active family travel,  family,  Travel

San Juan – A Caribbean Beauty Rich In History #IFWTWA

San Juan is one of the can’t miss areas of the Caribbean that anyone traveling to the area should incorporate into their travels. Located between the Dominican Republic and the British Virgin Islands, Puerto Rico shares some prime Caribbean real estate, and its capital, San Juan is a show-stopping destination.


San Juan, Puerto Rico – Two Sides of One Amazing Coin

When we visited the Puerto Rican capital for the first time, I didn’t know what to expect. Puerto Rico, in general, had been on my travel bucket list for five years or so. I figured that since it was an excursion stop on our cruise, it would be nice for the entire family to explore a new destination. The city – and the country, in my opinion – are highly underrated Caribbean locations. Much love is reserved for places like Jamaica, the US and British Virgin Islands, rightfully so because these are stunning family travel favourites, but don’t overlook Puerto Rico and its capital. San Juan has a rich history with glorious beaches. It’s also a photographer’s dream that should be on every Caribbean traveler’s list.


Old San Juan

If you love history, architecture and the feel of age, then Old San Juan is for you. Walking through this part of the capital city is like stepping back in time. As you walk down the streets, you’ll take in brightly colored homes that pop in vibrant shades of red, yellow, and other primary colors. Continue through the area, and you’ll find museums, landmarks, plazas, restaurants, and shopping. And through it all, you’ll experience that friendly, welcoming vibe that permeates everything in the city. You’ll also be able to experience the festive events that occur almost weekly. It’s an amazing experience in history and culture.


We began our day tour of Old San Juan at the port of San Juan of course on our most recent cruise. From the port to the major landmarks in the city, it was a very short drive. First up was the National Historic Site. I could have spent all day just photographing and walking around the walled city.

In fact Old San Juan remains one of the prettiest and most captivating capitals I have ever seen. There’s so much history here that my teenager and my tween were extremely interested. They both found the National Historic Site, the public art and monuments and the stunning President’s Walk truly memorable. We will try to return to Puerto Rico next time for a lengthier visit.


New San Juan

This amazing city has two sides – the old and the new. And if you’re less about history and more about dynamic contemporary cities, then New San Juan is the place for you. This bustling Caribbean metropolis is constantly on the move, ever growing and ever changing. In contrast to the old world architecture and feel of its counterpart, the modern side of the city features luxury hotels, posh beaches, upscale shopping and dining, and vibrant nightlife.


San Juan – Beautiful on Every Level

Whether you want a laid-back, island time experience or a super hot, super posh getaway, the Puerto Rican capital has what you’re looking for. We were on a family trip, so we kept mostly to Old San Juan, but for honeymooners or single travelers, New San Juan is definitely the place to be. Wherever you choose, you can’t go wrong in this city of contrasts.

Mom of two beautiful active girls, traveller, fitness junkie, social media consultant, and keeper of the sanity.


  • Roger Willis

    I’ve heard San Juan, Puerto Rico, is a beautiful place! I’ve traveled mostly in Europe, when I was in the military and was a single soldier. PR is one of those places I’d like to visit. Your pictures of the city, beaches and its historical areas are incredible! There’s something magical about pictures of rustic buildings and beaches. Great job on personalizing your photos on your travel experience!

  • Melanie

    This looks fun and educational for a family getaway! We are hoping to travel more as our kids get older, and this is a place to put on the bucket list for sure. We would probably stick to the historic side if taking the kids.

  • Ali Rost

    We’ve been to a number of places in the Caribbean .. but haven’t made it to San Juan yet. I didn’t realize there were both old and new parts. I can see my husband getting lost in the history of the old part. Me? I’d probably be in the new part on the beach!

  • Tiara Wilson

    I cannot wait until we go visit this upcoming year! Once a year, my husband’s family likes to take a big trip and they usually plan it. This year we are going to San Juan and I am so intrigued now, by what we’ll be doing based off your post!

  • Jenn @ EngineerMommy

    Traveling more is definitely something I’d love to do. In fact, visiting San Juan sounds like a wonderful vacation for me and my family in the next few months. I have a friend who vacationed here and she raved about what a wonderful experience she had. There is so much to see and do here!

  • Censie Sawyer

    One of my good friends is in San Juan right now. The photos that he is sharing are simply amazing. After watchign his travels and now reading this post I am so ready to book a trip to San Juan soon!

  • Victoria

    I have heard of San Juan, but it is never a place that I have been. It’s nice to learn more about it from your post though. I hope one day to be able to experience it for myself.

  • Amanda Kee

    I have only left the country once and it was this year. I can’t wait to leave the country again and see the beautiful places in this world. My brother was in PR once and he actually wasn’t a fan. He loved the resort but he wasn’t happy with when he left the resort! San Juan looks like a beautiful place to visit!