Just 30 minutes from Fort Myers, Pine Island is the largest island on Florida’s Gulf Coast, yet it still feels like a hidden gem. Unlike nearby Sanibel and Captiva, you won’t find sandy beaches here. Instead, you’ll discover mangrove shorelines, tropical fruit farms, and a resilient community dedicated to preserving Pine Island’s Old Florida charm.

Coastal charm, deep-rooted history, and Old Florida character make Fernandina Beach a must-visit. Located on Amelia Island’s northern tip, this historic town helped launch the modern shrimping industry and is part of the famed Isle of Eight Flags. With a walkable 50-block historic district and the oldest hotel in Florida, it’s the perfect place to slow down and explore.

Just 30 minutes west of Orlando, Winter Garden feels like a total change of pace. With its small-town charm and walkable, historic downtown, it’s the kind of place you’ll want to keep coming back to. Here are six spots worth checking out on your next visit!

Micanopy may be small, but it holds a big place in Florida’s history as its believed to be the state’s oldest inland town. Just south of Gainesville, it’s the perfect escape, where time slows down and antique shops line the streets.