Top Things to Do in Pensacola This Fall & Winter (2025 Guide)
Pensacola is known for its sugar-white beaches and vibrant summer tourism, but the fun doesn’t stop when the weather cools down. In fact, the fall and winter seasons in Pensacola are some of the best times to explore the city, thanks to fewer crowds, cooler temperatures, and unique seasonal events.
If you’re planning a trip—or if you’re a local looking for ideas—here are the best things to do in Pensacola during the offseason.
1. Take a Sunset Dolphin Cruise
Yes, dolphin cruises run year-round! Cooler weather makes for crisp, beautiful evenings on the water. Fall sunsets over the Gulf are some of the most colorful of the year, and dolphins are still active in the bays and nearshore waters.
2. Glow Paddle After Dark
One of the most unique activities in Pensacola is night kayaking in clear-bottom kayaks with LED lights. Even in the offseason, Glow Paddle runs nightly tours, letting you see the water in a whole new way. The lights attract fish and give the bay a magical glow—perfect for couples or small groups.
👉 Reserve Your Glow Paddle Adventure
3. Explore Historic Pensacola
Take advantage of the cooler temps by walking through Historic Pensacola Village and the nearby Pensacola Museum of History. You’ll learn about the city’s Spanish, French, and British influences while exploring restored homes, museums, and interactive exhibits.
4. Visit the National Naval Aviation Museum
Rainy day? No problem. The National Naval Aviation Museum is one of the largest in the world, featuring more than 150 restored aircraft. Best of all—it’s free to enter. Keep an eye out for the Blue Angels practice schedule, which often continues into the fall.
5. Enjoy Offseason Events & Festivals
Pensacola’s offseason is packed with local events that showcase the city’s culture:
Pensacola Seafood Festival (September) – Fresh Gulf Coast seafood and live music.
Pensacola Interstate Fair (October) – Rides, games, and fair food classics.
Great Gulfcoast Arts Festival (November) – Over 200 artists, live entertainment, and food vendors.
Pensacola Winterfest (December) – Holiday parades, lights, and family activities.
6. Relax on the Beach Without the Crowds
One of the perks of visiting Pensacola Beach in the fall and winter is the tranquility. You can enjoy a quiet morning walk along the shoreline, go shell hunting, or simply watch the waves roll in without the summer crowds.
Why Visit Pensacola in the Offseason?
Lower prices on hotels and rentals
Cooler weather that’s perfect for exploring
Local vibe with fewer tourists
Year-round activities like dolphin cruises, Glow Paddle, and historic tours
Plan Your Offseason Trip Today
Pensacola in the fall and winter is just as special—if not more so—than the busy summer months. From sunset dolphin tours to holiday events downtown, there’s no shortage of things to do.
