When the Puritan settlers arrived in Boston Harbor in 1630, their leader, John Winthrop, delivered a now-famous sermon. He dreamed that Boston would be a “city on a hill,” a shining example to the world. Today, the city remains true to Winthrop’s vision as a beacon for innovation, boasting a sports scene almost religious in nature and alive with sites pivotal to the American story.

The newly reimagined View Boston atop the Prudential Center is the perfect spot for groups to begin their tour. View Boston is a three-story observatory that includes a restaurant, can’t-miss interactive experiences, open-air viewing space, and a cocktail bar—all offering panoramic views of the city. Meanwhile, the outdoor observation deck, dubbed “The Cloud Terrace,” offers visitors a 360-degree look at the city from the illuminated Citgo sign at Fenway Park to the lights of the Zakim Bridge and the nearby TD Garden arena. An entire floor of View Boston is dedicated to interactive exhibits, such as “Explore Boston,” a discovery tool that helps visitors build an itinerary of things to do and a 270-degree theater that showcases points of interest across Boston’s neighborhoods. Before departing, visitors can pick up a personalized itinerary for their city-stay.

Floor 52 at View Boston,
Credit: View Boston

Another way to begin an itinerary is with Boston’s Old Town Trolley Tours, which provides visitors a real taste of the city with stops in all the major areas, including Beacon Hill, Back Bay, the Waterfront District, and the historic North End. The 18 designated trolley stops ensure that your group is only steps away from some of the city’s must-see sites.

The Waterfront District is home to the New England Aquarium and its thousands of aquatic creatures. This is also the departure point for an active ferry service that takes visitors out into Boston Harbor to explore the forts of the Harbor Islands or right to the doorstep of the new Encore Boston Harbor casino resort. Boston’s Seaport District is a redeveloped stretch of the South Boston waterfront, where groups can enjoy a nightcap on one of the rooftop bars or take in a performance at the Leader Bank Pavilion, one of the city’s largest outdoor amphitheaters. History-minded travelers will appreciate the immersive Boston Tea Party Ships & Museum where visitors can adopt the identity of a revolutionary figure and learn more about that fateful December night.

Seaport District,
Credit: Kyle Klein

The North End is home to delectable Italian eateries and an incredible food scene highlighted by the dueling bakeries of Mike’s Pastry and Modern Pastry on Hanover Street, where a cannoli is a must-eat treat. Meandering through the North End, groups can follow the red-bricked Freedom Trail, an iconic 2.5-mile walk that connects 16 nationally significant historic sites like the Paul Revere House and the Old North Church.

Boston Common,
Credit: Massachusetts Office of Travel & Tourism

The heart of the city is the Boston Common, a massive green space that carpets Beacon Hill from the gold-domed State House to the Public Garden, the first public botanical garden in the United States. A series of parks known as the “Emerald Necklace” stretches out through the Back Bay Fens area to offer visitors a tranquil oasis in the bustling city. Along the way, visitors can appreciate some of the city’s premier cultural institutions. The Museum of Fine Arts Boston contains more than 8,000 paintings and over 450,000 works of art, and thematic group tours make the expansive galleries accessible. Famous perhaps for the great unsolved art heist, the Isabella Stewart Gardner Museum includes paintings, sculptures, tapestries, decorative arts, and a courtyard that evokes a Venetian palace. 

Written by Michael McLaughlin

Main image: Boston Skyline; Credit: Boston Harbor Association