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Exploring Old Town St Augustine, Florida: The Oldest City in America

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America is a teenager compared to the matured and seasoned countries found elsewhere in the world. But it may surprise you to know the city of St Augustine, Florida dates back to 1565! In fact, Old Town St Augustine is the oldest continuously occupied settlement in the United States. Ok, so that’s still young compared to a city like London or Rome but it’s pretty impressive for North America.

Visiting St Augustine Old Town is a great addition to any Florida road trip, especially for anyone who likes historical sites. But there’s so much more to this beautiful city. After a day exploring the cobblestone streets, National cemeteries, and interesting museums in Old Town you can enjoy a delicious meal at one of the acclaimed restaurants followed by a nightcap or maybe some live entertainment at an atmospheric pub or wine bar.

Plus, once you’ve had your fill of the history and charm of Old Town you can relax at the beautiful St Augustine Beach, have fun in the sand dunes at Anastasia State Park, take a tour of the St Augustine Distillery or have a tasting at the San Sebastian Winery. There are so many reasons for this town to be on every Florida bucket list.

There is something to please every age and taste in St Augustine, Florida including a wide range of accommodations. If romance is the goal, a charming Inn or B&B in historic Old Town is a good choice. Family or group vacation? No problem with the variety of hotels in St Augustine for every budget. You can even stay at a resort on the beach if that appeals to you.

Top Sights of Old Town St Augustine

Old Town St Augustine’s Historic Streets

Pretty cobblestone street in Old Town St Augustine
Aviles Street in Old Town St Augustine

When visiting historic towns our favorite thing to do is wander the streets and Old Town St Augustine is perfect for that. The most popular one to explore in St Augustine is St George Street which is full of historic homes, boutiques and restaurants.

Cordova Street is full of tourist sights including one of the cemeteries and museums listed below. Avenida Menendez is an interesting street with a variety of international restaurants and great views of the Bridge of Lions and the St Augustine Lighthouse.

Also worth a look are Aviles Street, the oldest in the country with some lovely restaurants, and Treasury Street which is the narrowest street in America at only six-feet wide.

Museums of St Augustine

Black and white striped lighthouse with red lamp on tip in St Augustine Florida
St Augustine Lighthouse & Military Museum

As to be expected in a historic town there are several good museums. The Colonial Quarter is a living history museum that will thrill kids and adults with an interactive journey through time illustrated by period costumed actors and guides.

The original St Augustine Lighthouse and Military Museum dates back to 1565. Today you can ascend 165 feet by climbing the 200+ steps to a great viewpoint and maritime exhibits.

The Lightner Museum was once the extravagant Alcazar Hotel built in 1887 for Henry Flagler. The museum now holds a collection of American and Asian art and artifacts as well as some impressive Tiffany glass pieces.

Kids will love the Pirate & Treasure Museum with the largest collection of pirate artifacts in the world. Architecture buffs will be impressed with the example of Moorish-Spanish revival displayed at the Villa Zorayda Museum and the St Augustine History Museum will take you on a journey of the cities 500 year past.

Cemeteries of Old Town St Augustine

Grave markers and American flags
St Augustine National Cemetery

We love visiting old cemeteries and we know we’re not alone in this unusual fascination. St Augustine has three lovely and interesting cemeteries. I was personally excited about the Huguenot Cemetery as my grandfather claimed we had ties to them somewhere along the line. It’s a small cemetery near the Old City Gate and is only open the 3rd Saturday of every month.

The Tolomato Cemetery contains almost 1,000 graves of every nationality to settle in St Augustine between 1777 and 1884. It is also only open to the public the third Saturday of every month but you can get a photo-worthy glimpse through the gate.

Unlike the other two cemeteries mentioned, the St Augustine National Cemetery is open to the public daily. It’s also the largest of the three and is a place of rest for members of the armed forces and their families. The most interesting sight here is the Dade Monument which consists of three pyramids of coquina stone which were erected in 1844 to commemorate the men who died in the 1835 massacre along with Major Dade.

More historic sites and attractions in St Augustine

Old Town St Augustine Flagler College
Flagler College in Old Town St Augustine

There’s a cornucopia of historic buildings in Old Town St Augustine. Flagler College, once the Hotel Ponce de Leon, tops the list with incredible architecture, vibrant color, intricate finishing details and 79 windows of Tiffany Glass.

Castillo de San Marcos is the only surviving 17th-century stone fort in America. It’s now a National Park Monument and offers reenactments including musket and cannon firing on weekends.

The elegant Flagler Memorial Presbyterian Church was built in 1889 as a tribute to Henry Flagler’s daughter, Jenny. The intricate Venetian Renaissance-style architecture and incredible interior details attest to the money spent on this labor of love.

As the name suggests, the Fountain of Youth Archaeological Park is home to the alleged healing spring found by Ponce de Leon. Aside from drinking from the “magical” fountain visitors can also enjoy historic recreations have a picnic and stroll a boardwalk through the marshes.

This is just a sampling of the many things to do in St Augustine, Florida. If historic sights aren’t your thing there’s a whole other list of leisure activities based around the beautiful beaches, wildlife and golf courses in the area. As we said, there’s something to please everyone in this southern city.

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