If you're dreaming of a coastal escape filled with seafood, sailing, and slow, scenic drives—let me tell you why you should explore Chesapeake Bay. When I visited, I found quiet harbors where time seemed to pause, crab shacks that served up the freshest bites I’ve ever tasted, and views that made me pull over just to soak it all in. I’ll take you through the charming towns, old lighthouses, and seafood feasts that made me fall in love with Maryland’s Chesapeake Bay region. If you’re like me and love a blend of history, salt air, and simple pleasures—you’re going to want to plan a trip here soon.
Best Time to Visit
I’ve found the sweet spot for visiting Chesapeake Bay is late spring through early fall (May to October). That’s when I could really enjoy the boating, seafood festivals, and those warm bay breezes that make you want to stay outside all day. You’ll get sunshine, fresh crab season, and a calendar full of local events—trust me, it’s worth timing your trip right.
How to Get There
- Driving? I usually take U.S. Route 50 or I-95—it’s an easy ride from Baltimore or D.C. In just an hour or two, you can be walking the streets of Annapolis, biking through St. Michaels, or grabbing lunch in Cambridge. You’ll want to keep your camera close—there are scenic byways all along the route.
- Flying? I recommend flying into Baltimore/Washington International Airport (BWI) for the western shore, or Salisbury Regional Airport if you’re heading to the Eastern Shore. Either way, you’ll be close to the water in no time.
- Boating in? I met several travelers who arrived by boat—there are marinas everywhere, and even water taxis that link up charming coastal towns. If you’ve got a vessel, you’ll love exploring by water.
Where to Stay
- Inn at Perry Cabin (St. Michaels) – I stayed here once and felt completely spoiled. The waterfront setting is pure tranquility, and I even took a sailing lesson—something I’d absolutely recommend if you want to experience the bay up close.
- Hyatt Regency Chesapeake Bay (Cambridge) – If you’re traveling with family, this place checks all the boxes. I loved how easy it was to relax while the kids splashed in the pool or watched the boats glide by from the marina.
Recommended Tours:
- Chesapeake Beach: Sunset Sailing Cruise with Snacks – I took this cruise on a whim, and I’m so glad I did. You’ll sail into the sunset, nibble on snacks, and maybe even spot dolphins or ospreys. Price: From $123 per person.
- Chesapeake Beach: Guided Walking Tour to The Cliffs – I joined this tour for the views and ended up learning so much history along the way. The cliffs are breathtaking, and the guide brought the area’s stories to life. Price: From $41 per person.
- Chesapeake Beach: Private Sailing Cruise on a 42-Foot Yacht – If you want to treat yourself (or impress someone special), I highly recommend this private cruise. It’s peaceful, luxurious, and lets you see the bay on your own schedule. Price: From $654 per group up to 6.
Best Things to Do in Chesapeake Bay
Unleash Your Inner Creative at the Academy Art Museum - Brush up on fine art where tradition meets modern expression.
Wander Wild at Adkins Arboretum - Hike, breathe, and reconnect with native landscapes.
Cruise Like a Local with American Cruise Lines - Sail past history and hospitality on Chesapeake waters.
Get Grounded with the American Chestnut Land Trust - Protect forests and hike trails where restoration thrives.
Raise the Sails at Annapolis Yacht Club - Navigate prestige and performance on historic waters.
Unlock Canal Secrets at the C&D Canal Museum - Discover the gritty ingenuity that moved America forward.
Dig Deep at Calvert Cliffs State Park - Hunt fossils and bask in coastal serenity.
Paddle Through Time on the Captain John Smith Trail - Trace history by kayak on this National Historic route.
Anchor Your Curiosity at the Chesapeake Bay Maritime Museum - Explore shipbuilding, oysters, and Chesapeake traditions.
Sip and Savor Along the Chesapeake Wine Trail - Toast Maryland’s terroir one glass at a time.
In Summary...
(and if you want to revisit my photo journey)- • Unleash Your Inner Creative at the Academy Art Museum
- • Wander Wild at Adkins Arboretum
- • Cruise Like a Local with American Cruise Lines
- • Get Grounded with the American Chestnut Land Trust
- • Raise the Sails at Annapolis Yacht Club
- • Unlock Canal Secrets at the C&D Canal Museum
- • Dig Deep at Calvert Cliffs State Park
- • Paddle Through Time on the Captain John Smith Trail
- • Anchor Your Curiosity at the Chesapeake Bay Maritime Museum
- • Sip and Savor Along the Chesapeake Wine Trail