Boston Travel Guide

With a dazzling city skyline lit up against the harbor, Boston, MA, is an idyllic city that belongs on every globetrotter’s radar. Catch a Red Sox game, navigate several historic landmarks, and shop ‘til you drop: Boston is a city where anything is possible.

The capital of Massachusetts is also a great choice for travelers who prioritize dining and entertainment. Feeling hungry? Find a spot to tuck into a New England-style clam chowder and lobster roll. Albeit a little quirky, be sure to try some of the city’s famous baked beans. (They don’t call Boston “Beantown” for nothing!)

Can’t wait to start planning your vacation? This complete Boston Travel Guide will give you all the inspiration you need, including ideas for what to see & do, where to stay, and when to visit.

Why Treksplorer? Founded in 2011 by Ryan O’Rourke, Treksplorer provides travel recommendations and advice to millions of readers every year. Our content is rooted in our writers’ firsthand experiences, in-depth research, and/or collaborations with other experts and locals. Read more about our editorial policy.

What to see & do in Boston

Freedom Trail

Even if you only have one day in Boston, the Freedom Trail is an attraction that needs to make the cut. This historic walking tour winds you through the city’s downtown streets to 16 important sites and landmarks from throughout American history.

The Freedom Trail

Throughout the journey along the Freedom Trail, you’ll learn about the Boston Massacre, Paul Revere, The Boston Tea Party, and much more. There’s even an important historic bookstore along the way that attracts bookworms from all over the world.

Spanning across 2.5 miles of city streets, packing a good pair of walking shoes is imperative, so don’t forget them at home! Well-suited to history buffs and bucket-list tourists alike, the Freedom Trail is unequivocally one of the best things to do in Boston; you’ll hit nearly every point on your must-see list in one afternoon!

Boston Common

If you love hanging out in urban parks, plan some time to relax in Boston Common. A great spot for a picnic, reading a book, or simply people-watching, this downtown greenspace is impressive. Covering 50 acres in the Beacon Hill neighborhood, Boston Common has multiple lawns, walking paths, water fountains, statues, and recreational facilities to explore.

Boston Common

Boston Common also frequently hosts festivals and special events. Don’t be surprised if you encounter an “Art In The Park” workshop, a performance from their neighborhood concert series, or an outdoor movie screening.

Traveling to Boston with your pets? Boston Common has an off-leash area for your companions to socialize and blow off some steam.

Quincy Market

Don’t have time to walk the Freedom Trail but looking for an enriching landmark to explore, nonetheless? Quincy Market offers a glimpse into America’s history, once serving as the hall where Independence speeches were given and one of the city’s first public markets. Talk about a rich background!

Quincy Market

What started as a prominent meeting place in the 18th century is now a hub for Boston-bound foodies and eclectic shoppers; you’ll find a little bit of everything at Quincy Market.

Looking for a quick lunch? The food colonnade at Quincy Market serves up plenty of Massachusetts’ most popular food dishes, like clam chowder and lobster rolls. You can’t leave without trying one of these Boston staples, can you?

Museum of Fine Arts

If you’re only going to visit one museum on your trip to Boston, let it be the Museum of Fine Arts. This extensive collection, comprised of over 500,000 individual works and 100 galleries, will leave art lovers enchanted. One of Boston’s must-see museums, it’s also among the top 20 largest art museums in the world, giving its visitors an extra modicum of bragging rights.

Museum of Fine Arts

Traveling exhibitions are one of the main draws to the Museum of Fine Arts. While these exhibits are constantly changing, the current exhibition—The Obama Portraits Collection—has been gaining much traction from critics and the media alike.

Located in Boston’s Fenway-Kenmore neighborhood, The Museum of Fine Arts is also quite beautiful, with impressive architecture, high ceilings, and grand showrooms. There’s so much to see & do in the gallery, you might want to stay all day!

Castle Island

If you have a little time to spare, why not add Castle Island, one of the most popular day trips from Boston, to your itinerary? Despite its name, this destination doesn’t include any castle. However, it is home to sprawling sandy beaches, a historic fort, and exciting sightseeing opportunities.

Castle Island

A trip to Castle Island is a big hit for young families, between the extensive playground, plane-watching opportunities, and, depending on the time of year, evening fireworks. For an impromptu beach picnic, you can visit Sullivan’s for some takeout seafood or a giant ice cream cone, a Boston classic.

Are you a waterbug through and through? You can also explore Castle Island from the waves by booking a sailing, whale watching, or harbor hopper cruise.

Where to stay

Figuring out where to stay in Boston is one of the biggest decisions you’ll make when planning your trip. Choosing the right neighborhood for you will set the tone for your holiday and impact which attractions, restaurants, and areas you’ll have easy access to. Chosen carefully to suit each type of traveler, here are some of the top areas you’ll want to consider:

Back Bay

Looking to add a taste of luxury to your Boston vacation? Back Bay is the “it spot” for tourists who love living the high life. The atmosphere in this neighborhood is quite European, between its historic buildings and cobblestone streets, while the accommodation scene offers nothing short of modern, world-class hotels.

Back Bay

Back Bay is also central to some of the city’s more sophisticated attractions like museums, the iconic Public Library, and high-end boutiques for an impromptu shopping spree.

Downtown Boston

Suitable for businessmen on work trips and first-time tourists alike, Downtown Boston is a great place to be if you want to see and do it all. As Downtown Boston is close to plenty of the top attractions, restaurants, and nightlife, you’ll never find yourself running out of things to do in this area.

Downtown Boston

Many of the hotels in this area are on the swanky side; be sure to budget a little extra if this is the neighborhood you’ve set your sights on.

Seaport District

For gorgeous views and a waterfront breeze, consider staying in the Seaport District. This neighborhood will put you at the front of the line for attractions like sailing the harbor on a historic ship or setting out on a whale-watching adventure.

Seaport District

Though you may need to search a little harder to find those on the more affordable end of the scale, the Seaport District has a wide range of accommodation options making this an attainable destination for any budget.

North End

For the perfect combination of historic charm and waterfront amenities, choose from the accommodations in the North End. You’ll find that this neighborhood, perched at the wharf’s edge, has a slower pace that’s well-suited to adults and couples on a romantic getaway.

North End

Hold hands as you walk to the local bakery for breakfast and settle into an authentic Italian restaurant for dinner by candlelight. By that measure, Boston’s North End is a great destination for foodies, too.

East Boston

If you’ve got an early morning flight or are arriving late at night, spending a night in East Boston might be a solid idea. Located close to Logan International Airport, this vibrant neighborhood sits across the harbor from the city center, about 20 minutes away by car.

East Boston

Even if you get “stuck” here, East Boston has plenty of its own charms. The vibrant neighborhood offers a slew of great restaurants covering a gamut of international flavors, tranquil city parks, and a selection of some of the most beautiful beaches in Boston.

When to visit

The best time to visit Boston is from May to October. Since the city has so much to do outside, visiting during the warmer months opens up a whole plethora of additional attractions.

Fall in Boston Public Garden

From festivals and markets to baseball games and sailing the harbor, these warm-weather activities are worth scheduling your holiday around. Plus, Boston is highly walkable and bikeable, so traveling during the warmer months allows you to save money on transportation and explore on foot.

Worried about the high costs of traveling to Boston through the summer? Avoid the inflated peak season rates by targeting the end of this range, from May to June or from September to October.


Getting there

By air

Boston is served by Boston Logan International Airport (BOS), located 5 miles northwest of Downtown Boston. Several major airlines offer direct flights to BOS from major U.S. and international destinations, including:

  • American Airlines
  • American Eagle
  • Cape Air
  • Delta Air Lines
  • Delta Connection
  • JetBlue
  • Southwest Airlines
  • Spirit Airlines
  • United Airlines

By road

Boston is well-connected by road to other cities in Massachusetts and other neighboring states. Popular driving routes to/from Boston and estimated driving times include:

  • Cape Cod, MA (2h4m)
  • Provincetown, MA (2h58m)
  • Worcester, MA (1h41m)
  • Providence, RI (1h47m)
  • Hartford, CT (2h26m)
  • Portsmouth, NH (1h38m)
  • New York City, NY (4h43m)

Getting around

Renting a car in Boston is not ideal. Like NYC, Boston isn’t a city you want to drive in. So, how should you get around? Boston has a fairly extensive and affordable public transportation system. The subway, locally known as the “T,” seems to be everyone’s favorite way to travel around Boston.


If you only have a weekend (or a single day) to explore Boston, you may also want to consider an alternate method of transportation. If you buy a ticket to one of the many hop-on-hop-off tour buses, you’ll be able to explore several of the city’s top attractions in a short period of time. Plus, you won’t need to worry about bus schedules or expensive taxi rides from point A to point B.


Ryan O'Rourke is a seasoned traveler and the founder & editor of Treksplorer, a fiercely independent guide to mid-range luxury travel for busy people. With over 20 years of extensive travel experience, Ryan has journeyed through over 50 countries, uncovering hidden gems and sharing firsthand, unsponsored insights on what to see & do and where to eat, drink & stay. Backed by his travel experience and in-depth research, Ryan’s travel advice and writing has been featured in publications like the Huffington Post and Matador Network. You can connect with Ryan on Twitter/X at @rtorourke.