Honeymoon Pt. 1 – Exploring the Streets of Old San Juan

Join us as we spend Day One of our Honeymoon exploring the blue cobbled streets of Old San Juan in Puerto Rico!

On August 7th, 2021, Laura and myself (Andrew) tied the knot! The very next day, we packed our bags and moved to the US Virgin Islands as Laura pursues her Master’s Degree in Marine Science at the local university in St. Thomas.

Although we moved to a tropical paradise for a minimum of the next two years, this was never considered a viable option as a proper honeymoon (much to my bantered efforts). So, when we finally got the chance the following May, we packed our bags for the nearby island of Puerto Rico!

Arriving in Puerto Rico

Puerto Rico is extremely close to the US Virgin Islands yet entirely different in terms of landscape, culture, and history. It’s a fascinating place, and certainly, one that captivated our attention as a potential home in the future.

Our first day was spent exploring the streets of Old San Juan. This is the historic district of the island’s capital city, San Juan, and the second oldest European settlement in the New World (Santo Domingo in the Dominican Republic is the oldest).

You’ll find centuries-old churches, fortresses, city walls and gates, and a plethora of other historic buildings along the blue cobblestone streets of the city. It’s a wonderful step back into history while providing modern amenities like restaurants, nightclubs, and duty-free shopping.

For more, check out our article on How to Spend One Day in Old San Juan, and be on the lookout for Part 2 of our Honeymoon in Puerto Rico!

Old San Juan: Photo Gallery

Old San Juan: Video Transcript

Welcome to our very first adventure in Puerto Rico! Today, we’re joined by my in-laws as we explore the streets of Old San Juan in celebration of Laura’s 27th birthday! Feliz cumpleanos, mi amor!

About Old San Juan

Old San Juan is the historic district of the island’s capital city, San Juan. Not only is it the oldest city within the United States jurisdiction, but it’s also one of the oldest in all of North America, founded by the Spanish explorer, Juan Ponce de Leon in 1521.

Today, much of the city is geared toward tourists as the colorful buildings feature streetside cafes, bars, and restaurants lining the cobblestone streets. The US National Park Service manages many of the historic structures including two impressive fortresses, many churches, and old city walls.

Pirague in Puerto Rico

And of course, the birthday girl needed her sweet treat for the day: Piragua. This Puerto Rican, shaved ice dessert is served by vendors throughout Old San Juan. I highly recommend trying it out for yourself!

One Day Itinerary for Old San Juan

You can easily spend an entire day walking around Old San Juan browsing through shops, snapping pictures at the Instagram-worthy sites, wandering through museums, and admiring the historical buildings. For a full one-day itinerary, visit the link below to our website.

Walking to El Morro via Paseo del Morro

My favorite scene of the day was the Paseo del Morro. After exiting through the city’s main gate, this path wraps around the city walls before ascending into Castillo San Felipe del Morro – one of the two main fortresses within the district.

Even if you don’t end up along this exact route, make sure to pack plenty of sun protection. It’s hot year-round and very few places in Old San Juan have shade.

San Juan National Historic Site

Much of San Juan National Historic Site is on the north side of Old San Juan overlooking the Atlantic Ocean. Most of the structures are free to enjoy but if you want to go inside the two fortresses, Castillo San Felipe del Morro or Castillo San Cristobal, you’ll need to pay a $10 admission fee. We decided against it as we were late to arrive in the day and would have limited time to explore inside. Instead, we took in the many sites peppering the coastline.

Tourism in Old San Juan

Old San Juan is the epicenter of tourism in Puerto Rico. It’s a great place to stay with many hostels, guesthouses, and restaurants nestled into the colorful buildings. At night, the neighborhood transforms into a lively atmosphere as salsa dancing from the clubs spills into the streets. Oh, you’ll even find your typical American conveniences like Marshalls.