Old Naples should be enjoyed at a strolling pace, credit cards at the ready. Fifth Avenue South and nearby Third Street South in downtown Naples combine charm, historic opulence and elegance. You’ll find the aura of small-town friendliness and historical landmarks amid the sophisticated boutiques, neighborhood shops, art galleries, antique shops, dining destinations and colorful buildings of downtown Naples. Enjoy the romance of Third Street in historic Old Naples, located in the southern section of Naples, between Naples Bay and the Gulf of Mexico. Fifth Avenue South is Naples’ main street and has become a popular place for visitors and residents alike to stroll along the freshly landscaped promenades and enjoy shopping and sidewalk dining.