Things to Do in Milton

At the age of 16, Matthew "Matty" Hughes became the youngest-ever licensed captain in the port of Boston. Funneling his passion into a career, he founded Boston Harbor Cruises in 1926 to lead tours up the Charles River. What began as a two-man, one-boat operation has grown tremendously throughout its more than 90-year history, now encompassing a 21-boat fleet and more than 250 employees who transport more than 2 million passengers.

The Boston Harbor Cruises's staff handles all things nautical, from whale watching and speedboat tours to wedding receptions and celebrations for special occasions. Because dolphins are hard to saddle and refuse to obey verbal commands, Boston Harbor Cruises also navigates the waters with ferries and harbor cruises that explore the historic and romantic sights of Boston.

Though the leadership has changed, Matty's grandchildren Rick and Chris Nolan still perpetuate the traditions of Boston Harbor Cruises, furthering one man's obsession with the harbor and inspiring future generations to create their own memories on its calm waters.

Local actors guide the three-hour Boston TV & Movie Sites Tour, dishing out behind-the-scenes specifics and juicy tidbits about 40+ TV show and movie locations peppered across Boston’s diverse neighborhoods. The tour bus comes outfitted with TV screens that roll video clips corresponding with passing sites, starting at Boston Common and continuing through the quaint brownstones of Beacon Hill, and onto South Boston, Back Bay, Copley, and the North and West Ends before ending back at Boston Common. Along the way, grab a bite to eat at the original Cheers bar, where everybody knows your Social Security number, or visit the L Street Tavern, the local pub frequented by Matt Damon and Ben Affleck’s characters in Good Will Hunting. Tour-goers can ogle at pavement made famous by films such as The Departed, Legally Blonde and a multitude of America’s Funniest Home Videos. Tours start rain-or-shine on Saturdays and Sundays at 11 a.m. in September and October and Saturdays at 11 a.m. in November and December.

Hop aboard a high-speed, rigid inflatable boat to journey the Boston Harbor Islands National Recreation Area with Flagship Adventures. Flagship's expert tour guides pepper the 90-minute adventure with interesting Boston Harbor factoids and their favorite porterhouse marinade recipes. Board ship at 200 Seaport Blvd. and venture through Boston Harbor, passing many national recreation area islands and peninsulas during your journey.

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.