Private Charters on Boston Harbor are great for any occasion. We would love to have you aboard Tupelo Honey for engagement parties, graduations, first dates, a girls’ night out or other fun events. CSAN offers a BYOB/F atmosphere- any food or drinks are welcomed! For more great ideas for a private charter on Boston Harbor please see below.

For any questions about any of our charters, see our FAQs.  Also please be sure to read our cancellation policy prior to booking

Private Charters

What’s a better way to celebrate any special occasion than to charter a sailboat on Boston Harbor? Come Sail Away Now can arrange for anything your heart desires for your Special Day . Invite up to 12 passengers on your private charter and enjoy your time aboard a beautiful boat. We encourage our guest of honor to BYOB/F and have a great time!

Charter Length: 2 hours minimum

*$75 Per additional Person over 12 Passengers/ 16 Passenger Maximum.

Island Sailing Adventure

Why not charter a sailboat for a 4 hour trip out to Spectacle Island.  We will motor out to Spectacle Island, which will take about 1 hour.  Once we arrive, you can spend about 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.  We will then spend the last two hours sailing back to Charlestown.  It is quite an experience you will never forget! 

Charter length: 4 hours minimum

*10 Passenger Maximum.

Bachelor/Bachelorette Parties

What better platform to host your bachelor/bachelorette party than aboard the Tupelo Honey! Book a private charter for 2 hours, half day or a full day to sail around Boston Harbor. Bring your closest friends, family, and party props aboard for a truly unforgettable experience.  Come Sail Away Now offers a BYOB/F atmosphere.

Charter Length: 2 hours 
12 people

*$75 Per additional Person over 12 Passengers/ 16 Passenger Maximum.

Romantic Charters for Two

Picture this: you and your honey are cuddled up on the bow of a 100 year old majestic Friendship sloop. The wind is skipping over the bow while the two of you share a bottle of your favorite wine. The view is breath taking, the stars are out to play and you can hear the waves gently slap against the hull of your privately chartered sailboat. The moon guides the captain as he makes your sail on Boston Harbor as peaceful and intimate as possible. You and your loved one can sit back, relax and take in the magical Boston Harbor skyline. Come Sail Away Now loves to be a part of anniversaries and couple surprises! Call now and we will help you plan your romantic private charter on Boston’s harbor.

Charter length: 1.5 hours

*2 passenger maximum.

Citylights/Moonlight Charter

See Boston in all its glory at night under the moonlight on our 90 minute Citylights/Moonlight Private Charter, which begins at 9pm.  Sail through Boston’s Inner Harbor and experience the spectacular nighttime views of Downtown Boston, the Seaport District and the historic Charlestown Navy Yard. 

Charter length: 1.5 hours

*10 passenger maximum.

Sailing Lessons

For those of you learning to sail, what could be more perfect than learning aboard a traditional sailing vessel from the turn of the century. You won’t be dangling from the rigging, but you will learn from the best in a safe, fun fashion. Lessons will be conducted aboard the Tupelo Honey under the tutelage of captain Don and his first mate. Lessons will be offered during charters so you will be learning during a real sail. 

Charter length: Approx. 3 Hours 


  • 30% off
  • 3 lessons
  • Pricing: $315.00/ $35.00 per hour


  • 40% off 
  • 5 Lessons
  • Pricing: $450.00/ $30.00 per hour


  • 50% off
  • 10 Lessons
  • Price: $750.00/ $25.00 per hour

Can't find what you're looking for?

For longer trips such as ½ day voyages or full day excursions or if you want more information about any of our other charters, please contact us.