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Exploring Perryville, MO in 5 Days Itinerary

Last updated: 2024 Jun 14

Historic Landmarks and Scenic Views

Morning

Begin your Perryville journey with a hearty breakfast at the local favorite Perryville Diner. Fuel up for a morning of exploration at the historic Fort Kaskaskia State Historic Site, where you'll step back in time to the 18th century and learn about the region's early history.

Afternoon

Savor a delicious lunch at Main Street Cafe before visiting the tranquil Chester, IL (Home of Popeye), the hometown of the famous cartoon character. Explore the small town's connection to the beloved spinach-eating sailor.

Evening

As the day winds down, enjoy a scenic dinner at Riverfront Bistro in Chester, overlooking the Mississippi River. Return to Perryville and take a leisurely stroll at Sunset Park, where the name truly comes to life with a beautiful view of the sun setting over the horizon.

Bedtime

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4.51
Chester, IL (Home of Popeye)
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4.54
Sunset Park
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Culinary Delights and Outdoor Fun

Morning

Kick off the day with a visit to Pere Marquette State Park, just across the river in Grafton, IL. Enjoy the morning breeze and take a short hike to immerse yourself in nature.

Afternoon

Head back to Perryville for a delightful lunch at Gourmet Grille. After your meal, spend the afternoon exploring the fascinating Cave Vineyard and Distillery, where you can tour the vineyards and enjoy some exquisite wine tastings.

Evening

For dinner, indulge in the succulent steaks at Steakhouse 45. End your evening with a bit of luck at the Lady Luck Casino in Cape Girardeau, where you can try your hand at the various games and enjoy the vibrant atmosphere.

Bedtime

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4.56
Lady Luck Casino
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A Day of Sights and Bites

Morning

Start with a delicious breakfast at Main Street Cafe before heading out to the Tower Rock Natural Area. Take a moderate hike to the top of Tower Rock for panoramic views of the Mississippi River.

Afternoon

Enjoy a casual lunch at Taco Time and then visit the Trail of Tears State Park to learn about a tragic chapter in American history. Walk the peaceful trails and visit the museum to gain insight into the Cherokee people's journey.

Evening

Dine at Pizza Palace for a taste of authentic Italian cuisine. Cap off the night with a visit to Weingarten Vineyard in Ste. Genevieve, where you can relax with a glass of wine and live music in a serene setting.

Bedtime

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4.80
Trail of Tears State Park
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Wine, History, and Riverfront Dining

Morning

Enjoy a delightful breakfast at Gourmet Grille before embarking on a day of wine tasting. Visit the Charleville Vineyard and Microbrewery in Ste. Genevieve to sample a variety of wines and craft beers.

Afternoon

Have a leisurely lunch at Burger Barn and then explore the Fort Davidson State Historic Site in Pilot Knob. Learn about the Civil War history of the region and walk through the well-preserved earthworks.

Evening

Return to Perryville for a scenic dinner at Sunset Park, where you can enjoy the river view as you reflect on the day's adventures.

Bedtime

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4.20
Charleville Vineyard and Microbrewery
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2.97
Fort Davidson State Historic Site
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Relaxation and Riverfront Dining

Morning

Start your final day with a leisurely breakfast at Riverfront Bistro. Then, take a short drive to Tower Rock Natural Area for a morning hike with stunning views of the Mississippi River.

Afternoon

Return to Perryville for lunch at Perryville Diner. Spend your afternoon exploring the charming shops and boutiques along Perryville Downtown Historic District, where you can find unique souvenirs and gifts.

Evening

As the sun sets on your trip, enjoy a farewell dinner at Steakhouse 45, savoring the flavors of the region. Reflect on your journey as you take a final walk along the river at Sunset Park.

Bedtime

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