Embark on an unforgettable Pony Tour adventure with seasoned Captain's Mike, Donnie, and/or Sandy. Boasting over 40 years of navigating Chincoteague and Assateague waters. Prepare for a full 2-hour exploration of the pristine coastline aboard state-of-the-art boats covering over 25 miles of scenic beauty. New luxury boats for 2026!

Get ready for an up-close encounter with the iconic Chincoteague ponies and a plethora of wildlife, from majestic eagles and ospreys to graceful herons and pelicans. Delight in the playful antics of dolphins and relish the breathtaking vistas of stunning sunsets.

As you cruise through the island's waterways, immerse yourself in captivating narratives about its rich history and the captivating personalities of its most famous equine residents, including the legendary “Riptide.” Traverse small guts and channels, reveling in the abundance of nature's wonders.

Captain Mike, the owner of Up The Bay Pony Tours is a resident of Chincoteague Island who grew up spending most of his summers with family members who lived on the island. He spent most of his time fishing, crabbing with his grandfather, and getting to know the back bays around Chincoteague and Assateague. Getting up at dawn and fishing all day was the norm.

Captain Mike’s excitement for fishing continued as he started his own fishing charter business. During the day he would take people out fishing for flounder and then when it got dark he would focus on shark fishing. Captain Mike found his true passion was touring the island and sharing his knowledge of the wildlife surrounding it. Mainly, the Chincoteague ponies.

Captain Mike knows the ponies by their names and consistently tracks the territories that they frequent most. He can recognize the stallions from the colors and markings on them. During the off-season, Captain Mike continues to explore and track the wild ponies as he is a Professional photographer that consistently hikes Assateague Island. You can view all his photos on his website Up The Bay Photography.

“Captain Donnie” holds a Master Captain's License and has lived his entire life on the Eastern Shore. At an early age of 5 he started to work with his dad who was a waterman on the back bays of Chincoteague. Along with knowing and understanding the waters around Chincoteague Captain Donnie also owned a forty acre farm for over 20 years managing over 30 horses. His farm gave lessons and training to many of our locals that lived on the Eastern shore. His first pony he ever owned was a 3 year old Chincoteague Pony Stallion named “Lucky.” If you tour with him he can tell you where the name came from! I know whoever tours with Captain Donnie will appreciate his knowledge and also his stories! Donnie is also an avid duck carver. If you are ever on tour ask him how I obtained one of his carvings!