The Old Soul of St. Augustine

A cultural kaleidoscope illuminated by pure Florida sunshine sets this exceptional small town apart from the rest

- VALERIE RAINS

Anyone who's ever loved a town knows its worth can't be counted in a census or measured in square miles. Instead, it's defined and distinguished by the precise combination of landmarks, lore, and even language that just couldn't exist in any other place of any size. With its Spanish colonial heritage, melting-pot population, and wealth of Gilded Age relics, there's truly no other town cut from the same cloth (or, perhaps, patchwork) as St. Augustine, Florida, this year's Best Small Town in the South. So when it came time to craft an itinerary through one of America's oldest destinations, I relied on the folks who know and love it best to help chart my path. I'd start each day with an expert recommendation and then strike up conversations on the go to determine where to head next. From picturesque brunch spots to windswept beaches, St. Augustine's fan club never steered me wrong.

DAY 1 Downtown Deep Dive

You wouldn't need an insider to point you toward St. George Street the steady foot traffic flowing through this pedestrian thoroughfare lined with colonial-era storefronts is as effective as a neon sign. But to find the sweet spot worth a stop amid all the souvenir shops and "olde tyme" businesses, I turned to Alex Drywa, whose small-group St. Augustine Experiences tours have consistently won both rave reviews and repeat customers.