Follow the famous red-brick route past some of Boston’s most historic sites, then end the day in the North End for classic old-school charm and plenty of great food. 

These adjoining green spaces are the heart of the city for strolling, people-watching, and taking in Boston’s classic scenery. In season, the Swan Boats are one of the most iconic Boston experiences. 

The Esplanade is a go-to for riverside walks and bike rides with skyline views, especially around sunset. Pair it with nearby Beacon Hill for cobblestone streets, historic townhouses, and that postcard Boston feel. 

Back Bay is built for wandering, from handsome brownstones to shopping and dining. Nearby, the Museum of Fine Arts is a top cultural stop, and Fenway’s game-day energy makes the area buzz when the Red Sox are in town. 

For modern waterfront vibes, head to the Seaport for harbor views, public spaces, and an always-growing lineup of places to eat. The Harborwalk connects much of Boston’s shoreline, so you can turn a simple stroll into a longer, scenic walk along the water. 

Just across the river in Cambridge, Harvard Square mixes historic college-town energy with bookstores, coffee shops, street activity, and plenty of spots to explore before you head back into Boston. 

On the downtown waterfront, the New England Aquarium is an easy add-on for families and anyone who wants a break from walking. It is known for a deep lineup of marine life exhibits and conservation work. 

Boston’s default speed limit is 25 mph on streets where no speed limit is posted, so assume 25 unless you see a sign. Highways around Greater Boston vary by segment and are typically posted higher, but speeds can change quickly near tunnels, ramps, and construction.

Downtown has plenty of garages, and those are often the simplest option for visitors. On-street meters are common, and most are active Monday through Saturday from 8 a.m. to 8 p.m., with time limits posted at the space. In neighborhoods, parking rules can be strict, so check for resident-only signs and street cleaning notices.

Late morning through early afternoon is usually the smoothest window. Weekday commutes and event traffic can stack up fast, so plan extra time if you are driving during morning or late-afternoon rush.

Logan (BOS) is just across the harbor in East Boston, so downtown is typically a short drive in light traffic. Many routes use the Sumner Tunnel or I-90 connectors depending on where you are headed, and tunnel traffic can impact drive time.

You may encounter tolls on common routes, including Boston-area tunnels and I-90. TollPass coverage for Massachusetts lists facilities like the Callahan and Sumner Tunnels and the Massachusetts Turnpike and Boston Extension (I-90). 

If Boston declares a snow emergency, you cannot park on designated snow emergency arteries and violations can be ticketed or towed. The City publishes snow emergency parking guidance and the list of restricted streets.