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 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 advance). We love to charter Tupelo Honey 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 Charters 


What’s a better way to celebrate your birthday, or the have a family day, than to charter a sailboat on Boston Harbor? All you have to do is invite 11 of your closest friends on your private charter to enjoy the fun. We encourage our guests to BYOB and have a great time. We cater to all ages on our sailboat, so don't leave anyone out! 

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 approximately 2 hours on the water and 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.

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.

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.