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An Epic Long Weekend in Puerto Rico

There is so much that is misunderstood about these islands. 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, this is still 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 here 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
Old Town

These islands are 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 his second trip while re-discovering the “New World” in 1493. History is around every corner in this beautiful capital city.

Old three-mast sailing ship in the old San Juan harbor

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 the islands 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 Town, 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.

Christmas display in a park during the holidays in Puerto Rico

Day 2 – Scuba Diving at Fajardo

We’re big divers, and the scuba diving here is among the best in the world. Head an hour to the east of the capital 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 is also possible. Or you could simply lounge at one of the Puerto Rican beaches and let the sand in between your toes. We recommend bringing your own equipment for snorkeling or diving with you. Check out our guide to snorkel equipment.

Laura scuba diving in the clear water of the Caribbean

Day 3 – Natural Activities in El Yunque National Forest

Not far from the capital 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), this 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 day trips from San Juan.

If you’re visiting Puerto Rico with kids, this makes a great destination. Start by hiking the Caimitillo Trail. And then end your visit by splashing in one of the waterfalls.

Day 4 – Casa Bacardi Distillery Tour

These islands are synonymous with rum. And there’s good reason for it. The Bacardi Rum operation occupies a massive section of shoreline on the western side of the 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 our gain.

Today, the Casa Bacardi Tour is one of the best things to do on the island – 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 weekend trip to Puerto Rico!

Small trail in front of the Bacardi factory building, a key highlight on your weekend in Puerto Rico itinerary
Small train that carries the rum

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 weekend trip to Puerto Rico packs a punch!

Holiday lights on the Governor's Mansion in San Juan
Governor’s Mansion during the holidays

Tips for Puerto Rico Vacations

Best Time to Visit

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 here 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

When it comes to visiting the island, a lot of people choose from one of the many 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 and staying at one of the Old San Juan hotels instead. Check current prices on hotels here.

Best Restaurants

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

What’s your favorite Puerto Rico itinerary? Why do you want to visit again? 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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Sunday 5th of November 2023

Can I still Scuba Dive even though I'm not certified?

Lance Longwell

Sunday 12th of November 2023

Short answer is yes. Longer answer is that many resorts and scuba dive shops offer an expedited "resort course" that will allow you to dive, however, if you ever want to dive again, you'll need to re-do the course again. A resort course will give you the fundamentals and you'll usually need to do some kind of pool or shallow ocean "check out" go make sure you are comfortable and won't panic.


Wednesday 19th of October 2022

I'm a food, so every local eatery, in the area. The flamingo dancers, the local Local Bamba, night life. Also the Ricon beach eatery and Ponce day life around the square weekends are a must.

Tonia Ross

Saturday 29th of October 2022

@Julieann, February 2023

Tonia Ross

Saturday 29th of October 2022

@Julieann, please tell me about a nice place to stay in Puerto Rico. I want to surprise my girlfriend with a 3 or 4 day bday vacation there. I just want a nice place to stay with 19 or more lady add to that surprise.


Thursday 14th of January 2016

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

Thursday 14th of January 2016

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

elaine schoch

Wednesday 6th of January 2016

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.


Monday 4th of January 2016

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

Monday 4th of January 2016

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.

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