Boston Harbor has come a long way since The Sons of Liberty’s famous Tea Party, but it remains an iconic characteristic of one of America’s oldest cities, and still boasts the best vantage point to capture Boston’s skyline. Offering multiple cruises, Classic Harbor Line, has something for every seafaring person.
Take your sea legs for a test with the Live Jazz Cruise, have a date night on the romantic Sunset Cruise, or experience a whole new perspective with the Boston Harbor Night Cruise. If you aren’t just here for the views, get to know your captain Brennon Hamilton, who is equal parts historian, tour guide, and funnyman. Here he is, with a few tips and tricks of the trade.
Did you always know you wanted to be a captain, and what excites you most about going to work each day?
I grew up in land locked Fort Worth, TX. I had no idea I would end up where I am, but the most exciting thing about going to work every day is knowing that I’m doing something I’m proud of.
How did you get into sightseeing cruises?
For a company party we rented a bicycle powered bar that pedals around downtown. After that experience, my then boss encouraged me to become a driver and tour guide on the beer bike. Realizing I could make money doing something I enjoyed, I moved to the Virgin Islands in search of more fun jobs and ended up on snorkel tour sail boats.
Credit: Tom Thrasher Photography 
Credit: Tom Thrasher Photography
What do you hope your customers get out of your cruises?
Getting out on the water is all about changing your perspective. To get out of the city without even leaving it. I hope every passenger that comes out with us takes in the best views of Boston, connects with the historic locations, and uses the new vantage point to relax, recharge, and be inspired.
What’s your #1 pro tip about captaining a yacht like the Northern Lights?
There are a lot of variables; the wind, waves, tides, currents, depths, and ship traffic. It’s easy to overthink everything. When I’m dealing with tough conditions I just calm my nerves and tell myself, “just drive the boat.”
When traveling, what is the one thing you never leave home without?
I never leave home without my Leatherman, and lens cleaning cloth. There is nothing I hate more than not having the right tool and smudged glasses.
Credit: Tom Thrasher Photography 
Credit: Tom Thrasher Photography
Why should somebody visit Boston?
Boston is where America went from an idea to a possibility. Getting to know Boston is like getting to know yourself as an American. Also, the people of Boston. There is something refreshing about a people so aggressively real.
What’s the #1 thing a visitor should do while in Boston?
Of course I’m going to say, “going on a boat ride with me or a sail on our schooner” is the #1 thing to do in Boston… but tied for first would be completing the Freedom Trail with a guide book or at least visiting the Bunker Hill Monument and reading the words of the farmers and tradesmen with hunting rifles who stood up against the world’s most advanced military force.
Lastly, where is the most breathtaking place you’ve ever captained a vessel?
Sailing our schooner Adirondack lll north on the Hudson River near West Point Academy in the Fall. The leaves had changed and we happened to pass between two mountain ranges during the golden hour of the sun setting.
Credit: Tom Thrasher Photography 
Credit: Tom Thrasher Photography