Closest will put you somewhere between Clearwater Beach to the north and St. Petersburg Beach to the south, although there are people who prefer to go just a little farther south, around Sarasota. Both Clearwater and St. Pete are fairly built up "resort beach" kind of places, but there are a lot of smaller communities in between them that are very relaxing and quiet. I used to live within walking distance of Indian Rocks Beach, which is pretty much halfway in between the two, so I spent a lot of time there. Now that I live near Orlando, I don't get to the gulf side as much as I'd like, since the ocean side is closer. If I do go to the gulf for an overnight, I like the Doubletree in North Redington Beach (about halfway between), and the Marriott Suites Sand Key (just south of Clearwater Beach). The Marriott is across the street from the gulf beach, but is right on the Intercoastal and the views are wonderful. There is a Sheraton on the beach side, but I've never stayed there.