Chincoteague Island Activities

Visitors to Chincoteague often remark that they are surprised by the abundance of activities on our small island, seven miles long and three miles wide. On Chincoteague Island, VA, you can fill your vacation with the perfect blend of relaxation and adventure. Chincoteague Island lies next door to Assateague Island, known for its pristine shores, wild ponies, and the iconic Assateague Lighthouse, with the only publicly accessible beach between Ocean City, MD, and Virginia Beach, VA.

Don't miss out on renting kayaks, paddleboards, and jet skis, or join boat tours to explore the island's waterways and the national wildlife refuge. Charter fishing boats offer a great way to experience the Atlantic Ocean's bounty. From fishing, boat tours, mini-golf, museums, pony swims, beautiful beaches, shopping, and Chesapeake Bay sunsets, there is truly something for everyone on Chincoteague. Explore all the activities our little beach town on the eastern shore of Virginia has to offer below.

Assateague Island

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Bait and tackle

Bait & Tackle

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Chincoteague Island biking


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Boat Tours

Boat Tours
Fishing rods

Charter Boats

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Nasa Wallop Rocket Launches

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pony swim

Pony Swim

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Kayak rentals


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Chincoteague Island surfing
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JS Expedition, Waterfowl Hunting, Chincoteague Island, VA

Waterfowl Hunting

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Andy's Guide Service, Waterfowl Hunting, Chincoteague Island, VA

Andy’s Guide Service

Andy Linton, a native of Virginia’s Eastern Shore, has been guiding hunting parties since 1965. Featured in “Disappearing Delmarva – Portraits of the Peninsula People,” The Washington Post, the television program “Virginia Outdoor Life,” and local newspapers, he is well respected and known as the Eastern Shore’s most experienced hunting guide. Licensed by the United States Coast Guard as a Master Captain, he provides a personal touch and is the sole guide for this business. His return clientele attests to his expertise and dependability.

Assateague Adventures Kayak Tours, Chincoteague Island, VA

Assateague Adventures Kayak Tours

Welcome to Assateague Adventures! Where they specialize in unforgettable memories! The tours are suitable for all ages and levels. Take a kayak tour to see the wildlife and wonder of Assateague while the guides share the beautiful history and folklore that the barrier islands have to offer. Get hands on education and interaction with the critters of the sea, while learning about your favorite pirates who once chartered these waters. Now including private paddle board lessons and tours (call for all paddle board inquires).

Assateague Explorer Boat Tour, Chincoteague Island, VA

Assateague Explorer Boat Tour

Where are the Wild Ponies? Since 2001, the Pony Express Nature Cruise has provided the best opportunity to observe wild ponies along the borders of Assateague’s extensive, calm western shoreline. Departing from the southern end of Chincoteague Island, the cruise spends more time along the best part of Assateague, looking for wild ponies, dolphins, eagles, shorebirds, and other wildlife. Enjoy a sunset wildlife cruise for a spectacular coastal experience or add a kayak tour for a more adventurous outing. Cruise/kayak packages and group/family discounts are available. Be sure to call ahead for reservations. Featured on the ABC “Good Morning America” show, Coastal Living Magazine, Southern Living Magazine, Family Fun Magazine, and more.

Assateague Explorer Kayak Tour, Chincoteague Island, VA

Assateague Explorer Kayak Tour

Escape to a nature haven where wild ponies roam freely on a kayaking adventure with Assateague Explorer. Guided tours start right across the channel from Assateague Island, the wildlife refuge. Kayak from the scenic dock overlooking the Assateague Lighthouse and explore the borders of Assateague’s extensive, calm western shoreline. Experience solitude, nature, and wildlife viewing on these unique island adventures. Paddle through the warm backwaters of barrier islands in premium sea touring or sit-on-top ocean kayaks. Search for famous wild ponies, eagles, shorebirds, and other wildlife as you navigate creeks, channels, and coves, or sometimes land on a remote beach at Assateague. No experience is necessary. It is a fun way to see great parts of the island with your family and friends.

Assateague Tours, Boat Tours, Chincoteague Island, VA

Assateague Tours

Assateague Tours offers the best Boat Tours and Kayak Tours along Chincoteague and Assateague Islands. They offer group tours as well as Private Exclusive Tours. They will take you to the most remote areas of the National Refuge for pony watching and birdwatching. Assateague Boat and Kayak Tours will get you up close and personal with the wild Chincoteague ponies and all the wildlife Assateague Island has to offer. They offer morning tours, pony tours, nature tours and sunset cruises. Assateague Tours will tour the great marshlands of Chincoteague & Assateague. They go around the islands to find the world-famous Chincoteague ponies, dolphins and the biggest selection of native birds on the east coast. Just call them at 757-336-6176 to make a reservation or visit for more info.

Bad Habit Fishing, Chincoteague Island, VA

Bad Habit Fishing

Captain Howard Rumbley has a beautiful and spacious 22-foot CHAWK fishing boat and is eager to help you catch some fish! Trips run daily during the fishing season, with all equipment provided. Captain Howard has over 30 years of experience on the waters of the Choptank and Chesapeake Bay, including 15 years in the waters surrounding Chincoteague.

Barnacle Bill's Boat Tours, Chincoteague Island, VA

Barnacle Bill’s Boat Tours

Come take a boat tour with Master Captain Barnacle Bill! Enjoy breathtaking scenery as you sail the waters of Chincoteague and Assateague Island in search of adventure and discovery. You will see Bald Eagles, wild ponies, the Assateague Lighthouse, dolphins, a large variety of birds and waterfowl, and some of the most beautiful sunsets you will ever experience. Being a native of Chincoteague, Bill can share many stories about life as it was years ago when his grandparents lived, worked, and even went to school on Assateague. “I am Barnacle Bill, your Captain, born and raised in the same house that my dad was born and raised in on Chincoteague Island.”

BluFin Bungalows and Marina, Chincoteague Island, VA

BluFin Bungalows & Marina

This brand-new vacation rental getaway and marina are like no other. Stay in your luxury bungalow on the water. Rent a boat slip for your stay, walk down the pier in the morning, and hop in your boat for a day full of fun. Get closer to Chincoteague Bay than ever before and admire the stunning sunsets! BluFin is in the heart of Chincoteague Island, surrounded by local attractions and amenities. Enjoy the luxury waterfront accommodations, Bungalows, Bungalow Boats, and access to the island’s best fishing spots.

Bottoms Up Tiki Tours, Chincoteague Island, VA

Bottoms Up Tiki Tours

HOW DO YOU TIKI? Bottom’s Up Tiki Tours is Chincoteague Island’s newest and most unique way to cruise the local waterways and experience Chincoteague Island Time! From a fun weekend brunch to a sunset wine tasting, enjoy great food, creative cocktails, and epic views from the water! Bottom’s Up Tiki Tours are the perfect way to celebrate any occasion—birthdays, proposals, wedding parties, girls/guys night out, graduation parties, team building, corporate meetings, retirement, bachelorette/bachelor parties, anniversary parties, or any reason you can think of… or for no reason at all. There are a multitude of different cruises and adventures to match your vibe. All cruises can be booked as a private charter if preferred. Give a call to create your personal specialty cruise.

Captain Dan's Around the Island Boat Tours, Chincoteague Island, VA

Captain Dan’s Around the Island Tours

Try the newly modified “Pony Tour,” now available daily in the afternoons. Search up to 21 miles of pony-viewing coastline, with ponies spotted at a distance of less than 100 yards over 90% of the time. On the “Around the Island Tour,” search for ponies, dolphins, wildfowl, and other local sights. Travel over 25 total miles of unique coastline, never passing the same area twice—see it all! All trips are 2-3 hours and include local history and commentary from your guide. The afternoon “Pony Tour” may be aboard the larger 14-passenger boat, while all other trips are aboard 6-passenger pontoon boats. Groups of more than 6 can inquire about a private tour aboard the larger boat. Board from the floating dock in the Downtown Park adjacent to Don’s Seafood Restaurant.

Captain Steve's Bait and Tackle Shop, Chincoteague Island, VA

Captain Steve’s Bait and Tackle

Captain Steve’s Bait and Tackle is your source for Chincoteague Island fishing tackle, bait and equipment. They specialize in surf, bay fishing (esp. flounder), and offshore fishing and carry a wide selection of rods, reels, lures and tackle for all local fishing needs. Here at Captain Steve’s, they also carry a variety of custom-made rigs which have been proven for years. The East Coast Flounder rigs have been the most popular rig for around 10 years now. The custom-made Assateague Mod. fish finder rigs have been the go-to rig for big fish off the surf. Swing on in and let their family help you have your most enjoyable fishing experience. Capt. Steve’s is your saltwater outfitter for surf fishing, bay fishing and offshore fishing!

Chincoteague Bay Adventures, Charter Boat Fishing, Chincoteague Island, VA

Chincoteague Bay Adventures

Offering an affordable, private, and fun fishing trip for the entire family on the inshore waters around Chincoteague. Fish for Flounder, Trout, Sharks, and delicious and fun-to-catch panfish. Capt. Tim has experience fishing throughout the U.S. and is a graduate of the University of Alaska Kenai Guide School and Orvis-endorsed Hubbard Guide School in Montana. Experience the difference training makes, where safety and comfort come first. Trips can be customized to your interests, whether it’s fly fishing, clamming, crabbing, or just riding around in the breeze. The vessel is a customized 22-foot Carolina-style skiff seating up to six passengers. For your convenience, Capt. Tim can meet at your waterfront location (weather conditions dependent).

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