At On The Boat Charters, we believe the best way to experience Martha’s Vineyard is from the water. Our private luxury charters are designed to combine the natural beauty of the island with elevated comfort, personalized service, and unforgettable moments at sea. Whether you are seeking a relaxing sunset cruise, a special celebration with friends, or a custom day exploring the Vineyard coastline, every charter is tailored to create a truly exceptional experience.

Led by Captain Donny Brice, guests can enjoy the confidence of cruising with an experienced local captain who knows the waters, harbors, and hidden coastal gems of Martha’s Vineyard. Captain Donny’s passion for boating and the island itself creates an experience that is both welcoming and refined, making every guest feel at home from the moment they step aboard.

Our vessel underwent a complete renovation in 2026, blending timeless coastal style with modern luxury and performance. Guests will enjoy updated luxury fittings, comfortable seating, premium finishes, and thoughtful amenities throughout the boat, all designed to create a sophisticated and relaxing atmosphere on the water.

Equipped with top-of-the-line navigation electronics and advanced marine technology, the vessel delivers a smooth, safe, and reliable cruising experience in a wide range of conditions. Every detail has been carefully considered to ensure comfort, safety, and peace of mind while exploring the beautiful waters surrounding Martha’s Vineyard.

From scenic daytime charters to unforgettable evenings at sunset, Discover The Vineyard by Sea offers a private boating experience that is elegant, effortless, and uniquely Vineyard. We look forward to welcoming you aboard.