Austin to Boston: Where to eat, drink, and explore

Austin to Boston: Where to Eat, Drink, and Explore For A Wicked Good Time

November 8, 2022 |

By Lola Hagopian

We recently took a trip from Austin to Boston and now we’re spilling the tea on where to eat, drink and explore. Much like Austin, Boston is the perfect city mixed with history, nature, art, and good food and drinks.

Here’s how to have a wicked good time in Boston!

Stay

We stayed in downtown Boston which we highly recommend. The Hilton Downtown/Faneuil Hall is perfectly locate as it’s close to just about everything. The hotel includes great accommodations so you don’t really need to go far for your morning coffee or a delicious meal. There’s a coffee shop off the lobby called Tradesman Coffee Shop and Lounge which serves up an amazing selection of coffee and teas in addition to delicious pastries. We recommend the Boston cream pie croissant!

The hotel also has a restaurant called Fin Point Oyster Bar + Grille which has an amazing raw bar among other fresh seafood dishes. There are so many reasons to stay at a Hilton, especially this one. The Hilton is always our number one choice in hotels because we love the comfort and consistency their hotels provide.

Eat and Drink

Boston is crawling with pubs and restaurants and you really can’t go wrong with any of them but there are a few standouts that we have to share!

We hit up Wicked Craft Co. on our first night in Boston and it set the bar high! Wicked stands out in its location in Boston’s Historic North End. Nestled between Italian restaurants and historic sites like Paul Revere’s House, Wicked is a little something more new age. While it isn’t the biggest restaurant, it makes up for its size in just about everything else, somehow balancing the fine line between aesthetic and quality. The cocktails and food don’t just look good, they taste good! The staff genuinely loves what they do and it really shows. Honestly, they all seemed like characters in a sitcom set in Boston and we kind of loved it! We tried a variety of food and drinks and we can’t say a single bad thing about anything we had, except that maybe the portions are too big. We’re not sure that’s a bad thing though. Did we mention the massive neon sign that says “Wicked”? It might as well scream, “Tourists this one’s for you!”

You can’t go to Boston and not have fish and chips, it’s kind of a crime. You also can’t say you’ve been to Boston unless you eat a cannoli (or three) from Mike’s Pastry, which has been a Boston staple since 1946. Don’t forget to pair your cannoli with some Dunkin’ Donuts coffee. There are two on every corner!

Even More Eats

While Italian culture might have a heavy presence in the city, so does the Irish. You might hear bagpipes while walking down the street, pass a pub playing “Galway Girl” or smell the distinct scent of Guinness. It often felt like we were back in Dublin. As Austin is the Live Music Capitol of The World, the amount of live music in Boston really surprised us. We even found live country music at a place called Lily’s, not too far from our hotel. While the food and drinks were good, the art is really what captured our attention. On the bar’s back wall are three unique portraits: One of Leonardo DiCaprio and Lana Del Ray, a second of Abraham Lincoln and a third of Elon Musk and Katy Perry. We’re not sure why these people were grouped together but it sure was fun trying to figure it out while we ate.

Tourist Musts

Boston has so much history that you can probably spend your entire trip just doing that. But if you’re like us, you like the cliff notes version. So we’re just going to talk about the places we think are worth it if you have the time and like history. We would definitely start with the Freedom Trail, it’s a 2.5-mile-long path through Boston, that passes by 16 locations significant to the history of the United States. The sites include:

Boston Common (America’s oldest public park)
Massachusetts State House
Park Street Church
Granary Burying Ground
King’s Chapel & King’s Chapel Burying Ground
Boston Latin School Site/Benjamin Franklin Statue
Old Corner Bookstore
Old South Meeting House
Old State House
Boston Massacre Site
Fanueil Hall
Paul Revere’s House
Old North Church
Copp’s Hill Burial Ground
USS Constitution
Bunker Hill

More Tourist Tips

Boston Commons is on the Freedom Trail but you should take extra time to explore it because it is absolutely beautiful. You can also walk to and from Newbury Street from there. We suggest going to the park before you hit up Newbury Street, so you don’t have to carry all your shopping bags with you. Newbury Street is full of fun shopping, cafes and more.

Harvard Square is a must. Not only did we live out our Gilmore Girls dreams (even though that episode was actually filmed at UCLA) but the campus is stunning and so full of history. Harvard was founded in 1636 making it the oldest college in the United States. We swear our IQ went up a few points just by being there. The square is also great for shopping, and grabbing a quick bite, but mostly for people-watching! For that, we highly recommend the window seat and a cappuccino at Tatte Bakery on the square.

Visit Salem

For more history and tourist must-sees, we suggest a trip out to Salem. From the witches on the cop cars, fire trucks and the school mascot, the entire town of Salem has fully embraced being known as “Witch City”. While visiting during Halloween would be best, we think that there are enough things to see and do that visiting during the off-season would be worth it! Read more about our trip to Salem here.

Pop-Culture Finds

Boston feels like a giant filming location because it’s been in so many movies and TV shows. So while there aren’t too many actual filming locations there are a few pop-culture things we just had to share!

Fenway Park falls in both the pop-culture and tourist category. Fenway Park opened in 1912 making it the oldest stadium in MLB and one of the most famous. In 2012, the park was added to the National Register of Historic Places – which doesn’t surprise us considering it’s one of the most well-known sports venues in the world.

But that’s just the stadium. The Boston Red Sox have a very large dedicated and sometimes angry fan base which includes a lot of celebrities – including well known Bostonians Ben Affleck, Matt Damon, Chris Evans, John Krasinski, and Mark Wahlberg. The team and their fans are so well-known that they even made a movie about it.

Watch Fever Pitch

We suggest watching Fever Pitch (2005) before your trip to Boston. It stars Drew Barrymore and Jimmy Fallon. When Barrymore’s character starts dating Fallon’s, a diehard Red Sox fan, she quickly realizes that dating him means she’s also dating the entire team and Red Sox culture. It’s a fun rom-com that mostly still holds up today.

Check Out Cheers

You might have heard of a little show called Cheers. The popular TV series, which aired for 11 seasons, was inspired by a bar in Beacon Hill called Bull & Finch Pub. It even used the exterior of the bar throughout the series. The NBC sitcom ran between 1982 and 1993 and has often been named one of the top TV shows of all time. If you’re unfamiliar with the premise, Sam Malone (Ted Danson) is a former relief pitcher for the Red Sox, who now owns and manages a bar. The problem is that he’s a recovering alcoholic. Almost 30 years after its final episode, Cheers is still as beloved as ever. The Cheers bar in Boston even includes a replica set upstairs where you can actually eat and drink. You’re not going to want to miss this nostalgic stop!

Have a Magical Adventure

What does Harry Potter have to do with Boston? The answer is nothing, really. But since we’re big fans of the books/ movies, we love finding Harry Potter related things during our trips. Boston was no exception! Newbury Street is known for beautiful brownstones, eateries, upscale shopping and more. It’s considered one of the most expensive streets in the world. So when we found the Harry Potter Shop there, it took us by surprise. The shop is tiny and we mean TINY but it has everything a Harry Potter fan could possibly want.

Speaking of the boy wizard, while we were in Salem we visited a wand shop called Wynott Wands. The store is set up to replicate Olivanders and while they had a selection of Harry Potter wands, the store was mostly their own creations. The clerk who assisted us was a magical woman who helps customers pick out the wand that’s right for you by asking a series of questions. Each wand is beautiful and intricate in its design. So, of course, we bought one!

During our trip to Salem we visited all the original Hocus Pocus filming locations. You can find that article here.

Texas Ties

We even found a little Austin in Boston. Loretta’s Last Call is a bar, restaurant and music venue “Deep in the heart of Fenway.” We knew it was a country bar going in but we had no idea we would be transported to Texas once we stepped inside. With icons like Willie and Dolly gracing the walls and Tito’s and Deep Eddy neon signs, you’ll feel right at home if you’re visiting from Texas. It’s a great brunch spot!

Travel Tips

Here are a few things we learned about taking a trip to Boston:

Don’t forget to pack an umbrella.
Make sure your phone is charged or you have an extra battery pack with you. You’re going to be using your maps a lot. The streets aren’t the easiest to navigate.
If you have a National Parks passport, don’t forget to bring it along! You can get stamps for things like the Freedom Trail! You can also just stamp paper or a sticky note and add it later like we did.
If you’re planning on spending time in Salem and are staying in Boston, plan accordingly. One day was not enough time in Salem.
Have a game plan together before you leave your hotel in the mornings. Check hours, some things close early and there are not a lot of late night dining options downtown. To avoid issues later, plan ahead.
Bring comfortable shoes. This one is kind of a given. Boston is a very walkable city so make sure your shoes are comfortable. Most of the time, it’s easier to walk than take a ride share.

Here’s how to have a wicked good time in Boston!