All the Trails

Dunedin

Dunedin · West Coast Florida

A charming Gulf Coast gem celebrating Scottish heritage. It is packed with independent craft breweries, seafood joints, and cozy inns right off the Pinellas Trail.

St. Augustine

St. Augustine · Northeast

America's oldest city features narrow, European-style pedestrian cobblestone grids completely closed to cars. It is packed with tavern style music, colonial architecture, and historic hotels.

Key West (Duval Street)

Key West · South Florida

Stretches from the Atlantic to the Gulf. Packed with legendary music venues like Sloppy Joe's and historic inns, you will never need a car here.

Ybor City (Tampa)

Ybor City (Tampa) · West Coast

A historic Latin quarter lined with brick streets and old-school streetcars. It transforms into a massive nightlife hub with live music clubs, cigar lounges, and boutique hotels.

Delray Beach

Delray Beach · South Florida

The ultimate walkable gold standard in South Florida. You can walk straight from upscale boutiques, rooftop cocktail bars, and energetic live music spots all the way down to the ocean beach.

Downtown St. Petersburg (Downtown / Central Avenue / West)

St. Petersburg · West Coast

Featuring a stunning waterfront, massive green parks, craft breweries, and indie music clubs, this area boasts one of the highest walkability scores in the state.

Downtown St. Petersburg (West)

St. Petersburg · West Coast

Just about a mile east but still on Central Avenue, this section is more focused on Breweries, with music venues and a wonerful outdoor environment. The Tampa Bay Ray's play at the stadium here and…

Tarpon Springs (Sponge Docks / Dodecanese Blvd)

Tarpon Springs · West Coast

Famous for its rich Greek culture. You can walk past authentic tavernas, traditional markets, bakeries, and local waterfront lodging.

Sarasota (Downtown / Main Street)

Sarasota · West Coast

A dense urban core right on the bay that offers an excellent arts scene, sidewalk European bakeries, live jazz lounges, and premium hotels.

Winter Park (Park Avenue)

Winter Park · Central Florida

Located just north of Orlando, this oak-shaded avenue faces a beautiful central park. It is famous for upscale French bistros, wine bars, and the historic Alfond Inn.

Mount Dora (Historic District)

Mount Dora · Central Florida

A hillside lakefront town that completely avoids chain businesses. It is highly walkable and allows open containers so you can stroll between tapas bars and historic B&Bs.

Lakeland (Downtown / Lake Mirror)

Lakeland · Central Florida

Beautifully framed by promenade paths and a historic square. It offers local taprooms, vintage cocktail bars, and boutique lodging.

Clermont (Downtown)

Clermont ·

Stuart

Stuart ·

Clearwater Beach

Clearwater Beach · West Coast