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SUGGESTED ITINERARIES

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  1. The Chesapeake Experience

    Experiencing the Chesapeake is all about getting your feet wet, tasting its flavors, and learning about its history.

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Renaissance Festival Renaissance Festival

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MONTHLY EVENTS

Looking for the best time to come to Annapolis? Learn more about local events by selecting a month below.

January
January

Get out of the chilly weather this January and enjoy the art and dining scenes in Annapolis.

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February
February

Ranked one of America’s Most Romantic Towns by Travel+Leisure Magazine, Annapolis is a great place to spend time in February.

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March
March

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.

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April
April

Spring has arrived! Get out on the water, dine outside, join a tour, or take part in the many events happening in April.

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May
May

From Blue Angel Flight demonstrations to food-packed events, May in Annapolis is all about being outside.

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June
June

As summer rolls in, come enjoy Annapolis’ art, dining, history, on the water activities, and the many festivals and events in June.

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July
July

July's sunny weather encourages locals and visitors alike to enjoy the area’s outdoor activities, events, and festivals.

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August
August

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.

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September
September

Fewer crowds and cooler weather in September makes for a perfect weekend getaway in Annapolis.

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October
October

Fall is here and so are the area’s seasonal festivals: Hayrides, haunted tours, and family-friendly events.

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November
November

Rated one of the best cities for the holidays by Travel+Leisure, Annapolis in November is a great way to kick start the season.

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December
December

With the holiday season in full swing, Annapolis is the perfect destination to find a special gift for everyone on your list.

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