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5 Days in Osprey Florida Itinerary

Last updated: 2024 Jun 14

Exploring Historic Spanish Point

Morning

Start your day with a visit to Historic Spanish Point. This 30-acre environmental complex offers a glimpse into Florida's past with prehistoric shell mounds, pioneer-era buildings, and beautiful gardens. It's a perfect way to understand the local history and enjoy some morning tranquility.

Afternoon

Head over to Casey Key Fish House for lunch. Enjoy fresh seafood with a waterfront view. After lunch, take a leisurely walk along the Blackburn Point Park for some scenic views and relaxation.

Evening

Dine at Rosebud's Steak & Seafood House for dinner. Known for its delicious steaks and seafood dishes, it's an excellent spot to end your first day in Osprey.

Bedtime

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Nature and Wildlife Day

Morning

Begin your day with breakfast at Max's Table. This cozy spot is known for its hearty breakfast options. Afterward, visit the Oscar Scherer State Park where you can hike or bike through trails while spotting local wildlife.

Afternoon

For lunch, head to Mad Moe's Sports Pub & Grill. Enjoy classic American fare in a relaxed setting. Post-lunch, explore the park further or rent a kayak to paddle along South Creek.

Evening

Enjoy dinner at Waterfrontoo Restaurant & Bar. With its stunning views and delicious menu options, it's an ideal place to unwind after an active day.

Bedtime

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Beach Day at Nokomis Beach

Morning

Start your morning with breakfast at Scrambles Café before heading out to Nokomis Beach. Spend the morning soaking up the sun or taking a swim in the Gulf of Mexico.

Afternoon

Grab lunch at Pop's Sunset Grill located nearby Nokomis Beach. This waterfront restaurant offers great seafood and American dishes. After lunch, continue enjoying beach activities or take a stroll along the shoreline.

Evening

For dinner, visit Captain Eddie's Seafood Restaurant on your way back from the beach. Known for its fresh seafood and laid-back atmosphere.

Bedtime

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Relaxation and Shopping Day

Morning

Begin your final day with breakfast at The Breakfast Cottage known for its charming ambiance and delicious menu options. Spend the morning relaxing or shopping around Osprey Village shops.

Afternoon

For lunch head over to Bentley’s Boutique Hotel’s restaurant which offers diverse menu options in a stylish setting. Continue exploring local shops or take another walk through nature trails if desired.

Evening

Conclude your trip with dinner at Roessler’s Restaurant offering fine dining experience amidst beautiful garden settings.

Bedtime

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Cultural Day in Sarasota

Morning

Drive up to Sarasota and start your day with breakfast at First Watch on Main Street before visiting The Ringling Museum of Art. Explore its extensive collection of art and beautiful gardens.

Afternoon

Have lunch at Owen's Fish Camp in downtown Sarasota known for its Southern-style seafood dishes. Afterward, visit Marie Selby Botanical Gardens which features stunning horticultural displays.

Evening

End your cultural day with dinner at Indigenous Restaurant which offers innovative American cuisine using locally sourced ingredients.

Bedtime

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