5 Unique Ways to Explore Boston’s Neighborhoods

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Whether you are a native Bostonian or here for a visit, there are always new ways to explore the city. Instead of taking a walk along the historic Freedom Trail, why not try a chocolate, wine or duck tour for a fun and memorable way to see all that Boston has to offer?

1 South End Wine Tour

City Wine Tours
City Wine Tours knows where to find the best wine in the city and now you can join them. They offer regular walking tours throughout Boston’s neighborhoods, including the South End, North End and Back Bay. We recommend the South End tour that starts off at Gaslight Brasserie where you can sip on some French wine at an authentic brasserie. From there, head over to nearby Cinquecento Roman Trattoria for a taste of Italian wines. The last stop on the two-hour tour, which runs every Saturday at 3 p.m., is at Masa for a sampling of wines from Chile, Argentina and Spain.
City Wine Tours 67 Mount Auburn Street Cambridge, MA 02138

2 Boston Chocolate Trolley Tour

Trolley Tours of Boston
The sweetest way to see Boston is by way of the Boston Chocolate Trolley Tour. The three-hour tour runs from January to April and departs from the Trolley Stop Store at the corner of Boylston and South Charles Streets at 11:30 a.m. and 12:30 p.m. on Saturdays. The first stop on the tour is Top of the Hub on the 52nd floor of the Prudential Center for a “chocolate surprise.” From there, you will visit Ghirardelli’s in Faneuil Hall and enjoy a gooey ice cream sundae before heading over to Café Fleuri at the Langham Hotel for the massive chocolate buffet. The all-you-can-eat spread includes everything from chocolate soup, white chocolate pudding and chocolate chip cookies to chocolate croissant bread pudding, bittersweet chocolate mousse and even a chocolate fountain.
Old Town Trolley Tours 3 Park Plaza Boston, MA 02116

3 Boston Duck Tours

Boston Duck Tours
One of the most unique ways to tour Boston is in a World War II amphibious vehicle that cruises the historic streets and ends with a splash in the Charles River. You’ll pass by several landmarks on the 80-minute ride, including the State House, Faneuil Hall, the Prudential Center and Boston Common before your tour “ConDUCKtor” drives you right into the Charles River for a fun finale. There are three Duck Tour locations in Boston – the New England Aquarium, Prudential Center and Museum of Science – and the tours run from March to November from 9 a.m. to sunset.
4 Copley Place, Suite 4155 Boston, MA 02116

4 Boston Segway Tours

Boston Segway Tours
Gather up five of your closest friends and book a group tour aboard Boston Segway Tours or just come alone for a fun way to explore the city. They offer one-hour tours throughout Back Bay as well as two-hour tours that include Chinatown and parts of the Freedom Trail. If you are an experienced Segway rider, you can rent one for a half or full day. They provide full training so you are entirely comfortable on it before venturing out into the city streets.
364 Boylston Street Boston, MA 02116

5 Off the Eaten Path Tours

Off the Eaten Path
Deciding where to dine in the North End can be a bit overwhelming. The Italian section of Boston has more restaurants and bakeries than any other neighborhood in town. If you aren’t sure where to go for some homemade pasta, some of the best arancini outside of Sicily or a cup of creamy gelato, Off the Eaten Path Tours will take you on a three-hour excursion that includes food and drink sampling as well as cooking demonstrations. The tours are held on Saturdays and depart at 10:45 a.m. from North Square across from the Paul Revere house.
43 Fleet Street Boston, MA 02109
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