Boston Harbor Sailboat Charters

Are you ready for some fun on the water?
We are! 

Our sister company, Boston Harbor Shuttle, is now part of Come Sail Away Now! Offering pub cruises, private charters and public trips out to Spectacle Island - we're very excited about this transition!

If you've purchased a GroupOn or Living Social voucher for Boston Harbor Shuttle, you can book directly through us. Just email us or give us a call at (617) 828-9005.

Calendar of Events


      Traditional Sailing Adventure
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. 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. 

Tupelo Honey allows for you and 11 other passenger’s 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.

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 bars that are difficult to have any kind of intellectual conversation. 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 breath taking views. For more information be sure to check out our specialty tours page.

Sailing Lessons

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.