Source: Old Town Trolley Tours

As the USA’s oldest city, St. Augustine is a vacation destination that draws visitors from all over the world. Steeped in history, natural beauty and a wealth of interesting sites and attractions, the Ancient City offers an unforgettable experience to people of all ages. Whether you’re here for a weekend getaway, a romantic escape or an extended family vacation, fall is one of the best times to discover all St. Augustine has to offer.

With nearly five centuries of history, St. Augustine offers a fascinating experience to all who visit any time of the year. From witnessing Flagler’s architectural majesty, the St. Augustine Alligator Farm, founded in 1893 and the city’s oldest attraction—to the many historical sites and cultural attractions, there’s truly something for people of all ages. Whether you’d like to stroll on a stretch of pristine shoreline, discover the Fountain of Youth or have a paranormal encounter, you’ll find that St. Augustine delivers. In the fall, the weather’s just a bit milder, allowing you to enjoy outdoor and indoor attractions more comfortably than in the summer. Here are some of the top sites and attractions that you won’t want to miss:

BEST ATTRACTIONS TO VISIT

TOUR THE OLD JAIL

One of Henry Flagler’s structures, the Old Jail served as the city’s prison from 1891 through 1953. In order to ensure that the guests at his new hotel, the opulent Ponce de Leon, felt safe, Flagler built the jail to look like anything but a prison. With its Romanesque Revival architecture, the building looked more like an elegant Victorian home than a place of incarceration.  While it was active, the Old Jail housed some of the city’s most violent and dangerous criminals, and was known for its harsh, sometimes brutal practices. Today, tours of the facility are led by costumed actors and provide a close up look at the men’s and women’s cells, the Sheriff and his family’s living quarters (adjacent to the prisoners), the gallows and a collection of weapons.
In the fall, tours operate beginning at 9am and ending at 4:30pm.

OLD JAIL AFTER DARK

Prepare yourself for a spine tingling night you’ll never forget at The Old Jail After Dark. This 45-minute chilling experience allows visitors to participate in an actual paranormal investigation of St. Augustine’s Old Jail. Recognized as one of the most haunted buildings in the country, the Old Jail is shrouded in mystery and lore. The historic building housed prisoners from 1891 to 1953 when it was closed due to its deplorable conditions and the inflicted cruelty on its residents. Eight documented hangings were carried out on this site and many other deaths that can only be described as unnatural. Perhaps these are why many believe the Old Jail is an epicenter for paranormal activity and why it has become a popular destination for ghost hunters everywhere.

CASTILLO DE SAN MARCOS

In the fall, when the air is brisk and there’s less humidity, it’s a great time to visit the Castillo de San Marcos, a historic fortress that stands on the shore of St. Augustine. This iconic structure was built between 1672 and 1695 to guard the coastline of the city from foreign invasion. The largest masonry structure of it’s kind in the continental United States, Castillo de San Marcos is a national monument. Visiting in the fall, you’ll have the opportunity to explore the many rooms that once housed Civil War soldiers and prisoners and to see the large courtyard and gun deck. You can also witness weapon demonstrations, cannon firings and enjoy ranger-led tours that take place every half hour on Friday, Saturday and Sunday beginning at 10:30am and ending at 3:30pm.

TAKE A SIP FROM THE FOUNTAIN OF YOUTH 

Enjoying the natural scenery of St. Augustine is particularly pleasant in the fall when the temperatures are lower. It only makes sense that the Fountain of Youth Archaeological Park is a top item on most folk’s September through November itineraries. You’ll have the opportunity to discover the original site that was first explored by Ponce de Leon and Pedro de Aviles. Located on 15 waterfront acres, the park features beautiful tropical gardens, living history exhibits, live cannon firings, a Timucuan Village, the Navigators Planetarium and of course, the Spring House, where you take a sip from the eternal water. Admission to the park is from 9am to 6pm, last ticket sold is 5pm.

THE SPANISH QUARTER

Also known as the Colonial Quarter, this historic attraction in St. Augustine is best explored when the fall weather is at its mildest, between September, October and early November. Within two acres, you learn about the rich past of the city brought to life in numerous ways including witnessing a blacksmith at work, participating in a musket drill with a live firing demonstration and a cannon drill, viewing the original Mesa-Sanchez house circa 1740 and climbing to the top of an interpretive 17th century watchtower. The park offers a journey through centuries of the city’s history and even features the opportunity to experience period fare at two restaurants. Guided tours of the Spanish Quarter take place daily beginning at 10:30am and ending at 3pm and of course you are free to roam and explore on your own throughout the day.

TAKE A PHOTO AT THE CITY GATES

The original gates to the city of St. Augustine, which were constructed in 1808, are still standing today, although they’ve been repaired and restored over the years. Located at the north end of St. George Street in the historic district, the Old City gates are a lasting symbol of how the city was once surrounded by strong walls and provide a glimpse of what life was like centuries ago. Worth a visit while you’re enjoying your fall vacation in St. Augustine, and a great spot for photos to remember your experience.

SHOP ON ST. GEORGE STREET

If you love to shop, there’s no better place to do it in St. Augustine than on St. George Street. And because it’s a pedestrian only mall, you’ll find it the idea place to relax and enjoy the wonderful fall weather. Here, you can dine, shop and visit some of the oldest structures in the city, including the Oldest Wooden Schoolhouse.

VISIT THE ST. AUGUSTINE LIGHTHOUSE

Built in 1874 and located at the end of Anastasia Island, the St. Augustine Lighthouse was preceded by a Spanish watchtower that was first constructed in the late 1500s. Many towers have been built through the centuries, but today’s lighthouse is St. Augustine’s oldest surviving brick structure and provides visitors a chance to learn about its unique history. Rising 165 feet above sea level, the tower contains 219 steps which guests are invited to climb to reach the top which provides spectacular views. In addition, guests can tour through the lighthouse keeper’s quarters that was constructed in 1876. Fall is an ideal time to visit the lighthouse and to enjoy their various events which are listed below.

TASTINGS AND TOURS AT SAN SEBASTIAN WINERY

Housed inside a building that was built by Henry Flagler in 1923, San Sebastian is Florida’s largest winery. For wine enthusiasts, this family owned and operated business offers an opportunity for an insider’s view of the winery as well as a chance to taste some of their wines. Tastings and tours take place Monday through Saturday from 10am-6pm and on Sunday’s from 11am to 6pm. The Cellar Upstairs Wine, Jazz and Blues Bar offers you an idyllic spot to enjoy the beautiful fall weather while sipping a glass of San Sebastian wine and listening to live music every Friday and Saturday night.

HAVE A FUN-FILLED FRIGHT NIGHT WITH GHOSTS & GRAVESTONES

Climb aboard Ghosts & Gravestones Night Tour for an evening of spooky fun as we transport you to some of the city’s most haunted spots. Your costumed ghost host will share the eerie tales of the ancient city’s haunted past and guide you as you discover the secrets of the Tolomato Cemetery. Be sure to keep a watchful eye while passing by the old City Gates. You might catch a glimpse of Elizabeth, a child victim of the yellow fever, waving to passersby. Arrive early to explore Cromwell’s Parlour of Paranormal Curiosities, St. Augustine’s only collection of the paranormal and unexplained.

WHERE TO DINE

As you might expect, St. Augustine has an array of restaurants to choose from that include family-friendly, casual and upscale dining. In the fall, most visitors to the city are looking for those that provide dining by the water or with a view. Some of the top places to dine in the fall are:

HENRY’S SEAFOOD BAR & GRILLE

Overlooking the bay, this local favorite serves up savory seafood infused with creole, Cajun and southern flavors.

BEACHES AT VILANO

Dine with your toes in the sand at this unique restaurant located directly on the beach. Beaches at Vilano features delicious American cuisine, signature drinks, live music and the ambiance of the tropics.

CAPS ON THE WATER

Voted Best Outdoor Dining on numerous occasions, Caps on the Water offers picturesque views and fresh local seafood masterfully prepared. Enjoy a fall sunset over the water as you sip your favorite cocktail.

THE REEF

Seaside tables overlook sand dunes and provide oceanfront views in this elegant St. Augustine restaurant. Dine al fresco in the fall, when the sea breezes will keep you cool as you enjoy their specialties.

AUNT KATE’S

Located on the bank on the Tolomoto River, Aunt Kate’s features outdoor dining under live oaks with lovely river views. Seafood, steaks, salads and more will please your palate.

WHAT TO PACK

When visiting St. Augustine in the fall it’s a good idea to bring along a light jacket or sweater and some long pants and long sleeve t-shirts. Of course, a swimsuit, shorts, t-shirts, a hat to keep the sun off and flip-flops or sandals are recommended, and a comfortable pair of shoes to wear while sightseeing. Don’t forget the sunblock- you can get a sunburn anytime of the year!

AVERAGE TEMPERATURES

• September: Low 72, High, 87
• October: Low 65, High 82
• November: Low 57, High 75