Summer days always bring us back to our childhood, when that last ring of the school bell signified the beginning of three months of freedom and long days where the sun went to bed long after we did. There was no hurry to do anything, because we had forever to do whatever we wanted, and our nights were spent in deep and dreamless sleep. We didn’t need to dream, because every day was a dream come true, and when you plan your own summer journey to Annapolis, we hope the trip brings you back to the carefree days of your youth as well!
Day 1: Stock Up on Snacks
As you pull into town, your first stop should be The Fresh Market at 2504 Solomon’s Island Road to stock up on food and snacks to keep you satisfied during your stay in our At Home Annapolis properties. Offering ready-made meals that are healthy, nutritious, and delicious, as well as those decadent snacks that sweetened your youthful days, everyone knows there are no calories in vacation food, so feel free to live it up during your summer journey!
Day 2: Water Slides, Sunburned Noses, and the Taste of Popsicles- Family Fun In Annapolis MD
Our favorite childhood memories always involve long days spent at the local water park: the exhilaration of speeding down the high slides, the feel of sunburned noses, and the taste of sticky popsicles enjoyed on a towel by the water. If you’re looking to relive your childhood, a visit to nearby Chesapeake Beach and the Chesapeake Beach Water Park is highly recommended! Located at 4079 Gordon Stinnett Avenue and offering everything a good waterpark should, your journey would be missing something if you didn’t play here! Click here and check out our favorite Annapolis water activities.
Day 3: Music in the Park
Summer nights and music go together like peanut butter and jelly, and Annapolis offers multiple free opportunities to jam! From the Rock the Dock series sponsored by the Art in Public Places Commission and held on Thursday evenings all summer long to the Maritime Museum’s Tides and Tunes, also held on Thursday evenings, your summer journey to Annapolis will be a musical interlude of magnificent proportions! This is one of the most favorite Annapolis things to do with the family.
Day 4: We’ve Got Crabs
And they taste FANTASTIC! Maryland is known the world over for having the sweetest and tastiest crabs in the nation, and for the last 74 years, Annapolis has been home to the world’s largest crab festival! Held the first Friday in August at the Navy-Marine Corps Memorial Stadium, this celebration of our favorite sea creature should not be missed! It’s the perfect activity to create memories of family fun in Annapolis MD. Also offering hotdogs, watermelon, barbecue, and beer in addition to over 320 bushels of crabs and 100 gallons of crab soup, this festival will be the highlight of your summer journey.
Day 5: Chesapeake Bay Activities
When you live on the bay, the activities in town tend to revolve around the water, and Annapolis is no exception. Summer is the high sailing season, and our Wednesday Night Sailboat Races are a tradition enjoyed by visitors and residents alike. If you’re more of a participant than an observer, J World Annapolis offers sailing courses that include an introduction to racing. This is one of the most exciting Annapolis things to do with the family. Could this be an introduction to your new obsession?
Day 6: Stay Home and Play?
Today is your last full day in our bayside village, and when you look back over the last five days, this summer journey has been an adventurous one, so no one would blame you for staying home and enjoying the comforts and amenities of your classic cottage. Rent a home that is located on the creek and spend the day fishing or sit on the screened-in porch with a book and a margarita and lose yourself on a slow summer day. Take a nap on the couch in front of the television in the comfortable family room or play a board game at the dining table, reveling in this unexpected family time. There’s no wrong way to spend your time in Annapolis; all we ask is that you have the time of your life!
Day 7: Farewell for Now
The day you’ve been dreading has finally arrived: It’s time to pack up your things and return to real life! Saying goodbye is always sad, but as you sit enjoying one last cup of coffee and contemplating the week, the smile on your face will be a testament to the good times that were had. Reserve your At Home Annapolis family escape today and start planning your summer journey to our favorite place on earth! Click here to browse through our vacation rentals with pools.