Sunday, April 19, 2026

Great Pedestrian Downtowns in Florida

3 mins read

Garden shop in Naples, FloridaFloridaSnapshot.com had a reader email us from near Canterbury, England. She is looking for a place to come with her husband for a few weeks this winter, to escape chilly Britain. And we don’t blame her.

The issue? They both hate to drive on the right, and they are both looking for walking-oriented places to stay where there is more to do than just a few T-shirt shops. They are Brits after all, and have to have walks! Yet they are also looking for a place on or near the beach.

On the Gulf Coast, places like Naples and St. Petersburg are the places that would be best for walking and extended stays, though obviously Sarasota’s Lido Key and Sarasota downtown are options as well. Also good places on the Atlantic are Delray Beach and Stuart. Of course, big cities like Fort Lauderdale and Miami Beach are easy for walking, but their pace is a bit fast.

A few ideas:

  • Sarasota, while not on the beach, is on Sarasota Bay, and shuttles to the beach are easy to use and inexpensive (just don’t say the service is regular, as the bus company is called SCAT). Downtown Sarasota is vastly improved from even 10 years ago, when it had a slightly seedy and empty feel, and has all manner of national and local retailers, multiplex movie theaters and even an art house theater, as well as live opera and theater. It also has a Whole Foods supermarket downtown, as well as dozens of restaurants. It also has a good library, the Selby Library.
  • Lido Key, Longboat Key and Anna Maria Island. Sarasota’s legendary island Longboat Key is great, obviously, but it is much more of a resort feel than a town feel. That’s great for some, but you have to REALLY love golf. Also north of Longboat Key is Anna Maria Island, with its delightful old cottages and laid back feel. Lido is loved for the beaches, and St. Armand’s Circle, the shopping district.
  • Naples. Also on the Gulf of Mexico is Naples. Downtown Naples is close to the water, and all things downtown are walkable. It is a large downtown for a medium-sized city, and the shops and restaurants are first rate. It has suburban shops and two in town shopping districts, the Third Street South district and the Fifth Avenue South district. Because of the immense wealth there, it has all the luxury places to eat and shop, but it is still not exorbitant if you look for the places the locals eat (pubs, etc). If you stay, there are a number of very nice one bedroom very nice flats that rent by week or month, all within walking distance. Obviously, Jan, Feb and March are most expensive. The main downtown area is not gated off at all, and quite democratic. Just because Naples is full of people who are rich, it doesn’t mean that the town feels inhospitable. In fact, the beach is medium sized, and not overly crowded. You will see all walks there, including Mexican migrants on their weekend family excursions, who feed parking meters just like the rest of us.
  • St. Petersburg. We would also recommend downtown St. Petersburg, but there is no beach. It has the benefit lots of museums and restaurants. It is also a big city, so you get a real metropolitan feeling and blocks and blocks to walk. It is not on the beach, but on Tampa Bay. It was home to Jack Kerouac.
  • Boca Grande. If you want secluded and quiet old town, Boca Grande in Charlotte County and Lee County is nice, but it is limited in terms of shopping and walking. This town on Gasparilla Island has a good small library, and a few restaurants. The Gasparilla Inn is legendary. The Boca Bay resort, developed by the railroad company CSX, is a good bet, too. Try the Temptation Restaurant.

On the Atlantic

  • Delray Beach in Palm Beach County is south of Palm Beach and Lake Worth, and north of Boca Raton. Anyone who visits will be charmed by the drawbridge in the middle of town. Good historical society, exhibits, and a downtown with NO chain shops. Great reastaurants and old hotels, as well as fancy Marriott. Delray is south of Palm Beach and North of Boca Raton, so it is fancy without looking new money.
  • Stuart is also a favorite walkable town on the East Coast. It is north of Palm Beach County and the Jupiter Tequesta area. The streets are all walkable.