Traditional New England Sailing at its Finest

“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 charter on Boston Harbor is a great way to create memories and new traditions. 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 that Boston’s magical harbor has to offer.

Private Charters

The Tupelo Honey is US Coast Guard certified for up to 16 passengers. Sail Boston Harbor and take in the city’s beauty from another angle. Private Charters are great for any occasion; sailing with family, friends, co-workers or a significant other is an experience you want to miss. The possibilities with a private charter on Boston harbor are endless. 

For more information be sure to check out our Private Charters page.


Our Signature boat, Tupelo Honey, is a 31 foot traditional Friendship sloop which sails on the Boston Harbor. She is a Coast Guard certified replica of the 1904 friendship sloop Dictator. The Dictator was one of the original lobster smacks that fished the coast of Maine. Captain Don aims to make the traditions and appreciation of classic sailing vessels of the late 1800’s available for everyone to experience and enjoy.

Learn More about the Tupelo Honey