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

Tupelo Honey allows for up to 12 passengers to 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 don’t 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.

Private Charters

Public Harbor Tours

Aside from our private charters, Come Sail Away Now has created unique Boston harbor cruises for your enjoyment. We provide a variety of harbor tours that allow you to mingle with new people while enjoying great food and beverages. A typical night on the town involves loud restaurants and boisterous bars that make heartfelt conversation impossible. A not-so-typical night sailing on Boston Harbor sweeps you away from the hustle and bustle of the city while enjoying good company and breathtaking views. For more information be sure to check out our Harbor Tours page.

Harbor Tours


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 Benoit aims to make the traditions and appreciation of classic sailing vessels of the late 1800’s available for everyone to experience and enjoy.

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