Specialties
Come sailing with 757 Sailing Charters. Experience the waterways of Hampton Roads and Chesapeake Bay from a 36.5 foot sailboat. We provide 2 or 3 hour day time and sunset sailing charters in Hampton Roads and Lower Chesapeake Bay for up to 6 people.
History
Established in 2020.
757 Sailing Charters started several years ago, when Captain Tom's and Captain Robert's wives wanted to get together for dinner and thought they would invite their husbands. They met for dinner at "The Deadrise," in historic Fort Monroe at Old Point Comfort Marina.
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." Captain Robert said, "I think that is a great idea! Doing something you love would be fun!" You see, they both love navigating the Chesapeake Bay, Hampton Roads and the surrounding waterways and they wanted to find a way to do it more frequently. 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 the Business Owner: Robert and Tom S.
Captain Robert has lived around water all his life. He is married with four children and three grandchildren. 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.
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. He holds a Captain's License for Uninspected Passenger Vessels.
We are looking forward to taking you, your family and friends out to enjoy the adventures of sailing.