Annapolis in May
Great time to visit
May might be peak Annapolis - gorgeous weather, the harbor buzzing with activity, and everything green and blooming. Crowds are manageable except during Commissioning Week, when the whole city transforms into a Navy celebration.
Weather
May delivers some of the best weather Annapolis sees all year - warm but not hot, low humidity, and those perfect blue-sky days that make the Chesapeake sparkle. Rain is minimal and usually quick afternoon showers. This is premium harbor-walking weather.
24°C high13°C low8 rain days
Crowds & Cost
moderate crowds
~$175/day average
Events & Festivals
- •Commissioning Week at Naval Academy
- •Spring sailing regattas
- •Memorial Day weekend festivities
May Tips
- •Commissioning Week brings thousands of Navy families - book hotels months ahead
- •Perfect time for Chesapeake Bay boat tours
- •Outdoor dining is at its absolute best
All Months
April through October gives you the best weather and full access to sailing season. May and September hit the sweet spot - warm days, cool evenings, and fewer crowds than peak summer. The Naval Academy graduation in late May brings thousands of visitors, so book early if you're planning around that. Summer means sailing weather, but also humidity and higher hotel rates. Commissioning Week in May is chaos - avoid unless you're there for the ceremony. Fall colors peak in mid-October around the Chesapeake Bay area. Winter can be charming for a quick historic walking tour, but many waterfront restaurants close or reduce hours. The holiday season brings colonial Christmas events and tours of decorated historic homes. Just bundle up - those harbor winds cut right through you.
Annapolis Scores
Solo
6/10
Couples
7/10
Families
8/10
Adventure
5/10
Budget
6/10
Luxury
6/10
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