See the Chesapeake Bay from above or charter a private boat for your group
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10 - 12 minutes
Up to 12 people
Choose a parasail flight or a private custom boat tour on the Chesapeake Bay in Annapolis. You can ride as a parasailer or join as an observer on the boat.
Parasail flights last 10–12 minutes, and you may be on the boat up to an hour as multiple flights run per trip. Double and triple flights require a combined weight between 225–450 lbs; observer weight limit is 285 lbs. No spray sunscreen or food is allowed on the boat; water bottles with a twist-closure lid are acceptable.
Full refund if the operator cancels due to weather or mechanical failure. You may cancel within 24 hours of your scheduled trip for a full refund. A 7-day cancellation notice is required for group and private charters.
Use GPS for Chart House, Annapolis; it will bring you straight to the check-in area at 300 Second St., Annapolis, MD 21403.
Yes. Street parking and onsite parking in the marina are available.
Dress appropriately for a boat outing. You may get splashed or come in contact with damp equipment (harnesses and life jackets). Storage can be minimal on a full boat, so limit what you bring. A water bottle is allowed.
Annapolis, MD
Howard and Audra run an exceptional parasailing operation that clearly knows how to make guests feel comfortable and welcome. Multiple reviewers mention how their warm, professional approach helps ease nervous first-timers, with Audra's personality particularly standing out for putting people at ease right from the dock. They're described as genuinely kind and engaging, creating an atmosphere where the experience feels fun rather than intimidating. The experience itself consistently delivers, with guests praising the generous air-time and spectacular views. Groups of all ages seem to have a blast here, from teenagers to visitors in their seventies. The team's professionalism shines through in how they take their time with guests and handle the technical aspects smoothly. It's worth noting they've also stepped up to accommodate last-minute bookings when other companies have fallen through, showing flexibility alongside their skill.
Amazing experience! Our entire family had a blast. We felt safe the entire time and our preteens said it was the most fun they’ve ever had.
Lauren Loomis
April 4, 2026
Amazing experience! Our entire family had a blast. We felt safe the entire time and our preteens said it was the most fun they’ve ever had.
Lauren Loomis
April 4, 2026