San Juan Family Vacation

An unseasonably cold start to the winter had us wanting a quick family getaway. We were thinking somewhere warm, somewhere that requires no passports from the US, a place we have never been, and a blend of city and beach. Being born and raised in NJ with quick access to New York City and Philadelphia, we are city people at heart and enjoy culture and city life when traveling. San Juan, Puerto Rico met all requirements and is where we decided to spend our family vacation to ring in 2023. Here is a recap of where we stayed, what we did, and of course what I wore!

Caribe Hilton Hotel

Only a few weeks away from New Year’s Eve, most of our top hotel choices were already booked, however our final choice winded up being perfect for our family. Our stay at the Caribe Hilton was a great first experience to the San Juan area. Only a 15 minute drive from the airport, this resort gave us the best of both worlds.

Private beach and infinity pool

The private beach area is key, as some hotels have public beaches. This beach has plenty of beach chairs available on the beach, as well as on the dock. The entire beach area is contained by a rock barrier so that the waves stay out further to sea, leaving the swimming area as calm as bath water. There is an inflatable tubing area for kids to play on just a short swim away, that my kids loved. For younger kids, there is a small playground on the beach. I remember how important playgrounds were when my kids were younger! This would have been one of their highlights!

Part of the beach also has a hammock garden as another option for relaxing. This is where we watched the New Years day fireworks and had s’mores for the kids. This is a great place to read a book under a palm tree.

There are 3 pools in the hotel that are not connected. You need to leave one to enter the other, although they are all right next to each other. The infinity pool is right in the middle and has the best views. The larger pool to the left has a basketball hoop for keeping kids busy, and the third, much smaller pool has a swim up bar for the adults. A great set-up for a family vacation.

Best Location for Beach and City

If you are looking for a beach resort with easy access to Old San Juan, Caribe Hilton is perfect. Only minutes from Old San Juan with taxi service right at the hotel lobby. We never waited more than 5 minutes for a ride. Anyone who’s ever done it before knows that wait time is key when traveling with kids.

Birthplace of the Pina Colada

Now this is debatable. In fact two places are claiming to be the birth place of the Pina Colada. The first being here at the Caribe Hilton hotel by bartender Ramon “Mochito” Marrero back in 1954. The hotel claims this was first served here at the Caribar. The second claim to the Pina Colada is in Old San Juan at the Barrachina restaurant by bartender Ramon Portas Mignot. I tried them at both places and they were equally delicious! In any event, the Caribe Hilton has a number of great restaurants on site. Probably one of the best hotel dining selections I’ve experienced.

Swim with the Sea Turtles

The Caribe Hilton is just a 5 minute walk to the Sea Turtle reserve at Escambron Marine Park, located right next to Escambron beach. This is a protected area where you can snorkel and get up close to the sea turtles. This is a perfect San Juan family vacation activity. While parts of the area can get up to 25 feet deep, most of the cove is fairly shallow.

Groups are divided up according to swim level, or families, as ours was. No need to swim at all here! Everyone wears a vest to keep them afloat, and gets a quick snorkel lesson before starting. It’s a very comfortable experience and was a lot of fun. Plus the turtles are not shy!

Exploring Old San Juan: Family Vacation

My most anticipated part of the trip was exploring Old San Juan. I love the colorful buildings and old architecture. Our cab driver told us that you are not allowed to have your home the same color as your neighbors. That makes for a truly colorful experience!

While Old San Juan can be very crowded, especially if the cruise ships are in, you will find many quiet side streets. Head down one or two to get away from the sun, or for a great photo op!

San Cristobal and El Morro Forts

The old forts are a must-see if you visit. There is a small entry fee that gets you into both forts if you go on the same day. We didn’t. We toured one end of Old San Juan one day and visited San Cristobal, and the other end on another day, visiting El Morro. There was no rush for us. Plus, traveling with kids, it’s nice to break it up as the climbs can be steep, especially at El Morro. Of the two forts, El Morro was most impressive. It’s the larger of the two and at the tip of Old San Juan. The views are amazing at both locations!

What to wear

Let’s get to my favorite part! I love knowing what other people pack for trips, so I hope this is helpful for you.

Light cotton clothing is always best for warm, humid weather. I packed an assortment of cotton dresses, and tops to be worn with shorts for both me and my daughter. The dresses got the most use. I love packing day to night dresses for easy dressing. Just swap out the shoes. In my opinion, they are the best choice for comfort from the heat, and style.

100% cotton is my favorite choice for travel as it does not wrinkle as much as linen, and it keeps you from overheating. Here are some of my favorite cotton dress choices:

Another travel essential is a packable day bag. I keep this one folded up in my suitcase until I’m ready to use it. It’s roomy enough to hold my camera, a water, wallet, sunscreen, and sunglasses. I even stuffed my kids hats in there.

Here I’m wearing the small version of the Pliage bag. I also have the large version that I use for all of my personal items on the airplane. Both are so easy to travel with since they fold right up!

Polo shirts for the guys are always a good idea for day to night. I bought UPF fabric shirts for my son and husband. Plus picked up a few new of my husbands favorite Peter Millar shorts. Both my son and husband packed their most versatile shoes (in both youth and adult sizes), sneakers, and a pair of sandals.

Wearing Shoes

Most guides will tell you to wear sneakers when touring old San Juan. The forts can be steep, and the city has some uneven pavements, with lots of cobblestone. Our first day in Old San Juan, I wore my trusty sandals and was fine for touring about 4 hours. We split most of our days between beach/pool and city. My kids wore their sneakers which was the best choice for them. I will say that El Morro fort is vast and pretty steep in sections. I wore my sneakers that day which was a smart idea.

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