See U in San Juan

Puerto Rico was not on my radar. I never had an interest, but I am learning after 2020, never say never. So this year, I started or better, attempted several times to visit San Juan, and each time sometime came up, I had to cancel. But you know what they say — the third time is/was always the charm. I finally made it, and it was definitely worth the wait.

Planning a trip to Puerto Rico

Why Puerto Rico? And I tend to answer a question with a question – Why not Puerto Rico? It is a U.S. territory, which means no passport, exchanging money, or updating your phone plan with an international feel. How can you go wrong with that? Also, with planning, you can find phenomenal airfare and hotel deals.

Before I get into all the details about my trip, I must mention that ugly 5-letter word — COVID. Since we are in a “COVID traveling season”, preparation and planning are the key to a successful trip. Regardless of your vaccination status, Puerto Rico requires all travelers to fill out a Travel Declaration Form on the Puerto Rico Health Department’s online portal, which produces a QR code to proceed. Since I am vaccinated, I only had to upload my card. If you are not vaccinated, make sure to research their policies. Before exiting the airport, passengers must present ID to ensure alignment with the Travel Declaration Form.

Where to stay in Old San Juan

Before we get into the itinerary, let’s talk about where to stay in San Juan. There are several touristy areas, and the most popular are Old San Juan, Miramar, Condado, and Isla Verde. I opted for Old San Juan because it is the “heart of the action”. However, if you want the beach/resort, Condado is your area. As for Old San Juan, the area is extremely walkable with lots of restaurants, bars, and nightlife. The best part is the history and architecture.

As for the accommodations, you can’t go wrong, especially if your preferences are boutique hotels and Airbnbs. I am more of a chain hotel traveler, and my choice was the Sheraton Old San Juan. The hotel has the charm of an old city and a view of the Port.

Things to do Old San Juan

In the age of social media, you can see what people are doing when they visit San Juan. I wanted to do something a little different, and this itinerary covers 3 nights and 2.5 days of activities. In other words, by the time the day was over, I was in bed by 7 pm. So if you like me, this blog will be right up your alley.

Day 1: Personal Photographer with Historical Tour

Since my flight arrived around 2 pm in San Juan, I started looking for an activity that started around 4 pm. Initially, I booked the Old San Juan Historical Tour, but they canceled it. That did not stop my plans. I went on Airbnb and found a personal photographer with a historical tour. I bet you didn’t know that Airbnb had that feature. The excursions are led by locals, and you can find some unique activities. The tour was informative, and I had my camera. No sharing and no asking strangers to take your pictures. I so loved it and will likely incorporate it into my travels.

Day 2: Hidden Waterfall Hike Adventure

Shhh… don’t tell my friends, but I am starting to like hiking. So, if there is an opportunity, I will find one. However, when doing my research, there were several hiking tours to El Yunque. I felt like it was the go-to activity, and I wanted to do something different. So, the Hidden Waterfall Hike Adventure was the perfect hiking tour.

The tour is described as “this amazing adventure will take you deep inside Puerto Rico’s thick forest mountains. Hike on a man-made trail to ultimately stand under one of the tallest waterfalls in Puerto Rico. I’ll be honest: this tour is not for the faint of heart. You will be climbing. The rocks will be slippery. You will be walking through mud and water. The hike to the waterfall is approximately one mile and takes about an hour roundtrip, but once you get to the waterfall, it will be worth it. The best part is the free time at the waterfall. So bring your bathing suit, a good pair of shoes, and a positive mindset.

Day 3: Let me show you MY island!

On my last full day in San Juan, I signed up for the Afro-Puerto Rican Heritage Tour. Unfortunately, it was canceled due to a medical emergency. Once again, the cancellation did not stop me, and I found the “Let me show you MY island tour.” This tour included an overview of Old San Juan, Loiza (the town where the Africans migrated to at the end of slavery), Maria de la Cruz Cave, El Yunque National Forest for a very short hike to the cliff and rope jumping. Don’t worry, I didn’t do the last part, but you can.

The tour was a combination of cultural and insightful. I ended up learning who is the perfect race. Go ahead and Google it 😉

Old San Juan

El Yunque National Forest

Where to Eat in Old San Juan

I stayed and ate in Old San Juan because they had a ton of restaurants and bars. I don’t have any recommendations, but I will tell you, explore your palate. The food is good and forget about the diet and healthy eating.

Fried Whole Snapper with sweet plantains

Pork Chops with Rice and beans

Stuffed Avocado with Shrimps and Rice and beans


The fact that my trip was from Sunday to Wednesday was perfect. There were not a lot of tourists, and I felt like I had Old San Juan and the tours to myself. I invite you to consider San Juan as a destination in its own right; there’s so much to do, as you can see in this itinerary! Whether you’re into history, food, art, or just chilling by the water, you can find it all in different parts of San Juan. Just writing this itinerary makes me want to plan another trip!

Thank you so much for reading this blog and joining me in my adventures! Make sure to check out my other blogs. Contact me when you are ready to travel domestically or internationally. I am here to curate a trip for you, your friends, and your family.

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