12 p.m. – Take a stroll through history
Immerse yourself in history as you walk down Palafox Street, the core artery of Pensacola’s downtown community which runs north and south through the city. Lined with 19th-century buildings and sprawling oak trees, this stretch – known as the gateway to Pensacola – is home to many local businesses, restaurants and entertainment.
With a hot coffee in hand, follow The America’s First Settlement Trail – a nearly five-kilometre marked path with 20 stops highlighting the history of the town dating back as early as 1756. As you’ll soon learn, Pensacola is often referred to as “The City of Five Flags” – a reference to the five governments who have ruled the city since the first non-Indigenous visitors landed in America in 1559: the Spanish, the British, the French, the Confederacy and the United States.
Along your walk, you will pass the site of the formal transfer of Florida from the rule of Spain to the United States, and further south, beyond the official path, you can find the statue of Don Tristán de Luna y Arellano. This Spanish explorer led the effort to establish Pensacola in 1559. Though this is six years before St. Augustine – the oldest city in the United States – was established, the two cities have continuously competed for the title of the most ancient metropolis, as Pensacola wasn’t continuously occupied in its early years.
Nonetheless, Pensacola takes pride in its deep history, with a collection of over 20 historical buildings and museums to explore along Historic Pensacola Village.
10 a.m. | Go Gulfing
Driving along the Gulf Islands National Seashore is otherworldly. Bright, sugar-white sand dunes – I like to call them Florida snowbanks – hug both sides of the winding road, with the Gulf of Mexico on one side and Pensacola Bay on the other. Experience the longest area of protected coastline in the United States as you make your way towards Fort Pickens – a massive military fortress on Santa Rosa Island built in 1834 to defend the bay. A five-bastion complex, Fort Pickens once housed Union troops and the Apache leader Geronimo. History buffs will surely enjoy exploring its winding tunnels, low ceilings and weathered brick arches.