Let's talk about Boston. People think it's just brick buildings and angry drivers. They're partly right about the drivers, to be honest. But the city itself is surprisingly small and easy to navigate. You're reading this boston travel guide probably trying to figure out if you need a car. You absolutely do not. The subway system (locals just call it the T) costs $2.40 a ride and gets you pretty much anywhere you need to go. Plus, walking is often faster anyway.
When friends ask me about the best time to visit boston, I always tell them to aim for October. Why? Here's why. Summer gets ridiculously sticky. We're talking 90°F (about 32°C) with 80% humidity. Winter is basically a frozen wind tunnel. But autumn? It's just right. The air is crisp, the leaves turn orange along the Charles River, and you only need a light jacket. September and November are solid backups too.
Alright, let's get into the actual things to do in boston. You're probably going to walk the Freedom Trail. Everyone does. It's a 2.5-mile red brick line painted on the ground that leads you past 16 major historical markers. It takes about two to three hours depending on how often you stop for coffee. And you should stop for coffee. The North End (our little Italy) is right on the trail, and you can grab a cannoli at Mike's Pastry for about 5 bucks. Some locals say Modern Pastry is better. It's an ongoing war. Try both and decide for yourself.
If you're making a list of places to visit in boston, don't just stick to the downtown stuff. Hop on the Red Line and cross the river into Cambridge. Yeah, it's technically a different city, but it's completely connected. Walking around Harvard Yard is completely free. Just don't rub the toe of the John Harvard statue. Tourists think it's good luck. College kids think it's a toilet after a night out. Gross, right? Just look at it from a distance.
Speaking of budgets, there are actually a ton of free things to do in boston if you know where to look. The Boston Public Library in Copley Square is basically a palace. You can walk right in, sit in the Bates Hall reading room with its green lamps, and just soak in the atmosphere. It costs zero dollars. Same goes for the USS Constitution over in Charlestown. You need to go through a security check, but walking around the oldest commissioned warship afloat is totally free. Honestly, these are some of the best places to visit in boston for free.
Let's talk food because you're going to get hungry. Seafood is the obvious choice. Legal Sea Foods is the big chain everyone knows, and it's fine. But if you want a really good lobster roll, head to James Hook & Co. on the waterfront. A roll will set you back about $30 to $35. It sounds expensive, but that's just what lobster costs now. It's packed with meat and totally worth it. For something cheaper, you'll find amazing dim sum in Chinatown for under $15 a person.
If you're in your twenties or thirties, you might be looking for fun things to do in boston for young adults. The Seaport District has exploded over the last five years. It used to be just parking lots. Now it's packed with rooftop bars, breweries, and expensive apartments. Check out Trillium Brewing. A pint is around $9, and they have huge outdoor patios. Or head over to Somerville (right next to Cambridge) and go to Bow Market. It's this cool outdoor courtyard surrounded by tiny independent food stalls and a natural wine bar. It gets super crowded on weekends, so go early if you want a seat.
What about the big tourist spots? Are they worth it? The New England Aquarium is great, especially if you like penguins. Tickets are around $34. Fenway Park is legendary. Even if you don't care about baseball, taking a tour of the stadium is pretty cool. It's the oldest ballpark in the country. The seats are tiny because people were smaller in 1912.
When you're figuring out places to go in boston, you should definitely spend an afternoon in Beacon Hill. Acorn Street is famous for being the most photographed street in the country. It's just real cobblestones and old gas lamps. Wear flat shoes. Seriously. The cobblestones will wreck your ankles if you're in heels.
Look, I get it. Planning a trip can be stressful. You want to see all the big boston attractions without feeling like you're stuck in a tourist trap. The trick is to balance it out. Do the big museums in the morning. The Museum of Fine Arts is massive. You could spend six hours there and not see everything. Then in the afternoon, grab a slice of pizza at Galleria Umberto in the North End (cash only, about $2.50 a slice, they close when they sell out) and sit in a park.
There are so many places to see in boston that you'll probably have to leave some for your next trip. Don't try to cram everything into 48 hours. Pick one neighborhood a day. Walk around the South End to see the massive Victorian brownstones. Get some tapas at Toro on Washington Street. Or take a walk around the Public Garden and look at the swan boats. The real charm of this city is just walking its weird, confusing, winding streets.
Anyway, if you want to know what sites to see in boston, just follow the water. Walk the Harborwalk. It stretches for nearly 40 miles, though you obviously won't walk the whole thing. The section near the Institute of Contemporary Art has great views of the harbor and the planes taking off from Logan Airport. It's loud, it's breezy, and it feels very Boston.
Let's talk about day trips for a second. If you're staying for more than three days, you might want to get out of the city limits. Salem is only a 45-minute train ride away on the Commuter Rail. Tickets are about $8 each way. Yes, it's famous for the 1692 witch trials, and October there is absolute chaos. If you hate massive crowds, do not go to Salem in October. Go in May. The Peabody Essex Museum is there, and it's incredible. Plus, the coastal views are great.
Getting from the airport to downtown is actually super easy, which is rare for American cities. Logan Airport is practically in the city. You can take the Silver Line bus for free from the airport into the Seaport and South Station. A taxi or Uber will cost you about $25 to $40 depending on traffic. And there is always traffic. I wasn't kidding about the angry drivers. We call them Massholes for a reason. But you won't care because you'll be on foot or on the T.
Another spot you shouldn't skip is the Isabella Stewart Gardner Museum. It's right near the Museum of Fine Arts. Basically, this eccentric millionaire built a 15th-century Venetian palace in the middle of Boston, filled it with art, and then left it to the public. But she put a rule in her will: nothing can ever be moved. Oh, and it was the site of the biggest unsolved art heist in history back in 1990. They just left the empty frames hanging on the walls. Admission is around $20. It's moody, weird, and absolutely fascinating.
If you're an architecture nerd, Copley Square is going to blow your mind. You've got the super modern John Hancock Tower right next to Trinity Church, which was built in the 1870s. The reflection of the old church in the glass of the new skyscraper is a classic photo op. Right across the street is the shopping district on Newbury Street. It starts out super high-end near the park (think Chanel and Rolex) and gets progressively cheaper and more indie as you walk west toward Massachusetts Avenue. You'll find great vintage shops and cheap falafel down that end.
