St. Augustine (pop. 12,707) is a rare Florida bird. Not only does this laid-back city offer some of the state's most consistent surfing; you can actually afford to buy a bungalow right on the sand (median price, $225,000). The town pier has a beginner-friendly beach break; you'll find bigger waves at the point break at Matanzas Inlet. Can't work in your pajamas? Jacksonville, 40 miles down the road, is home to several Fortune 500 companies.
Matanzas Inlet

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Kite Surfing is so sweet at the Matanzas inlet, and sea kayaking of every type is available out your front door as well. There is a good vibe between the surfers and kiters, and lots of waves for everyone. You'll sweat your sock off on the mainland, but on the water it is sweet, 80+ degree water in the summer, white beaches. As a bonus, Florida has some of the worlds best cave diving (inland). St. Augustine (the city, as opposed to the beach areas like Augustine, Butler & Crescent) is a
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