All About the Hop-on Hop-Off in Boston

Boston trolley at Congress Street bridge


A Hopping Good Time: Tips to Explore Boston on the Hop-On, Hop-Off Trolley

At 48 square miles and boasting plenty of sidewalks and quaint cobblestone alleys, Boston is definitely a walkable city. However, all those cobblestones can wreak havoc on little feet. If you and the brood are visiting The Hub, consider one of the hop-on, hop-off tours to maximize sightseeing and minimize dealing with weary kiddos. You'll also be privy to scenic views as you cruise down the city's narrow streets. Here's what you need to know before booking.

You Have Options

There are two year-round hop-on, hop-off trolley tours in Boston. Old Town Trolley Tours is slightly more expensive but offers the most comprehensive route focusing on both historic and modern attractions, while CityView Trolley Tours is shorter and places more emphasis on the major attractions. Both offer discounts when booking online as opposed to buying a ticket at one of the street kiosks. So plan ahead!

Read the Fine Print in a Good Way

Your tickets will get you significant discounts at nearby attractions such as the New England Aquarium, city museums, whale watching cruises and haunted tours. Be sure to read the exceptions, as many of those discounts are valid only on the same day as the tour.

Consider the Season

Summer is the best time to visit Boston. The temperatures are warm, the skies blue and there's minimum rain. It's also high tourist season, meaning lots of families vying for seats. Early morning or late afternoon are the least crowded. Spring and fall in Boston offer their own special sights. The Public Garden and historic neighborhoods are in full bloom in spring, while fall brings fiery foliage. If you think winter is awful in Boston, you are right. However, if you've got a family trip planned from December to February, a hop-on, hop-off tour may be the best bet. Boston is notorious for unplowed streets and messy sidewalks, and a trolley is the easiest way to see the snow-covered city.

Map Out a Munchies Route

Don't fall victim to being stuck in a neighborhood void of kid-friendly food at the moment when everyone in tow decides they can't go on without a snack. Copley Square, Faneuil Hall and the area near the New England Aquarium offer the most family-friendly food options. You'll find plenty of sit-down options near the Aquarium, while Faneuil Hall boasts an entire building full of food vendors, from pizza and cupcakes to clam chowder and sandwiches.

Don't Walk in a Straight Line

You probably don't want to spend the entire day walking the city, which is possible if you decide to hop off at every location. Instead, zigzag around the city in the areas that are most interesting. Are you kids history buffs? Spend more time walking around the North End and Beacon Hill to retrace the steps of the Founding Fathers. Love sailing and pirate lore? Take time to walk around Boston Harbor and the USS Constitution. Bonus points if your tour guide delves into the details of William Fly, the city's most notorious pirate.