things to do in Chesapeake, VA

Softtop boards with free swaps and local delivery

Celebrate from the sky with a float landing and golden-hour views

Rent a beach cruiser with a lock, with delivery available

Fly over Chesapeake Bay and arrive dockside for waterfront dining

Fly to a working oyster farm and taste Virginia oysters fresh from the water

Paddle at your own pace with flexible kayak rental periods

Choose your board size and get free swaps during your rental

Paddle together with included gear and optional delivery

See the Peninsula’s fall colors from a private seaplane

Take on cooler-season waves with close instructor attention

Cast for Chesapeake Bay fish with gear, bait, and tackle included

Learn proper SUP technique, then follow a guided route on calm waters

Explore Virginia Beach by jet boat with a 2-hour minimum rental

Rent a Polaris Slingshot for 24 hours with 250 miles included

Cast a line with gear, bait and licensing included

Cruise Virginia Beach Bay in a 5-seat JetCar rental

Make the water your private pub, with your own drinks and a certified captain

Paddle Chesapeake Bay waters with a stable sit-on-top kayak

Battle sharks with captain-led guidance for anglers of every skill level

Share a private farm evening with your own meal and time with the cows

Explore the water at your own pace in a single sit-on-top kayak

Soar in an open-cockpit WWII trainer for 20 thrilling minutes above coastal Virginia.

Cast a line on Chesapeake Bay with gear, bait, and deckhand guidance included

Private SUP surf lesson tailored to your skill level in Virginia Beach