Air & Water

(8 activities)
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    Earn Your Wings Flight Package

    Have you always wanted to feel the thrill of free falling without having to... well, jump out of an airplane?! What if you could feel the adrenaline rush of skydiving MINUS your totally understandable fear of heights? Well, here's your chance! iFLY is an indoor skydiving facility that creates true free fall conditions. You'll float inside iFLY's 1,400 hp vertical wind tunnel -- with absolutely NOTHING attaching you to planet earth. And with the Earn Your Wings package, you'll get the ultimate beginner-level package for a great introduction to indoor skydiving: 2 unforgettable flights, plus hands-on assistance and a comprehensive training session from your personal flight instructor. You'll even get to take home a personalized flight certificate to show off to your friends. This is one indoor aerial experience you don't want to miss! Note: You will need to arrive 1 hour prior to flight time for a training session. Includes use of all the flight gear. If you have had a prior shoulder dislocation, back, or neck problems you should not fly. Those less than 6 feet tall must weigh less than 230 pounds, and those over 6 feet must weigh less than 250 pounds. Flyers can be as young as 3 years of age; there is no upper age limit. Discounted rate offered to groups of 8 or more. Please visit our website for more information.
    Earn Your Wings Flight Package

    2412 Pacific Ave, Virginia Beach

    • Experience the adrenaline rush of skydiving without having to jump out of an airplane
    • Benefit from the ultimate beginner's package, with everything you need to have a great first flight
    • Feel safe and prepared with hands-on assistance from your personal flight instructor
    • Channel your inner super hero as you float in iFLY Virginia Beach's 1,400 hp vertical wind tunnel
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    Flatwater Tour (Stand-Up Paddleboarding Tour)

    Take a small-group, guided Stand Up Paddleboard tour through the peaceful waters of First Landing State Park. Little or no experience is necessary to use Chesapean's Stand Up Paddleboards to explore the backwaters of First Landing State Park in a way that few get to see. Guides will help you launch and navigate the park for 1.5-hrs while you take in beautiful sceneries and see herons, ospreys, and other animals that call First Landing State Park "Home."
    Flatwater Tour (Stand-Up Paddleboarding Tour)

    313 Laskin Rd, Virginia Beach

    • Learn to Stand-Up Paddleboard (SUP) in pristine, refreshing water
    • Get tips on SUP technique and stance from a friendly tour guide
    • Take in the beautiful views of First Landing State Park
    • Have a chance to see and splash around with wildlife
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    Stand Up Paddleboard Lesson & Tour

    Getting restless from lounging on the beach? Stand up and try Stand Up Paddleboarding! Explore islands, bays, sounds, creeks and the protected estuaries of KH Woods and scan the lush seasonal flora to see many types of birds, otters, fish, crabs, eels, turtles, butterflies and more. Paddle out to the Salt Marshes into KH Bay overlooking the Albemarle Sound & the Wright Memorial and practice your SUP technique. Take in this scenic, protected environment with your instructor on a guided eco-tour. This adventure is educational, protected, safe, great for field trips, and all inclusive with a guide/instructor and a ground school to get you up and moving. C'mon lazy bones. In the words of the late Bob Marley "Get up, stand up" on a paddleboard!
    Stand Up Paddleboard Lesson & Tour

    1207 Duck Rd, Duck

    • Try out Stand Up Paddleboarding (SUP) in a beautiful area
    • Learn how to balance and practice effective paddling technique from the experienced guide
    • Keep on the lookout for friendly critters and wildlife
    • Take in the gorgeous views while learning a fun new hobby
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    Club 21+ Pirate Cruise

    Bring your own booty to this pirate-themed event and be prepared to shake it! This themed booze cruise takes place off the shores of Virginia Beach aboard a 65' replica of a Spanish Galleon! Mix and mingle with other guests and dance to modern tunes. Enjoy bawdy pirate performances that will leave you in stitches and adult beverages that are available for purchase. Altogether, you can expect well over an hour of raucous entertainment! The waters off of Virginia Beach offer plenty to see, including the glowing city skyline. This innovative outing is a great way to spend some quality time with old friends and maybe, make a few new ones! Shiver me timbers, this is going to fun!
    Club 21+ Pirate Cruise

    308 Mediterranean Ave, Virginia Beach

    • Embark on a raucous booze cruise aboard a replica pirate ship
    • Watch rowdy pirate skits that will leave you in stitches
    • Enhance the fun with adult beverages and dancing
    • Bring your old friends and make some new ones
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    Dolphin Tour (Stand-Up Paddleboarding Tour)

    Experience the ultimate Stand Up Paddleboard adventure that only Chesapean Outdoors offers. Combine the thrill of Paddleboarding with the joy of Dolphin Watching and never have to fight the tide or wind. This is the only tour in Virginia Beach that allows you to paddle down current for an hour and a half while dolphins cruise alongside you. Instead of paddling back to your launch spot, Chesapean will shuttle you back to your vehicles while our guides take care of the equipment. This is the ultimate SUP experience, but we recommend some paddling experience or taking one of our flatwater tours first. You'll love the beautiful ocean views and crisp air, as you splash around with the friendly ocean mammals. SUP offers a unique perspective so you can see it all from your feet. Don't support the injustice of aquariums -- see the sea creatures you love where they are free!
    Dolphin Tour (Stand-Up Paddleboarding Tour)

    313 Laskin Rd, Virginia Beach

    • Stand Up Paddleboard (SUP) through the pristine waters of Virginia Beach's north end shoreline
    • Splash around with atlantic bottlenose dolphins during their migration
    • Learn proper SUP technique from your friendly tour guide
    • Relax and take in the beautiful sights and crisp ocean air
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    Dolphin Tour (Kayak)

    Enjoy the thrill of kayaking with Atlantic Bottlenose Dolphins off the North End Shoreline of Virginia Beach with the company that's been specializing in dolphin Eco-tours for 20+ years.These small-group, guided kayak tours last 2 hours and allow you to see these magnificent animals up-close in their natural environment. Little or no experience is necessary to use Chesapean's sit-on-top kayaks to explore the coastal waters of Virginia Beach and get closer to wild dolphins than you have ever been before. Guides will help you launch and navigate along the coast while you partake in breathtaking scenery and unforgettable experiences with wild Bottlenose Dolphins.
    Dolphin Tour (Kayak)

    313 Laskin Rd, Virginia Beach

    • Kayak through the pristine waters of Virginia Beach's north end shoreline
    • Splash around with atlantic bottlenose dolphins during their migration
    • Learn about the beautiful area from your friendly tour guide
    • Relax and take in the beautiful sights and crisp ocean air
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  • Give the gift of fun with a Vimbly gift card!
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    First Landing Tour (Kayak Tours)

    Kayak the tranquil waters of First Landing State Park and witness the beauty of this unique tidal environment in a way that few ever experience. These small-group, guided kayak tours last 2 hours and lead you past awe-inspiring views and native wildlife such as: herons, egrets, kingfishers, ospreys, and even dolphins and bald eagles on occasion. Paddle under majestic oaks covered in Spanish Moss until you reach Eagle Point, one of the tallest dunes in Virginia Beach, where you will be greeted with a breathtaking view across White Lake and the marshes of First Landing. Your guide will touch on some local history as well as any local wildlife you may encounter.
    First Landing Tour (Kayak Tours)

    313 Laskin Rd, Virginia Beach

    • Ride a bike along Virginia Beach and into to the beautiful First Landing State Park
    • Ogle at the majestic sea-side mansions and cottages along the coast
    • Get a chance to see amazing wildlife like Osprey and Heron
    • Enjoy a nice, relaxing bike ride through diverse, gorgeous landscapes
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    Family Fun Pirate Cruise

    Ahoy there! Aargh ye ready for some fun? Cut loose and hit the high seas with Captain Jack aboard a custom-designed replica of a 65' Spanish Galleon! Outfitted to look like a pirate ship, The Lost Pearl sports water cannons along the deck. You'll help man these cannons to defeat the nefarious Blackbeard and recover a stolen treasure in the process! You'll also enjoy a pirate show, sing pirate songs, and scarf down delicious (not-so authentic) pirate grub, such as hot dogs and popcorn! What, you were expecting cackle fruit and salmagundi? Dolphins are also frequently spotted, as are numerous other vessels cruising these pristine coastal waters. Bring the kids -- this themed tour is all about wholesome, family-friendly fun!
    Family Fun Pirate Cruise

    308 Mediterranean Ave, Virginia Beach

    • Partake in a family-friendly cruise aboard a replica pirate ship
    • Play games, sing songs, and enjoy a pirate show
    • Scarf down snacks such as hot dogs and popcorn
    • Check out dolphins swimming alongside the ship
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