Best 241 things to do in Annapolis, MD

Flexible paddleboard rentals for your time on the water

Celebrate your occasion aboard a private party boat on Chesapeake Bay

Pair two hands-on rage activities under one roof

Break, throw, and paint your way through three indoor activities

Private Chesapeake Bay sailing aboard a 1935 ketch

Paddle Back River coves with a short safety introduction

Paddle Back River's coves with an included safety introduction

See Baltimore’s skyline and harbor from a guided jet ski

Explore Baltimore’s harbor by jet ski with a certified guide

Walk Easton's haunted past through its notorious Tragedy Triangle

Sharpen your pickleball skills with targeted drills and live coaching

Paddle the Anacostia River while helping remove floating trash

Taste Capitol Hill’s culinary history through dishes from neighborhood restaurants and markets

Taste your way through Eastern Market with vendor bites and local favorites

Cruise the DC Waterfront with premium onboard entertainment and bow seating

Taste house-made wines while creating a different Sunday project each week

Taste five house-made wines and see how an urban winery brings them to life

Taste five house-made wines and see how an urban winery works after hours

Cruise the Potomac in a private cabin boat for up to 6 guests

Cruise the Potomac at sunset on a private boat for up to 6

Fish private “secret” Potomac River spots on a Grady White (up to 6 guests)

Follow Black Broadway’s jazz, literary, and intellectual legacy

Build polished headshots with posing, client prep, and retouching techniques

Frame neon, desert relics, and dam architecture with a Las Vegas pro