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An Epic Long Weekend in Puerto Rico


Puerto Rico. There is so much that is misunderstood about this island. Yes, it’s a territory of the United States. But to think of it as merely the “American Caribbean” is to miss the whole point of this all-star island and its charming capital city, Old San Juan. Here is our must do Puerto Rico itinerary for a long weekend.

First off, Puerto Rico is technically the United States. You don’t need a passport to visit. You don’t need foreign currency. And just about everyone speaks English. So, traveling to Puerto Rico is easy, even for a long weekend. But that doesn’t mean it isn’t rewarding too.

The rampart walls of Old San Juan, Puerto Rico. The fortifications are one of the top things to do in Old San Juan Puerto Rico.

San Juan

Puerto Rico is historic. The capital, San Juan, is a UNESCO World Heritage Site. The three fortifications (San Felipe del Morro, San Cristóbal and San Juan de la Cruz) guarding the harbor are pristine examples of early Caribbean architecture. Christopher Columbus arrived in San Juan, on the second of his trips to Puerto Rico while re-discovering the “New World” in 1493. History is around every corner in Puerto Rico.

Old San Juan harbor in Puerto Rico.

Our Ideal Puerto Rico Itinerary

Day 1 – Explore the Historic City of San Juan

Old Town San Juan is one of the most beautiful cities in the Caribbean. It’s also one of the oldest cities in the Americas. By day, Old San Juan is filled with charm as visitors wander the cobble-stoned streets peeking into a few stores and doing a little shopping. Understanding the history of San Juan begins on the broad esplanade in front of the San Felipe del Morro, with its stunning views of the ocean and San Juan harbor.

As the sun sets on Old San Juan, we were able to take in the festive holiday lights around Plaza de Colon and sample some of the local gastronomy. In the summers, the party is just getting started as patrons fill the bars and restaurants before carrying the festivities through the streets.

Puerto Rico is a great destination around the holidays.

Day 2 – Scuba Diving at Fajardo

We’re big divers, and scuba diving in Puerto Rico is among the best in the world. Head an hour to the east of San Juan to the town of Fajardo. This oceanfront community is the launching pad for a lot of dive trips. The closest and most common trips are to the La Cordillera Reef, where divers can explore the reefs, submerged caverns and walls. The massive coral formations have abundant marine life and there’s also the chance to see manatees in the wild. The area around Fajardo is known for its extremely clear water and extreme visibility.

If you’re not a certified scuba diver, snorkeling in Puerto Rico is also possible. Or you could simply lounge at one of the Puerto Rican beaches and let the sand in between your toes.

Laura scuba diving in the clear water of the Caribbean.

Day 3 – Natural Activities in El Yunque National Forest

Not far from San Juan on the slopes of the Sierra de Luquillo Mountains, the El Yungue National Forest is the only tropical rainforest under U.S. National Forest Service control. This is a chance to go hike, take in waterfalls and the flora and fauna of the rainforest.

For those into birding (we’re not birders), Puerto Rico is the only place in the world to see the elfin woods warbler. We’ll stick to the waterfalls, like the La Mina Falls. El Yunque Forest is one of the top Puerto Rico day trips from San Juan.

Day 4 – Casa Bacardi Distillery Tour

Puerto Rico and rum are synonymous. And there’s good reason for it. The Bacardi Rum operation occupies a massive section of shoreline on the western side of San Juan harbor. Originally started in Cuba by Spanish immigrants, the Bacardi family moved the recipe and production out of Cuba just before the communist revolution nationalized all assets in the country. Cuba’s loss was Puerto Rico’s gain.

Today, the Casa Bacardi Tour is one of the best things to do in Puerto Rico – and makes a great stop before heading to the airport and flights home.

On the Bacardi factory tour, you board a little open-air bus that drives you about 100 yards, let’s you off to explore a four room museum (which begins with a 7 minute video). Unfortunately, you can’t see any of the rum production (due to food production and hygiene), but the Case Bacardi creates a magnificent experience center. They also have one of the most extensive gift shops we’ve ever seen and make perfect souvenirs to take home from your trip to Puerto Rico!

A highlight of any Puerto Rico itinerary is a visit to the Casa Bacardi Rum distillery. If you're wondering what to do in San Juan Puerto Rico, most people will consider on the Bacardi Tours Puerto Rico. This is also one of the top San Juan excursions for cruise ship visitors, so it can be quite busy in the middle of the day when cruises are in port.

There are so many things to do on this all-star Caribbean island; it’s tough to narrow down everything to a single weekend. However, our must-do Puerto Rico itinerary packs a punch!

Don’t forget, you can live your own 5-star vacation in Puerto Rico.

San Juan, Puerto Rico during the holidays.

San Juan during the holidays

Tips for Puerto Rico Vacations

Best time to visit Puerto Rico

Given its location, the island can be impacted by storms during the autumn hurricane season in the Caribbean (such as Hurricane Maria in 2017, which devastated the island). For us, the best time to travel to Puerto Rico is near the end of hurricane season, but before Spring Break (so, from mid-December through the end of February). The weather is warm without being too hot.

Best places to stay in Puerto Rico

When it comes to visiting the island, a lot of people choose from one of the many Puerto Rico all inclusive resorts (such as these). While these resorts can be extremely popular because they simplify your trip, we recommend skipping the all inclusive resorts in Puerto Rico and staying at one of the Old San Juan hotels instead. Check current prices on San Juan hotels here.

Best restaurants in Puerto Rico

Food is Puerto Rico is far more than just mofongo and you have to try out all the dishes (check it out at the local restaurants).

Why do you want to go to Puerto Rico? What’s your favorite Puerto Rico itinerary? Post a comment below and tell us!

From scuba diving to visiting a rain forest to learning about history, there are so many things to do in Puerto Rico. Check out this great visiting Puerto Rico itinerary for an epic weekend.

This brought to you by visit Puerto Rico Tourism and is based on our experiences on the island.


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What do you think about An Epic Long Weekend in Puerto Rico?

  1. Danielle December 27, 2015 at 3:51 pm #

    I would love to go to Puerto Rico and spend time on the beaches and time hiking in the national forests.
    The rich history of the territory would be fascinating to explore, as well.

    • Lance Longwell December 27, 2015 at 4:19 pm #

      Thanks Danielle. We loved the history! Hope you get the chance to visit.

  2. mark December 29, 2015 at 4:59 pm #

    looks like a great place to spend a few days

  3. Warren December 30, 2015 at 12:18 pm #

    My wife and I visited Puerto Rico several times back in the 1990s, but haven’t returned since 2000. The Old Town was beautiful and I’d love to see it again. I always thought that statehood seemed to be just a matter of time, and frankly I’m surprised that Puerto Rico isn’t already our 51st state.

    • Lance Longwell December 30, 2015 at 2:46 pm #

      We agree that the Old Town San Juan is charming!

  4. Amanda December 31, 2015 at 2:41 pm #

    I loved exploring Old San Juan. It would be great to return to check out Puerto Rico’s scuba diving! Hadn’t heard of La Cordillera Reef, but it looks beautiful.

  5. Lesley January 2, 2016 at 1:13 pm #

    I loved the view from San Felipe del Morro and walking around the shops in Old San Juan. Unfortunately, I didn’t scuba dive there. I guess it’s another reason to go back.

  6. arvin January 2, 2016 at 2:20 pm #

    Puerto Rico is on my bucket list, and a 4 day get away is perfect, Bacardi Distillery Tour would be on top my things to see, thanks for the guide to Puerto Rico

  7. melody pittman January 3, 2016 at 4:43 pm #

    I’ve been to Puerto Rico a few times and how on Earth after all my visits could I have missed the amazing Bacardi factory tour?? It must have escaped me. Thanks for the reminding me for my next trip. I also enjoyed the Old Town and did a most fun tapas & mojitos walking tour. So much history in PR. Looks like you know a lot about it!

  8. Mags January 3, 2016 at 9:18 pm #

    I’ve only spent a day in San Juan during a cruise. I would love to go back and spend some real time getting to know Puerto Rico. I loved what little time I had there.

  9. Greig January 4, 2016 at 10:32 am #

    The scuba experience around Fajardo sounds really nice. Happy to hear that despite the uptick in tourism here the water clarity seems to have remained!

    On another note, you mention the local gastronomy throughout Old San Juan. What are some of the main food staples in the area that are worth trying?

    • Lance Longwell January 4, 2016 at 11:02 am #

      Well, the Pina Colada was born in San Juan, so that’s a “must drink.” For our tastes, we also recommend trying the local Cuchifritos – fried pork bits – which is native to the Capital region.

  10. elaine schoch January 6, 2016 at 2:56 pm #

    I love Puerto Rico! It’s one of my favorite winter time spots to visit. 😉 Old Town is always a lot of fun to explore and the beaches, well I can spend most of the days there.

  11. Kelly January 14, 2016 at 8:43 pm #

    We took a small charter plane to Culebra. I would highly recommend doing this! It’s so much faster than the ferry, and the views are breath taking. The beach is the one of the most beautiful beaches in the world! Next time hope to get to Vieges for a bio bay tour.

    • Lance Longwell January 14, 2016 at 9:37 pm #

      I really want to get to Vieques! Perhaps that will be on our next trip.

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