About - 757 Sailing Charters

Our Story

757 Sailing Charters started several years ago, when Captain Tom’s and Captain Robert’s wives wanted to get together for dinner. The two women frequently got together for lunch or coffee, but they had the bright idea, “Let’s invite our husbands to dinner.” Feeling some hesitancy from their beloved spouses, they sweetened the deal: agreeing to stroll on the docks and boat-watch. So the guys agreed and everyone met for dinner at “The Deadrise,” a waterfront restaurant in historic Fort Monroe at the Old Point Comfort Marina.

During the stroll on the docks the conversation turned to what they wanted to do when they grew up. Captain Tom said, “When I was a kid I use to love taking people out on my dad’s boat. Now I would like to buy a sailboat and take people out sailing. That’s what I want to do next.” Captain Robert, wanting to be encouraging, said, “I think that is a great idea! Doing something you love would be fun!” You see, they both loved navigating the Chesapeake Bay, Hampton Roads and the surrounding waterways and they wanted to find a way to do it more frequently. So, several years later, Captain Tom and Captain Robert would partner together to buy Sailing Vessel Freedom. And that, my friend, is how 757 Sailing Charters got started. The two Captains think their wives might regret it now.

Meet our Captains!

Capt. Robert

Captain Robert has lived around water all his life. He is married with four children and three grandchildren. He has operated many types of small craft using various forms of propulsion. He enjoys most water sports, finds the area’s history fascinating, and is an amateur birdwatcher. He is a retired U.S. Coast Guardsman and holds a Captain’s License for Uninspected Passenger Vessels.

Capt. Tom

Captain Tom has lived around water all his life also. He is married with four children and four grandchildren. He grew up in Hampton and has enjoyed boating all of his life. He learned how to operate a boat from the many trips out with his dad as a little kid. Captain Tom has been remodeling and building houses for over thirty years and is now getting to take people out sailing. He also holds a Captain’s License for Uninspected Passenger Vessels and is looking forward to taking you, your family and friends out to enjoy the adventures of sailing.