Experiencing the Chesapeake is all about getting your feet wet, tasting its flavors, and learning about its history.
Try typing in a phrase above, and we’ll make suggestions to get you back on course.
Looking for the best time to come to Annapolis? Learn more about local events by selecting a month below.
Get out of the chilly weather this January and enjoy the art and dining scenes in Annapolis.
Ranked one of America’s Most Romantic Towns by Travel+Leisure Magazine, Annapolis is a great place to spend time in February.
Winter is coming to an end, and March is a wonderful time to beat the crowds and get a taste of the unique character of Annapolis.
Spring has arrived! Get out on the water, dine outside, join a tour, or take part in the many events happening in April.
From Blue Angel Flight demonstrations to food-packed events, May in Annapolis is all about being outside.
As summer rolls in, come enjoy Annapolis’ art, dining, history, on the water activities, and the many festivals and events in June.
July's sunny weather encourages locals and visitors alike to enjoy the area’s outdoor activities, events, and festivals.
Visiting Annapolis in August means one thing: Get out on the water! Climb aboard a sailboat or rent a kayak/paddleboard and cool off in the breeze.
Fewer crowds and cooler weather in September makes for a perfect weekend getaway in Annapolis.
Fall is here and so are the area’s seasonal festivals: Hayrides, haunted tours, and family-friendly events.
Rated one of the best cities for the holidays by Travel+Leisure, Annapolis in November is a great way to kick start the season.
With the holiday season in full swing, Annapolis is the perfect destination to find a special gift for everyone on your list.