The Essential Itinerary: Pensacola, Florida

A three-day guide to exploring the diverse culture, rich history and beautiful beaches of America’s first settlement

  • Mar 14, 2023
  • 1,153 words
  • 5 minutes
A man surfs next to Pensacola Beach Gulf Pier. Though Pensacola’s waters aren’t typically known for surfing, the city usually has between 150 and 200 choppy, rideable days a year.
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Nestled in the westernmost point of the Florida Panhandle lies the quaint town of Pensacola. It’s a place where white quartz sand meets turquoise waters, a bustling downtown meets relaxed oceanfront dwellings, and heritage buildings meet vibrant arts and music festivals.

Alongside boasting incredible natural beauty across 80 kilometres of coastline, Pensacola also takes pride in its rich history – from pre-Civil War forts to the title of America’s first settlement. With countless landmarks to see and an endless amount of shoreline to enjoy, it can be difficult to decide where to begin. So here’s how to make the most of three days in this unique town.

Day 1

10 a.m. | Get caffeinated 

Before you officially set out on a day of exploring, grab a coffee (or two) at one of the city’s many coffee houses. Pensacola has long been known as a “caffeinated” town – with Spanish coffee among the most popular products sold at local markets during the 1800s. Even today, independent coffee shops outnumber Starbucks in this town of more than  53 thousand people.

Alongside many other premiere coffee vendors, Fosko Coffee Barre, The Nest, Bodacious Brew and Buzzed Brew are four shops worth stopping in. From dark roasts to cold brews to oat milk cappuccinos, there are many drinks to choose from. In particular, you can enjoy some brews from Black & White Coffee Roasters at The Nest, tasting the product of founders Kyle Ramage and Lem Butler, who placed first in back-to-back United States Barista Championships in 2016 and 2017.

If you want to try a sip of everything, consider a Seville Savories coffee tour, which provides the chance to experience an abundant range of flavours from specially selected destinations across historic downtown Pensacola.


The cortado, a coffee drink with origins in Spain, consists of espresso mixed with steamed milk. It’s one of many beverages on the menu at The Nest.
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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.

Day 2

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.

Visitors at Fort Pickens can take as long as they want following a self-guided tour.
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The world-famous Blue Angels are based at Naval Air Station Pensacola, and can be seen practicing on select days throughout the year.
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5 p.m. | Time to glow

To wrap up your day, rest your feet with one of Glow Paddle’s LED-lighted clear kayaks. Illuminate Little Sabine Bay with neon colours and glide over the shallow and tranquil waters as you enjoy an experience unique to this area under a sky full of stars.

Glow Paddle offers a magical experience out on the water.
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Day 3 

Noon | Festivals galore 

No matter what time of the year you visit Pensacola, there’s a big chance it might coincide with one of the town’s many festivals and cultural events. Every November, for example, Foo Foo Fest celebrates and showcases all types of art and music for 12 days. This past fall, visitors could enjoy Bubble Alley – a floating public art exhibition featuring 4,000 18-inch diameter multi-coloured vinyl balloons suspended from wire grids. Nearby, at the Pensacola Museum of Art, the Vandals to Vanguards art exhibition spanned the entire second floor and featured contemporary masterpieces by artists such as Andy Warhol and Keith Haring. And at the Pensacola Little Theatre, audience members could enjoy an immersive theatrical production of Unrequited, based on William Shakespeare’s Romeo and Juliet. Initially envisioned as an entity that would help boost cultural tourism in the city, Foo Foo Fest has certainly lived up to its purpose, attracting locals and visitors to the heart of Pensacola every fall.

Bubble Alley was one of many attractions at the 2022 Foo Foo Festival.
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6 p.m. – Enjoy a beverage 

In 1821, Rachel Jackson – the wife of former U.S. president Andrew Jackson – wrote a letter to a friend about the beauty she had discovered in Pensacola. “Pensacola is a perfect plain: the land nearly as white as flour but productive of fine peaches, oranges in abundance, grapes, figs, pomegranates, etc,” she described. “The town is immediately on the bay, the most beautiful water prospect I ever saw, and from 10 o’clock in the morning until 10 at night, we have the finest sea breeze. There is something in it so exhilarating, so pure, so wholesome; it enlivens the whole system.”

The first line of that letter inspired Perfect Plain Brewery’s name, with a passage of Jackson’s letter printed on the wall behind the bar. The love locals have for their city is evident in their pride in their businesses, with Pensacola’s best-rated margarita found at the establishment. Right next door, you can enjoy Scuba Steves at The Well Cocktail Bar – a lounge specializing in modern twists on Floridian cocktails. ⁣

Bartender Drew prepares six Scuba Steves at The Well.
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A Scuba Steve, consisting of cucumber, mint and blue curacao, is a must-order drink.
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Hilton Pensacola Beach, overlooking the Gulf of Mexico, provides stunning balcony views.
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Where to stay in Pensacola: Hilton Pensacola Beach 

For an incredible sunset experience, check in to Hilton Pensacola Beach. Overlooking the Gulf of Mexico, this beachfront hotel offers immaculate views of Pensacola Beach Gulf Pier and the recognizable beach ball water tower. Alongside two outdoor waterfront pools, the hotel is a stone’s throw from the beach below, where you can swim, surf, or lounge on the beach as the sun sets beyond the horizon.


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