Trip Recap: Chesapeake Bay & Colonial Virginia 2017

By: JD Conroy

Last week I returned from an 8-day trip to the Chesapeake Bay & Colonial Virginia. I was joined by an amazing group of American Classic Travelers on this trip. We saw so much and had a lot of fun. I wanted to share some of our experiences with you! Enjoy reading this Trip Recap!


Our Route

Washington DC --> Baltimore --> Annapolis --> St. Michaels --> Virginia Beach --> Norfolk --> Charlottesville --> Skyland National Park --> Washington DC



Mary and JD met each American Classic Traveler curbside at O'Hare to start our trip to Chesapeake Bay & Colonial Virginia. We had a quick and easy group check-in before taking off for Reagan National Airport in Washington DC. 


Fort McHenry

Our first stop on our trip to Chesapeake Bay & Colonial Virginia was Fort McHenry. Located on the Baltimore Harbor, Fort McHenry has a long and storied history. It played a crucial role in the War of 1812 as the American Army successfully defended Baltimore from a British invasion, a pivotal turn in the war. It was this battle at Fort McHenry that inspired Francis Scott Key to write the Star Spangled Banner.


An Impromptu tour of Baltimore

Our flight landed about a half an hour early in Washington DC, so we had a little bit of time to spare before arriving at dinner. Our motorcoach driver, Kevin, is a Maryland native, so he showed us around Baltimore. We saw Baltimore's iconic row houses, Camden Yards, the campus of Under Armour Headquarters, Federal Hill, the Inner Harbor, and the Emerson Bromo-Seltzer Tower. 


Crab Feast at Bo Brooks on the Baltimore Harbor

We enjoyed a delicious meal and tremendous views of the Baltimore Harbor at Bo Brooks Restaurant. Our feast included: Maryland Crab Soup, Potato Salad, Cole Slaw, Roasted Corn with Cilantro Butter, BBQ Chicken, Jumbo Lump Crab Cakes, Steamed Crab, Watermelon Wedges and Fresh Baked Cookies!


The Loews Annapolis

We enjoyed a pleasant 2-night stay at the Loews Hotel in Annapolis. There are 23 Loews Hotels in the United States. Each Loews is decorated thematically to match the character of the city in which it is located. The Loews Hotel in Annapolis is decorated with blue colors and sail decorations, representing the marine culture of Annapolis. 


Guided Tour of Annapolis

Home to the naval academy, old cobblestone streets, quaint boutiques, and uniform, red-brick architecture, Annapolis is a charming coastal town definitely worth visiting!


Cruise the Chesapeake Bay

We enjoyed beautiful weather on our Lighthouse Cruise of the Chesapeake Bay.  We cruised under the Chesapeake Bay Bridge, and we saw a number of the bay's iconic lighthouses including: Sandy Point Lighthouse, Baltimore Harbor Lighthouse, and Thomas Point Lighthouse.


Guided tour of the Naval Academy 

We took a guided tour of the United States Naval Academy. We learned about the academy's history, it's stunning architecture, and the daily routines of the men and the women who attend the academy. 


Dinner at Mike's Crab House

Ideally situated on the Severn River in Riva, Maryland, Mike's Crab House is famous for their delicious Crab Cakes. We had two choices of entree:

1) Seafood Combo - Broiled Crab Cake, Shrimp, Scallops, and Orange Roughy. 

2) 8oz. New York Strip Steak and Stuffed Shrimp. 

For dessert we had a choice of: Cheesecake, Key Lime Pie or Apple Pie. 


Ride on the Chesapeake Bay Bridge

The Chesapeake Bay Bridge is said to be the scariest bridge in America to drive across. Spanning almost 5 miles in length, the Chesapeake Bay Bridge sits high above the water carrying over 60,000 passengers on its back every day. 


Chesapeake Bay Maritime Museum and Free Time in the Charming Town of St. Michaels

The Chesapeake Bay Maritime Museum tells the ecological, economic, and social history of the Chesapeake Bay and the people who have called it home. After we visited the Chesapeake Bay Maritime Museum we had a couple of hours to explore the small, seaside town of St. Michaels, Maryland. Lined with charming boutiques, ice cream shops, and authentic restaurants, St. Michael's Talbot Street is a precious hidden piece of Americana. 


Chesapeake Bay Bridge Tunnel

Since its opening in 1964, 116 million passenger and commercial vehicles have crossed the Chesapeake Bay on this engineering masterpiece. Measuring over 17 miles in length, the Chesapeake Bay Bridge-Tunnel is the largest bridge-tunnel complex in the world. The video above shows aerial views of the drive we took from the Delmarva Peninsula to Virginia Beach. 


Virginia International Military Tattoo

We attended the Virginia International Tattoo at Norfolk, Virginia's Scope Arena. A military tattoo is a celebration of military bands and performers. Bands from 7 nations performed this year at the Virginia International Tattoo. Both patriotism and global unity are celebrated by powerful performances from bands, vocalists, drill teams, and dancers. This show is definitely an American Classic! The video above is from the 2016 Virginia International Tattoo.


Check-In to DoubleTree Virginia Beach

After the Virginia International Military Tattoo we checked into the DoubleTree in Virginia Beach. With a modern look and a clean feel, this DoubleTree made for a relaxing 1-night stay. 


Old Cape Henry Lighthouse And Memorial

We began Day 4 of our trip by visiting First Landing Point at Cape Henry. First Landing Point is the first place the English landed in America before heading inland towards Jamestown. It is also the sight of the first federally-funded construction project - the Old Cape Henry Lighthouse which was commissioned by President George Washington in 1792. A few American Classic Travelers climbed 191 steps to the top of the Old Cape Henry Lighthouse for a view of the ocean and the New Cape Henry Lighthouse. 


Guided Tour of Yorktown

We visited the brand new, 6-week-old American Revolution Museum in Yorktown. This state-of-the-art museum is filled with amazing artifacts and exhibits explaining the southerners' motivations for rebelling against the British crown. After we explored the museum we went outside and watched a live cannon demonstration. The video above shows the cannon demonstration. 


Campbell's Tavern in Colonial Williamsburg

We enjoyed a beef tenderloin meal at Christina Campbell's Tavern in Colonial Williamsburg. Rumor has it that Campbell's Tavern is frequented by President George Washington, at least that's what Mrs. Campbell claims!


Guided Tour of Jamestown

On our guided tour of Jamestown we explored the rich history of the Jamestown Settlement. 


Colonial Williamsburg

Williamsburg is home to the largest living history museum in the world. As we explored this 18th century colonial city, we met artisans, road on horse and buggies, watched craftsmen at work, and ate at the local town taverns. History comes alive at Williamsburg.


King's Arm Tavern

Our main course at King's Arm Colonial Tavern was pan seared chicken. After our meal we took a group photo outside the tavern. 



Thomas Jefferson decided to call his estate Monticello (Italian for "little mountain") because it sat atop the scenic hills of Central Virginia. Monticello was Jefferson's "essay in architecture" as he designed, redesigned, and was constantly tinkering with his home throughout his life. By visiting Jefferson's home we learned a lot about the man: his love of the sciences, his attitudes towards slavery, and so much more.


the Skyland Lodge

The Skyland Lodge sits atop Shenandoah National Park in the mountains of Virginia. We enjoyed tremendous views from our rooms, a delicious dinner at the lodge, and the peace and quiet of this secluded national park. 


Scenic Travel Along the Skyline Drive

We started our day with a scenic ride on the famous Skyline Drive atop the Blue Ridge Mountains. Off to Mount Vernon and Washington DC!


Mount Vernon

During our visit to Mount Vernon, we learned about the life of our 1st President including his military career, his relationship with his wife Martha, his business ventures, and his whiskey distillery.


Dinner at Filomena's

Filomena's was amazing! Our 3-course meal started with an abundance of gourmet appetizers including: Arancini, Calamari, Sandi Ravioli, Bruschetta, Shrimp Scampi and more! For our main course we chose from a variety of Italian dishes. To top it off, we had just about every dessert imaginable: multiple cheesecakes, tarts, and pies were passed around our table. We topped off our meal with some Sambucca and Amaretto!


the AC Hotel in Washington DC

The AC Hotel is located in Washington DC's up-and-coming National Harbor area. The AC Hotel is a new Marriott brand known for it modern look, European design, and its unique approach to creating a relaxing ambiance and social environment for its visitor. 


Guided Tour of Washington DC

We finished our trip with a guided tour of Washington DC. Our local guide, Bill, showed us around our nation's capital with stops at the White House, Capitol Building, Lincoln Memorial, Washington Monument, World War II Memorial, Korean Memorial, and Vietnam Memorial. 


Flight Back to Chicago

Back home to Chicago! If you look closely at the picture above you can see an awesome, aerial view of the National Mall. 


A special Thanks to Our Awesome Group of American Classic Travelers


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