The Kessler Collection

St. Augustine: Modern Gems Breathe Life into This Ancient City

Casa Monica - Hotel exterior

St. Augustine is a city so full of firsts that its most popular attractions read like a list of bragging rights. As the first continuously settled city established in the U.S. in 1565, it boasts Florida’s oldest home, the nation’s first wooden schoolhouse and the oldest masonry fort, to name a few. While the city certainly has a lot to be proud of, you won’t find a hint of smugness about town. The locals here share a quiet friendliness, a deep appreciation for history and a passion for telling their city’s story—even if that means donning a costume for a period reenactment. The city’s history is fascinating, but a deeper look uncovers a more modern side to “The Ancient City” which includes hip cafés, craft distilleries, cultural gems and vibrant nightlife hidden among its cobblestoned streets.

With a variety of cozy B&Bs, quaint seaside inns and historic hotels, St. Augustine provides an interesting and endless list of options for lodging. But the city’s ancient past practically begs for accommodations not only historical, but majestic. The Casa Monica Resort & Spa is both. Originally built in 1888, this hotel is part of the National Trust Historic Hotels of America and has been completely renovated to honor the spirit of the past, right down to each of its 138 completely one-of-a-kind guestrooms. From its painted frescoes to its ornate chandeliers, your stay will make you feel like royalty. And the location is pretty great too—just a short walk away from the iconic landmarks and monuments in St. Augustine’s historic district.

When in St. Augustine, a trip to St. George Street is a given. And the earlier you head there the better, especially if you want to avoid crowds and the sweltering Florida sun. If you arrive in time for breakfast, start your day at The Bunnery. This charming café will deliver your morning caffeine in any form you choose—espresso, latte or even smoothie. And their pastry lineup, including German chocolate brownies and house made croissants, provides the perfect bite to fuel your morning of window shopping. If sleeping in is more your style, Hyppo will help you beat the heat on St. George Street. This popsicle shop specializes in a rotating menu of completely outrageous flavor combinations. From hibiscus-honeydew to pineapple-cilantro, your curiosity will be rewarded with a taste of something interesting and completely unexpected.

In the afternoon, head downtown for a different kind of experience and some much-needed air conditioning at St. Augustine Distillery. This locally owned distillery handcrafts award-winning rum, bourbon, gin and vodka, all inside a restored turn-of-the-century ice plant. Guests enjoy free tours and sampling of local spirits seven days a week.

When night falls, downtown St. Augustine comes alive with music, drinks and dancing. Nestled on Aviles Street (one of the oldest streets in America) lies Cellar 6, a local favorite. With a full bar, a wine list featuring more than 100 selections and live music nightly, it’s not hard to see why. For a more laid-back vibe, head to the renowned patio bar at Scarlett O’Hara’s. While there, make a trip upstairs to the Ghost Bar, rumored to be haunted by the man who originally built the place in 1879. Whether you come for its storied past or a bit of fun, St. Augustine has a history of delivering both for hundreds of years.