One Week Annapolis Itinerary

Sometimes spending a week in a place you’ve never visited before can be overwhelming, as you try to find the perfect balance between seeing it all and still managing to get in enough rest and relaxation. Our one week Annapolis Itinerary for your getaway helps you find that balance and come away with a vacation you will never forget.

Day 1

Your first day in Annapolis will probably be spent traveling and getting settled in to your At Home Annapolis cozy cottage, so don’t feel guilty for grabbing takeout from nearby House of Hunan and settling in for the evening. Watch the sunset over eggrolls and take a moonlit stroll down by the creek before calling it a night.

Day 2 of your Annapolis Itinerary

Your second day in our Annapolis Itinerary consists of a tasty breakfast at the Iron Rooster; their Crab Cake Benny is the perfect introduction to the wonderful crab dishes you’ll find here in Maryland. Make sure you are wearing your most comfortable walking shoes, because the best way to get to know a new city is by taking advantage of the tours they offer. Watermark Tours offers walking tours of Annapolis designed to make you feel comfortable with your temporary home. By the end of the day you will be ready for a hearty meal at O’Leary’s Seafood Restaurant and then another early night.

Day 3

After a restful night’s sleep, Miss Shirley’s Café will be calling. Their service is quick, which is a good thing, as you have a full day ahead of you! Today’s adventures will take us to museums all over the city. From the William Paca House & Garden to the Hammond-Harwood House and finishing off with a visit to the Chase Home, it’s all about the beginning of our country’s history.

Day 4

Your fourth day of your Annapolis Itinerary is enjoying some delicious breakfast at Evelyn’s, lunch at Harry Browne’s Restaurant (keep an eye out for your favorite politician, this is a favored lunch location for our nation’s leaders), and dinner at Galway Bay Irish Restaurant & Pub is on the menu today. Now that your meals are figured out, you can spend the day concentrating on the great outdoors. Chesapeake Bay is a huge draw, and you’ll find plenty of things to do as you head to its shores; rent a kayak, take a boat tour, or simply walk along the shores enjoying the beauty of our town.

Day 5

Today we’ll take it slow. Head back to Miss Shirley’s Café and take your time over a Born on the Bay-O Bloody Mary and Miss Shirley’s famous Crab Happy Chesapeake Chicken Sammy. Summer visitors should head back to Chesapeake Bay and the Annapolis Sailing School; it’s time to learn to sail! Lunch at Middleton Tavern for some oyster shooters to go with your craft beers may have you heading back to your vacation rental for a nap!

Day 6

As your seventh day will probably be filled with traveling, day six is going to be your last day of adventures in Annapolis, and we say stay home! Our vacation rentals are designed to be lived in, offering luxury amenities and comfortable surroundings that will make you feel content with being a homebody for a change! Your last night’s dinner should be a memorable one, so a romantic and delicious meal at Carrol’s Creek will be the perfect ending to a perfect vacation. It’s time to say farewell to historic Annapolis for now, but your memories of this town in our vacation homes will last forever. Reserve your stay today!