Historic Districts

If Southwest Florida did an ancestry test, it would discover in its genes Indigenous Americans, immigrants, creative geniuses, railroad and hotel magnates, soldiers, pioneers and adventurers. Diversity and vintage architecture keep the past alive in five of the region’s historic districts.

Downtown Naples

Fifth Avenue South and Third Street South have held the heart of historic Naples since the 1920s when distinguished visitors and winter residents arrived by boat to the Naples Pier and traded with Seminole natives, where today glamour shops sell jewelry, fashions, home accessories and other wares in historic buildings.

The neighborhoods, too, are known for their fashionable sidewalk restaurants and cultural venues. Famed downtown Naples has spread in recent years to include the Naples Design District. Like nearby Fifth Avenue South, it blends vintage vibes with modern trends and is famed for its galleries, home craftsmanship and contemporary spots to eat, socialize and spend the night in luxury.

Downtown Bonita Springs

Old 41 Road has seen heydays come and go ever since its youthful tourism era. Today, its magnetism has returned, built on the very foundation of historic hotels and the nature attraction that brought the Everglades wilds to a main street in the 1930s, it’s now undergoing a rejuvenation as Wonder Gardens.

Today, Shangri-La Hotel stands as a symbol of Bonita Springs’ healthful reputation and 20s alluring hospitality. Around it, historic buildings have turned into fine restaurants, craft breweries, cocktail lounges and a new food truck park that overlooks the town’s lifeblood, the Imperial River. Discover here Bonita Springs’ deep roots at Riverside Park, devoted to olden days and new waves of festivity and vigor. Looking to the futILure, the town continues to build a party reputation as Sugarshack Downtown – a combo live music stage, craft brewery and restaurant – prepares to open any minute now.

Fort Myers Historic River District

Like many downtowns of a certain age, there came a time when Fort Myers’ urban sprawl left its core looking a little abandoned. Wiser heads prevailed, however, to save the Historic River District with all its vintage gems from falling victim to trends and “out with the old” attitudes.

Thanks largely to the endurance of the Edison & Ford Winter Estates at its fringe, the historic downtown was renewed. An old, handsome federal building became an art center, a vaudeville house circa 1915, and a theater. Stores and restaurants moved into buildings dating back to the late 18th century, as was the case with The Veranda, a gracious restaurant that lives in two pioneer homes.

Bars and lounges today draw a young crowd to frenzied hangouts such as the Sky Bar and Downtown Social. The new Bay Street Yard takes the party outside.

The Historic River District continues to take full advantage of its waterfront beauty and bygones intrigue as hotels move in and people of all ages come out for its monthly street parties and annual festivals.

Downtown Punta Gorda

The wide and placid Peace River separates old from new in Charlotte County, where Punta Gorda dates to the 19th century and tells its story through a series of vibrant murals. Marion Avenue, the pretty and picturesque main street, lines up eclectic shops and eateries like The Perfect Caper and Celtic Ray Public House, each with its unique charm. It overlooks the river and the county’s newest attraction on the opposite shore – Sunseeker Resort Charlotte Harbor, a vital entertainment center for visitors and residents alike.

Along the riverfront in Punta Gorda, Wyvern Hotel’s rooftop bar and Four Points by Sheraton with TT’s Tiki Bar maintain the lively atmosphere. Laishley Park and its crab house cater to sea enthusiasts and families, complementing the extensive bike trails along the river.

Boca Grande

The railroad, tarpon fishing and the grande dame Gasparilla Inn first brought captains of industry to tiny, island Boca Grande at the turn of the century. The railroad has transformed into a path for bicycles and golf carts, while the historic depot holds boutiques, an ice cream shop and Keylime Bistro.

Within its three-block-long area, downtown Boca Grande holds historic gems well beyond the circa-1913 Gasparilla Inn. You can easily stroll or bike around its beautiful churches, pink-hued Johann Fust Library and handsome Community House, then along canopied Banyan Street and to the beach. The Port Boca Grande Lighthouse & Museum encapsulates local history, overlooking tarpon-rich Gasparilla Pass. n