9 Ideal Chesapeake Bay Destinations for a 3-Day Weekend in 2024

Looking to spend your next vacation with a splash? You cannot go wrong with Chesapeake Bay, the United States’ largest estuary! With a rich maritime history, gorgeous waterfront views, delicious seafood, and water activities fit for all ages, spending a 3-day weekend here would be a blast.

From touring historic seaports and museums to tanning on the beach and dining on blue crabs, there is a long list of what you can do in this Mid-Atlantic holiday crown jewel. Scroll down to see some well-recommended spots, activities, and accommodations at these nine ideal Chesapeake Bay destinations for your next weekend getaway. Grab your sunnies and sunscreen, and let us go!

Annapolis, Maryland

Historic architecture, cobblestone streets, and a beautiful harbor make Annapolis the go-to city for a picturesque destination in the Chesapeake Bay. Start your trip by acquainting yourself with the town through Annapolis Tours, operated by Towne Transport. After seeing the century-old Georgian-style buildings, drop by the Maryland State House and the William Paca House and Garden for a lesson on Annapolis’ role in American history. You can even stay at The Annapolis Inn to immerse yourself in the city’s 19th-century charm. The inn is the only historical landmark accommodation nearby!

Meanwhile, boat lovers will enjoy the Annapolis Maritime Museum and Park, where you will learn about the importance and boons of the Chesapeake Bay. Got a boat to flaunt? Cruise in the waterway Ego Alley at City Dock, then enjoy a rum and a herbed grouper at Pusser’s Caribbean Grill. Now that is worthy of a hearty yo-ho-ho!

Smith Island, Maryland

Teetering between the territorial waters of Maryland and Virginia, Smith Island is the perfect Chesapeake Bay vacation if you want to unplug from your tech-dependent life. For starters, this archipelago is only accessible by boat from Crisfield or Point Lookout in Maryland. Phone signals can be weak in the area, but in return, you will have the best scenic location for kayaking, sunset cruises, and birdwatching pelicans.

While there are no Hilton-level hotels on Smith Island, the Smith Island Bed & Breakfast is the best family-friendly accommodation in the area. After a day of swimming, fishing, and kayaking, hit the Bayside Inn Restaurant for striped bass and steamed soft-shell crabs! Before leaving, do not forget to try Maryland’s official dessert—the 8-10 layer Smith Island cake.

Chestertown, Maryland

Founded in 1706, this port-hub-turned-college town is the perfect getaway for those who love history and the arts. Start with a self-guided walking tour to learn about the town’s 18th-century buildings, iconic Fountain Park, and even a tavern that served George Washington. You can also tour Washington College, visit the many art galleries, like MassoniArt Gallery, that dot the town, or take a river cruise along the Chester River.

Around May, the town has a festival that reenacts and celebrates the Chestertown Tea Party, when their forebearers dumped tea in Chester River as a form of protesting the British Parliament's closing of the port of Boston. During the Christmas season, the town turns into a two-day Dickens-themed festival where they transform the town into a Christmas imagined by Charles Dickens. Take it further with the immersion by staying at the Great Oak Manor Bed & Breakfast or Inn at Mitchell House, both well-preserved 18th-century structures.

Cape Charles, Virginia

From relaxing cruises and beach parties to fishing and kayaking, Cape Charles is one of the most ideal Chesapeake Bay destinations to visit for water activities. You can book romantic sunset cruises with The Schooner Windsong or fishing excursions with Tidewater Charters. Meanwhile, Southeast Expeditions offers rentals to kayakers and paddleboarders.

If you would rather just tan or splash at Cape Charles Beachfront, stay at The Northampton Hotel to be near the beach. Those who like cozy bed-and-breakfast options have Bay Haven Inn and Fig Street Inn to choose from. Want to celebrate the end of summer with a bang? LOVEFest is the festival to be! But if you like the peace of museums, Cape Charles also has you covered with its museum.

Havre De Grace, Maryland

Where historical attractions meet a quaint downtown, prepare for an incredible stay at Maryland’s Havre De Grace. Only a short drive from Washington D.C. and Baltimore, start with Havre De Grace’s most prominent monument—the Concord Point Lighthouse. The Decoy Museum and Maritime Museum are just a stone’s throw away and will tell you more about the town’s history and fascination with wooden ducks.

After a day of history, drive north to find some of the town’s most popular waterfront establishments. Artsy folks will appreciate Arts by the Bay Gallery for celebrating local artists. Bayside Antiques and Brookbend have vintage collectibles, while Tidewater Grille offers a view of the Susquehanna River while dining. As for accommodations, you will not find typical hotels in Havre De Grace. Instead, there are historical and charming inns, like the Vandiver Inn and the Spencer Silver Mansion.

Saint Michaels, Maryland

Known as “the town that fooled the British,” Saint Micheals is a great Chesapeake Bay destination for its riveting maritime history, as preserved in the Chesapeake Bay Maritime Museum and the St Michaels Museum. Just a few hours’ travel from New Jersey and Philadelphia, you can stay at the Log Canoe Inn or at the Victoriana Inn. They are both 18th-century buildings with excellent river views that can help you immerse in the town’s history.

While museum hopping is fun, no trip to the Eastern Shore is complete without a boat tour via Sail Selina II. Seafood, particularly oysters, are a big thing in Saint Michaels—you can even learn how they are caught through the oystering at the Chesapeake Museum. But if you would rather gorge on them, you best head to The Crab Claw, the Carpenter Street Saloon, and Foxy’s Harbor Grille.

Deltaville, Virginia

Dubbed the “Boating Capital of the Chesapeake,” those who love to sail and fish should make Deltaville their next summer getaway. The town’s numerous marinas are always accommodating with visitor boats, but sailing newbies—whether kids or adults—can also take classes with the Junior Sailing Camp by Fishing Bay Yacht Club.

If you would rather be out of the water, Deltaville still has other things for you, too. Catch a game of America’s favorite pastime sport at the town’s vintage baseball park, the Deltaville Ballpark. Get to know the city more through the Deltaville Maritime Museum and its chronicles on the town’s boat-building origins. Lastly, stay at Deltaville Dockside Inn and dine like the locals on the freshest seafood at J&W Seafood or Deltaville Tap and Raw Bar. Make sure to try the crab cakes!

Chesapeake City, Maryland

Steeped in Chesapeake-Delaware canal history, this quaint coastal town in Maryland can be best enjoyed through a Chesapeake Water Tours canal cruise where you will see the city in a different light—especially during sunset! Its rich history is kept in the C&D Canal Museum, the Chesapeake City Museum, and even the town’s historic 19th-century bed and breakfast—the Blue Max Inn.

The only Maryland town situated by the canal, almost everywhere in the city has top waterfront views, like Pell Gardens Park, the Bayard House Restaurant, and the Ship Watch Inn. Do not leave till you have had all-you-can-eat crabs at The Tap Room and handcrafted ales at the town’s sole brewery, Bayheads Brewing Company.

Chesapeake Beach, Maryland

Settled as a resort community at the last stop of the town’s old railroad, Chesapeake Beach City continues its resort-like allure today with its water park, seafood restaurants, postcard-perfect beach trail, and stunning waterfront accommodations.

Start your weekend with a history lesson at the Chesapeake Beach Railway Museum. Those who want to do their cardio can jog at the town’s gorgeous beach trail with a perfect view of the water. If you cannot get enough of that view, the Rod’ N’ Reel Resort has beachfront rooms and boating excursions. It even has a tab machine game room and bingo night for the grown-ups! As a cherry on top of this paradise-like vacation, eat your seafood fill at Traders Seafood Steak and Ale and Abners Crab House.

Why the Chesapeake Bay Should Be Your Next Weekend Getaway

Not only is the Chesapeake Bay blessed with impressive beachfront views and rich seaport history, but many of its cities are also primed and ready for tourists looking for a great weekend getaway. These 9 ideal Chesapeake Bay destinations are oozing with charm, character, and plentiful attractions and activities perfect for any traveler of any age.

In addition, a study actually showed that simply viewing a body of water—say, a beach, river, or bay—can boost relaxation and lower blood pressure and heart rate. With Chesapeake Bay’s many beaches, canals, and rivers, you will wash away your daily life’s stresses while having fun!