In St. Augustine, Take a Trip Back in Time
St. Augustine shines during the holiday season.
Image: Sean Pavone/Shutterstock.com
St. Augustine, the oldest continuously occupied settlement of Europeans and African Americans in the U.S., may turn 458 this year, but the city is young at heart. With a bevy of fun live music venues and festivals, hip bars and restaurants and plenty of historical sites to explore, this city is gorgeous, walkable and lively, making it an ideal destination for a long weekend away.
When to Go
Anytime, really, but the city shines (pun intended) during its annual Nights of Lights celebration, which takes place from November to January. During the event, roughly 3 million Christmas lights are switched on each night, creating a twinkling spectacle.
The colorful Collector Inn has nine historic buildings that date back to the 1700s and a stunning pool and patio area.
Image: Joe Vaughn
Where to Stay
If price is no object, you can’t go wrong with a reservation at the Casa Monica Resort & Spa, a towering edifice that debuted all the way back in 1888. Staying here grants you access to the nearby Serenata Beach Club and the Palencia Golf Club, if that’s your thing. Or just stay in and book a day at the spa. The Collector Inn is another excellent choice, with nine historic buildings that date back to the 1700s and a stunning pool and patio area, primed for relaxation. The city is also home to plenty of cozy B&Bs and inns, like Lions and Lanterns, a rehabbed home where each of the six rooms has a unique look and vibe as well as private entrances.
Castillo de San Marcos was built in the 1600s
Image: Barbara Smyers/Shutterstock
What to Do
If you enjoy live music, try to time your visit around a show at the St. Augustine Amphitheatre, an outdoor venue located on Anastasia Island, just a short hop from downtown. The venue has recently hosted top-shelf rock acts like Vampire Weekend, Parquet Courts and The National. During the day, bone up on the city’s incredible history by touring the Castillo De San Marcos, a Spanish fort constructed in the 1600s, and Fort Mose Historic State Park, a settlement for Africans fleeing enslavement by the British in the 1700s that became the first free Black community in what would become the United States.
Where to Eat
St. Augustine’s compact city center is teeming with restaurants and bars that cater to tourists looking for a wild night out. For a quieter meal, head to Preserved, where chef Brian Whittington serves impeccable dishes that blend Southern ingredients with French techniques in a restored Southern mansion. Over at The Floridian, things are more laid-back, with inventive cocktails named after lyrics by the band Silver Jews and novels by Thomas Pynchon. Huge sandwiches, addictive biscuits and satisfying salads round out the menu. The Ice Plant, meanwhile, is located next door to the St. Augustine Distillery, which offers fun and informative tours, and it’s no surprise that the emphasis here is on the drinks. But the food is no slouch, with great bar fare like fried chicken and a short rib grilled cheese.
Know Your History
Fake (but cool) Spanish doubloons are a perfect St. Augustine souvenir.
Image: Studio Casper/istock
A Book to Pack: Harry Crews’ brutal yet lyrical memoir A Childhood: The Biography of a Place mostly takes place in southeastern Georgia and Jacksonville, just up the road from St. Augustine.
A Record to Put On: The city’s huge Sing Out Loud live music festival takes place each September and October. Spin something by The Black Keys or Mumford & Sons, two bands that headline this year’s event.
A Movie to Watch: The 1988 screwball comedy Illegally Yours brought together leading man Rob Lowe and legendary director Peter Bogdanovich for a story set and filmed in St. Augustine. Not a highlight in either’s filmography, but the movie offers a whimsical look at St. Augustine in the 1980s.
Must Have Souvenir: Fake (but cool) Spanish doubloons.
