Massachusetts Guide and Deals

David Goldstein could be considered a renaissance man: he's organized skiing trips and city bar crawls, founded a murder-mystery dinner theater, and led team-building exercises—one of which focused on sharing his passion for chocolate. As this particular venture garnered public demand, he began traveling across the country to meet with chocolatiers and cocoa experts. In 2009, he returned to Boston and focused his findings and theatrical flair into sweets-focused tours—what he now refers to as his passion business.

Today, his team includes chocolate-experience designer Caitlin, two chocolate tour guides, Count Chocula, three pastry-chef chocolatiers, and a wine expert who teaches wine-and-chocolate pairings. The guides lead guests on walking tours and a cupcake crawl through three of Boston's historic neighborhoods, taking them to boutique chocolate shops, bakeries, ice-cream parlors, and a cosmetics company that uses chocolate in its products. In hands-on workshops, chocolatiers teach students how to form truffles, make fillings, hand mold chocolate, and package confections.

Cambridge Historical Tours unearths nearly 400 years of history during informative jaunts that cast light on the area's captivating, funny, and sometimes gory past. Sheathed in authentic puritan attire, guides lead groups on 90- and 120-minute treks back in time, fusing wholesome doses of humor with laboriously researched facts. Guests raise an imaginary glass at the house of John Hicks, a participant in the Boston Tea Party, and absorb the eerie ambiance of the Cambridge Burial Ground, where many of Harvard's early presidents are buried. The extended 120-minute tour reveals such sights as the picturesque Longfellow House, which was seized in 1775 to become George Washington's quarters, presumably so he could practice his putting game on the property's lush lawns.

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.

Saba Alhadi was visiting her retired father when she received the phone call. A man on the other end, with a British accent, informed her he'd seen her photos of the city of Boston. He worked with Random House and wanted to publish her work—provided she write a book about the city and furnish it with her photographs of 16 historic sites. More than five years later, Saba's book, Boston in Photographs can be found on gift-shop shelves in the Old State House. Formerly a travel agent, she began building her portfolio as she turned her lens on the city and developed photography walking tours through historic neighborhoods.

On each of her tours, she reveals historic details such as brick sidewalks, verdant cemeteries, Romanesque courtyards, and flower-packed window boxes, and encourages those on her tour to look for unlikely subjects. Meanwhile, she interlaces the history with photo tips on how colors on different buildings complement each other, how a reflection of a historic church in a window can become a composition, and how to keep a historic interpreter from startling when the shutter goes off. She also devises scavenger hunts throughout Victorian neighborhoods, sending participants scattering to decode cryptic clues that draw on notable local facts, such as which districts were once home to wealthy citizens and which homes have pools in the backyard.