St. Augustine is nothing if not enduring. The city’s brick-lined streets, horse carriages, forts and grand hotels have charmed generations of visitors for many years. From the romantic restaurants and walkways, to the family-friendly attractions and activities — there are plenty of things to do in St. Augustine for every type of traveler.
St. Augustine is full of adventure and activities for the whole family. Walk around St. George Street, with its coquina stone pillars that mark the historic city gates. The ancient street is closed to vehicles, allowing kids to run back and forth between the shops. Then head to the Oldest Wooden School House — the cedar and cypress planks of the more-than-200-year-old building are washed by weathering, but the structure’s history remains. Learn how the schoolmaster and his wife lived above the classroom, and see some of the textbooks that students used centuries ago. Next, find the Colonial Quarter, where blacksmiths and woodworkers roam about the 18th-century courtyard, giving demonstrations and entertaining groups.
Weekend with Friends
Enjoy dinner and drinks at the torch-lit courtyard of Harry’s Seafood. For a fun adventure, check into the Pirate Haus Inn, a hostel right in the middle of the historic district. The next morning, head to Castillo de San Marcos. Built by the Spanish from 1672 to 1695, it is the oldest masonry fort in the U.S. A tour of Flagler College is also a great attraction. The former 1887 Hotel Ponce de Leon is now on the National Register of Historic Places.
Cap off the night with the Old Town Trolleys Ghosts and Gravestones ’"Frightseeing" Tour of nighttime St. Augustine. Aboard the trolley of the doomed, you’ll encounter "ghosts" at historic sites like the Old Jail.
Check into the Kenwood Inn B&B. The 1880s house is in the historic district just one block from the Intracoastal Waterway, which you may see from your suite. Take a sunset cruise on the Schooner Freedom, a 72-foot sailboat. The cruise leaves from the marina across from the Inn and includes hors d’oeuvres and wine.
For dinner, try the velvet-draped Costa Brava — an elegant restaurant located in the beautiful Casa Monica Resort & Spa. Built in 1888, the Casa Monica was restored to its former glory and re-opened in 1999. As you leave the restaurant, you’ll see the impressively lit Lightner Museum. It is another of Henry Flagler’s former grand hotels (this one, the Alcazar) and today it holds a wonderful "collection of collections" featuring one of the world’s largest displays of cut glass — as well as Victorian art and furniture.
Finish your romantic evening with a walk along the dimly lit streets of the historic district. Close out the night at Prohibition Kitchen, a retro-chic gastro pub with craft cocktails and gourmet pub grub.