Check out our new sister company....
Cityside Harbor Shuttle!
Come Sail Away Now with Captain Don aboard the sailboat, Tupelo Honey. Get out and cruise Boston Harbor with your closest friends and family. A private charter on Boston Harbor is a great way to create memories and new traditions. Tupelo Honey’s first mate, Ann Flannery devotes her time to making your sailing tour truly special and unique. Our goal is to share our love of sailing and to create an experience on Boston Harbor you won’t forget. This is your memory in the making and we want you to experience all of what Boston’s magical harbor has to offer.
Private Charters
Specialty Tours
Yes, we do it all while sailing Boston harbor and that includes you at the helm too! Tupelo Honey’s crew is experienced and willing to teach you the tricks of the trade. We are so passionate about sailing that we want you manning the sheets with us. Sailing lessons are great for anyone and especially great for family or corporate bonding. For more details about sailing lessons on Boston Harbor check out or sailing lessons page.
Click here to visit the Purchase page and buy your tickets today!