I moved to Boston in 2008 and started guiding tours in 2015. I've talked with thousands of people about this city, giving suggestions and directions. I thought I'd summarize some of what I often share into one handy dandy guide to Boston.
What to Do
I wrote a recent post about this, which is especially helpful if you’ve only got 72 hours (or less) in Boston. That said, keep an eye out for a future post of my picks of things you absolutely must do; the things that make Boston the place it is.
Best Neighborhoods to Explore
Boston has 23 different neighborhoods. Some, like Bay Village, are tiny and easy to miss. Others, like Dorchester, are enormous and comprise many smaller neighborhoods within it. I’m someone who loves nature and you’ll find the most amount of it in Jamaica Plain. There is Jamaica Pond, the Southwest Corridor Park, Forest Hills Cemetery, Arnold Arboretum, and Franklin Park. Too, there are some great restaurants like Tres Gatos (tapas), Blue Nile (Ethiopian), Chilacates (Mexican) and The Haven (Scottish). It’s also home to my favorite bar in the city, The Brendan Behan.
Where to Eat
I recommend any of the places I mention in the post about restaurants in the North End. Also, all the restaurants in Jamaica Plain mentioned in the last section are great!
Where to Drink
Of course, there are plenty of options in and around the North End, which I recounted here. I also recommend Yvonne’s and The Last Hurrah for cocktails. If you’re downtown, check out Democracy Brewing. It's a small, local brewery with some good food and an atmosphere reminiscent of a German beer hall.
Where to Drink with the Locals
If you want to get down and dirty, try Biddy Early’s. They’ve got the grossest bathroom in the city but the drinks are so cheap it’s hard to believe. The food is so-so, but the staff is nice. It’s a slice of life place and I love it for that.
Where to Stay
Boston has very pricey hotels. But if money isn’t an issue, I recommend Marriott Vacation Club’s Custom House. It’s an urban resort right in the heart of the city located in an almost 200-year-old building. It has great amenities and awesome views from most of the suites. The Liberty Hotel is another option. It’s built in the old city jail but is pure class. There are several bars and restaurants inside including Clink and Alibi. (Do you see what they did there?)
Best Markets & Shopping
I love the Haymarket for cheap fruits and veggies. You can read more about it at the post about things to do around the North End. Right next to it is the Boston Public Market, which I wrote about in the same blog post. It also comes recommended for its unique New England foods and goods.
As for shopping, your best bet is Newbury Street. As comedian Marc Maron once said, “It’s the Rodeo Drive of Boston.” You’ll find everything from Tiffany and Co. to Urban Outfitters. The stores stretch for blocks and there are cafes and restaurants to grab a bite to eat.
Events & Festivals
Most weekends in August and September in Boston’s North End there are feasts for different Catholic saints on the weekends. These include Fisherman’s Feast, Madonna Della Cava, St. Agrippina di Mineo, San Gennaro, and others. The biggest, though, is St. Anthony’s, called the “Feast of all Feasts” by National Geographic. Many of these feasts are over 100 years old. What they amount to are huge block parties. Thousands of people come out for the energy, food, and entertainment. Dozens of Italian food vendors descend upon the streets. There are marching bands, fireworks, processions, musical artists, games, and an air of fun throughout the neighborhood.
Best Area for a Night on the Town
If you’re into live music, check out the further-out neighborhood of Allston. There you’ll find O’Brien’s Pub, Paradise Rock Club, and Brighton Music Hall. If you want to hit the big dance clubs, head straight for the Theatre District or the Seaport. If you’re looking for some jazz, check out Wally’s in the South End. It's a hole-in-the-wall that showcases some great musicians. This sometimes includes students from the nearby Berklee College of Music.
Tours, Sightseeing & Passes
Obviously, you need to take a tour with Historic Boston Crime Tours! But outside of that, if you’ve never been to the city, Old Town Trolleys will give you a good overview. If you’re interested in hitting up the main attractions in town, the Go Boston Pass will give you the best bang for your buck.
Boston is America’s walking city. It’s very easy to get around on foot and the T (the subway). A 7-day pass costs $22.50 for unlimited rides on the subway or bus. A 24-hour pass is $12.75 for unlimited rides. A one-way ride will run you $2.40.
Traveling to Boston
It’s rare for someone to say they like an airport, but my experiences in and out of Boston's Logan Airport have always been pleasant. It’s near downtown and I’ve never had to wait more than 10 or 15 minutes in line for security. There are many food options (some of which are very good), and several are Boston-based. Logan has direct flights to Europe, Asia, and throughout North and South America.
If you’re coming from somewhere in the Northeast, taking a bus is an option. I like Megabus but I’ve taken everything from the cheap Chinatown buses to and from New York City to the Greyhound.
Amtrak is also a possibility, but can be pricey, especially if you’re coming from New York City.
Drive if you must, but Boston is best appreciated by walking around. Not to mention, parking is expensive. Besides, our mass transit system is robust and affordable.
Favorite Side Trip
Salem. It’s accessible on the Commuter Rail Line and the price for a round trip ticket is reasonable. The train station in Salem is a ten-minute walk from all the action. Like Boston, the city is quite walkable. While Salem has thrown their lot (haha) in with the whole witch theme, it has a lot of other great things to offer. The Peabody Essex Museum always has great art exhibits. There are some restaurants making delicious food including Life Alive and Jodi Bee Bakes. Salem is also home to Notch Brewing and Far From The Tree cider. Finally, if it’s the summer, get a rideshare service to take you a few miles up the road to The Willows. It’s a throwback to the old arcades of yesteryear, with boardwalk food options. It’s also located right on the water, which creates a nice setting.
Best Time to Visit
All the seasons have their pros and cons as a time to visit Boston. However, I’d argue fall is the best time to see the city. While the weather is hit and miss as far as rain, most tourists have left by September. I’m one who likes cooler temps and even early November can be a good time to experience Boston. You can take in the historic sites, walk the city, and spend time at one of our many museums if the weather takes a turn for the worse.
Best insiders tip
I have a few:
1. Don’t drive. Take the T, walk, or use a rideshare service.
2. Don’t call it Little Italy. It’s the North End.
3. Go to the Harbor Islands.
I Love Boston because...
there's so much history. Don’t be fooled, though. There’s way more to Boston history than just the Colonial tales we're taught in US History classes. In fact, I talk about some of them on the North End Tour!