Brookline, MA Outdoor Activities

From the hallowed field at Fenway Park to the educational havens of Harvard and M.I.T, Boston's history is written across its skyline. The area's nearby waterways allow for mostly unencumbered views of these sights, and guided boat tours let sightseers experience the city in a relaxing way. To this end, Charles Riverboat Company's vessels embark on journeys across the Charles River and Boston Harbor. Captains and crews point out historic sights such as famous architecture or the 100-story kettle used during the Boston Tea Party. Under the warm glow of a sunset, evening tours wind through the river as music plays. Charles Riverboat Company also charters their boats for groups of up to 150.

Docked adjacent to the New England Aquarium, the Liberty Star and the Liberty Clipper might look a bit obscure. The Liberty Star measures 67 feet long and can hold up to 39 passengers, and the Liberty Clipper measures 125 feet long with a capacity for up to 100 passengers. The massive schooner is an authentic replica of an 18th-century Baltimore clipper ship, thoroughly modernized to transport passengers on Boston Harbor sails and longer private charters. They sail daily throughout the harbor for public and group outings, along with private charters for special events, such as weddings or corporate proms. For a longer respite, they hoist the sails of the Liberty Clipper and steer her southward, cruising through the Bahamas and the Virgin Islands on all-inclusive luxury sailing vacations.

Freewheeling around historic hallmarks and architecture, Boston By Segway, formerly Boston Gliders, has led more than 100,000 sightseers through Bean Town atop intuitive, easy-to-maneuver segways. Tours, which kick off every half-hour, range from one to two hours; the shorter version trundles down Boston's Harborwalk, and the longer sojourn ventures past historic hotspots including Faneuil Hall and Bunker Hill. To get acquainted with the segway, all upright rollers speed through a half-hour how-not-to-crash course, getting acquainted with the natural, fluid steering and learning how to propel the vehicle forward using a carrot tied to a stick. Armed with digital cameras, the urban sherpas snap shots throughout the tour for purchase afterward, and customers may take their own pictures as long as they briefly hop off the segway.

When Valerie Beck was in kindergarten, there was only one way to get her to drink her milk: mixing in chocolate. As she grew up, her passion for the sweet treat only deepened. During a five-year stint living in Europe, she sleuthed out the most delectable chocolate shops and bakeries, eventually bringing friends along with her on trips to chocolate hot spots. After returning to the United States, she broadened her scope to create Boston Chocolate Walking Tours, focusing on the city’s increasing number of premium chocolatiers.

Valerie’s team of tour guides reveals Boston's best chocolate spots to guests on 2.5-hour tours around the Newbury Street neighborhood. They embark from Teuscher Chocolates of Switzerland, walking or canoeing across the city's historic chocolate canals. The tour changes daily, hitting five–six spots, such as DeLuca's Market and Emack & Bolio's, though the Lindt shop is always on the list.

Boston CityWalks’ owner, Alan Maltzman, loves to show his passion and knowledge for his city. At Boston CityWalks, he and his coterie of guides lead six different tours that roam the city’s historic cobblestones, highlighting areas such as Harvard Square, the waterfront, Beacon Hill, and various Jewish cultural sites. He can also design a custom tour for any occasion such as family vacations, engagements, birthdays, reunions, and business meetings.

Boston’s Finest Tours unveils the City on a Hill’s hidden charms to residents and visitors with five unique seasonal tours. Native Bostonians John Feeley and Cheryl McDonald lead tours dressed as their midcentury counterparts, Jonathan Wendell Holmes and Frances Appleton, while sharing tales of the city’s history and culture. The ghost tour of Beacon Hill thrusts patrons into close encounters with specters, and on the Irish Heritage tour, trolleys roll through Eire-influenced sites including the Boston Public Garden and Fenway Park. The Beacon Hill tour begins with a sighting of the State House’s brilliant gold dome before groups stroll down the brick sidewalks of Mount Vernon Street, the cobblestone corridor of Acorn Street, and the legendary Boston Strangler’s daily jogging route.