Sometimes we spend months, even years planning trips. Sometimes we spend a day. That was Puerto Rico. Waiting for your passport to renewal  to come through while having your finger hovering over the “book” button on any travel website, is a unique form of torture- the lesson here boys and girls is renew eaaaaarrrrrrlllly. Do it.

Its rare, but sometimes procrastination pays off, and in this case Puerto Rico was our reward. No passport required.

You don’t hear much about Puerto Rico unless, its bundled together with words like, Zika, and hurricanes. But you should or maybe you shouldn’t, maybe thats what makes this place great.

A relatively small island ( 100 miles long X 35 miles wide) you can drive across the entire place in a day  (theoretically- we’ll talk about the insane driving in Puerto Rico a little later). With 7 days, and the keys to a trusty rental Toyota Corolla- we set out on an epic Puerto Rican Road Trip.

* Short on time?  If you want just the basic trip itinerary, click hereor jump on over to our trip video.


Just like all destinations, traveling to Puerto Rico can be easy or difficult, quick or arduous depending on where you’re flying from. As Southern East Coasters, our total travel time should have been 3 hours tops, but we’re all about the savings and flying North to Philadelphia first saved us a bundle in the long run, the downside is it also increased our travel time to almost 7 hours. A small price to pay to save nearly $400 per ticket. Thank you American Airlines!


Day 1: Old San Juan

STAY:  Whenever possible we take up the offers of friends, family and neighbors to couch surf and crash at their residences to cut back on costs. On this trip we were fortunate enough to have generous friends who own a vacation rental in the city share their residence with us! If you’re looking to book the best hotel in the city, scroll down to day 7, to learn more about the unbelievable El Convento. If you’re on the hunt for comfortable, affordable and clean accommodations, the city offers a huge array of hotels. A quick trip advisor search brings up tons of viable options. ( Travelers tip: hotel rates on the weekend in the city skyrocket, book the weekdays for a more reasonable budget friendly price.)

PLAY:  The longer flight times got us to San Juan around 3 in the afternoon, the airport is small and super easy to navigate. If you’re in the market for a rental car- which you really should be, Puerto Rico has very limited public transport, and a car is a necessary commodity if you want to see anything other than your hotel pool- look no further than Target Rental Cars. So what I’m saying is yes, Target rents cars, but no its not that Target. This locally owned, family run business will make you feel like family and with rental prices at almost half the costs of all the other international brands, they just can’t be beat. Bonus points, they’ll pick you up at the airport! It took us entitle less than 2 hours from the arriving at the airport, to picking up our bags, the rental car, and navigating our way to our rental flat in San Juan- which is pretty remarkable if you’ve ever attempted a similar feat in any other international destination.


The colorful streets of Old San Juan!

After settling in to your accommodations put on your walking flip flops and head out to explore the city under the stars. A relatively safe city, with lots and lots of nightlife, especially on the weekends. This vivacious city like most caribbean city centers is a mixing pot of old world architecture, new world vibes, and youthful spirit. Take a break at ANY of the many local bars and cool off with a frozen Pina Colada and chat up the locals. Our favorite spot to grab a drink was an open front bar over looking the harbor. The name? No name, just damn good drinks, and friendly folks.  With a city steeped in centuries of rich history and colorful buildings galore, a nightime stroll is the perfect way to work up an appetite- on that you’re going to need for whats next on the list!


Fresh Pina Coladas & Coco Frio ( fresh cold coconut) are too good to pass up!

EAT: Dinner at Prillo Pizza Rustica – Are you thinking, “Pizza, dumbasses, don’t you know you’re in Puerto Rico”. Yes, yes we do. And we think you should eat here to.

It’s been another long standing tradition of ours to try the pizza everywhere we travel- this internationally loved food can vary as much as the taste of Coke ( if you didn’t already know that, that’s a thing, it is). With a cozy old world atmosphere and portions big enough to share, you’ll be enchanted, and your stomach will thank you. Order the Argentinian Empandillas as an appetizer and then move on to the Chorizo Calzone, it’s amazing. Wash it all down with local Medalla beer and or a Quinepa (Spanish Lime) Margarita. I promise you will NOT be disappointed.                                                                                                                 Prilio Pizza 201 Fortaleza Street, Old San Juan                                                                              (787) 721-3322  * Call ahead for reservations, if you’re not in the mood to wait, they can get busy.

Day 2: Old San Juan 


El Morro

STAY:  Keep your accommodations from day 1. For as much as hotels, guest houses, and inns cost. Enjoy your location, embrace your accommodations as a part of your vacation, not just  a place to lay your head. Choose wisely, and you will be rewarded time and time again.

PLAY: See the city sights. Just like the rest of Puerto Rico its incredibly easy to underestimate Old San Juan. Walking this city will take you ALL day. Learn from my mistake and wear sunscreen, its easy to forget you’re only 18 degrees above the equator and with all the distracting sights, the sun will catch up to you. Start your day with an incredible breakfast at Caficultura, then head over to Castillo San Cristobal, the larger of two enormous fortified structures that guards the old city. The views are staggering, the architechure amazing, and the rewarding breeze from the top is well worth the visit. $5.00 gets you into both Castillo San Cristobal and its younger cousin Castillo El Morro. Walk the city wall between the two, once you arrive at El Morro take in the sights. The sprawling lawn in front of the fortification is a favorite location for kite enthusiasts, on any given day you can see hundreds of kites flying high above the fort. Cart vendors nearby sell kites on the cheap, if you’re dying to be a part of the action too!  After a full day of exploring this amazing city, you will be hot, you will be tired, and your feet will hurt. These are all good things, I promise. Use those aching dogs as an excuse to grab an early afternoon drink … mmmmm, Pina Coladas… and wander back to your hotel stretch out by the pool or the beach- if you go back home without a tan that just wouldn’t seem right 🙂

Explore the grand fortresses of Old San Juan- Castillo San Cristobol & El Morro

EAT: Breakfast at Caficultura. I could write an entire post just about this amazing Cafe. Its one of those places, that when you sit down and browse the menu you can’t fathom having to possibly choose just one thing- think, coconut-milk French toast with pineapple jam and coconut shavings, yeah, I know. We munched on an array of pastries and some of the BEST coffee I have ever had, all for less than $10. Eat outside and you get a gorgeous view of Castillo San Cristobal.



We love local! Caficultura is the best, and gives back to their community while serving up insane coffee and breakfast dishes! 

Grab a snack at any of the many street vendors that abound across the city. One thing is for certain Puerto Ricans love to eat. If you ever find yourself hungry while in Puerto Rico then you’re doing something wrong! If you hear a bell ringing across the way, don’t hesitate, just head straight for it. Heldado vendors ( gelato) can be found all over the city. $3.00 gets you a heaping serving of one of three flavors, Coco (coconut),  Pina (Pineapple), or my favorite Parcha ( Passion Fruit) or mix it up and try them all!

Dinner at Cafe Puerto Rico. The name seems cheesy and like a place to avoid, but the food is divine. With old world ambiance, beamed ceilings, and hearty local fare, you don’t want to skip this one. Eat outside for views of the Plaza Colon. If you’re ready to try Mofongo  (mashed fried plantains stuffed with awesomeness), this is the place to do it, choose from one of many filling options, the pork was amazing!                                                                                  Cafe Puerto Rico                                                                                                                                          208 Calle O’Donnell 

Day 3: El Yunque National Forest 

STAY: El Escondido Guest House, only 30 minutes outside of the city but miles and miles and miles away. I don’t even know where to begin, other than to say that if you don’t book a room here you’ll be sorry. Nestled on the edge of the rainforest, you fall asleep nightly to the sounds of singing Coqui frogs, and rain dripping through the forest canopy. You will feel like a Lost Boy in Neverland. For only $90 a night including breakfast this 5 room guest house is one of a kind. The downside is you are about 45 minutes from the beaches on the East side of the island, but if you are willing to drive a short distance this is your place. We loved it so much I was convinced that when it was time to leave we were going to be reenacting one of those silly commercials… DJ was going to have to pry me out of there against my will, for sure.                                                                                                    El Escondido                                                                                                                                          Hato Puerco, Canóvanas


Even our trusty Corolla “Nina” was sad to leave El Escondido!

PLAY: El Yunque National Forest is the ONLY tropical rainforest in the US Forest System, and well worth spending a day hiking through. Think waterfalls, tropical plants, and stunning mountain top vistas. El Yunque has it all. (Travelers Tip: get there early, parking is limited and it can get busy fast.) Keep an eye out for our upcoming post on what to do and  see in this special place!                                                                                                                                                     El Portal Visitor’s Center                                                                                                                           PR-191, Río Grande

Magic in El Yunque

EAT:  There are small kiosks located along the road into El Yunque where you can easily grab a quick snack or meal for a few dollars. BUT if you’re coming from El Escondido Guesthouse take the advice of its proprietors Nike and Scott, and go by the local grocery store Supermercado Unico for a sandwich to go. Here sandwiches are huge, and insanely delicious. While you’re there grab some local style snacks to munch on with it- eat like a local with favorites such as chicharonnes ( deep fried pork skins), or a bag of plantain chips.                                                                                                                                               Supermercado Unico                                                                                                                                  PR-957, Canóvanas 


Cuban sandwhich from Supermercado Unico + Quinepas ( spanish limes) + a rainforest = joy!

For dinner get local, the difference between in Canovanas versus a more popular resort area is that you have the chance to connect to the local culture, without the influence of the tourist industry, this equals authenticity. The boys at El Escondido can point you in the right direction, but there are an array of local choices including a Puerto Rican BBQ pit, that slow roasts its meat for 20+ hours, it will literally melt in your mouth.

Day 4: East Coast Beaches & The Best Mofongo Ever

STAY: Spend a second night at El Escondido, sleep with the windows wide open and listen to the song of the forest. Try a midnight swim in their 24 hour pool – look up and don’t miss that gorgeous sky full of stars!

PLAY:  Spend the day lounging on the beaches in Loquillo, there are a lot of options to chose from but personally, we found Balneario La Monserrate to be the best. Parking is $4.00 per day, but with maintained facilities and gelato vendors galore, its well worth it.

Beachside gelato, and happiness in Loquillo!

* What we missed: The ferry to Culbera. Ferry systems are unpredictable in Puerto Rico and locals get priority tickets, that means that attempting to get a ride across to the insanely popular island of Culebra home to Flamenco Beach ( 3rd most beautiful beach in the world) can be entirely impossible. If you can go, you should go. We didn’t want to waste a day getting up at 1 am to wait in line for tickets, so it didn’t work out for us. Flights are also available to the island, but make trying to visit for a day trip a bit tricker to plan. We may have missed it this time but Culbera is most certainly on the list for the future!

You’ll hear a lot about Bioluminescent Bay Tours in Puerto Rico. Tiny micro-organisms that make the water glow are cool, no arguing that. If you’re a bit of an environmental science nerd like I am or a fan of adventure travel, a bio bay tour may leave you a bit disappointed. Keep an eye out for a more detailed review coming soon. But if you’re looking to just have a fun time on the water after dark and learn a little something along the way, check out Pure Adventure Tours, for this unique experience. A copy owned and run by marine biologists who not only know what their talking about but actually care to try and protect it.

EAT:  One the coolest things about Loquillo is the Kioskos, also known as kiosks. This line of small scale restaurants is equivalent to the American version of a Food Truck Rodeo. Food is cheap and plentiful, and its here you’ll find the best Mofongo in all of Puerto Rico.  For dinner stop in and eat at Terruno, the food is amazing ( are you catching on to the Puerto Rican food theme here, seriously these people know how to cook). Try the coconut rice and fish they’re well known for or explore the culinary wonder that is mofongo further, and dive in- the chicken with garlic sauce will make you clean the plate  its so incredible!                                                                                                                                               Terruno, Kiosk #20                                                                                                                                    Loquillo


This looks amazing, doesn’t it? That’s because it was.

Day 5: The Long Drive West

STAY: The Blue Boy Inn Rincon is everything a guest house should be and more. If you want  resort style accommodations, but without having to actually stay at an over touristy resort than this is where you need to be. We loved it. Loved it. While not directly on the beach Blue Boy is literally steps to Las Tres Palmas Beach. Proprietors, Karen and Wes have thought of everything with snorkel gear, coolers, grills and more all available to their guests.                                                                                                                                                            The Blue Boy Inn                                                                                                                                     556 Black Eagle Street, Rincon

The amazing art at the Blue Boy in- capturing all the wonders of Rincon

PLAY: Road Trip Puerto Rico! You could easily drive from Canovanas to Rincon in less than 3 hours, but with all the things to see and do along the way, why would you want to? Heading out from El Escondido Guest House there are so many stops you can make, visit the pork highway in Guavate, The Puerto Rican dry forest in Guinacia for incredible ocean views ( we saw manatees while we were there), and don’t miss Cabo Rojo- visit the lighthouse, and the amazingly beautiful pink salt flats.  With stops this drive will take you most of the day, dropping you off in Rincon, just in time for one of the West Coast’s famous sunsets.

Gorgeous views of the Caribbean Sea roadside in the Dry Forest & The pink salt flats of Cabo Rojo

EAT: For Dinner visit the Beach Bar in Rincon. This little surf town has lots to offer, but one of the things its known best for is its beautiful caribbean sunsets. Perched a top a hill over looking the caribbean sea this little bar serves up traditional style bar food, tacos, burgers, beer, with a side of one of the best views in town. No address for this one! Take the drive to the Rincon lighthouse and you’ll find this awesome little place on the right.

Day 6: Under The Sea! Diving Desecho Island

STAY: Blue Boy Inn 

PLAY: Take a dive! If you’re a certified diver you’re in for a treat, and even if you’re not you’re going to love this! The boys at Tiano Divers (literally right next door to The Blue Boy Inn) will treat you right, with an incredible day of adventure exploring the waters of Derecho Island. The Island itself is a National Wildlife Refuge, federal law prevents you from actually stepping foot on to the island, but you won’t need to once, you’ve had the chance to explore the wonder of the underwater caves and gorgeous reefs surrounding the island.  Taino Divers offers 2 tank dives to certified divers, a discover dive program for those looking to learn but don’t yet have certifications and snorkeling if you want the same adventure but are looking for a more laid back experience.                                                    Taino Divers                                                                                                                                               564 Calle Black Eagle, Rincon


Taino Divers, Rincon.

EAT:  Breakfast is covered! Aside from having the most relaxing pool I have ever plunged into, and an insanely comfortable mattress your stay at Blue Boy Inn also offers incredible breakfasts. Think made to order omelettes, pancakes, and fresh fruits. Yum.

A long day on the water requires refueling and there is no better place for traditional Puerto Rican fare in Rincon than The Red Flamboyan Restaurant. Just like everywhere else on the island you the Flamboyan serves up heaping plates of Mofongo along with a variety of other amazingly delicious dishes.  Maybe this is just the way it is in Puerto Rico, but by the time we reached the Red Flamboyan we had eaten our way across the rest of the island and every place we ate, made it harder and harder to narrow down what to order off the menu- I almost never say this, but during our whole 7 days on the island we never had a bad meal.     The Red Flamboyan                                                                                                                                     Apartado 11, Rincon

Day 7: Road Trip Back To Old San Juan

STAY: Hotel El Convento Im not even sure how to begin, because it is hard without having shared this experience with you to truly convey in a few short sentences the awesomeness that is Hotel El Convento so I won’t try- keep an eye out for an upcoming post on where to stay in Puerto Rico- until then however know this: if you’re ok with a splurge and want a garuntee that you will get your money’s worth BOOK THIS HOTEL, seriously why are you still reading? Do it now! Housed in a restored 17th century convent, and directly across the street from Catedral De San Juan Bautista, you won’t find the same combination of history, stunning city views and or 5 star service anywhere else in the city like you will here. We were fortunate to receive and upgrade at check-in and spent a glorious night in the Pablo Casals Suite, were treated to a wine and cheese reception before dinner, and took in the sights and sounds of the city from the terrace top pool. Book your stay in Old San Juan here. NOW. You won’t be sorry.                                                                                                            Hotel El Convento                                                                                                                                  100 Cirstobol Street, Old San Juan


The view of the Cathedral from the Pablo Casals Suite’s balcony- Hotel El Convento

PLAY: The road from Rincon to Old San Juan is literally overflowing with options of things to do and see. In fact there are so many places to visit you’ll have to pick and choose, since you won’t have the time to do them all.  The list for our stops included, a late start out of Rincon ( mostly because we loved it and Blue Boy Inn so much we wanted to languish in the experience and Karen’s amazing Nutella pancakes a little longer), a few hours lounging  on Crash Boat Beach- while you’re there don’t miss out on fresh cold coconut, “Coco Frio”- and wrapping it all up with a spectacular views at  Las Cuevas De Indios. We could have easily spent a full day at each of those locations, and I am still lamenting the ones we missed- Arecibo Lighthouse and Historic Park, Camuy Caves, and Cueva Ventana, plus many, many more.


Cueva De Los Indios: If this isn’t enough to convince you to visit, I don’t know what is!

EAT: For breakfast, don’t miss out on one last chance at fresh Nutella Pancakes, seriously don’t.

For dinner you’ll be back in the city, and once again just like with the rest of Puerto Rico your options are endless. On this trip, we broke one of our own golden rules of travel ( and I’m not ashamed to admit it). We always say,  NEVER, EVER EAT AT THE SAME PLACE TWICE – we did it, sorry, not at all sorry. Ever since our first meal there, I had literally been dreaming about the food at Prilo Pizza.– crazy I know, but true. Round 2 at Prilo included lots of chorizo based appetizers, and another incredible pizza for dinner. It was amazing.  But if you’re looking to avoid the travesty of breaking such a steadfast rule try one of the two restaurants housed within Hotel El Convento- El Picoteo or Patio del Nispero. The smells alone will draw you in!                                                                                                                                    El Picoteo & Patio del Nispero                                                                                                              100 Cristobol Street, Old San Juan



After 7 days in this amazing land, we boarded our plane to head home. Like ending all journeys it was bittersweet. Sad to go, but excited for the future and all the new adventures on the horizon.  Puerto Rico was like no place I had ever experienced before, part caribbean island paradise, part old world European city, and maybe a teeny tiny part any typical American city. This is a special place.If you’re looking for something different, book your trip now!

Been to Puerto Rico? Got tips and tricks to add? Let us know, in the comments below!


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