I would like to surprise my husband w/ a long weekend trip to Florida. Any suggestions on nice towns or resorts close to beaches. We like nice restaurants, taking long walks and relaxing. We are going to Naples in May so any other suggestions would be greatly appreciated.

Gotta be South Beach in Miami Beach. We stayed at the Lowes which was wonderful and north enough to be out of the 4am party zone, but close enough to walk to that zone. People watching is hilarious and there are many great restaurants and shopping and of course the beach!

Would you be flying or driving and how long would you have? Also, when would you go as it can be very cold in north Florida December and/or January. Do you want beach walking in bathing suit or sweat suit?

We would be flying and would be staying for 4 nights. We do not necessarily need to be in bathing suits but we do love to walk.

You may want to try Key West. The whole island is 4 miles long by 2 miles wide, so you can walk anywhere. In fact, there is a "walking guide" that can be ordered thru the Chamber of Commerce.
KW has plenty of nice restaurants and plenty of attractions to keep you occupied thru the weekend. Don't miss the sunset celebration every evening at Mallory Square. There are all sorts of entertainers and arts,crafts, food and drinks!

Ft. Lauderdale(Lago Mar or Marriott Harbour Beach); West Palm(The Breakers)

Here are my two cents:

Anna Maria Island
Amelia Island
Sanibel / Captiva

It does depend on when. I went to Amelia Island in early January and it was way too cold to go outside never mind walk on the beach.