Fora’s Take
Discover Pensacola's unexpected charm with a quaint downtown reminiscent of a larger Gainesville. Explore lively bars, restaurants and the Naval Base and Museum, reflecting Pensacola's naval heritage. Relax on white sandy beaches and don't miss the iconic Flora-Bama bar. Ideal for couples seeking a laid-back getaway with coastal vibes and historical intrigue.
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Day 1: Arrival
Arrive in Pensacola with a quick flight, experiencing the vibrant nightlife of downtown. Start the evening at Perfect Plain, a local brewery known for its patio ambiance, live music, and great beers like the South by Northeast saison.
Enjoy other downtown hotspots like O'Rileys, World of Beer and Intermission Bar, each offering a unique atmosphere and local charm.
Insider tip: Stay downtown to easily explore bars on foot and experience Pensacola's lively nightlife scene. Perfect for couples seeking a memorable evening out in Pensacola.
Day 2: National Naval Aviation Museum
Start with delicious donuts from Milton Quality Bakery before heading to the National Naval Aviation Museum, a must-visit with over 4,000 artifacts and 150 restored aircrafts.
Insider tip: Check out the Blue Angels jets and catch their daily practice at 10:30 am if you're lucky.
After the museum, enjoy lunch at the iconic Flora-Bama Bar and Grill, known for its lively atmosphere and the famous Bushwacker drink.
Explore the beach bar's multiple stages and grab dinner back in downtown Pensacola at Seville Quarter, featuring a dueling piano bar for a memorable night out. Perfect for couples looking to explore history and enjoy Pensacola's vibrant scene.
Day 3: Sand Island
A day spent on the beautiful Sand Island in the bay, accessed by renting a Pontoon Boat for a relaxing day on the water.
Insider tip: Ensure your phone is protected from water damage with a waterproof case or a ziplock bag.
Renting a pontoon boat and enjoying a beach day at Sand Island is a must-do for couples looking to unwind and explore Pensacola's scenic bay areas.
Day 4: Relax Before Heading Home
Begin with a delightful brunch at Blackwater Bistro, a charming spot known for its wholesome atmosphere and bottomless champagne option, perfect for a relaxing morning before heading home.
Insider tip: Opt for the bottomless champagne if you prefer a lighter mimosa.
Need to know
For additional brunch options in Pensacola, consider The Fish House or George’s Bistro.
If you're near the beach, Flounder’s Chowder House and Crabs on the Beach are recommended spots.
For those interested in Irish pubs, McGuires Pub is worth a visit.
Lastly, consider attending the Hangout Music Festival in nearby Orange Beach for a lively music experience during your stay.
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This itinerary is part of our ongoing series on travel to Florida. Looking for more travel inspiration? Check out Amanda Peter's guide, Florida's Hidden Gem: Vero Beach