Puerto Rico Flag Street

Puerto Rico Itinerary: The Ultimate Vacation Guide

Share This

Looking for a vacation destination with beautiful beaches, friendly locals, flavorful cuisine and a solid dose of culture and history? Well, look no further than the island of Puerto Rico! Our seven day Puerto Rico itinerary will give you relaxing days, cocktail-filled nightlife and old-city exploration. Feeling excited? You should be.

Really and truly, when planning a trip to Puerto Rico, understand this place has a little something for everyone. Fun for families, romantic for couples and adventures perfect to share with friends!

Easily accessible from the United States, a short flight to Puerto Rico will have you saying, “Why didn’t I visit Puerto Rico sooner?!” At least that’s what we said 🙂

Puerto Rico Itinerary

Day 1 – Arrive into Puerto Rico

Wherever you’re located in this big beautiful world, plan to fly into Puerto Rico’s main international airport, Luis Munoz Marin. This airport is closest airport to Old San Juan, making it a popular jumping off point for tourists.

Once at Luis Munoz Marin, you can catch a 15-20 minute Uber or Taxi ride to Old San Juan. Don’t worry about renting a car, for this Puerto Rico itinerary. Uber and your two feet will be all that you need to get you around.

Once in town, get settled into your accommodation and rest up, you have a busy day tomorrow! Plan to grab a bite to eat at Birra & Empanadas and catch the sunset at Castillo San Felipe del Morro.

A few Old San Juan accommodations that are nice to call home for the next few days are…

Puerto Rico Sunset

Check Out: Puerto Rico Vacation Planning and Travel Guide to get great travel tips to plan your ultimate Puerto Rico vacation.

Day 2 – Explore Old San Juan

No trip to Puerto Rico is complete without wandering the blue-bricked streets of Old San Juan. The stacked colorful houses, the Spanish music playing in the air and the sound of the Pina Colada’s being made in the distance all make up the quintessential vibe that is Old San Juan.

Start your day with a Puerto Rican coffee and a mallorca at La Bombonera. Once you’ve devoured your breakfast, tie those shoes. You have some walking to do!

A popular Old San Juan activity is the Old San Juan Walking Tour. A great option for folks wanting to see popular Old San Juan attractions and learn more about the rich history and culture of Puerto Rico with a local tour guide.

If an Old San Juan tour is not your thing, no worries! Walking Old San Juan is completely doable yourself.

Our suggestion? Hit a few (or all) of the below Old San Juan must see attractions.

From forts, to small houses, to some of Puerto Rico’s most instagrammable locations, click on and follow the purple dots on the map above. The purple dots will lead you to some of the best things to do in Old San Juan 🙂

Old San Juan Flag Door

Where To Eat in Old San Juan

As you walk around Old San Juan, you’re inevitably going to get thirsty and hungry. Head over to La Barrachina, the place that invented the Pina Colada, for an authentic rum soaked Pina Colada. Still thirsty? Mosey your way over to El Batey for the coldest Medalla you’ll have in a Puerto Rico dive bar.

For food, El Jibarito is a perfect pitstop for lunch. It’s authentic Puerto Rican food and it’s oooh sooo good! Order the empanadas and mofongo.

If you’re looking for an Old San Juan restaurant for dinner, Verde Mesa or La Taberna Lupulo is it! Verde Mesa is a farm to table restaurant that sources local, fresh ingredients where La Taberna Lupulo offers tasty bar food and has the biggest craft beer selection in the Caribbean.

Check out our San Juan nightlife guide as well as the best places to eat in San Juan.

Day 3 to 4 – Beach It Up On Culebra

There are a handful of beautiful beaches that lay waiting for you around Puerto Rico. A short ride from Old San Juan, you’ll find Playa El Escambrón. Great for snorkeling, catching a tan and a rum drink, Escambrón is one of the closest beaches to Old San Juan.

Hoooweevverrrr, while you could go to Escambrón and have a great time, one of the best beaches in the world is nearby! Interest peaked? We thought so.

Located on the island of Culebra, Flamenco Beach is known for its shallow turquoise waters, white sand and palm tree forest line. It’s no wonder why this place is considered a Caribbean gem and one of the worlds best.

Check Out: The best things to do on Culebra, Puerto Rico

Flamenco Beach, Culebra

To get to Flamenco Beach, you’ll beed to catch a 28 minute prop-plane flight from Luis Munoz Marin or a 45 minute ferry ride from Ceiba. Or, you can take a snorkeling tour from Old San Juan to Culebra.

Don’t think beachin’ is the only thing you can do on Culebra. Culebra is home to some of the best snorkeling and scuba diving in Puerto Rico.

If you’re a certified diver, or want to be, check out Aquatic Adventures or Sea Ventures Pro Dive Center to book your scuba dive or snorkeling trip.

Puerto Rico Scuba Diving

Planning to stay the night on Culebra Island? A few places to check out are Mamacitas Guest House and Hillbay View Villas.

Day 5 – Fall in Love With Santurce

Located 10 minutes from Old San Juan, Santurce is a must visit for a true taste of Puerto Rican art & culture.  

Spend your day wandering the mural lined street of Calle Cerra or visiting the art museums of Museo de Arte de Puerto Rico and Museo de Arte Contemporáneo (aka the MAC).

Check out: Santurce Street Art – A Guide to San Juan Graffiti Neighborhood

Outside of Santurce’s amazing art scene, there are a plethora of amazing restaurants and bars to try.

La Placita is a marketplace by day but come night, it turns into the most epic street party. Lined with cafe’s and bars, a visit to La Placita is a must if you want to be one with the locals.

If cocktails are your thing, don’t you dare miss Jungle Bird. Great vibe and killer tiki cocktails. What more can you want?

If you’re looking for a bite to eat, don’t miss Lote 23. With it’s food truck-like experience, choose from a handful of different cuisines. Food kiosks offering anything from traditional Puerto Rican food to pizza and sushi bowls.

San Juan Street Art
Santurce Murals

Day 6 – Back To Old San Juan

Back in the beautiful city of Old San Juan. Now, there are a few ways to end your last day in Puerto Rico. You can enjoy the Flavors of Old San Juan food tour and the Puerto Rico Craft Cocktail Walk. Or, if you’re looking for a more “hands on” experience, a Puerto Rico cooking class is a great way to learn about the food and culture.

Regardless, if want to satisfy your tastebuds, those experiences above are it.

Looking to get outside of Old San Juan? Puerto Rico has some wonderful outdoor adventures waiting for you! If you’re an adventure enthusiast, consider hiking to a hidden waterfall or swimming in a bioluminescent bay. We will go out on a limb and say that no trip is complete without seeing an unforgettable sunset. Set sail on a sunset catamaran cruise around Old San Juan to see the city from a different perspective, by sea.

For a full list of other fun day trips, check out our “9 Can’t Miss Day Trips from San Juan“.

Last but certainly not least, get a night cap at La Factoria. Made of a maze of speak-easy style bars, La Factoria consists of 6 different bars all offerings different vibes and drinks. Once there, you’ll see why La Factoria was voted as one of the best bars in the world.

Grab a drink, “salud” to an amazing trip as you sip rum while listening to Spanish music play in the background.

Old San Juan Puerto Rico Street

Day 7 – Depart

As with any trip, the day always comes when it’s time to leave. We hope you enjoy your trip and this Puerto Rico itinerary as much as we did! Puerto Rico’s truly an amazing island that has it all – rainforests, beaches, culture and history. Sheesh, Puerto Rico is awesome. When are we going back?!

Old San Juan Fort

Where to Stay in San Juan

San Juan is made up of many neighborhoods/districts. Depending on the type of traveler your are, you may want to stay outside of Old San Juan.

Below is an overview of the different districts that make up this incredible place.

  • Santurce: Authenticity, art and a hipster, local vibe
  • Isle Verde: Luxury resorts, home to three of San Juans beaches
  • Miramar: Close to the beach, mostly residential
  • Condado: High-end hotels, located between Old San Juan & Isla Verde
  • Ocean Park: Mostly residential, great beaches, not close to attractions
  • Old San Juan: Great location, higher prices, beautiful & charming

Regardless of where you stay, getting too and from each neighborhood is walkable, in some instances. When it’s not walkable, that neighborhood lies a short Uber ride away.

Is Puerto Rico Safe?

Just like anywhere else in the world, you can expect to find petty theft, like pickpocketing and carjackings, in Puerto Rico. With such a high influx of tourists, pickpocketing is common in touristy areas, beaches and on public transportation.

Our biggest tip is to be aware of your surroundings, avoid sketchy streets or alleyways and always keep your belongs zipped up and out of sight.

Just like other destinations, we highly recommend getting travel insurance before visiting Puerto Rico. We use World Nomads and it’s definitely come in handy a time or two for us


9 Can’t Miss Day Trips from San Juan

Things To Do On Culebra, Puerto Rico – Your Complete Travel Guide

The Best Place to Eat in San Juan: A Foodie’s Guide

San Juan Nightlife: The Best 7 Bars in San


Puerto Rico Itinerary Pin

For more travel tips, guides and awesome travel shots, be sure to poke around our site, follow us on Instagram @wanderingstusPinterest and on Facebook. Oh and if you have any questions, let us know in the comment section. We’re happy to answer. Or, just leave us a positive note!

Happy Travels,

– Lauren & Jesse Stuart (The Stüs)

Share This

Similar Posts


Questions?! Let us know. Leave us a comment!

This site uses Akismet to reduce spam. Learn how your comment data is processed.