- One of the nation’s oldest cities
- Very walkable with a great subway system
- Teeming with historic landmarks dating back to the Revolutionary War
Metro Population: 4.7 million (#10 in the U.S.)
When To Visit: April-October
Climate: Very seasonal – with a hot summer, cold snowy winter, and cool spring and fall
The largest city in New England, Boston has no shortage of cool landmarks to explore – from the ultra-modern John Hancock Tower to Paul Revere’s grave. Most of the central neighborhoods of the city preserve stunning Victorian-era homes and buildings – making for beautiful walks wherever you go.
Photo: Boston Common
Where To Go in Boston
The Freedom Trail winds through Boston’s center, connecting dozens of important landmarks to the city (and the country)’s history.
- Massachusetts State House: This National Historic Landmark built in 1798 serves as Massachusetts’ capital building. Tours of the beautiful interior are available Monday-Friday. Free.
- Boston Common: The city’s most prominent park (pictured above), Boston Common sits beneath some of Downtown’s most prominent skyscrapers and has great walking trails and a walk-in fountain for the warm months. Free.
- Boston Public Gardens: Next door to the Common is this serene collection of gardens – with hundreds of flowers during the warm season, historic statues, and a pond on which you can rent adorable swan boats. Free.
- Granary Burying Ground: You’ll find Paul Revere, Samuel Adams, and John Hancock’s graves in this cemetery with over 2,000 graves dating back to 1660. The old-fashioned thin tombstones are an incredible sight. Free.
- Faneuil Hall Marketplace: This market is filled with fun vendors and tasty food and it has an amazing past as a frequent meeting place for the 18th century Sons of Liberty. Free.
A walk through this historic area which has been continuously inhabited since the 1630s is a must – every building looks like a historic landmark. It is a hub for Italian Americans in the area, so there’s great Italian food to be found.
- Old North Church: The oldest standing church in Boston, this small but stunningly beautiful and unique building has the most unique pews you’ll ever see. Open to the public at most times, $3 donation suggested. 193 Salem Street. (617) 523-6676
- Paul Revere House: This museum features great exhibits on the city’s history and the chance to walk through a typical 18th century Boston home and gardens. $5 admission. 19 North Square. (617) 523-2338
An upscale neighborhood in the center of the city, Beacon Hill is one of Boston’s most desirable and stately neighborhoods.
- Boston African American National Historic Site: Walk through the African Meeting House, the oldest black church in the country where Frederick Douglass delivered a famous anti-slavery speech in 18060. Free admission and guided tours. 15 State Street. (617) 742-5415
This wealthy neighborhood has some of Boston’s best shopping, eats, and homes.
- Newbury Street: The 8-block stretch of this throughfare from Massachusetts Avenue to Arlington Street is the hub of the neighborhood’s businesses. Free.
- Boston Public Library: One of the most exquisite libraries in the country, most every room of this building has stunning architecture and murals. Free.700 Boylstown Street. (617) 536-5400
- Charles River Esplanade: A popular 3-mile path that takes you along the Charles River, providing excellent nature and city views. Free.
This large city just across the Charles River from Boston is home to two of the nation’s premier universities and a host of luxurious homes and fun businesses.
- Harvard: This prestigious, world-famous Ivy League university dates back to 1636. Take a walk through the historic campus on your own or as part of a free guided historical tour. Free.
- MIT: One of the top STEM-focused colleges in the world, MIT has a fittingly futuristic looking campus. Don’t miss the Ray and Maria Stata Center, which looks like it came out of a Dr. Seuss novel. Free.
Boston Cheap Eats
Boston restaurants and fast casual eateries popular with locals where you can get a full meal for under $15. I always highlight some vegan or vegetarian options – cutting down on the amount of meat you eat is by far the #1 way you can reduce your environmental impact and contribute less to animal cruelty.
Boston Burger Company: Locals call this “the best burger you’ll ever eat.” There’s nearly 30 options and if that isn’t enough, you can even build your own. Their veggie burger is to die for. 37 Davis Square, Somerville. (617) 440-7361
Masa: It seems too good to be true, but this fun Mexican restaurant has an exquisite $9 2-course brunch and you can also purchase bottomless coffee. 439 Tremont Street, South End. (617) 338-8884
Il Mondo Pizza: Thin crust gourmet pizzas are the main draw at this cheap fast casual spot that is popular among locals and generous with toppings. 682 Huntington Avenue, Fenway. (617) 277-7161
Bova Bakery: Whether you’re looking for a sandwich or a dessert at this 24-hour bakery that’s been around for over 80 years, you’ll find just the right thing for your craving. 134 Salem Stree, North End. (617) 523-5601
Mike’s Pastry: Boston’s most famous dessert – the cannoli – is a must and this longtime favorite among locals is the best place to try one. Choose from dozens of flavors and enjoy! 300 Hanover Street, North End. (617) 742-3050
Boston bars, lounges, and clubs that are popular with locals and meet one or more of these criteria: A) Unique, unlike anyplace you’ll find in another city B) Fun and lively, sure to be a good time C) Beautiful decor or view
Drink: This hipster bar is known for not having a drink menu, but no shortage of unique cocktail creations in a trendy setting. There are often lines. 348 Congress Street, South Boston. (617) 695-1806
The Black Rose: Boston has a large Irish American population and no shortage of Irish pubs. This iconic neighborhood spot is one of the best – with on-point food and beer. 160 State Street, Downtown. (617) 742-2286
The Alley: One of Boston’s largest gay clubs, this two-floor venue is a great place to let loose and dance. It’s bear-friendly, but has a wide variety of clientele. 14 Place Alley, Downtown. (617) 263-1449
Harpoon Brewery and Beer Hall: You’ll get superb views of Boston and great beer at this popular brewery. Tours are $5 and include tastings. 306 Northern Avenue, South Boston. (617) 456-2322
Top Of The Hub: This swanky 52nd floor lounge connected to a pricey restaurant has some of the best views of the city and live music every evening. Tables have a $24 per person minimum after 8pm, but you can circumvent this by sitting at the bar. 800 Boylston Street, Back Bay. (617) 536-1775
Nearby Side Trips from Boston
New England Road Trip: Read my blog from my fall foliage road trip from Boston through Massachusetts, Vermont, New Hampshire, and Maine
Salem: This small city a half-hour to the north was the site of the infamous Salem Witch Trials and is teeming with historical landmarks.
Acadia National Park: New England’s only national park, Acadia (4.5 hours north of Boston) features the tallest mountain on the East Coast, tranquil beaches, and supreme outdoor adventures.
New York City: Just 3.5 hours to the southeast, the nation’s largest city has some of the best (and most trendy) food, nightlife, and entertainment in the country as well as five boroughs to explore.
Mohawk Trail: For Massachusetts’ most scenic drive, head 1.5 hours west to Greenfield and then take Highway 2 to Williamstown, making frequent stops along the way to soak in the beauty.
Portland, Maine: This small city 1.5 hours north is actually Maine’s largest and has a cute downtown area and great seafood. Stop in the town of York to see an epic lighthouse on an island.
White Mountains: 2.5 hours north of Boston, this mountain area is the crown jewel of New Hampshire, with incredible hiking, camping, and boating opportunities.
Burlington: Drive 3.5 hours northwest to Vermont’s largest city to see a historic downtown, America’s version of Stonehenge, and views of giant Lake Champlain.