You could spend a week exploring all that Boston has to offer. The city’s small size, however, makes it easy to see different parts on the same trip. If you’re only stopping in for a few days on your New England road trip, here’s your ideal Boston itinerary.

looking up at the front gate of the Massachussets State House

The Massachusetts State House. Photo © Jen Rose Smith.

Day 1

Start your day in America’s oldest park, Boston Common, where you can sip a cup of coffee with a view of the gleaming, gilded Massachusetts State House. Get your bearings by following the Freedom Trail through the city’s most important historic sites, with stops to pay your respects to Paul Revere and John Hancock at the Granary Burying Ground, visit the Old State House and site of the Boston Massacre, and stroll Faneuil Hall. By the time you reach the Italian American enclave of North End, you’ll be ready for a sub sandwich with all the fixings from Monica’s Mercato followed by a classic North End dessert—choose between a sugar-dusted cannoli from Modern Pastry or zesty Italian ice from Polcari’s Coffee (or try them both).

Get back on the trail for an afternoon in Charlestown, where you can tour the USS Constitution and learn about real-life “Rosie the Riveters,” then climb to the top of the Bunker Hill Monument to get a patriot’s-eye view of the entire city. Head back into downtown Boston the easy way, on a ferry ride from the Charlestown Navy Yard to the waterfront, then finish the night in one of downtown’s creative eateries.

courtyard garden

The Isabella Stewart Gardner Museum is full of European and American paintings. Photo © Jen Rose Smith.

Day 2

Now that you’ve covered the city’s essential sights, slow down at one of Boston’s great museums: see Impressionist masterpieces at the Museum of Fine Arts, learn about a history-making art heist at the Isabella Stewart Gardner Museum, or pitch some tea into the harbor at the Boston Tea Party Ships and Museum.

If you’re visiting Boston with kids, don’t miss the fabulous New England Aquarium, where hands-on exhibits and walk-through tanks get you up close and personal with the East Coast’s wildest underwater creatures.

For your last afternoon in the city, stock up on picnic supplies for an alfresco lunch in the Boston Public Garden, where you can watch the city drift by from a shady patch of grass, then take a lazy turn around the duck lagoon on a classic swan boat. When the sun goes down, join the boisterous local scene at one of Boston’s many dive bars, where dim lights and televised sports pair well with pints of cheap beer or Irish whiskey. Start at The Tam and see where the night takes you, or go colonial-era at Union Oyster House, whose downstairs bar is the perfect place to slurp locally harvested oysters.


Excerpted from the First Edition of Moon New England Road Trip.