Consider Pensacola
We owned a 30' Hunter in Pensacola for 3 years and loved it. Many sailors we met there feel that Pensacola Bay is one of the best places to sail in the US, I agree, here is why. Cheap, it is a decent city, major interstate comming in all the way to the water, many marinas to choose from, the sailing is fantastic: Tons of National Seashore Beaches, only really accessable by boat. By sailing in the intercoastal and big lagoon you can anchor if protected coves just north of the Gulf. We would anchor, short walk across the beach, no roads and you are sitting on a white sand, uninhabited beach overlooking the gulf of Mexico, on the intercoastal side, calm waters, good swimming, fishing, the best of both worlds. Inside the bay there are at least 5 excellent restaurants that you can easiliy get to by boat, you can get to Pensacola Beach and great nightlife, you can watch the blue angel air showes from your boat, if you want open water sailing you just cruise out into the Gulf, if you like small waves and good winds, Pensacola Bay is the BEST. The restaurants are all within 2-3 hour sails, perfect for company, cruise up in your boat, eat, head back with the sun setting over the water in the East. We own a boat now down here in the Carribbean and the virgin islands are great, but we miss pensacola. I think it is the best place. Lastly, the town of Pensacola (downtown) which is easy to access by boat is a neat place, they have shops, frequently have small festivals, they have a symphony, etc. Neat place.
