Private Charters

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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 information on our Public Harbor Tours, please click here.


   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! 

   Birthday Charters

What’s a better way to celebrate your birthday than to charter a sailboat on Boston Harbor? Come Sail Away Now can arrange for anything your heart desires for your private birthday cruise. Invite up to 15 passengers on your private charter and enjoy your big bash. We encourage our guest of honor to BYOB/F and have a great time!

   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.

   Family Fun Charter

A private charter is a great way to spend time with family. In today’s fast paced world it is easy to lose touch with even your immediate family members. Time spent on a sailboat, privately chartered for your family, allows you to reconnect while creating new memories. You can also surprise a family member with a sailing charter to celebrate new accomplishments such as a graduation, promotion, or athletic success. Charter the Tupelo Honey today and let the family sailing traditions begin!

   Corporate Team Building Charter

In business it is crucial that your staff is able to work as a team. Sailing a boat on Boston Harbor takes the same effective communication and team work needed in the corporate world. Our private charter for corporate bonding is designed to challenge your employees to overcome tasks by effectively communicating and working together as a unit. Your employees will leave with a sense of accomplishment and the skills needed for successful team work. If your employees can sail a boat on Boston Harbor, they can surely work together to tackle any project on the job!
Chartering a sailboat on Boston Harbor is also a great way to impress new or existing clients. Why bore your clientele with the traditional overpriced dinner and event tickets when you can impress them with a private sailboat charter on Boston Harbor? Call today and let us handle your next outing. Your clients will surely feel appreciated aboard a Boston Harbor private boat charter.

   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.

   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.  Give us a call to book this unique experience:  617-828-9005