As I’ve mentioned before, I love to travel with my dog, Kuma, wherever I go. I can’t take her on the plane with me, so I’m limited to bringing her on road trips. Luckily, St. Augustine, America’s oldest city, is not too far from Tampa, so I was able to take her with me to this dog-friendly town.

St. Augustine is actually America’s oldest city. Florida usually isn’t known for American history like the northeast, but surprisingly this place was founded by Spanish explorers in 1513. Juan Ponce de Leon believed he found the mysterious Fountain of Youth in St. Augustine.

Today, you can still see the Spanish influence and architecture scattered throughout the historic city.

I was traveling with some friends who also had a dog and found a cute little cottage on Airbnb that was perfect for 4 people and 2 dogs. The 2-bedroom home had plenty of room for the dogs, a vintage kitchen, dining area and a backyard with a little grill and covered pool. We loved the vintage design of the home. Whoever designed the home definitely knows how to antique shop!

The cottage is located about 1.5 miles from the center of downtown St. Augustine, so we alternated between walking and taking an Uber, which was about $6 - $8 one way.

This was my third time visiting St. Augustine and it’s usually pretty busy with tourists, but this Thanksgiving weekend was insanely busier than usual. The locals were even a little overwhelmed with all the visitors as we experienced restaurants running out of food and Uber drivers getting stuck in traffic. Not sure if this will be happening every Thanksgiving, but I would try not to visit during this time to avoid the crowd.

There was so much on our list that we wanted to do in St. Augustine, but with the tourists, traffic, rainy weather conditions and dogs, we had to cut down some things from our list. Either way, we still had fun! Here's the itinerary we accomplished:

DAY 1 / THURSDAY

We arrived at our Airbnb cottage and explored all the rooms and debated on which room to take. Kind of like what the MTV Real World kids do, but on a much smaller scale.

DAY 2 / FRIDAY

There are tons of things you can do with your dog in St. Augustine! The coolest thing we got to do was ride on the Scenic Cruise with our dogs. The dogs walked with us for 1.5 miles, so by the time we got to the boat, they were pretty tired, which was a good thing since Eli is still a 6-month old hyper (huge) puppy. We enjoyed the relaxing scenic cruise as the boat guide showed us the gigantic cross, the lighthouse and beaches.

After the boat tour, we walked to the Spanish Bakery. Out of all the times I've been in St. Augustine, I have never stopped by here because it is tucked away on St. George Street, but I'm glad we found it this time! It's a cute little bakery with empanadas, sausage rolls and sandwiches. They keep the menu very simple and cheap. The bread is made fresh daily and you can certainly tell when you have that first bite. I enjoy these smaller restaurants way more than the bigger, fancier restaurants. 

Later in the day, we indulged in some waffles and milkshakes at Cousteau's Waffle and Milkshake Bar. Everyone must visit this heavenly place. I wanted to cry (yes, I cry for good food) because these waffles and milkshakes were so darn good. I just got the plain 'ol Waffle Bites (silly me), but everyone else ordered more of the interesting ones like 'Life on Mars' with coconut ice cream espresso and the 'Whirlybird' with bourbon whipped cream. So yummy!!

We did a little more walking around St. George Street and then walked back home as we enjoyed St. Augustine's Nights of Lights with all the pretty Christmas lights decorated on the buildings and streets.

DAY 3 / SATURDAY

We walked to St. George Street again and after hearing my colleague, Kat, rave about The Floridian, I had to check it out. The Floridian has a very cute vibe to it as soon as you see the sign and outdoor patio. Indoors, the restaurant is filled with bright colored walls, wooden tables, and alligator decorations. I was immediately attracted to the Fried Green Tomato Bruschetta and Ryan ordered his favorite cheese tray, the Georgia Cheese Board. Everything was very creative, beautifully plated and delicious!

We later visited the Castillo de San Marcos fort with the dogs. You can't take the pups inside the fort, but you can walk around the site, which is still pretty cool to see. I love history and St. Augustine is the perfect place for history lovers. It's the oldest city in the United States. The construction of this fort began in 1672! It's always surreal to me to think of how long ago that was and how awesome it is to see this huge piece of history in front of you.

After the fort, we walked around St. Augustine a little more with the dogs and came across some fun fake snow on the streets. 

After we took the dogs back home, we enjoyed some barbecue at Mojo BBQ. The locals love this place and I can see why! The best BBQ I've ever had and everyone at the table agreed. I'm not a huge fan of BBQ sauce, but their sauce is amazing.

As we walked back to the cottage, we stopped by San Sebastian Winery since we heard lots of laughter and music coming from the rooftop. The winery has a very spacious rooftop bar with a jazz band, although they weren't really playing jazz music. Maybe they changed the vibe when we walked in because we were a bit younger than most of the crowd. Either way, we had some good, cheap drinks and enjoyed watching the older crowd dance the night away.

There's definitely more to do in St. Augustine and we'd love to go back again someday when it's not so crowded. For our Thanksgiving trip next year, we're planning on meeting up in either Asheville or Charleston. Can't wait!