Capital SUP's founders and head instructors aren't just all Annapolis-area natives—they're also all experienced in aquatic fitness and local history. It may come as no surprise then, that they've found a way to teach standup paddleboarding and the rich history of Annapolis at the same time. They offer a trifecta of guided tours, beginner and intermediate paddling lessons, and equipment rentals.

Daytime tours begin at the South Annapolis Yacht Centre, the city's oldest operating marina. After a brief training session, groups set off to explore the city's creeks and rivers, passing under the shadows of docked yachts and centuries-old stone buildings. Tours visit historic sites such as St. Mary's Church and the US Naval Academy, balancing aquatic adventure with a history lesson and the occasional Roman mock naval battle. Nighttime tours add a little drama with colored lights affixed to the bottom of each board and nonstop music throughout the tour. CapitalSUP goes beyond basic paddleboarding, though: fitness classes start with dynamic land exercises before using the boards as a floating gym, and FloYo classes work through yoga poses out on the water.