There are many historic ways to explore Boston on your own, but only a few unique options to discover the city by tour. Instead of taking a solo walk along the Freedom Trail, sign up for one of these group sightseeing excursions that will provide a new perspective of the city.
On Saturdays, chocoholics meet for a two-and-a-half hour walking tour with Boston Chocolate Tours of the Back Bay. The adventure begins with a history of chocolate at the Hotel Chocolat on Newbury Street, followed by a sampling of the treats on offer. Tour guides move participants along to nearby Teuscher Chocolates of Switzerland, which includes a taste of the decadent Dom Pérignon champagne truffles. They also stop at iconic Ben & Jerry’s, to learn about the fair trade chocolates used in the national ice cream brand. More stops, including a peek into Sweet Cupcakes and the Gourmet Boutique at the Westin Copley Hotel, ensure that no sweet tooth will go unsatisfied.
Families can sign up for a ride aboard the Boston Duck Tours. With three daily operating tours that launch from the Prudential Center, the Museum of Science and the New England Aquarium, these amphibious land and water World War II vehicles are more than just an interesting ride. Tours pass assorted historic sites like the Granary Burying Ground and the Old State House, and are narrated by humorous “conducktors,” who encourage on-board quacking and put everyone’s knowledge of the city to the test. The tour culminates with a watery drive straight into the Charles River.
For cinema buffs, On Location Tours’ TV and Movie Sites Tour offers a three-hour journey (both on foot and by bus), where well-informed tour guides – who are working actors as well – highlight some of Boston’s most notable moments on screen. The tour stops at various locations like Fenway Park, the Cheers bar and, of course, the L Street Tavern made famous in Good Will Hunting. Make sure to clear your weekend calendar, though, since On Location tours operate Saturdays only.
Finally, wine connoisseurs and wannabe aficionados alike can unite on a walking tour throughout one of the city’s select neighborhoods, including the North End, South End, Back Bay and Harvard Square. Along the two-hour excursion, oenophiles learn the basics of wine tasting while sampling six wines and snacking on food pairings at three different restaurants. There’s Legal Sea Foods on the Back Bay tour, with its 10,000-bottle wine cellar, Gaslight Brasserie du Coin on the South End tour, Aragosta for those in the North End and Nubar in Harvard Square. Not a bad way to spend a weekend afternoon in Boston.