Folks who come to St. Augustine for the beaches stay for the history—and vice versa. With 42 miles of stunning sugar-sand shores, this city of 13,400 on Florida's northeast coast is also America's oldest continuously occupied European settlement, founded nearly 450 years ago by the Spanish. Colonial influences still permeate the town's graceful architecture and narrow redbrick lanes. That makes for awesome sites, including centuries-old churches, forts, and even Ponce de Leon's storied Fountain of Youth. (Visitors can take a sip from the Spring of Eternal Hope at the archaeological park.)
St. Augustine's dining scene is as vibrant as its history. The Spanish Bakery on St. George Street has served up its famous empanadas and smoked sausage (not to mention the homemade lemon, almond, and cinnamon cookies, and large loaves of fresh bread) for nearly 40 years.
Locals and visitors also revel in those endless sands, beachcombing at Crescent Beach, surfing at St. Augustine Beach (and hitting its many surf shops), exploring beautiful Anastasia State Park by canoe, or playing along the super wide, quiet stretches of the shore that locals try to keep secret—Vilano Beach.
Where to Stay: A historic downtown hotel, the Casa Monica is pure luxury set amid Moroccan fountains and frescoes. Rates start at $199; 888-213-8903 or casamonica.com.