How to Spend Summer In Annapolis

How to Spend Summer In Annapolis

The historic streets of Annapolis burst to life in the summer. Countless locals and tourists gather throughout the city for family activities and weekend entertainment. There’s no shortage of things to do near the Chesapeake Bay, especially in the hot season. Here are a few ideas to inspire your summer-time schedule.

Come Sail Away

Water’s an obvious theme for recreation when you’re located seaside in the Chesapeake Bay. “The Sailing Capital Of The U.S.” allows boat owners in the area to take advantage of every sunny day. If you don’t have your own boat and slip in the harbor, you can charter a vessel for a few hours, a weekend, or longer.

Boat charters are a popular choice for families looking to entertain guests during the summer. From an afternoon of sailing lessons to a week-long ocean excursion, the boating possibilities are endless.

When you charter, you’re renting the yacht or sailboat in one of two ways; bareboat or skippered. A bareboat charter means you’re at the wheel, while skippered means you have a small crew accompanying you.

Walk Through History

Most of Annapolis’ charm comes from its historical buildings and patriotic past. Stroll through the Colonial Annapolis Historic District for a fun and enriching tour of the city. Wine tours, candlelight tours, and garden tours are some of the most enjoyable ways to get to know this slice of Americana.

Take in the elegant architectural style of the old buildings in the city. Many Sturbridge Homesborrow design ideas from these classic structures. Do you see similarities in the traditional brick styling?

Celebrate Independence Day

What better way to celebrate July 4th than with fanfare and fireworks at the Annapolis Harbor? The historical setting is the ideal backdrop for parades, foodie events, live music, sailing cruises and a professional fireworks display.

Waive the stars and stripes while you explore the busy downtown area. Or hop on the Watermark Yacht and watch the shenanigans from the water. You could even host a celebratory barbeque in the comfort of your Sturbridge Homes backyard.

Chill At A Concert

Do you have musical ear? Enjoy live music in the fresh seaside air! Listen to a variety of bands and genres weekly, hosted by the Annapolis Maritime Museum.

From jazz and rock, to folk and soul, the Tides & Tunes Summer Concert Series has a range of performers great for every audience.

Entrance to the concert is free. If you donate you’ll be supporting the museum’s education efforts. Delicious bites and refreshing cocktails are on site for purchase. Music floating through the breeze and a margarita in hand? Sounds like the perfect summer night.

Wind Down At The Faire

Wrap up the final days of summer by partying like it’s 1529. Only 15 minutes away, Crownsville, MD is home to theMaryland Renaissance Festival, the 2nd largest of its kind in the United States.

Raise a glass of ale as you cheer on knights in a jousting competition. Feast like royalty while you mingle with faeries and bards. Be entertained by improv comedy and musical acts on 10 different stages. If you’ve never experienced a renaissance fair, this is one of the most immersive and elaborate events in the country!


Ready to call Annapolis your home? Find yourdream house in this vibrant and festive part of the country. Contact Sturbridge Homes today!