere so tropical, and I knew the hiking, waterfalls, and nature would enrapture me. That’s not even mentioning the architecture, beaches, and food!

So yeah…it was 2 weeks for me.

Days 1-4: Vieques

We flew right to Vieques (rather than taking a ferry later), rented a Jeep, and explored the island for four days. And I’d still go back! There are remote beaches, crazy history (half the island is off limits because it was a bombing range), snorkeling, and a big rum distillery. There’re also wild horses, a national wildlife refuge, and pretty lighthouses.

You’ll want to visit Black Sand Beach (Playa Negra) and Sea Glass Beach. Stay in Esperanza (the south side of the island, away from the ferry dock); don’t worry, the island is tiny and you can explore the north side, too.

Adding Vieques made our trip much more expensive, but it was well worth it. We made a few new friends, swam with sea turtles, drove a Jeep out to empty beaches, and snuck into abandoned lighthouses.

Can’t wait to get back there one day. I’ll probably spend more time sitting on the beach and wading in the turquoise waters, when we do return.

Days 5-7: Old San Juan

We flew early from Vieques to Old San Juan, so we had a whole day to hang out in the new place.

Over three entire days, we took tours, explored historic sites (most on this OSJ scavenger hunt), and ate good food. No rental car was needed for this portion: Old San Juan is walkable. This is another place I’ll return to. It’s very close to the airport and you don’t need a rental car. Just Uber from the airport to your hotel or Airbnb, and then Uber back when your trip is over. Anyone could spend a week in OSJ and be happy.

Days 8-10: El Yunque

Don’t skip the rainforest if you’re in Puerto Rico for more than a week, mostly because of El Hippie. We hiked, swam in waterfalls, ate passionfruit from the vine, and listened to the millions of famous coqui frogs each night singing in the treetops. I enjoy mountains and stomping around in wild places, and El Yunque did not disappoint. Check out my El Yunque guide right here.

Days 11-12: Driving to the West Coast, Staying in Rincón

After hanging in El Yunque, we drove roughly this route across Puerto Rico to Rincón, a beach town popular for surfing. We hung in Rincón for a couple days, eating some good food and watching awesome sunsets (you’ll be on the west coast, after all). Rincón has a whole boardwalk and lighthouse park seemingly dedicated to sunset. While there’s ample parking, you’ll see crowds gathering for that beautiful end of day. The park is right here: Apple Maps | Google Maps

Rincón is a happening little town that I’d want to spend more time at, possibly for surfing lessons. And definitely to watch more sunsets.

Days 13-15: Playa Buye

We ended our trip in the most relaxing fashion: lounging around one of the most loved beaches for west coast Puerto Rico tourists: Playa Buye. It’s a crowded little white sand beach with amazing sunsets. Here’s a whole guide on visiting it, if you’re in Cabo Rojo. Cabo Rojo is home to salt flats, crazy cliffs, and lots of iguanas, too.

Playa Buye, even though it’s on the opposite side of Puerto Rico, was only a few hours drive to the airport. If you can, I recommend spending some time on the west coast. On your way, check out Ponce, Yauco, and Mayagüez, too.

Any questions? Shoot me an email!

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George Callahan is the creator of Pine Tree Poet. He is an author of fantasy stories and an adventure poet. He prefers mountains and pine trees to most other things, and usually takes his dog Cowboy along for the ride.

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