The Overseas Highway runs 113 miles along the Florida Keys, from Key Largo south to Key West. This was the one thing my husband wanted to do in the Keys and the thing I probably researched the most. I had read dozens of ideas of places to stop and things to do along the way and after much debate narrowed it down to 8 potential activities. We only did 3 of them (and 2 of them begrudgingly). But such is the nature of a road trip with tired kids and competing interests. Much like Key Largo itself, my expectations of …

Key Largo is the northern-most island of the Florida Keys. It is the largest of the keys at 33 miles long and is the self-proclaimed “Diving Capital of the World”. Water sports are extremely popular here, from diving and snorkeling to fishing and boating. I will be the first to admit that I did not fully understand the Florida Keys before our visit. I read about the beautiful Overseas Highway connecting all the different islands and pictured each island having its own town and individual vibe. I was really surprised to find that, with the exception of Key West, there …

As the oldest city in the US, St. Augustine holds a lot of other “oldest” distinctions within the city, among them the oldest masonry fort in the continental US. Castillo de San Marcos was built by the Spanish starting in 1672 following an English raid of the city that caused significant damage and exposed its vulnerabilities. (In total, 9 wooden forts had been burned to the ground by invaders over the years.) Construction spanned 23 years, and upon completion, the fort’s 12-foot thick coquina (shell and limestone) walls were a formidable defense that proved both impenetrable and fire-resistant. The fort …

We stopped in the St. Augustine Pirate & Treasure Museum on a whim as we walked by. The line was long and it was pricey ($15 for adults and $8 for kids 5-12) but we decided to visit anyway. The theming was great, even in the entrance and gift shop, and it looked to be really well done. And kudos to them for being covid-safe and requiring masks (and doing it in a clever fashion!). The museum was laid out like a pirate ship and had several different rooms with artifacts matching that section of the ship. It was really …

Founded in September 1565 by Spaniard Pedro Menendez de Aviles, St. Augustine is the nation’s oldest city. It’s Spanish heritage is still evident in its architecture, from the Castillo de San Marcos, a Spanish Colonial landmark, to the original Ponce de Leon Hotel, a Spanish Renaissance Revival masterpiece. Although best known for its Spanish-style buildings featuring red clay terra cotta and ornate trimmings, the city of St. Augustine has a varied and unique architectural heritage that has been remarkably well preserved. When touring the city, the first architectural landmark you will probably come across is the Old City Gates. After …

Located across the Tolomato River from Saint Augustine, Vilano Beach is a wonderful place to watch the sunset. We headed over there for dinner and the sunset to end our first evening in Florida, and the sunset did not disappoint. We ate dinner outside at Vilano Grill 180. The food was good but the real excitement of this restaurant was the roaming neighborhood chickens. They wandered along the streets and sidewalks of the area, clucking and being generally loud. They were highly entertaining to the boys, especially when they surprised us all and flew into the trees and hung out …

We arrived in St. Augustine a little before 4:00 and wanted to squeeze in an activity on our first day. After quickly checking into the hotel, we headed over to the St. Augustine Lighthouse. Since we planned to spend the next day exploring the city on foot, a visit to the lighthouse made perfect sense for our arrival day. Located across the Bridge of Lions about 2 miles from downtown St. Augustine, the lighthouse is more easily reached in a car than on foot. The lighthouse was open until 6:00 so we had about an hour and a half there …