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Chesapeake Beach

Looking to soak up some sun and sand on the Chesapeake Bay? Look no further than Chesapeake Beach! With its charming boardwalk, water park, and seafood restaurants, this seaside town is the perfect spot for a relaxing beach getaway. Don't miss the annual Rod and Reel Tournament for some fishing fun!

Recommendations

Landmark4.3/5

North Beach Boardwalk/Beach

Welcome to the North Beach Boardwalk and Beach! Grab your sunscreen and flip-flops for a day of sun, sand, and sea. Enjoy scenic views of the Chesapeake Bay, stroll along the picturesque boardwalk, and cool off with a dip in the water. Don't forget your camera for Insta-worthy snapshots!

Culture4.7/5

Chesapeake Beach Railway Museum

Hop aboard nostalgia at the Chesapeake Beach Railway Museum! Nestled at 4155 Mears Ave, this charming spot unveils the delightful history of the railway that once chugged through Chesapeake Beach. Explore fascinating exhibits, vintage artifacts, and the cutest train-themed memorabilia. It's a fun-filled pit stop that’ll have you chugging along memory lane—perfect for the young and young-at-heart!

Landmark3.9/5

Chesapeake Beach Water Park

Welcome to Chesapeake Beach Water Park, where the sun shines bright and the waves are just right! Nestled in Chesapeake Beach, Maryland, this family-friendly park offers thrilling water slides, lazy river relaxation, and plenty of snack shacks to keep you fueled up. Don't forget your sunscreen and get ready for a splashtastic time!

Eat$$$4.4/5

Skipper's Pier Restaurant & Dock Bar

Eat4.4/5

Chesapeake Market & Deli

Chesapeake Market & Deli is a beloved local gem, known for its fresh seafood, homemade sandwiches, and charming atmosphere, making it a must-visit spot for both locals and visitors in North Beach, MD.

Eat$$3.9/5

Abners Crab House

Eat$$3.9/5

Rod 'N' Reel Restaurant

Eat$$4.2/5

Traders Seafood Steak & Ale

Craving a hearty meal by the water? Look no further than Traders Seafood Steak & Ale in Chesapeake Beach, MD! Indulge in fresh seafood, juicy steaks, and a wide selection of ales while taking in the picturesque views of the bay. Don't forget to snap a selfie with your mouthwatering meal!

Eat$$4.4/5

the bakist

Eat$$4.6/5

Cold Stone Creamery

Eat$$$4/5

City Sliders Steakhouse at the Westlawn Inn

Eat$2.2/5

Dunkin'

Stays

Stay4.5/5

Rod 'N' Reel Resort

Stay5/5

Chesapeake Beach Art House

The Chesapeake Beach Art House is a vibrant cultural hub, showcasing local artists and unique exhibitions, while offering breathtaking views of the Chesapeake Bay, making it an iconic destination for art enthusiasts and nature lovers alike.

Stay4/5

Breezy Point Beach & Campground

Nestled along the stunning Chesapeake Bay, Breezy Point Beach & Campground offers beautiful sandy beaches, scenic views, and family-friendly activities, making it a perfect destination for relaxation and outdoor adventure.

Things To Do
Provided by

5/5

48 h

Exclusive 2-Day Private Journey: Marrakech to Berber Villages

This is a private Atlas trekking tour so it means nobody else will travel in your group. You will discover the high mountain in Morocco and north Africa on these two days by the climb in Mt Toubkal.

$164.60

5/5

1 h 30 mins

Chesapeake Beach Guided Walking Tour - Railway Trail

Chesapeake Windsail Tours, a division of Chesapeake Windsail Cruises, is offering a wonderful way to enjoy Chesapeake Beach, with a stroll back into time down the old railway trail that once brought visitors from Washington DC, Baltimore and other destinations to the beaches. You will enjoy the peace and quiet of the marshland off Fishing Creek, where you will have many opportunities to photograph the habitat of the Chesapeake Bay region. You will visit the site where the war heroes of Chesapeake Beach are honored. This tour will end with a visit inside the Chesapeake Railway Museum. Learn about life in the early 20th century, before the Chesapeake Bay Bridge and why people came down to visit and to stay here. These are just a few of the sights on this tour. We are not responsible for the operation hours of the museum. You must call 24 hours before your tour time to see if the minimum requirement of 4 walkers has been met.

$41.00

5/5

2 h 30 mins

Themed and Special Event Cruise in Chesapeake Bay

This cruise is a unique way to celebrate that special event in your life while cruising on your very own private sailing yacht. You and a guest or you and 5 of your best friends will all help you celebrate that birthday, anniversary, promotion or a honeymoon; all of this with the scenic historic Southern Maryland as your background. Complimentary snacks and water will be served along with a small cake to help you and your guests celebrate.

$790.00

4.8/5

2 h 30 mins

Sailboat Cruise on Chesapeake Bay

Enjoy the peaceful sounds of the waves gently breaking off the hull of Eternal Hope as she glides through the waters of the bay, powered only by wind! This cruise sails at 9 am, 12 Noon and 3 pm, Tuesday - Sunday and on Mondays for Memorial Day and Labor Day. You must call 24 hours before your cruise time to see if the minimum requirement of 4 passengers has been met.

$116.00

4.7/5

1 h 30 mins

Chesapeake Beach Guided Walking Tour - The Cliffs

A great way to see the Cliffs of Calvert, historic Chesapeake Beach, the beautiful homes built on the Cliffs, the wildlife of the region and Chesapeake Beach's elevated Boardwalk overlooking, the third largest estuary in the world and the largest in the United States, the Chesapeake Bay. You must call 24 hours before your tour time to see if the minimum requirement of 4 walkers has been met.

$41.00

4.5/5

Private Washington DC City Tour | Monuments Tour

Crown DC Limo Service provide extensive tour of Washington DC at affordable rates. We will take you to explore the beauty of DC. Experience the best tour service with exotic limos at lowest rates. We are #1 Rated tour operator in Washington DC.

$342.00

4.4/5

2 h 30 mins

Chesapeake Bay Private Cruise

This private cruise for up to 6 persons is great for family outings, friends in town, a girls or guys day out on the water, or just to have the cruise to yourself! Enjoy the peaceful sounds of the waves gently breaking off the hull of Eternal Hope, a 42 ft sailing yacht, as she glides through the waters of the Chesapeake Bay. We are only a 42 minute drive from Washington DC, 30 minutes from Annapolis, MD and one hour from Baltimore, MD, so bring your own food or you can order food for this two and half hour cruise. The time and the boat are all yours. Complimentary snacks and water will be served.

$736.00

4.4/5

2 h 30 mins

Sunset Cruise on Scenic Chesapeake Bay

Watching the sunset over the twin beaches on the Western Shores of the Chesapeake Bay! A great way to close out a summer day with beautiful photos of the sunset. You must call 24 hours before your cruise time to see if the minimum requirement of 4 passengers has been met. Rates for the Sunset Cruises, September 9 thru 21 are lower and the cruise duration is shorter due to the time of Sunset. Sunset Cruises, September 23 thru October 30th will sail at 3 pm and may be shorter due to the time of sunset.

$139.00

4.2/5

120 h

Civil War Battlefields Self-Guided Audio Driving Tour Bundle

This captivating bundle of self-guided audio tours immerses you in the battles of Gettysburg, Antietam, and Vicksburg. Discover how the Americans finally defeated the mighty British empire in the decisive battle of the Revolutionary War. Then jump forward in time to two of the bloodiest battles of the Civil War, when brother fought against brother. Hear about the generals, unsung heroes, and blow-by-blow accounts of how it all unfolded. Recommended: Purchase one tour per car. Everyone can listen at the same time! After booking, check your email/text to download the separate Audio Tour Guide App by Action while connected to WiFi or mobile data. Enter the password, download the tour, and enjoy it offline. Follow the audio instructions and route from the designated starting point. This is not an entrance ticket. Check opening hours before your visit. New, Lifetime access, no expiry. Use it anytime, on any trip, as many times as you want.

$39.99

4.1/5

Antietam National Battlefield Self-Guided Driving Tour

Recommended: Purchase one tour per car, not per person. Everyone listens together! Explore and understand the Antietam Battlefield with this self-guided driving tour. See where Union and Confederate lines clashed, over and over, in a desperate struggle to maintain control. Feel the poignancy of the sacrifices made on the single bloodiest day in American history during the Civil War. After booking, check your email/text for a special password and setup instructions. Download the Audio Tour Guide App by Action while connected to WiFi or mobile data. Enter the password, download the tour, and once it's complete, you can enjoy it offline. Just open the app, hit the road, and follow the audio instructions! New, Lifetime access, no expiry. Use it anytime, on any trip, as many times as you want. This isn't an entrance ticket. Check opening hours before your visit.

$14.99

North Beach Historic - Guided Walking Tour

The tour includes a stroll on the board walk, the pier where famous entertainers were discovered, the town & historic points of interests and will end in the Bayside History Museum. Just a few of the sights on the tour. You must call 24 hours before your tour time to see if the minimum requirement of 4 walkers has been met.

$41.00

North Beach Scenic - Guided Walking Tour

The scenic tour includes a stroll around the bayside Sunrise Garden, visit to the tranquil Wetland Overlook Park, a walk on the pier where many famous entertainers were discovered, and continue throughout the bayside town as other scenic points of interests are reviewed. Enjoy the beautiful homes and cottages around the town. These are a few of the sights on this tour. This 60-90 minute tour starts at the Welcome Center on the Board Walk and will end with a visit to the Bayside History Museum. We are not responsible for the operation hours of the museum. You must call 24 hours before your tour time to see if the minimum requirement of 4 walkers has been met.

$41.00

2 h 30 mins

Private Sunset Cruise on Chesapeake Bay with Snacks and Drinks

Your Private Sunset Cruise offers a truly unique and intimate experience on the Chesapeake Bay—the nation’s largest estuary. Unlike standard group tours, our cruise is completely private, giving you and your guests uninterrupted time to relax, celebrate, and soak in the stunning natural beauty around you. As the sun sets over the Bay, you’ll enjoy complimentary sparkling cider, light snacks, and refreshing sparkling water, creating an atmosphere that feels both luxurious and personal. Designed for couples, families, and friends, this experience blends comfort, exclusivity, and unmatched scenic views. With limited availability, our sunset cruise provides a rare opportunity to create unforgettable moments on the water—making your evening not just a tour, but a cherished memory.

$797.00

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