Boston Harbor Public Tours

Come Sail Away Now offers a variety of incredible harbor tours. Each one is designed for your relaxation and sailing pleasure! Enjoy the tranquility of the morning on our weekend brunches or experience the gorgeous sunset colors against the Boston harbor skyline. Wine tastings and night time harbor cruises let you witness the stars twinkle on Boston Harbor during your boat tour. Our Boston Harbor Tours are an exciting way to take pleasure in the other side of Boston. Enjoy your sail and take in the cities spectacular views while the crew navigates their way around Boston Harbor. For information on our Private Charters, please click here.


Traditional Sailing Adventure on Boston Harbor!
 
 

Come Sail Away Now with Captain Don aboard the sailboat, Tupelo Honey. Captain Don has been sailing all of his life and was a commercial fisherman in Gloucester, MA.  The Tupelo Honey is a 31 foot traditional gaff rigged 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.  Ever wonder how lobstering was done before motors?  Rigging was done so the sails could be back winded (stand still in the water) while pulling traps.  Sails were tied down with the line and hoisted by sheer strength.  Trees were cut down for masts.  Captain Benoit aims to make the traditions and appreciation of classic sailing vessels of the late 1900’s available for everyone to experience and enjoy. Get out and cruise Boston Harbor with 11 of your closest friends and family. A traditional sailing adventure 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. Captain Don is there to share with you some of the traditions of sailing if you wish.

2 Hour Adventure on Boston Harbor 
Call for dates & times & to book! 



Island Sailing Adventure on Boston Harbor!


Come Sail Away Now with Captain Don aboard the sailboat, Tupelo Honey for our Island Sailing Adventure. If 2 hours on the harbor is not enough for you, then join us on this 3 hour trip out to Spectacle Island. Spend approx an hour on the island, where you can visit the museum, hike a trail to the top of the island (where there are superb views of the harbor and outer islands), go kite flying and sea-glass hunting and even go swimming.

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. 

3 Hour Adventure 
Call for dates & times & to book!