Extended Weekend Getaways By Kathy Barnett
Editor-in_Chief
Today, its preserved historic districts, coastal forts, and maritime museums offer visitors the chance to walk through more than 460 years of layered Spanish, French, British, and American history while enjoying scenic waterfront streets and cultural attractions.
Celebrating USA 250: From the 1500s, With Love
As the nation gears up to celebrate the 250th anniversary of independence, Pensacola has teamed with St. Augustine in the “From the 1500s, With Love” campaign, highlighting their roles as America’s earliest European settlements. This collaborative initiative encourages travelers to explore historic landmarks, museums, and educational programs tied to the Semiquincentennial. From colonial forts to restored homes, Pensacola invites visitors to experience firsthand the city that was shaping America centuries before 1776. (floridashistoriccoast.com)
Historic Attractions to Explore
(While our last visit was last fall during the government shutdown, we were unable to visit some of the places we originally planned. However, the beach is always there whenever you go and we did get to explore the historic village with definate intentions to return. )
Historic Pensacola Village
Just steps from downtown, this living history complex preserves more than two dozen historic buildings spanning colonial, territorial, and early American eras. Brick streets, restored homes, and museum exhibits offer a vivid glimpse into daily life from Spanish colonial days through the early 20th century.
Pensacola Museum of History
Located in the former city hall, the museum explores Pensacola’s founding, European control shifts, and its strategic military importance. Artifacts from early Spanish settlements help visitors understand why Pensacola is known as the “City of Five Flags.”
Fort Pickens & Fort Barrancas
Both coastal fortresses offer a window into the Gulf Coast’s strategic past. Fort Pickens, built in the early 1800s, later held Apache leader Geronimo as a prisoner of war, while Fort Barrancas showcases Spanish and U.S. military architecture from the late 1700s onward. Visitors can tour ramparts, tunnels, and defensive structures while taking in panoramic bay views.
Pensacola Lighthouse & Maritime Museum
Climb 177 steps for sweeping views of Pensacola Bay and explore exhibits on shipwrecks, naval history, and maritime heritage that shaped the Gulf Coast.
National Naval Aviation Museum
One of the world’s largest aviation museums, featuring more than 150 historic aircraft. Interactive exhibits connect Pensacola’s centuries-old strategic role to its current status as the “Cradle of Naval Aviation.” The flight line behind the museum is used to view the U.S. Navy Blue Angels’ practice flight demonstrations. Throughout the year, the Blue Angels can be spotted flying high as they practice for their famous air shows and can be caught cutting through the blue skies, front row, on Pensacola beach. For more information on the Blue Angels’ performance schedule in 2023, visit USNavy Blue Angels
Staying Downtown
During our visit, we stayed at the Holiday Inn Pensacola Downtown – Historic District, right on 122 East Main Street. Its location makes it easy to explore historic streets, museums, and waterfront parks on foot. The hotel includes a hot buffet-style breakfast, which is far more than the usual continental fare—self-serve hot selections ensured we started the day energized for full sightseeing adventures. A popcorn machine and cookies were also available in the lobby for evening snacks. Sometimes, you just have to have a quiet escape to rest and wind down from all the exciting travel destinations. This hotel was the perfect spot – clean, quiet and very hospitable.
For travelers who just need to unwind outdoors, take to the sugar-white sand beaches nearby that Pensacola is known for.
Dining Highlight: Tuscan Oven Pizzeria
No visit to Pensacola is complete without a stop at Tuscan Oven Pizzeria, where the open-fire Italian oven is visible from the dining area. Watching pizzas bake to perfection adds to the experience, and the authentic Italian menu does not disappoint. The friendly staff, generous portions, and reasonable prices make it a well-worth-the-stop addition to any extended weekend itinerary. (theTuscanOven.com)
Walking Through History
Pensacola’s historic downtown, anchored by Seville Square, offers travelers a rare opportunity to walk the streets where America’s earliest European settlers once lived. Archaeological discoveries confirm the location of the original 1559 settlement, and combined with restored forts, museums, and interactive exhibits, visitors can engage with centuries of history while participating in USA 250 commemorations. Whether exploring colonial streets or learning about naval aviation, Pensacola makes the past feel alive and inviting.
For more information, please visit https://www.visitpensacola.com
For those looking for more adventure above or below the surface, visitors can enjoy outdoor activities like Pensacola’s SCUBA diving experiences or a fishing expedition to reel in a tide to table meal. Visitors can also take the family to experience a closer look at history at Pensacola’s Historic Village or take the fun inside at the National Naval Aviation Museum, where
Now through summer 2023, New York Yacht Club American Magic will call Pensacola its home base for training, and they are currently considering calling Pensacola a permanent winter training location as they prepare for the America’s Cup in 2024. Visitors can experience the 75-foot sailboat, Patriot, flying over the water at speeds of more than 50mph in Pensacola Bay. Pensacola was chosen as a winter training base due to its geography and wind conditions, making it a perfect spot to train. The America’s Cup is one of the most prestigious sailing race events in the world, featuring boats that are on the cutting edge of sailing technology.
From winter travel to a spring break getaway, or those looking to plan ahead for a visit in late 2023, 
Pensacola has a variety of lodging, food, and entertainment deals available year-round.
Attractions and activities for guests of all interests and abilities include the Pensacola MESS Hall, the Gulf Breeze Zoo, a number of museums and art galleries.
For more information on Pensacola or how to plan a visit in 2023, visit visitpensacola.com.
