Annapolis Harbor
R. Matthew McKinney

Bay, Beach & Beacons

Explore Maryland's Eastern Shore

Annapolis Harbor
R. Matthew McKinney

Day 1

A Day By The Bay
Start your day in Annapolis, on the shores of the Chesapeake Bay.  Let an Annapolis Tours by Watermark attired guide take you back to the 18th century. They will lead you through the Old Senate Chamber, in the Maryland State Capital Building, where in 1783 George Washington resigned as Commander-in-Chief. Travel through the gates of the United States Naval Academy, founded in1845, and home to 4,000 of our country’s future naval leaders. Your visit will include the Naval Chapel, the Crypt of John Paul Jones and Bancroft Hall. Free time at City Dock, eat at the Dry Dock Restaurant and/or take a Watermark Cruise to see the shores of the USNA and Annapolis Harbor. Enjoy getting on the water and catching a glimpse of the Chesapeake Bay Bridge. This 40-minute cruise is the perfect ending to your time in the Capital.  See the Thomas Point Light House (Beacon) Travel to Ocean City.  Arrive at your oceanfront hotel and enjoy a welcome reception while your baggage is delivered to your room.  Refresh and get ready for a delicious dinner overlooking Assateague Island, at Harrison’s Harborwatch Restaurant.  Afterward, enjoy a stroll on the Boardwalk before heading back to your hotel to relax for the evening.

Day 2

Crisfield, Crab Cake & Smith Island Cake (Cake + Cake Tour)
Enjoy breakfast and meet with your step-on guide to depart for Crisfield, the “Crab Capital of the World.”  Begin by visiting the historical J. Millard Tawes Museum and taking a driving tour of this historic town.  For lunch, The Crab Place brings a special treat of a famous Maryland Crab Cake with all the fixins’ for a delicious meal.  During lunch, there are demonstrations on crab steaming, crab picking, crab cake making and the icing on the cake – a visit from a Smith Island Cake maker.  Learn what goes into making this fabulous dessert and have a piece of your very own.  You will return to Ocean City to relax, dine or free time to explore Ocean City’s finest attractions.

Day 3

Country House & Crab Feast
Travel to Salisbury and immediately take a step back in time at Poplar Hill Mansion, a Federal-style home.  Then visit the largest country store in the East, The Country House, and a pleasure waiting to happen.  Lunch will be in the area at one of the local restaurants.  Walk through the Salisbury Zoo, which has been called "one of the finest small zoos in North America."  A short ride through the lovely countryside will take you to the sleepy waterfront village of Whitehaven and the Red Roost Restaurant.  A real treat is in store as you enjoy an "all-you-can-eat" dinner of steamed hard crabs, shrimp, corn on the cob and much, much more.  Some evenings offer sing-alongs, banjo playing and entertainment.  

Day 4

St. Michaels
Enjoy breakfast, board the coach and travel to Tilghman, one of the last small fishing villages left on the Chesapeake Bay.  At Bay Hundred Seafood, there will be a tour of the last crab-picking plant in Talbot County.  Visit a crab wholesaler and learn how workers separate the sooks (females) from the jimmies (males) and grade the crabs by size and shell hardness. Watch the preparation of live crabs to go to seafood markets.  Next is a tour of Phillips Wharf Environmental Center to learn about the life of a crab - molting, doublers, peelers, and more.  Then it’s St. Michaels and the Chesapeake Bay Maritime Museum.  After learning the traditions of boat building, fishing, water fowling and going into a 100-year old screw-pile lighthouse, you’ll board the Patriot for a tour of the Miles River. 


Noon Formation at U.S. Naval Academy - Annapolis
Visit Annapolis
U.S. Naval Academy

Travel through the gates of the United States Naval Academy, founded in1845, and home to 4,000 of our country’s future naval leaders.

Ward Museum of Wildfowl Art
The Ward Museum

The Ward Museum programs bring people of all ages together through exploration of art, nature and tradition.

Enjoy the hands-on exhibits and overnight programs at the lighthouse at this museum.

Discover the heritage of oystering and crabbing at the Chesapeake Bay Maritime Museum. The museum displays a large collection of working and recreational watercraft and hosts exhibits on bay history and waterfowl hunting.