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. He is a USCG Licensed Master and is certified to captain a motor, towing, or sailing vessel of up to 100 tons.

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 1800’s available for everyone to experience and enjoy.


Tupelo Honey in the news!
Get a taste for the sea with this lobster snack, but it’s no roll, bisque or bake. The Tupelo Honey is a replica 1904 Dictator model Friendship sloop, a traditional New England ship used by lobstermen in the late 19th-century. Today it sails Boston Harbor giving small groups of would-be sailors great views of city sights on harbor tours, brunch cruises, sunset cruises, private & public cruises. Where Boston tells you all about us!

We have also been featured on Chronicle. Check Us Out! 

“Captain Don and Crew, You are amazing! Our experience was the highlight of our weekend. I am sitting here at dinner thinking life could not get any better. You certainly live the dream! May God bless you, keep you and His face shine upon you. Best wishes on all your adventures.”  ~Scott and Jolene Daniels

“Captain Don & Ann – Thanks so much for including us in the wine cruise – it was something memorable to add to our Boston trip and we’ll certainly suggest our friends look you up when they ask, ‘What’s there to do in Boston?’! – Cheers, Bev & Jon” – Windsor Ontario

“To the best Captain and first mate around, thanks so much for our romantic evening sail. By far the best thing we have ever done. A perfect anniversary for sure. Thanks for making it all so great.” – Meredith B.

“Just wanted to say thank you again for yesterday’s sail – we had the best time and can’t wait to have reason to celebrate again on the water!” – Andrea K.

“Thanks for such a great sail this past Sunday! We all had a blast and it was by far the highlight of our weekend. What a lovely way to spend 2 hours – can’t wait to make my next trip back to Boston and join you again!” – Rosie S.

“We had a great sail today – we loved the sights of the city and the kids loved when we got close to the airport and the planes were landing overhead. With the sails up and the motor off it was so relaxing. What a great way to spend our last day in Boston!” – Adrian C.

“These guys do it right – we went sailing Sunday and had a blast! The boat is really something special and Ann and Captain Donald treat you like family…in a good way.” – Brian P.

“Thanks to Captain Don for introducing me and my wife to sailing on such a terrific boat. Watching him and Laura work the sails gave me a new appreciation for the art of sailing.” – Jim H.

“Sailing around the harbor on Tupelo Honey is an exquisite experience. Don and Ann are highly trained owners/crew. They accommodate 8-12 people comfortably and offer both private and small group tours. Both ways, we have enjoyed cruising on this historic boat and have met wonderful people. For example, yesterday, a young couple was celebrating an anniversary and had received a gift certificate for the cruise from their family. What a unique idea. Others were just looking for a get-away to relax for two hours on the water. Thank you for lovely memories and we look forward to sailing again.” – Juli Ann, Scott and Rich

“I had one of the best days of my summer last season with the folks at Come Sail Away Now. This was an amazing Boston sailing experience because 9 of my friends and I got to go sailing in Boston harbor on a 100 year old sloop. We were able to select what wine we wanted on the cruise and they brought it to the dock for us, chilled and served it, and they supplied a cheese and cracker plate as well. We were sailing Boston Harbor and watched the sunset behind the downtown Boston skyline. Truly amazing Boston sailing experience, next time I’m in Boston, I’m bringing my girlfriend and all my friends our for a Boston sailing experience we can never forget! 5 out of 5 stars!” – Aaron T.

“Dear Don & Ann – Thanks for making my birthday cruise such a success! Everyone had a wonderful time, as you could tell, and you both did everything to make the whole experience really special. Wishing you all a wonderful rest of the summer! – Francine”

“Dear Ann & Captain Don – We had a wonderful time on the 7/30/11 Big Sister Sailing Trip. Your generosity is much appreciated! Lsis (Little Sister) has added “Owning a sailboat” to her list of life goals and she has not stopped raving about her special day. Thank you – Kerry & Lsis”

“Dear Ann & Captain Don – Thank you for a wonderful, magical few hours on your beautiful boat. Janieka loved it and it seems so did everyone else. It was a great day! Sincerely – Monika”

“I went out on the Tupelo Honey last week and had a great time! The captain and his sailing partner were really friendly and put us at ease. They were flexible with timing and the trip we took down the Boston waterfront. They even sailed us back around so we could see the sun set over the Boston skyline. I would definitely recommend Come Sail Away Now if you are looking for something unique for a special occasion or just to have a good time!”

“For my girlfriend’s birthday I booked a private “voyage” with CSAN for us and our friends. Captain Don and crew were very accommodating and friendly from the moment I contacted them about booking to stepping off at the dock at the conclusion of our two hour tour. The boat comfortably sat all 12 of us along with all the beer and wine we could carry (a pretty great perk that comes with the private tour if you ask me). After boarding we quickly headed out on the bay. Soon after the sails were raised, and with the engine finally cut it was unreal. It was so quiet that you could hear every splash of water, the creaking hull and far away sounds of the city. I loved every minute of it. Plus, once we set sail they allowed us to sit on the bow of the ship two at a time, which I didn’t expect and really made the trip unforgettable. At the conclusion of the tour everyone was very happy and a little tipsy. Looking back, I hope we weren’t too rowdy, but it was hard not to have a great time. If they’ll have us again we’ll definitely be back for more!” – Jason

“Dear Ann & Captain Don, we just wanted to thank you again for taking us on such an exciting sailing trip! Mariysa was so proud she conquered her fear of boats! We so appreciate you taking the time out of your busy schedule to host us – it was a gorgeous day on the water (and we both have suntans to prove it.) Thanks again for everything!”

“My family and I had the most amazing time on Saturday!! Your sail boat is beautiful and you both (Don & Ann) were terrific hosts! We look forward to next year’s trip. I’ve been telling all my family and friends about your company so hopefully you’ll be getting some new business” – Jessica Murphy

“Thank you so much for hosting our family’s sailing cruise Sunday. The weather was with us as your knowledge, experience and warm, welcoming personalities made our sailing experience a fond memory…I would highly recommend Come Sail Away Now for any party or reason to get out on the water. The BYOB is perfect giving you the option of tailoring to your personal needs and desires. Thank you again and we’ll definitely keep you in mind for future cruising!” – Cathy Schaeffer

“Thanks to all for a wonderful time today! It was perfect…I was so happy and my husband was surprised and delighted too! Best of all the weather couldn’t have been more beautiful! Thanks for making his 50th Birthday so special and memorable!!!!” – Lisa Comis