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Exploring Chesapeake, VA in 7 Days

Viewed by 153 travelers

Day 1: Downtown Discovery

Chesapeake, VA

8:00AM

Breakfast at The Egg Bistro

Start your day with a delicious breakfast at The Egg Bistro, known for their hearty omelets and pancakes.
$$, 1 hour

10:00AM

Visit Great Dismal Swamp National Wildlife Refuge

Explore the serene beauty of the Great Dismal Swamp, home to diverse wildlife and beautiful nature trails.
Free, 2 hours

1:00PM

Lunch at Cutlass Grille

Enjoy a taste of the Caribbean at Cutlass Grille with their flavorful jerk chicken and plantains.
$$, 1 hour

3:00PM

Shop at Greenbrier Mall

Indulge in some retail therapy at Greenbrier Mall, offering a variety of shops and boutiques.
$$, 2 hours

6:00PM

Dinner at Passion The Restaurant

End your day with a gourmet dinner at Passion, known for their seafood dishes and elegant ambiance.
$$$, 1.5 hours
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Day 2: Western Branch Wonders

Chesapeake, VA

9:00AM

Breakfast at The Egg Bistro

Fuel up for the day ahead with another delicious breakfast at The Egg Bistro.
$$, 1 hour

11:00AM

Explore Oak Grove Lake Park

Spend the morning at Oak Grove Lake Park, a picturesque spot for a leisurely walk or picnic by the lake.
Free, 2 hours

1:00PM

Lunch at Mi Hogar

Try authentic Mexican cuisine at Mi Hogar, known for their flavorful tacos and fresh guacamole.
$, 1 hour

3:00PM

Visit Chesapeake Arboretum

Discover the beauty of nature at Chesapeake Arboretum, featuring a variety of plants and walking trails.
Free, 1.5 hours

6:00PM

Dinner at The Butcher's Son

Enjoy a hearty dinner at The Butcher's Son, known for their steaks and comfort food dishes.
$$, 1.5 hours
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Day 3: Deep Creek Delights

Chesapeake, VA

8:30AM

Breakfast at Sunrise Pizzeria Family Restaurant

Start your day with a cozy breakfast at Sunrise Pizzeria, known for their delicious pancakes and breakfast pizzas.
$, 1 hour

10:00AM

Explore Deep Creek Lock Park

Discover the historic Deep Creek Lock Park, featuring a scenic canal and walking paths.
Free, 2 hours

1:00PM

Lunch at The Barking Dog

Savor gourmet hot dogs and creative toppings at The Barking Dog for a unique dining experience.
$, 1 hour

3:00PM

Visit Battlefield Park

Explore the Civil War history at Battlefield Park, home to historic sites and walking trails.
Free, 2 hours

6:00PM

Dinner at Lockside Bar & Grill

End your day with a waterfront dinner at Lockside, offering fresh seafood and scenic views.
$$, 1.5 hours
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Day 4: Discovering Greenbrier

Chesapeake, VA

9:00AM

Breakfast at Zeke's Beans & Bowls

Start your day with a healthy breakfast at Zeke's, known for their acai bowls and specialty coffee.
$, 1 hour

11:00AM

Shop at Towne Place at Greenbrier

Explore the shops and eateries at Towne Place, a vibrant shopping destination in Greenbrier.
$$, 2 hours

1:00PM

Lunch at Baker's Crust

Enjoy a delightful lunch at Baker's Crust, known for their artisanal sandwiches and freshly baked bread.
$$, 1 hour

3:00PM

Visit Chesapeake City Park

Relax in the green spaces of Chesapeake City Park, with walking trails and recreational areas.
Free, 2 hours

6:00PM

Dinner at The Butcher's Son

Return to The Butcher's Son for another delicious dinner, this time trying their signature burgers.
$$, 1.5 hours
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Day 5: Historic Great Bridge

Chesapeake, VA

8:30AM

Breakfast at Sunrise Pizzeria Family Restaurant

Enjoy breakfast at Sunrise Pizzeria before heading to the historic Great Bridge Battlefield & Waterways Museum.
$, 1 hour

11:00AM

Explore Great Bridge Lock Park

Visit Great Bridge Lock Park for a scenic stroll along the Intracoastal Waterway and wildlife viewing.
Free, 2 hours

1:00PM

Lunch at The Culpepper

Indulge in Southern comfort food at The Culpepper, known for their fried chicken and homestyle sides.
$$, 1 hour

3:00PM

Tour Historic South Norfolk

Explore the charming streets and historic buildings of South Norfolk, reflecting the city's past.
Free, 2 hours

6:00PM

Dinner at The Plaid Turnip

End your day with a farm-to-table dinner at The Plaid Turnip, featuring seasonal dishes and local ingredients.
$$$, 1.5 hours
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Day 6: Hickory Hideaways

Chesapeake, VA

9:00AM

Breakfast at Metro Diner

Start your day with a hearty breakfast at Metro Diner, known for their classic American breakfast options.
$$, 1 hour

11:00AM

Visit Northwest River Park

Explore the natural beauty of Northwest River Park, offering hiking trails, canoeing, and a petting zoo.
$, 2 hours

1:00PM

Lunch at Big Ugly Brewing

Enjoy a casual lunch at Big Ugly Brewing, pairing craft beers with their delicious pub fare.
$$, 1 hour

3:00PM

Discover Hickory Ridge Farm

Experience farm life at Hickory Ridge Farm, where you can pick seasonal produce and enjoy farm activities.
$, 2 hours

6:00PM

Dinner at The Cutting Edge Cafe

Enjoy a cozy dinner at The Cutting Edge Cafe, known for their creative dishes and warm atmosphere.
$$, 1.5 hours
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Day 7: South Mills Serenity

Chesapeake, VA

8:30AM

Breakfast at The Egg Bistro

Start your day with a familiar favorite breakfast at The Egg Bistro before heading to South Mills for a day of tranquility.
$$, 1 hour

10:00AM

Explore Dismal Swamp Canal Trail

Embark on a peaceful hike or bike ride along the Dismal Swamp Canal Trail, surrounded by nature.
Free, 2 hours

1:00PM

Picnic at Northwest River Park

Enjoy a picnic lunch amidst the scenic beauty of Northwest River Park, with waterfront views and lush greenery.
$, 1 hour

3:00PM

Visit Cornland School

Learn about the local African American history at the historic Cornland School, a preserved one-room schoolhouse.
Free, 1 hour

6:00PM

Dinner at The Culpepper

End your day with a comforting dinner at The Culpepper, savoring their classic Southern dishes.
$$, 1.5 hours
Find Hotels in Chesapeake
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12 days in Chesapeake, VA — December
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