The best places to visit on the Chesapeake Bay

Enjoy the best of what America has to offer by exploring the Chesapeake Bay!!
. . . . . . . . . . . . . . . . . . . . . . . . . . .

What comes to your mind when someone says that they vacationed on The Bay?
Is it “what bay?”
or
“Why?”
maybe even
“you mean San Francisco Bay?”

If you are not a East coaster than the likely hood of you having personal experience with the Chesapeake Bay is slim to none but that is why I am here to educate you on what you are missing out on!  It is also a great escape for people living in the Washington, DC area because it is so close!

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* Lets start with the towns/cities on the Bay *
  • Cape Charles on the Eastern Shore

Yes, that is literally how big the town is.

Their very quaint downtown – make sure you stop at the only wine shop for a fantastic selection of wines!

Cape Charles is a small, sleepy village on the Bay that offers you the down home, southern quaintness you expect from a coastal town.  
I recommend by experience:
Staying at:
Eating at: 
Kelly’s Gingernut Pub – an old bank turned into bar/restaurant 

Land activities:
Water activities:
South East Expeditions – go for an eco tour via kayak!

  • Inner Harbor – Baltimore, Maryland

Everyone has heard of Baltimore but not everyone has visited there.  Their downtown is one of my favorite places to visit along the East coast.  It is urban and trendy yet the city still has managed to keep the history and coastal attributes.  You can take a boat ride to a restaurant that is said to still house “spirits” in the upstairs.  Or view where pirates used to hang out.

I recommend: 

Staying at: 
Eating at: 
The Capital Grille for amazing seafood!

Daytime land activities:
You HAVE to visit the National Aquarium!

Daytime water activities:
Cruise the Inner Harbor aboard the Big Red Boat through Watermark Cruises!

  • Tangier Island, Virginia 

The tiny island of 700 residents is known as the “soft-shell capital of the world” and many of the locals make their living solely off oysters and crabs.  In order to visit the 3 mile long island you will have use either boat or plane and once you get there do not expect a ton of amenities – there are only a few gift shops, restaurants, hardware stores, grocery stores, and B&Bs.  Also, there are only a few cars so primary transportation are golf carts and bikes.  You may be asking yourself why visit then?  Well, for a nature lover it is going to absolute heaven!

I would recommend:

Staying at:
The Chesapeake House – the offer golf cart rentals!

Eating at:
Lorraine’s – lunch and dinner

Activities:
kayaking, boating, fishing, swimming, shelling, photography, crabbing, sleeping, reading

  • Easton, Maryland

Easton is your quintessential waterman town of the Chesapeake.  It was founded in 1710 but unlike other sleepy towns, has been able to progress with time.  It is sophisticated, with fantastic shopping and delicious dining!

I would recommend: 

To Stay and eat:
The Inn at Easton

Activities:
Eat, drink, shop, boat, fish, hike, lay on the beach


  • St. Michaels, Maryland



This place reminds me a lot of Beaufort, North Carolina, it looks like a village Norman Rockwell would have loved to paint.  It comes equipped with all the perfect little boutiques, restaurants, churches, and B&Bs.  Basically, a postcard town!  It has evolved from a shipbuilding center to a fishing village and now to a tourist destination.    

I would recommend:

To stay:
Inn at Perry Cabin by Belmond – I would die and go to Heaven and never want to leave here!

To eat:
208 Talbot for American, seafood cuisine 

Activities:
eating, drinking, shopping, reading, relaxing, swimming, fishing, boating, sailing, kayaking, shelling



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