3 Days in Annapolis

Three-day weekends and vacations make our normal 9 to 5 jobs bearable, and when you can combine the two with a special getaway to Annapolis, life becomes that much more of an adventure. For your 3 days in Maryland, Annapolis offers exciting activities, amazing sights, and delicious restaurants all waiting to be discovered, and this helpful guide will ensure you don’t miss a single one of them!

Days in Maryland – Day 1: Raring to Go!

After a good night’s sleep in one of our At Home Annapolis vacation escapes, you’ll want to start out your first day of adventures with a hearty breakfast at Miss Shirley’s Café, an Annapolis tradition for almost 15 years. After filling up on her Oysters Rockefeller Eggs Benedict and perhaps a breakfast cocktail or two, we like to advise people to head to the bay. Chesapeake Bay is a huge draw, and when you catch sight of it, you’ll understand why.

Take a sailing tour with Schooner Woodwind Annapolis Sailing Cruise and explore by water the areas you may want to explore on land later in your stay! After grabbing a quick lunch, it’s off to the US Naval Academy for their 2 PM free tour, where you will learn the history of the academy and how today’s academy students become tomorrow’s heroes. As the sun sets over the bay and hunger pains remind you how long its been since lunch, dinner at O’Leary’s Seafood Restaurant will be a fitting end to your first day; go for the crab cakes, they are a Maryland specialty!

Day 2: Historic and Beautiful

Have it your way at Evelyn’s for breakfast, where special orders are no problem, and then it’s time to hit the streets with a tour of Annapolis Historic District. Make sure you are wearing comfortable shoes because today we are going to walk a LOT! As luck would have it, though, the shops, restaurants and art galleries found in this beautiful district will help to keep your mind off any pain in your feet! Take a peek at the latest fashions at Lilac Bijoux, admire the talented works of local artists at the McBride Gallery, and when you start to feel hungry, enjoy a burger, fries, and a milkshake at Chick & Ruth’s Delly. These are all businesses housed in buildings that have been around almost as long as we have been a country. Your exploration of the historic district will take up most of your second day from you 3 days in Maryland, if you do it right, and dinner at Galway Bay Irish Restaurant & Pub will give you the perfect ending to your second day in our historic city.

Day 3: Enjoy Every Second!

On your last day in town there’s no need to be sad, as we have adventures planned that will have you enjoying every second! Today’s adventures will give you a deeper glimpse into the history of our town and our country; it’s museum day! The following homes and museums can be visited in no particular order but be sure to see them all.

The Annapolis Maritime Museum promises to be a hit as you learn about the history of the water men who have made their living on the bay. The Chase Lloyd House, constructed in 1769, was the home of one of the signers of the Declaration of Independence, Samuel Chase. The thrill of walking in the footsteps of a man who was instrumental in our freedom never grows old and we visit as often as we can, learning something new from each visit. And if you can’t get enough of homes owned by signers of our Declaration of Independence, the Charles Carrol House, constructed in 1687, will be the perfect way to end your tour of homes! Mr. Carrol is famous for being the only Catholic to sign that revered piece of parchment, and his home is only open for tours on weekends from June through September, so be sure to have your trip coincide with those times or you will be extremely disappointed!

Dinner on your final night is sure to be a memorable one when you choose Cooper’s Hawk Winery & Restaurant. Offering an extensive wine menu and a large selection of American-style dishes, be sure to leave room for the Reese’s Ice Cream Cookie. There are no words for how delicious this dessert is!

The Best Part of Your 3 Days

Of all the adventures you will have during your three days in Maryand, the best part of your trip will take place in our At Home Annapolis vacation escapes! Warm and welcoming, comfortable and stylish, memories will be made that you will never forget. Reserve yours today!

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