By
Travel & Leisure
updated 11/15/2011 1:15:39 PM ET 2011-11-15T18:15:39

Day 1: Jacksonville to St. Augustine (38 miles)

Fly into JAX, then drive south along the coast to the oldest European settlement in America.

Lunch: Angie’s Subs
Memorable sandwiches in a nondescript mini-mall popular with surfer types. 1436 Beach Blvd., Jacksonville Beach; 904/249-7827; lunch for two $15.

See: Castillo de San Marcos
Imposing 17th-century fort that makes a good jumping-off point for a walking tour of St. Augustine’s historic downtown.

Snack: The Hyppo
Artisan ice pops made from seasonal ingredients (try the pineapple-cilantro) and modeled after Mexican paletas. 15 Hypolita St., St. Augustine; 904/217-7853; ice pops for two $7.

Dinner: The Floridian
Husband-and-wife team Jeff McNally and Genie Kepner put their own spin on trusted Southern favorites. Grab a bottle of biodynamic wine from the bar next door to pair with the shrimp and grits. 39 Cordova St., St. Augustine; 904/829-0655; dinner for two $40.

Stay: Casa Monica Hotel
Great Value Moorish-style grandeur in an 1888 property once owned by railroad tycoon Henry Flagler, who developed much of Florida’s eastern coast. Doubles from $199.

Best Town Crawl: The Tasting Tours’ Vittles and Vino($76), a three-hour feast through the city’s top restaurants and food shops.

Copyright © 2012 Amex

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