I should admit at the outset that I’m rather biased toward St. Augustine. My wife and I fell in love there. It was October 2008, a brief respite from the election season I was reporting on, and our first vacation together. We ate at Collage, one of those meals you remember for years afterward. We indulged at Spa Laterra in the World Golf Village, availing ourselves of the pool and the hot tub and the cabanas and copious amounts of wine. We drank and danced at Tini Martini Bar, where Sinatra filled the room and (too much) vodka filled our glasses. We walked around the über-quaint historic district’s seemingly endless array of shops. (And we stayed at a Days Inn well outside of town, because we were poor.) We held hands and remarked on how at ease we felt. It was all very charming.

In the years since, we’ve gone back many times, whenever the opportunity presented itself. We’ve sought out new places and experiences (the Ice Plant Bar, Sangrias Wine & Tapas Bar) and revisited favorite haunts. And it continues to be charming each and every time, in a way few tourist traps (and St. Augustine is most certainly a tourist trap) do.

You can’t talk about the Ancient City without talking about its history, about the fact that it is the oldest continually operated European-established settlement in the New World, about Castillo de San Marcos and the St. Augustine Lighthouse and even the seminal role this place and its people played in the Civil Rights Movement. You can sense that history on its streets and in its storefronts, almost like it’s infused in its very being, and maybe that’s part of it. But I like to think there’s something else, something almost magical about this little city, something that cues all the right endorphins, something that, as old as St. Augustine is, makes the world feel new again. Then again, I am biased.




Acapulco Mexican Restaurant (12 Avenida Menendez)

The Black Molly Bar & Grill (504 W. Geoffrey St.)

Candlelight South (1 Anastasia Blvd.)

Collage (60 Hypolita St.)

Columbia Restaurant (98 St. George St.)

The Floridian (39 Cordova St.) 

Georgie’s Diner (100 Malaga St.)

Hurricane Patty’s (69 Lewis Blvd.)

Michael’s Tasting Room (25 Cuna St.)

Sangrias Tapas & Piano Bar (35 Hypolita St.)



A1A Ale Works (1 King St., Ste. 101)

The Ice Plant (110 Riberia St.)

Kings Head British Pub (6460 U.S. 1 N.)

San Sebastian Winery (157 King St.)

St. George Tavern (116 St. George St.)

Tini Martini Bar (24 Avenida Menendez)



Anastasia Books (81C King St.)

Antique Warehouse (6370 U.S. N. Highway 1)

High Tide Gallery (51 A&B Cordova St.)

St. Augustine Outlets (500 Outlet Mall Blvd.)

St. Augustine Premium Outlets (2700 S.R. 16)

The Way We Were (86 Charlotte St.)



Anastasia State Park 

Spa Laterra @ WGV (500 S. Legacy Trail)

St. Augustine Alligator Farm (999 Anastasia Blvd.)



Castillo de San Marcos (1 S. Castillo Drive)

Crisp-Ellert Art Museum (48 Sevilla St.)

Basilica Cathedral of St. Augustine (38 Cathedral Place)

Lightner Museum (75 King St.)

Mill Top Tavern & Listening Room (19 1/2 St. George St.)

St. Augustine Lighthouse & Museum (81 Lighthouse Ave.)