Private Boston Harbor Sailboat Charters

Private boat charters on Boston Harbor are great for any occasion. The crew of Tupelo Honey works to meet your specific needs during your cruise around the harbor of Boston. A private charter aboard the Tupelo Honey allows for you to BYOB/snacks or have your cruise catered by one of the local area restaurants. We are happy to have food and beverages arranged for your sail if notified in advanced. We love to see Tupelo Honey chartered for engagement parties, graduations, first dates, a girl’s night out or other fun events. For more great ideas for a private charter on Boston Harbor please see below. For information on our Public Tours, please click here.

Private Birthday Charter


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. All you have to do is invite 11 of your closest friends on your private charter to enjoy the big bash. We encourage our guest of honor to BYOB and have a great time. We cater to all ages on our sailboat charters and have charters designed especially for children’s birthdays. 

Check out our Ultimate Peter Pan Experience Tour:  

What could be more enjoyable for a family outing than a fun filled sail around Boston Harbor?  Come Sail Away Now offers the Ultimate Peter Pan Experience catered especially towards children!  The Ultimate Peter Pan Experience departs from Charlestown, sails for 2 hours and returns back to port.  The boat is designed to look exactly like the ship in Peter Pan – from the crocodile to Tinker Bell to Wendy walking the plank.  The captain and crew will be in character as Peter Pan, Captain Hook, and other classic icons from the story to make the experience authentic!  Kids of all ages will love spending the day in Neverland!  The Peter Pan experience is also great for birthday parties!  You can fill the boat with up to 12 people to celebrate your child's birthday. 
For Pictures of our Peter Pan Tour please click here.

Romantic Private Charter 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 for you to reconnect while creating new memories. You can also surprise a family member with a sailing charter to celebrate new accomplishments such as graduations. Charter 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 feeling with a sense of accomplishment and the skills needed for successful team work. If your employees can sail a boat charted 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 over priced 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 private boat charter.