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Ultimate 10-Day Pensacola Adventure with Nearby Cities

Ultimate 10-Day Pensacola Adventure with Nearby Cities Itinerary

Last updated: 2024 Jun 14

Historic Pensacola Beginnings

Morning
Start your journey with a hearty breakfast at The Leisure Club Coffee & Brunch Bar. Afterward, immerse yourself in history at the Pensacola Lighthouse and Maritime Museum. Climb to the top for a panoramic view of the bay and learn about the area's maritime past.
Afternoon
For lunch, head to Jaco's Bayfront Bar & Grille and savor their fresh seafood. Spend your afternoon exploring the Historic Pensacola Village, where you can visit the T.T. Wentworth Jr. Florida State Museum and several historic homes.
Evening
Dine at The Wine Bar On Palafox and enjoy their extensive wine selection. Afterward, take a leisurely stroll down Palafox Street, often recognized as one of the best streets in the U.S., and explore its shops and galleries.
Bedtime
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Family Fun and Beach Time

Morning
Grab breakfast at Ruby Slipper Cafe to fuel up for a day of excitement. Spend your morning at Sam's Fun City, where you can enjoy amusement rides, go-karts, and water activities.
Afternoon
For a casual lunch, visit BJ's Restaurant & Brewhouse for their wide selection of food and handcrafted beers. Afterward, relax at Pensacola Beach, known for its white sand and emerald waters.
Evening
Experience the vibrant atmosphere of Pensacola Beach Boardwalk. Dine at The Bistro - Eat. Drink. Connect.® and then enjoy live music at one of the beachfront venues.
Bedtime
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Nature and Wildlife

Morning
Start with breakfast at Carmen's Lunch Bar & Tapas. Then, take a drive to the Gulf Islands National Seashore and spend your morning exploring the pristine beaches and coastal habitats.
Afternoon
Pack a picnic from South Market and enjoy it at the park. Afterward, take a guided eco-tour to spot dolphins and other marine life with Key Sailing.
Evening
Head back to Pensacola and have dinner at Union Public House, known for its elegant yet relaxed atmosphere. End your day with a serene walk at Big Lagoon State Park, where you can witness a beautiful sunset.
Bedtime
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Day Trip to Gulf Breeze

Morning
Cross the bridge to Gulf Breeze and have breakfast at 86 Forks Bar + Table. Then, spend your morning at the Gulf Breeze Zoo, where you can see a wide variety of animals in a lush, natural setting.
Afternoon
Enjoy a delightful lunch at Intermission, a local favorite. Afterward, take a scenic drive through the Gulf Islands National Seashore and make a stop at Naval Live Oaks Nature Preserve to stretch your legs and learn about the area's natural history.
Evening
Head back to Pensacola for dinner at McGuire's Irish Pub, a must-visit for its lively atmosphere and delicious pub fare. If you're up for some entertainment, catch a show at the Pensacola Little Theatre.
Bedtime
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Historic and Haunted Evening

Morning
Start with breakfast at O'Brien's Bistro, and then delve into the haunted history of Pensacola with a guided tour by Go Retro. Visit the city's most haunted sites and hear chilling tales of the past.
Afternoon
For lunch, head to George Bistro + Bar for a sophisticated dining experience. Afterward, take a step back in time at the National Naval Aviation Museum, where you can see over 150 restored aircraft and learn about the history of naval aviation.
Evening
Dine at Rosie O'Grady's Inc, and then enjoy an entertaining evening at the Seville Quarter, a historic entertainment complex with multiple bars, live music, and a vibrant atmosphere.
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Culinary Delights and Sunset Cruise

Morning
Enjoy a delightful breakfast at The Wine Bar On Palafox. Then, explore the local farmers' market for fresh produce and artisanal goods.
Afternoon
Have a leisurely lunch at Pensacola Beach House, and then spend your afternoon on a Dolphin Cruise to see these majestic creatures in their natural habitat.
Evening
Dine at Miller's Ale House and then take a romantic sunset cruise aboard a Sail Wild Hearts catamaran, complete with live music and complimentary drinks.
Bedtime
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Day Trip to Orange Beach, AL

Morning
Cross the state line and have breakfast at O'Riley's Uptown Tavern. Then, spend your morning at Adventure Island, a family fun park with go-karts, bumper boats, and mini-golf.
Afternoon
Enjoy a beachside lunch at The Leisure Club Coffee & Brunch Bar, and then relax on the sandy shores of Orange Beach.
Evening
Head back to Pensacola and have dinner at Elbow Room, a local favorite known for its laid-back atmosphere and delicious food. Cap off the evening with a walk at Perdido Key State Park, where you can see the stars reflected in the calm waters.
Bedtime
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Arts and Culture Day

Morning
Start with breakfast at The Bistro - Eat. Drink. Connect.®, and then visit the Pensacola Museum of Art to admire a diverse range of visual arts.
Afternoon
For lunch, head to Union Public House, and then spend your afternoon at the T.T. Wentworth Jr. Florida State Museum, where you can explore the history of Florida through various exhibits and artifacts.
Evening
Dine at South Market, and then enjoy a live performance at the Vinyl Music Hall, a premier music venue in downtown Pensacola.
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Relaxation and Reflection

Morning
Enjoy a leisurely breakfast at The Leisure Club Coffee & Brunch Bar. Then, take a morning yoga class at Abhaya Yoga Center to start your day with mindfulness and relaxation.
Afternoon
For lunch, visit Carmen's Lunch Bar & Tapas, and then spend your afternoon at Pensacola Beach Dog Park, where your furry friend can run and play in the sand.
Evening
Dine at 86 Forks Bar + Table, and then take a peaceful evening walk at Plaza De Luna, enjoying the waterfront views and gentle sea breeze.
Bedtime
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Farewell to Pensacola

Morning
Have a final breakfast at The Wine Bar On Palafox, and then take a morning stroll at Perdido Key Beach, reflecting on the memories you've made in Pensacola.
Afternoon
Enjoy a leisurely lunch at Intermission, and then spend your afternoon at Perdido Key State Park, soaking in the sun and the tranquility of the Gulf Coast.
Evening
Dine at George Bistro + Bar, and then head to Flora-Bama to experience the unique and lively atmosphere of this iconic beach bar, with live music and a range of drinks to choose from.
Bedtime
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