America’s largest estuary, Chesapeake Bay offers miles of stunning shoreline, world-class sailing, and incredible seafood across Maryland and Virginia. The Chesapeake Bay watershed spans six states and Washington, DC: Virginia, Pennsylvania, Delaware, Maryland, New York, and West Virginia, with the bay itself primarily in Maryland and Virginia.
This means that when you visit, you’ll never run out of interesting places to explore! Whether you’re enjoying outdoor adventures, checking out historic towns, or savoring local food, the bay region promises an incredible visit.
A tour we think you'll love
There’s so much to do in Chesapeake Bay, you’ll want to stay forever! Here are some fun things to do on your vacation:
1) Learn To Make Waves With Norfolk Sailing
What makes Chesapeake Bay special? It’s not just another body of water and SailTime Virginia isn’t your average boat charter company. We not only offer tours, but we also let you drive the boat. Our elite instructors welcome both landlubbers and sailing pros who want to refine their skills. You’ll learn how to dock, sail near the coast and navigate the water.
If you’d rather relax, kick back and enjoy the sunshine and bay breezes, set sail on one of our charter yachts. They’re the most luxurious in the region. Have the sailing experience of a lifetime and contact us today!
2) Soak Up The Sun At World-Famous Virginia Beach
Going on a family vacation? A romantic retreat? A solo trip? Virginia Beach has something for everyone. Virginia Beach is a coastal city on Virginia’s Atlantic coast, near where the Chesapeake Bay meets the ocean, on Virginia’s southeast corner.
It has 38 miles of sparkling beaches and the iconic Virginia Beach boardwalk, a bustling three-mile-long stretch lined with restaurants, resorts, souvenir shops, and hotels. Besides the main beach, the city also has:
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Sandbridge Beach – This quiet coastline beach is perfect for birdwatching, spotting playful dolphins, and enjoying peaceful walks along the shore. It’s a great spot to unwind and soak in the natural beauty away from the crowds.
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Croatan Beach – Near the Oceanfront Beach, Croatan Beach has pristine sand and crystal-clear water. A surfers’ mecca for decades, there is a side for surfers and a side for swimmers, so everyone stays safe.
Fun Fact: Camp Pendleton State Military Reservation is near the beach, so you might hear shooting practice nearby. Don’t worry, it’s all safe and part of the training exercises for the military base just a short distance away. Adds a bit of excitement to your beach day!
3) Restaurants – A Foodie’s Paradise
Not only is Chesapeake Bay known for its stunning beauty, but it’s also renowned for its delicious food. The area is famous for its fresh seafood, especially legendary blue crabs. Spanning everything from simple crab shacks to fancy eateries, the bay has restaurants for everyone, including:
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Waterman’s Surfside Grille, Virginia Beach – This is a casual restaurant with outdoor and indoor seating. It also has a patio bar serving tasty seafood, burgers and steaks. Don’t leave Waterman’s without sampling their signature Orange Crush Cocktail. It’s a tangy blend of orange juice, triple sec, lemon-lime soda and orange-flavored vodka splashed over crushed ice.
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Pirates Cove Restaurant and Dock Bar, Galesville, Maryland – Combine scenic, dockside dining and luscious, fresh seafood, and you’ve got Pirates Cove. It’s also a great place to dance the night away to live music on the weekend.
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Oyster Farm Seafood Eatery, Cape Charles, Virginia – Offering spectacular views of the Coastal Virginia bay, the Oyster Farm has an impressive setting and delicious, fresh fare. Try their yummy Virginia oysters, shrimp and grits and she-crab soup.
Fun Fact: Oysters purify water by filtering things like nitrogen, sediment and even some heavy metals. A single oyster filters approximately 50 gallons of water daily, playing a crucial role in maintaining the bay’s health.
4) Discover The Bay’s Epic History
One of the interesting things to do at Chesapeake Bay is exploring its history. The Chesapeake Bay area has a rich heritage embodied by attractions including:
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Chesapeake Bay Maritime Museum – The Chesapeake Bay Maritime Museum is on the bay’s eastern shore in a beautiful, park-like setting. Discover its fleet of over 100 historic boats, 12 exhibition buildings and a working shipyard.
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Whitehall Mansion – Whitehall is an ancestral home built in 1764 for Governor Horatio Sharpe. It’s a gorgeous Georgian-style mansion decorated with antique colonial pieces and reproductions. The historic site is located near Annapolis, Maryland.
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Ft. McHenry National Monument and Historic Shrine – Ft. McHenry is known for its crucial role in the Battle of Baltimore in 1812. The courageous defense of the fort inspired Francis Scott Key to write “The Star-Spangled Banner.” Enjoy the fort’s history with re-enactments and tours.
Fun Fact: The flag that was flown during the Battle of Baltimore measured 30 feet high and 42 feet wide.
5) Shop Till You Drop
If you need a little vacation retail therapy, you’re in the right place. Whether you’re looking for charming local boutiques, funky stores or a large mall, you’ll find it in the Chesapeake region. Get ready to give your credit cards a workout at:
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Greenbrier Mall – Greenbrier has 144 stores including JC Penney, Macy’s and GNC. It also has a food court and a movie theater.
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H.E. Williams Candy Company – Handcrafting old-fashioned hard candy since 1919, the family-owned store is known for its famous Peach Buds, peach-flavored candies filled with chewy coconut. Their candy is inexpensive and a great gift to give your friends.
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Vintage Trixie – Vintage Trixie is a quirky store featuring “all things odd, curious, whimsical and just plain strange.” Trixie carries everything from handcrafted items, old photos, vintage toys and crystals to tapeworms in formaldehyde and spiders in plexiglass. Trixie also offers unique classes including tarot reading and insect pinning.
Ready for some shopping? Check out Chesapeake Bay’s unique boutiques and shops for exclusive finds. Start your adventure today and bring home a piece of the bay!
6) Norfolk, Virginia – A Mix Of Old And New
Norfolk is a vibrant seaport city in Virginia’s Hampton Roads region. The maritime city of Newport News is also located there. The town is home to Naval Station Norfolk, the world’s largest naval base. It also has the North American headquarters of NATO (North American Treaty Organization).
It’s one of Virginia’s largest cities, with about 226,000 people. It is known for its history, culture, arts, entertainment scene and seven miles of gorgeous beaches.
There are limitless attractions to discover in this fantastic city. Here are a few ideas:
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Nauticus and USS Wisconsin – This waterfront maritime museum features interactive exhibits and the enormous World War II battleship, the USS Wisconsin.
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Botanical Garden – The Botanical Garden is a 175-acre wonderland filled with 60 gardens. These include a magical butterfly garden, herb garden and rose garden.
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Ocean View Beach Park – This is a scenic, 6.5-acre park with a boardwalk, tranquil beach and calm waters where you can relax with your family. In the summer, it comes to life with festivals and concerts.
Norfolk’s lively downtown has a great mix of places to eat, shop, and enjoy entertainment. It’s a perfect spot for visitors who want to experience local culture and relax by the water. Whether you’re walking along the waterfront or joining a local festival, Norfolk has something fun for everyone.
7) Explore Chesapeake’s Great Outdoors
Chesapeake Bay is a beautiful place, so it’s perfect for outdoor activities. Whether you’re an avid nature lover or just looking to unwind, there’s something here for everyone. From peaceful strolls along sandy shores to adventurous hikes through lush forests, the bay offers endless ways to connect with the great outdoors. Here are some ways to spend your day:
Enjoy Magical Chesapeake Bay Bird Watching
The Virginia Birding & Wildlife Trail – South Chesapeake Loop is a fantastic place for bird watching. It’s also an important stopover for birds that are flying south for the winter. You might see birds such as:
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Nuthatches – Small birds that climb trees headfirst, easy to spot and fun to watch in the woods.
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Great blue herons – Big, tall birds with blue feathers that stand still by the water waiting to catch fish.
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Ruby-throated hummingbirds – Tiny birds that fly fast and have bright red throats, often near flowers.
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Wood ducks – Colorful ducks that swim quietly on the water, easy to notice because of their bright feathers.
Good To Know: Spring and fall are the best times to see birds that are flying south for the winter. Winter is a great time to see waterfowl.
Scenic Trails And Breathtaking Views – Hiking At Chesapeake Bay
Chesapeake Bay offers many trails, from easy shoreline strolls to difficult climbs up mountains. Here are some trails to explore:
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Dismal Swamp Canal – Contrary to its name, this is an enjoyable hike with a historic canal, bird watching and cypress swamps. It’s 16 miles out-and-back on a comfortable, paved path.
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Terrapin Nature Park – Terrapin Nature Park is an award-winning nature preserve. It has an easy walking trail that meanders through wildflower meadows, woodlands and sandy shores. It also has amazing views of the Chesapeake Bay Bridge.
Parks And Natural Wonders In Chesapeake Bay
The bay’s parks offer great ways to spend time in nature:
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Kiptopeke State Park – Located on Virginia’s eastern shore, Kiptopeke has boat ramps that let you go directly into the Chesapeake Bay. On an important bird migration route, this is one of the parks that’s great for birdwatching.
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Sandy Point State Park – Sandy Point State Park and its beach are renowned for their panoramic bay views. The park has something for everyone, whether you swim, fish, picnic, hike or boat.
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Trap Pond State Park – Trap Pond State Park in the Chesapeake region is known for its beautiful baldcypress swamp. You can follow a paddling trail to explore these graceful trees up close. The park also has hiking trails, camping, biking, fishing and volleyball.
Reel In The Fun – Fishing In Chesapeake Bay
Chesapeake Bay is a dream-come-true for fishermen of all ages and skill levels. The bay offers a wide variety of fish, whether you’re going to catch from a boat or shore. Here are some perfect places to fish:
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Lower Bay – Great spot for speckled trout and Spanish mackerel; perfect for both beginners and seasoned anglers looking for a fun day on the water.
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Middle Bay – Known for flounder and bluefish, this area offers exciting fishing adventures and beautiful views to enjoy while you cast your line.
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Upper Bay – Ideal for catching catfish and striped bass; a favorite among locals who love peaceful fishing spots with plenty of wildlife around.
Unforgettable Boating Adventures On Chesapeake Bay
With a body of water as big as the Chesapeake Bay, there’s no shortage of boating activities:
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Motorboating – A motorboat is great if you want to explore riverfront towns, coves and rivers.
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Kayaking – Glide through small rivers and shallow areas where you can see animals and marine life up close.
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Sailing – The bay is renowned for its sailing. Steer your boat toward a great destination such as Annapolis, “America’s Sailing Capital”.
Come Sail Away With Us!
Ever dream of sailing a boat? Well, SailTime Virginia can make that dream come true. We have courses from docking to guiding a catamaran to coastal navigation. Our seasoned instructors will help you learn while keeping you safe.
As an American Sailing Association (ASA) certified school, you can rest assured that you’ll be getting high quality lessons. If you want to sit back, relax and let someone else steer, we have the area’s most luxurious charter yachts. Your adventure is only a click away!
