What to do in Chesapeake, VA

Activities, attractions and tours

Colorful sunset over riverside resort in Cambridge Maryland USA
Sundown at the Beach
Baby Canada Goose walking along a beach on the Chesapeake Bay
Blue Heron on a Chesapeake Bay beach at sunset
The Jordan Bridge over the Elizabeth River on the border of Norfolk and Chesapeake Virginia against a beautiful red, purple, pink, and blue sunset

Chesapeake Attractions

Let Expedia help you experience the best that Chesapeake has to offer! If you’re looking for fun itinerary ideas, we can provide you with a list of the top sightseeing attractions, as well as helping you to find unmissable activities. Whether you’re travelling with your family, planning a romantic trip with your loved one, or visiting on business, we’ll make it easy to plan an unforgettable holiday that checks all the boxes.

Activities and Tours

Chesapeake is crammed with must-see places to visit and things to do. We can help you decide where to stay, and make it a breeze to explore the surrounding areas with our guides on where to go, what to see and when to see it. No matter how long your stay, it’s easy to find places of interest in Chesapeake to make sure that you enjoy your experience to the fullest and don’t miss a thing. Leave the local knowledge to us and leave the hassle behind.

If you’re planning a visit, why not check out our handy guides to places of interest in the area? You can browse lists of things to do, learn about the most popular attractions, and get help with planning the details of your trip. Expedia makes it easy for you to check out all the top sights.

Chesapeake Attractions

Expedia has something for everyone, so whether you’re planning to get active on a summer holiday, put a spring in your step with a romantic rendezvous, or pamper yourself with a leisurely winter trip, you’ll find plenty of attractions to keep you entertained. In addition to scheduling local tours, booking reservations and scoring advance event tickets, Expedia makes it easy to book your flight, hotel and rental car in advance, all on one consolidated travel itinerary, making for hassle-free travel and freeing you up to explore the sights of Chesapeake.

Looking for things to do can be time consuming, but we can take the hassle out of planning your holiday. Whether you’re looking to get active in the great outdoors, sample the cuisine or catch up with the vibrant local culture, our guides to Chesapeake attractions ensure that you’ll have a successful trip, whatever the season.

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Most fun & popular experiences in Chesapeake

Tours & day trips

See all 11 activities
City Cruises Norfolk: Signature Brunch Cruise

City Cruises Norfolk: Signature Brunch Cruise

Activity duration is 2 hours
8.8 out of 10 with 25 reviews
Price is CA $133 per adult
City Cruises Norfolk: Signature Brunch CruiseOpens in new tab

Food, drink & nightlife

See all 3 activities
City Cruises Norfolk: Signature Dinner Cruise

City Cruises Norfolk: Signature Dinner Cruise

Activity duration is 2 hours and 30 minutes
7.6 out of 10 with 57 reviews
Price is CA $116 per adult
City Cruises Norfolk: Signature Dinner CruiseOpens in new tab

Cruises & boat tours

See all 3 activities
City Cruises Norfolk: Signature Dinner Cruise

City Cruises Norfolk: Signature Dinner Cruise

Activity duration is 2 hours and 30 minutes
7.6 out of 10 with 57 reviews
Price is CA $116 per adult
City Cruises Norfolk: Signature Dinner CruiseOpens in new tab

Recommended things to do in Chesapeake

Number of things to do
19
Cheapest thing to do on Expedia
Awesome Norfolk Scavenger Hunt: Mystery of Norfolk: CA $21
Top 5 things to do
Half-day tours
With kids

What to do in Chesapeake

Discover the most popular places to visit in Chesapeake

Greenbrier Mall

Greenbrier Mall

You can browse for the perfect souvenirs at Greenbrier Mall during your visit to Chesapeake. Stroll along the beautiful beaches or attend a sporting event in the area.

Greenbrier Mall
Chesapeake Square Mall

Chesapeake Square Mall

You can find the perfect gifts to bring home at Chesapeake Square Mall during your trip to Chesapeake. Discover the top-notch restaurants and acclaimed theater scene in this family-friendly area.

Chesapeake Square Mall
Chesapeake Conference Center

Chesapeake Conference Center

After visiting Chesapeake Conference Center, make a plan to see the other sights and activities in Chesapeake. Experience the area's acclaimed theater scene and great live music.

Chesapeake Conference Center
This is a new bridge over the indian creek in Chesapeake virginia. Near northwest river campground

Chesapeake City Park

Chesapeake City Park is just one of the places to see in Chesapeake, so why not enjoy the other things to explore during your travels? Stroll along the area's beautiful beaches or experience its great live music.

Chesapeake City Park
A bald cypress tree in Lake Drummond in the Great Dismal Swamp Wildlife Refuge, Virginia

Lake Drummond

Commune with nature and explore the great outdoors at Lake Drummond during your travels in Chesapeake. Stroll along the beautiful beaches in this romantic area, or check out its top-notch restaurants.

Lake Drummond
Oak Grove Lake Park

Oak Grove Lake Park

After visiting Oak Grove Lake Park, make a plan to see the other sights and activities in Chesapeake. Experience the area's great live music or attend a sporting event.

Oak Grove Lake Park

Chesapeake Golf Club

Enjoy a round of golf in Chesapeake at Chesapeake Golf Club. Experience the acclaimed theater scene or attend a sporting event in this family-friendly area.

Chesapeake Golf Club

Dismal Swamp Canal

Dismal Swamp Canal is just one of the places to see in Chesapeake, so why not enjoy the other things to explore during your travels? While in this family-friendly area, you can enjoy the coffeehouses.

Dismal Swamp Canal

Chesapeake City Hall

After visiting Chesapeake City Hall, make a plan to see the other sights and activities in Chesapeake. Stroll along the beautiful beaches or attend a sporting event in the area.

Chesapeake City Hall

Explore areas of Chesapeake

Default Image

Deep Creek South

Suburban community with a rural touch, Deep Creek is connected to the historic Dismal Swamp Canal, a National Historic Civil Engineering Landmark. Located along the original U.S. Highway 17 route, it offers easy access to nearby attractions.

Deep Creek South
Greenbrier

Greenbrier

If you're spending some time in Greenbrier, Greenbrier Mall and Chesapeake Arboretum are top sights worth seeing.

Greenbrier
Vertical lift bridge for railroad over the Elizabeth River on the border of Norfolk and Chesapeake Virginia against a beautiful red, purple, pink, and blue sunset

Greenbrier East

While visiting Greenbrier East, you might make a stop by sights like Greenbrier Mall and Jillian's Billiards.

Greenbrier East
Newport News, Virginia, USA

South Norfolk

South Norfolk might not have many top sights, but Chesapeake Conference Center and Greenbrier Mall are two attractions nearby that you can check out.

South Norfolk
Greenbrier West

Greenbrier West

If you're spending some time in Greenbrier West, Bowlero Chesapeake and Rivercrest Play Area are top sights worth seeing.

Greenbrier West
Aerial panorama of Chesapeake Bay Bridge Tunnel at sunset. CBBT is a 17.6-mile bridge tunnel that crosses the mouth of the Chesapeake Bay.

Western Branch North

4/5(1 area review)

If you're spending some time in Western Branch North, Chesapeake Square Mall and Bowlero Western Branch are top sights worth seeing.

Western Branch North

 

Looking for fun things to do nearby? Check things to do near me to find and book the best things to do, fun activities, and top attractions wherever you happen to be.

 

 

Day trip destinations from Chesapeake

Norfolk

Norfolk

Virginia Beach

Virginia Beach

Frequently asked questions

Is Chesapeake worth visiting?
One of the most common things to do in Chesapeake is visit Portlock Galleries at SoNo. Tick this top attraction off your list, then experience more of the area's hiking and nature.
How do I spend a day in Chesapeake?
When you've checked off popular attractions like Jillian's Billiards and Portlock Galleries at SoNo, spend some time exploring the retail and food options in Chesapeake.
What is the top tourist attraction in Chesapeake?
Don't leave without visiting Portlock Galleries at SoNo, rated the top tourist attraction in Chesapeake.
Is three days enough to stay in Chesapeake?
Three days in Chesapeake is enough to visit the city's leading attractions. Many travellers book for two days on average. Portlock Galleries at SoNo, Jillian's Billiards and Chesapeake City Park are among the most popular sights. Like to discover more? Stick around a bit longer to explore nearby hotspots like Norfolk - Virginia Beach.
Is Chesapeake a walkable city?
With major attractions like Portlock Galleries at SoNo nearby, Chesapeake is every bit a place to explore on foot. Like to visit some vibrant neighbourhoods within walking distance of downtown? Greenbrier West is around 3 kilometres away.
What are some activities to do in Chesapeake with kids?
Planning what to do in Chesapeake with kids has never been simpler. Whether you're travelling with toddlers or teenagers, there are plenty of family-friendly attractions to keep everyone happy here.

What to do in Chesapeake for adults?
Whether you're a culture enthusiast, avid foodie or outdoor adventurer, there are plenty of things to do in Chesapeake for adults including Chesapeake City Hall.
Are there free things to do in Chesapeake?
One of the top ways to learn about free things to do in Chesapeake is to speak with a local tour guide. You'll get insider recommendations on interesting neighbourhoods, parks and other major attractions you can enjoy without reaching for your wallet. Portlock Galleries at SoNo is one place that doesn't have an admission fee.