First-Timer’s Traveling San Juan, Puerto Rico In 5 Days

Last Updated on January 11, 2025 by Erin Donahue

If you’re planning a trip to Puerto Rico and only have five days to explore, you’re in for a treat! The Island of Enchantment is only about the size of Delaware and Rhode Island combined, offering a perfect blend of history, culture, and natural beauty.

This was my first time visiting, and while the stay was nice, the flights to and from on JetBlue were an absolute nightmare! Both inbound and outbound flights had six-hour delays, so my travel tip moving forward is always to book the earliest flight of the day. While it’s a miserable existence to wake up at 4 a.m. to get to the airport, those flights indeed tend to have the fewest delays and issues.

 

U.S. Colonies Still Exist

Before fully jumping in, as a professional traveler, I think it’s important to point out Puerto Rico’s unique position geopolitical position. Not that this is my area of expertise, but it is the elephant in the room. The island is a U.S. territory that uses the dollar and doesn’t require a passport for U.S. citizens, yet it maintains a rich, distinct culture that sets it apart. However, this relationship is complicated. Despite being U.S. citizens, Puerto Ricans on the island can’t vote for president and lack representation in Congress. Correct me if I’m wrong, but most Puerto Ricans want sovereignty. It’s a situation reminiscent of other places like Hawaii.

Similar to many beautiful tourist destinations, Puerto Rico grapples with the double-edged sword of tourism. The economy has become dependent on the industry and that presents many challenges. During my visit to Old San Juan, I witnessed massive cruise ships docking, flooding the streets with tourists who seemed unfamiliar with travel etiquette.

Another contentious issue is the influx of mainlanders taking advantage of tax incentives like Act 60 – benefits unavailable to local residents. This is just one example of the ongoing economic and political challenges facing the island. These issues are complex and deeply rooted in history. As visitors, it’s crucial to be aware of this context. However, Puerto Rico also offers incredible experiences that shouldn’t be overshadowed. With this understanding, let’s explore the beauty and culture this enchanting island has to offer.

 

The Capital City of Puerto Rico

For my initial Puerto Rico 5 day itinerary, I only stayed in San Juan. It’s the capital and largest city and is also one of the oldest European-established cities in the Americas. However, Puerto Rico was originally inhabited by the Taino people, and they called the island Boriken which translates to “The land of the brave lord.”

The historic district, Old San Juan, is a UNESCO World Heritage site, and a port city. San Juan itself is a vibrant mix of old and new. Spanish might be the primary language, but English is widely spoken, especially in touristy areas. The local culture is a fascinating fusion of Spanish, African, and indigenous Taíno influences, reflected in the food, music, and festivals.

Inventors of the Pina Colada

Speaking of food, did you know that the piña colada was invented in Puerto Rico? For a taste of history and flavor, many visitors head to Barrachina, where the drink was supposedly created in the 1950s. It’s a must-visit spot for first-timers, but I found an even better piña colada at Raices. Their version is thicker, which I prefer, and is reminiscent of the best one I’ve ever had in Curacao. I suspect their secret is a generous dose of coconut cream. Plus, it’s only $6 for a virgin piña colada and $8 with alcohol. What a steal! While Raices is known for its drinks and has even hosted Anthony Bourdain, Make sure to only eat the traditional Puerto Rican dishes here rather than their attempts at other cuisines.

Where to stay in San Jan, Puerto Rico 5 day itinerary

Don Rafa Boutique Hotel

During my five-day itinerary in San Juan, I stayed at two distinctly different hotels. First up is the Don Rafa Boutique Hotel & Residences. Situated in the historic district of Miramar, this is where urban living comes to life. Inspired by the 1950s ambiance, this hotel is where essence and nostalgia meet to elevate your experience through carefully curated details and personal attention.

While its aesthetic is stunning, it’s more about style than function. The rooms are cozy, and ideal for solo travelers or couples, but storage space is limited and bathrooms are compact. I only stayed for one night and since my travel companion was British, her accent was able to sweet talk the front desk to upgrade us to a bigger room without charge. I have the worst luck so on my own that would never happen! It’s also worth noting they have a photography policy so I didn’t get much content.

 

Fairmont El San Juan

Next up is the hotel I spent most of my time during my Puerto Rico 5 day itinerary because I ended up doing a partnership with them to create content. Positioned on Isla Verde Beach, the Fairmont El San Juan Hotel has been a mainstay feature of the island since 1958. Originally opened as the San Juan Intercontinental Hotel, it’s now a Historic Hotels of America member. The hotel’s rich history is evident in its Mid-Century Modern architecture, including a stunning hand-blown chandelier from Czechoslovakia that still graces the lobby today, and is impossible to miss. It’s literally the first thing you see walking into the lobby!

The hotel is a convenient 15-minute ride to and from Old San Juan, but the property campus is also a great place for an all-day retreat, with four pools, numerous restaurants, like Caña and The Lobby, beach access, and a beach club. You can eat either a breakfast buffet or a la carte at Caña in the mornings, and for dinner, there’s a new menu created by Chef Jose Enrique. I woke up at sunrise every morning to enjoy a walk along the beautiful beach before the sun got too high.

 

Poolside Villa Balcony Room

Each guest room and suite on the property pays homage to San Juan’s heritage, and I stayed in a Poolside Villa Room where you can lounge on the private balcony for an elevated island retreat. There are Le Labo Rose 31 fine fragrance-scented soaps provided to wash with which I thought was a nice branded touch.

True 5-Star Luxury?

If you’ve read this far, I’m going to give some honest thoughts…Since the Fairmont brand is a high-end luxury brand, I was expecting more from this hotel. To be frank, the clientele at this particular hotel are people you would typically see at all-inclusive or cruises, basically, people who don’t travel much. That is pretty evident in the breakfast offering that’s more continental, and less mofongo. I overheard people say this was the “best hotel they ever stayed at” so there’s a clear difference in standards. It’s not just that. The hallways need updating, and in my room, it was clear some parts haven’t been cleaned in a very long time.

Now, it’s worth noting that while Fairmont Hotels & Resorts manages the property, it’s still owned by ESJ Resort LLC. The hotel joined the Fairmont portfolio in January 2020, after Hilton ended its franchise agreement. Despite its historical significance and 5-star luxury designation, the current state of the hotel doesn’t quite live up to those expectations. It seems the transition to the Fairmont brand is still a work in progress. I’m glad I traded my services to be able to stay here because if I was a paying customer, I wouldn’t have been happy with the standard given that the room I stayed in was pricey. Besides that though, the staff I interacted with there were awesome!

Party Hotel Vibes

During my stay, the hotel hosted some high-profile events, including Miss Universe Puerto Rico and a launch party for reggaeton queen Ivy Queen. What are the chances one of Puerto Rico’s biggest stars was right in front of me as I ate my guac and chips? While these events are cool, they’re not typically what you’d expect at a 5-star luxury hotel, at least not so visibly. There’s also a 15,000-square-foot casino, but that’s part of the hotel’s legacy. Despite my reservations, the hotel’s rich history and beautiful location can’t be denied. It’s a property with great potential, and I hope to see it fully live up to its luxury designation.

 

Unique Activity – Learn to Sail

Outside of the hotels, for a unique and must-do experience during a Puerto Rico 5-day Itinerary, consider taking a sailing trip around the island. It’s a fantastic way to appreciate the island’s coastline and crystal-clear waters. This wasn’t something I was originally planning on doing but said travel companion told me she always has to get on a boat when she travels, and I’m not one to turn down an adventure so that’s what we did.

We booked a private boat, and it was fun because my friend knew how to sail so the captain deemed it ok that we sail out into the Atlantic Ocean. So my first time ever sailing was out with some big swells! I ended up needing to steer longer than I anticipated because I started getting seasick, which had never happened to me before when I was out on the boat. The best way to combat that is to steer because it gives you something else to focus on since seasickness is mostly mental.

 

A Place of Contrasts

Puerto Rico is a place of contrasts – a blend of familiar and foreign, of rich history and modern challenges. It’s a destination that invites you to look beyond the surface, to appreciate its beauty while also acknowledging its complexities. Puerto Rico is navigating a path between preserving its cultural heritage and adapting to tourism industry pressures. I hope this glimpse into my Puerto Rican adventure has inspired you to explore this unique corner of the Caribbean!

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