Today we’d like to introduce you to Bobby T.
Bobby, can you briefly walk us through your story – how you started and how you got to where you are today.
It’s really my passion for boats and boating that drew me to this fun industry. I learned to sail, canoe, waterski, and drive boats from an early age in New England. Boating and sailing is something that I’ve always loved. For me, getting out on the water is such a pleasure… so relaxing. It’s like all my worries and problems disappear, and I’ve entered a world that is tranquil and beautiful. Out on the water, I have the opportunity to experience the world in a totally different way.
Previously I had a company for a decade in the gift industry as a manufactures rep, selling to New England retailers from small individual stores to companies like TJ Maxx, LL Bean, catalog houses and many of the larger retail chains. After this, I worked as a musician. One of my regular gigs was at the Ritz Carlton. My music can be found on Amazon, iTunes, YouTube, and CD Baby. I still get to play occasional concerts and private events. Before getting into the gift industry I worked as an actor and taught martial arts. I’ve trained in a Japanese style called aikido since I was a teenager and currently hold the rank of a 6th-degree black belt and teach aikido at MIT.
But back to my company Boston Charter Boat where I book about 100 charter events a year. All our boats come with captain and crews. We don’t own or manage any boats – we are an independent charter event broker and work with all the boat companies in Boston from individual boats and yachts to event vessels for up to 1,100 guests. Clients tell us that our website BostonCharterBoat.com is easy to navigate, where they quickly can see all the charter boat options that are available. There’s a surprisingly wide variety to choose from in Boston.
We enjoy helping setup water-based events. Everyone loves getting out on the water, whether for a corporate event, social events such as weddings, graduations, large family events, bachelor and bachelorette parties, a romantic cruise, or just a couple of friends looking to have a fun day together. As well we often set up overnight trips to Cape Ann, the North Shore, PTown and beyond.
In addition to an event on a boat, there are 34 harbor islands in Boston that offer a wide variety of fun event options. We’ve booked weddings and corporate events on a number of harbor islands with groups up to 300 guests. We start with the company’s budget and put everything together for them, including catering (lobster/clam bakes are popular), bar, entertainment, tents (in case of inclement weather or hot sun), fun games and activities on the beach, and of course boat transportation to and from the islands.
There are so many different boating options in Boston and our clients are always excited and intrigued at the prospect of seeing Boston harbor and the beautiful harbor islands. It’s such a pleasure to help people get out on the water. Everyone’s in a good mood and feeling upbeat throughout the planning process – culminating in a pleasurable and unique event where they get to commune with nature and experience the world in a totally different way.
Great, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
We started off working for another charter broker’s company and built up their business as well as our reputation in the industry and went out on our own about three years ago. It was difficult at first, but once we set up our website and marketing it’s been smooth sailing. A good website is the key and we are constantly tweaking it and adding new vessels.
Please tell us about Boston Charter Boat.
We specialize in corporate and social events, but we also book boats for as little as one person. Company parties are a big part of our business and there are a variety of boats that are available year-round for holiday parties and other events.
For smaller groups (up to 12 guests) we have lot’s of fun options and activities available. There’s sailing, sailing instruction, fishing, swimming, island picnics, harbor tours, Charles River tours, team-building activities and more. You can bring your own food and beverages on all of our smaller yachts, sailboats and motor boats. Many of them also offer catering, and we work closely with Boston’s best caterers.
Our 55′ Sea Ray offers swimming, paddle boards, a giant fun inflatable raft (fits up to 10), as well as a fun and fast 3-person jet ski (at no additional charge). How fun is that. This yacht and others can bring you out to many of the 34 Boston Harbor Islands (most are part of the National Park system), where activities like hiking, swimming, fishing, picnics and more are available. There are also day-trips to the North Shore, Ptown, and beyond as well as fun overnight and multi-day excursions.
We have all kinds of fun and exciting sailboats. Some can take up to 12 guests, and some up to 115 guests! Most captains will let you take the helm and sail the boat. A couple of our sailing yachts are as fast exciting as the international 12-meter racing boats and in addition to our usual 2-4 hour charters, are available for overnight and week-long or multi-week charters.
Of course, the striped bass, bluefish, flounder, and tuna are abundant in Boston and we can set up fishing for groups up to 20 guests. Some captains are licensed commercial lobstermen and we have a number of boats that offer lobstering activities where you can take home whatever you pull up in their traps. One of our captains specializes in trips to some of the outer islands that few people get to experience and then prepares a freshly steamed lobster picnic with views that are extraordinary.
However, there’s one activity that we really enjoy setting up and that’s surprise engagement cruises. Most people choose a romantic sunset cruise for this. We supply the champagne and hors-d’oeuvres.
We are proud of our wide-selection as well as our close relationships with the captains, crews and management companies. We are also proud of the fact that many corporate groups, universities, and family groups come back year after year to book boats with us. We feel that our commitment to our clients, our knowledge of all the boats and our ability to put together such a wide variety of events and options sets us apart from others.
Do you look back particularly fondly on any memories from childhood?
The first time that I sailed a boat on my own.
Pricing:
- Small charter boats start at $200/hour + tip (includes captain, all tax and harbor fees).
- Boats for larger groups (100 – 1,100) start at $1,500/hour. All provide catering and entertainment, and you can bring your own food and entertainment on some.
Contact Info:
- Website: BostonCharterBoat.com
- Phone: 617-913-9036
- Email: bt@BostonCharterBoat.com
- Facebook: https://www.facebook.com/BostonCharterBoat/

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