things to do in Annapolis, MD

Build pickleball skills through coaching and social play

Sharpen your pickleball skills with targeted drills and live coaching

Mix up your doubles partners and track your results

Mix up your matchups with rotating partners

Paddle the calm Washington Channel from The Wharf with board, paddle, and PFD included

Bring your own drinks and cruise Annapolis on a private tiki boat for 8–16

Walk DC’s U Street and trace the legacy of “Black Broadway”

Walk Capitol Hill to see Union Station, the Supreme Court, and the Library of Congress

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

Taste U Street’s culinary history along Black Broadway

Charter a private DC boat tour from The Wharf for up to 6 guests

Paddle a stable canoe on the Washington Channel

Cruise Chesapeake Bay with your own drinks, music, and flexible stops

Private cruising with your playlist, swim stops, and bring-your-own drinks