ITINERARY: THE ULTIMATE GUIDE TO PUERTO RICO
I lost my passport while moving apartments in 2021. I know, that’s basically a sin to a traveler, especially during COVID when the renewal process takes far longer than it used to. That’s why over this Thanksgiving I opted to go to Puerto Rico. As a U.S. citizen, I can travel there using just my government-issued driver’s license rather than a passport but I figured it would be more fun than heading home for the holidays.
As U.S. citizens, I think many of us take Puerto Rico for granted because it’s a U.S. territory and think of it like home, but I’m here to tell you that this couldn’t be further from the truth. While Puerto Rico is a U.S. territory and has a lot of similarities to the U.S. because of that, it is rooted in its Spanish and indigenous heritages that shine through in the culture you see there today.
Below is my comprehensive 8-day itinerary to Puerto Rico, inclusive of sandy beaches, waterfall adventures, and city strolling.
Looking for more inspiration for your next trip to Puerto Rico? Check out my Ultimate Guide to Culebra Island and my Street Art Walking Tour of the Santurce Neighborhood for tips.
SAN JUAN
Day 1
Quick tips:
Airbnb: I’d opt for staying in an Airbnb and would recommend staying in Old San Juan. It’s easily walkable and extremely quaint so the perfect place to stay if you want to get immersed in the city
Renting a Car: Don’t. Driving in Old San Juan is a nightmare and Uber is extremely accessible. Even if you want to take a day trip to El Yunque (which we did on Day 2), you can do that via a guide that picks you up in the city. I’d just avoid the hassle of a car altogether.
Eats:
- Lunch: La Vergüenza
- Dinner: El Jibarito
For us, day 1 was primarily a travel day and then an opportunity to begin getting to know San Juan. We chose an Airbnb in Old San Juan for the first leg of our trip. This walkable part of the city is full of rich history and lively nightlife, making it the perfect place to start our trip and spend our first weekend and remote working days.
Once we unpacked at our Airbnb, we headed to lunch at La Vergüenza near the La Perla neighborhood for our first of many mofongos and pina coladas of the trip. The view from La Vergüenza is awesome and was my favorite part of the lunch.
After lunch, we were lucky enough to discover that San Juan was celebrating its 500th anniversary since its founding – complete with various street fairs and performances all around Old San Juan. We spent the afternoon touring those before grabbing some beers and enjoying the sunset at El Morro Fort (which quickly became our nightly tradition in Old San Juan).
Then, we enjoyed a late dinner at El Jibarito, our favorite Puerto Rican restaurant in Old San Juan and definitely not one to pass up (be sure to go for the garlic chicken, it’s to die for). We then tucked in early to prepare for our day 2 adventures.
EL YUNQUE NATIONAL FOREST
Day 2
Quick tips:
Schedule a Tour: Since we didn’t rent a car in San Juan, we opted for the tour. Once we got to El Yunque, we noticed that’s what everyone else did as well and it’s definitely the best way to see the rainforest.
What to Wear: Warning – you will be trekking through rivers and mud, so don’t wear brand new shoes on this excursion! They’ll likely get ruined. I started in shorts and a t-shirt and by the end was just trekking in my swimsuit.
Be Ready for Adventure: It’s important to note that this tour is not for the faint of heart. There’s climbing, sliding, jumping, and swinging involved, so be ready for an adventurous day if you’re going to book it.
This was by far one of my favorite adventures in all of Puerto Rico! We purchased this Viator tour where our guide picked us up in San Juan and took us on an adventure tour of the national forest. Throughout the day, he shared insight into the history of Puerto Rico, his experience in the jungle, and helped us through the tricky paths of the jungle. This tour is definitely not for the faint of heart or those with new shoes — you’ll be trekking through rivers and mud, jumping off cliffs, swinging on rope swings, and sliding down natural water slides throughout the day. I’d recommend booking a guide for this – we got to meet a lot of other travelers and it made traveling to the forest stress-free.
OLD SAN JUAN
Day 3 – Remote Working Day
During our trip to Puerto Rico, I worked remotely for these two days. Our Airbnb in Old San Juan made it easy for me to work most of the day but also capitalize on short breaks and tour the city a bit.
Before starting my workday, we chose to do a free walking tour of Old San Juan. Wherever I go I always try to find free walking tours. The tours are entirely based on tips and the well-trained, local guides give great overviews of the history of the city, guidance on where to eat, and tips and tricks that you wouldn’t find elsewhere. Most of the tours meet in Plaza Colon of Old San Juan and last for about two hours.
Once my workday was over, we watched the sunset at El Morro Fort with a beer and then headed to La Factoria for their famous cocktails and salsa dancing on Mondays.
Quick tips:
Free Walking Tours: Pretty much anywhere I go I try to take advantage of the free walking tours. These are available in most cities and provide you with a great baseline for getting to know the city and understanding its history.
Remote Working: Whenever I work remotely from somewhere, it’s vital to choose the location of your Airbnb or hotel wisely. We opted for Old San Juan because it’s small and walkable, so I was still able to walk around the city at lunch and during breaks and not feel like I wasted my whole day working inside. Another bonus was that our Airbnb had a great rooftop that I could work from as well.
Salsa Dancing: On Mondays, La Factoria – the most famous local bar in Old San Juan – hosts salsa dancing nights. It’s very informal and you can participate as much or as little as you want, but it’s a fun sight to witness.
OLD SAN JUAN
Day 4 – Remote Working Day
For my second and final remote working day of the trip, I was only able to explore Old San Juan during brief breaks throughout the workday. However, my boyfriend was able to escape for a while to snorkel at the nearby Escambron Beach, about a 30-minute walk from our Airbnb. The crystal clear waters were ideal for snorkeling and he didn’t have to venture too far from shore to find them. After the workday was over we watched the sunset at El Morro Fort again and then went to Deaverdura, a local haunt, for a classic Puerto Rican dinner.
Quick tips:
Sunset at El Morro Fort: Every night in San Juan we watched the sunset at El Morro Fort. The fort is surrounded by a huge open field where locals and tourists alike convene on a daily basis to fly kites and just enjoy the sunshine and views.
Eats: Dinner at Deaverdura
CULEBRA
Day 5
Need a deeper dive into the ins and outs of Culebra Island? Check out my Ultimate Guide to Culebra Island here.
With remote working done, it was now time for adventure! For the second half of our trip, we took a prop plane tour to Culebra, an island off the east coast of mainland Puerto Rico that has some of the best beaches in the world.
The prop plane leaves out of SJU airport and is only a 30-minute flight over gorgeous blue waters to get to the island. Once you’re there, you rent a golf cart or a Jeep and just start exploring!
We started our trip at the famous Flamenco Beach, with white sands and pristine aquamarine waters. Then we hopped over to Tamarindo Beach to snorkel and watch the sunset on the west side of the island.
Quick tips:
Getting to Culebra: Whatever you do, take the prop plane to Culebra instead of the ferry! The ferry leaves from the east side of mainland Puerto Rico and if you didn’t rent a car it’ll be just as expensive to Uber there as it would to take the prop plane. Plus, the view from the plane is u-n-b-e-l-i-e-v-a-b-l-e.
Getting Around: You have to rent your Jeep or golf cart at least a few weeks in advance of your trip to Culebra, or you’ll be left wandering around the island on foot, which isn’t easy. We went with a golf cart from Jerry’s Jeeps which cost about $85 a day and was completely worth it. The island of Culebra is also incredibly safe, so we just left our luggage strapped to the golf cart while we went to the beach and never had an issue.
Beaches: Start with Flamenco Beach (one of the 50 best beaches in the world) for some nice relaxation and then head to Tamarindo for great snorkeling.
CULEBRA
Day 6
For our only full day on Culebra Island, we spent the day on a 5-hour scuba and snorkeling tour via Aquatic Adventures tour guides. They took us to two different dive spots and supplied us with both lunch and all the necessary equipment for our dives. Better yet, the full day only cost about $110 for a diver and $65 for a snorkeler, and we saw stingrays, manta rays, coral, nurse sharks, and tons of fish.
Quick tips:
Where to Stay: We stayed at Island Charm Culebra, a quaint little hotel not far from the main town on the island. They supplied us with towels, chairs, a cooler, and this amazing hammock and view during our stay – I’d recommend booking the sea turtle room if you’re there!
Scuba and Snorkeling: Culebra has fantastic scuba and snorkeling all around the island. Be sure to book a full-day tour with Aquatic Adventures during your time there.
Eats: Everything on Culebra closes super early. If you can put your name into Dinghy Dock restaurant about two hours early (by 6pm) then you should get a table. If not, try Mamacita’s. We missed out on both and had to cook dinner for ourselves.
CULEBRA
Day 7
For our only full day on Culebra Island, we spent the day on a 5-hour scuba and snorkeling tour via Aquatic Adventures tour guides. They took us to two different dive spots and supplied us with both lunch and all the necessary equipment for our dives. Better yet, the full day only cost about $110 for a diver and $65 for a snorkeler, and we saw stingrays, manta rays, coral, nurse sharks, and tons of fish.
We then ended our Culebra journey with a sunset flight back to San Juan, pina coladas in hand.
SANTURCE, SAN JUAN
Day 8
For our final day in Puerto Rico, we spent it in the Condado and Santurce neighborhoods of San Juan. These neighborhoods give you better insight into how the locals actually live in San Juan. They’re full of high-rise apartment buildings and hotels, shopping, dining, and some great nightlife.
Throughout the Santurce neighborhood, you can go on a self-guided scavenger hunt of the street art. At the end of the day, we joined some of the locals and tourists in a block party of sorts that happens every night in the neighborhood. I’d also recommend grabbing dinner at Lote 23, which is full of food trucks where you can get everything from local Puerto Rican cuisine to Philly cheesesteaks and everything in between.
Quick tips:
Street Art: Go to Santurce and do a self-guided tour of all of the great street art around every corner.
Eats: Head to Lote 23 for a ton of food trucks and varying cuisine.
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ABOUT ME
Welcome! I’m Natasha, a 27-year-old living in Manhattan and constantly itching to get out. I created Exploring Elsewhere to inspire those like me, 20-something women with shallow pockets and too few vacation days, to take adventurous solo trips in far-off lands.