This 450-year-old city on Florida's Gulf Coast is feeling brand-new, with a walkable downtown, great theaters, and up-and-coming neighborhoods.
1 of 6Photographer: Shooter/Alamy
Like much of the Florida Panhandle, Pensacola's beaches have powdery, sugar-white sand. But what sets it apart from other cities along this stretch of the Gulf Coast is its deep sense of history. Founded in 1559, Pensacola has rigorously preserved its historic architecture, from New Orleans- and Spanish-influenced buildings downtown to neighborhoods chockablock with Craftsman bungalows. Maintaining the historic core has paid off, as small businesses, new restaurants, and an emerging art scene take off.
2 of 6Map: Matt Caserta
Anchored by the renovated and expanded 1925 Spanish Baroque Saenger Theatre, this street in studded with restaurants, bars, and clubs.
North Hill, East Hill, Old East Hill
A dense collection of early-20th century bungalows attracts families to the historic residential neighborhoods.
Santa Rosa Island
Pensacola looks across the bay to the town of Gulf Breeze and Pensacola Beach, located on this razor-thin barrier island. You can get from downtown to the beach in eight minutes by car (paying a dollar toll on the bridge).
3 of 6Photographer: Chris Ellenbogen
There are plenty of beaches to choose from, but Fort Pickens—located on the western edge of Santa Rosa Island, and part of the protected Gulf Islands National Seashore—features silky-smooth sand and secluded, undeveloped dunes.
4 of 6Photographer: Chris M. Rogers
Where to Eat & Drink
The Leisure Club
Hit this retro-styled spot for expresso or brunch (pictured). 1151 Office Woods Drive, 850-912-4229 ortheleisureclub.net.
Jaco's Bayfront Bar & Grille
With views of Pensacola Bay and the Palafox Pier Marina, Jaco's is the spot for sunset dining. 997 S. Palafox St., 850-432-5226 orjacosbayfrontbarandgrille.com.
A local favorite for for surf-and-turf fare, such as steak topped with fried green tomatoes and crabmeat. 400 S. Palafox St., 850-469-9898 orjacksonsrestaurant.com.
5 of 6Photographer: Chris Ellenbogen
Where to Stay
Solé Inn and Suites
The inn is located in the shell of an old roadside motel (with the pool in the parking lot), but the building has been updated with sleek interiors. Rooms start at $89/night, 888-470-9298 orsoleinnandsuites.com.
Lee House Bed & Breakfast
Recently built in the historic district in the Old Florida style, with two levels and wraparound porches, the inn features nine suites with chic European linens, WiFi, and iHome audio systems. Rates start at $165/night, 850-912-8770 orleehousepensacola.com.
6 of 6Photographer: Chris Ellenbogen
What to Do
Try catching a show at the Saenger Theatre (pictured at left), home to performances ranging from Broadway's Monty Python to the Pensacola Symphony Orchestra. Take the kids to a musical at the Pensacola Little Theatre. Browse the paintings at Pensacola Museum of Art in the Old City Jail building. Attend one of the many local events, such as the Pensacola Crawfish Festival in late spring, or head to the Palafox Farmer's Market on Saturdays. And, there's always the beach.