A Long Weekend in Puerto Rico Itinerary

Are you dreaming of a little fun in the sun? Puerto Rico is the perfect destination for a long weekend of sunshine and exuberance. A warm and welcoming place, there is so much to explore and experience – too much for one weekend. But this Puerto Rico itinerary will help you make the very best of the time you do have, so you can experience the amazing place that is Puerto Rico.

Puerto Rico Itinerary – Day 1, Old San Juan

I suggest you stay in Old San Juan and use it as your base for your time in Puerto Rico. It is a fun and historic area, especially for first-time visitors. Old San Juan is beautiful, with buildings in various bright and colorful shades, and easily walkable. There are plenty of Airbnb choices, but I really loved our stay at “the Blue Room”. This Airbnb is located right next door to La Fortaleza, the Governor’s residence. From here, or another Airbnb nearby you can walk to all destinations around Old San Juan.

Start your day with a delicious breakfast – I suggest Spiga, a recommendation from our Airbnb hosts that I loved – before you head out to explore. Once you’ve filled up – head to Castillo San Felipe del Morro. This is a historic citadel that was created to defend the island. Spend a few hours walking through and around it, enjoying the beautiful views and learning something about its history. Also, take time to enjoy the expansive field in front of it on which you will certainly find families having picnics and flying kites.

After touring Castillo San Felipe del Morro, head back into San Juan to spend the afternoon shopping and cooling off! Walk through the streets and visit the local stores where you can find all sorts of interesting souvenirs and works from local artists. Make sure to pick up some truffles at Chocobar Cortés and perhaps a vejigante mask? For dinner, grab something delicious from Princesa – Cocina Cultura then stroll along the Paseo de la Princesa. This is a beautiful area of the city that really comes alive at night! Enjoy the lively sounds of the city, the outdoor shopping stalls, and perhaps a delicious cocktail.

Day 2, El Yunque National Forest

Day 2 is a day for adventure! Leave old San Juan bright and early to head over to El Yunque National Forest. I highly suggest you book the wilderness adventure tour with Montana Explora. The crew from Montana Explora are highly skilled and educated about the National Forest and will take you on a thrilling trip into it, including repelling down rock faces, ziplining, and swimming over, through, and around waterfalls.

The Montana Explora guides are absolutely fabulous and will tailor the trip to your group’s needs. Every “adventure” activity is optional or tailored to your physical abilities. All you need is to show up with an adventurous spirit, water, and snacks! All that excitement is sure to work up an appetite. El Yunque is such a beautiful and wild place – it is a must-do for any Puerto Rico itinerary.

After an exciting day in El Yunque, return to Old San Juan for dinner and some nightlife. Check out La Factoría, where the music video for the hit song “Despacito” was filmed. Enjoy their delicious drinks and have some fun dancing!

Puerto Rico Itinerary – Day 3, Bacardi Bioluminescence

For your last day, enjoy the morning around Old San Juan. I suggest checking out the wonderful walkway path, Paseo del Morro. This is a beautiful sea level path, where you might spot some of the many cats that roam Old San Juan. If you have the time after, perhaps visit a few other historic spots on San Juan or visit the beach for an early splash.

For the afternoon, schedule a trip to Casa Bacardi! This is the home of the famous Bacardi rum. They offer tours, mixology classes and more! It is a great way to spend an afternoon – learning about the history of the Bacardi family and perhaps enjoying a drink in their outdoor pavilion.

For your last night treat yourself to something really special. Puerto Rico is home to 3 of 5 places bioluminescent bays in the world! The best way to experience these magical waters is via kayak. Book a night tour with a group like Caribbean Breeze Adventures who provide all the needed equipment and will offer interesting information on the tour. It is extremely hard to capture the fantastical glittery water on camera so enjoy this as an unplugged adventure and be in the moment! I can promise it will be like nothing you’ve seen before!

After your night kayaking, head back to your lodging and enjoy one last relaxing night in Puerto Rico. I hope you love it as much as I did! For more fun itineraries check out my Vancouver long weekend itinerary or my two-week Iceland itinerary.

— Lauren