There’s something effortlessly glamorous about the Fenway Hotel — like stepping into a slice of 1920s Florida with a modern coastal twist.

Originally opened in 1927, this historic waterfront hotel helped put Dunedin on the map as a luxe winter escape. Today, it blends vintage charm with boutique sophistication — Art Deco details, airy coastal design, and golden-hour views over the Intracoastal.

The rooftop bar is the real crown jewel — sunset cocktails here feel cinematic, with sailboats drifting by and that soft Gulf breeze setting the mood. Whether you’re planning a romantic staycation, a girls’ weekend, or just stopping in for drinks, the Fenway delivers.