This post contains affiliate links.
Summer is here, and the best way to thank the warm air and shining sun for banishing our winter blues is by soaking them both up on a Boston rooftop bar crawl.
These three routes combine the three best things in the world – alcohol, the outdoors, and stellar views – to take you on a boozy journey through three of the city’s best neighborhoods. All of them can be done on foot, too, so leave your car at home and get ready to get rowdy.
Whether you want to drink your way through Cambridge, Back Bay, South Boston or all three, these Boston rooftop bar crawl routes are the perfect guide to your next weekend out!
1. Cambridge Rooftop Bar Crawl Route
Walking Time: 8 minutes
Walking Distance: <1 mile
Bars Visited: The Sinclair, Felipe’s Taqueria, Daedalus
The first route in Cambridge covers about a half-mile and begins at The Sinclair, continues to Felipe’s Taqueria, and then finishes at Daedalus.
Start your Cambridge rooftop bar crawl at The Sinclair with brunch on Saturday or Sunday from 11 am to 3 pm or dinner starting at 5 pm. The Sinclair is smack in the middle of Harvard Square and though it’s best-known as a music venue you don’t need show tickets to snag a rooftop table here on your Cambridge bar crawl.
Next, walk two minutes to Felipe’s Taqueria where the food is a bit more budget-friendly. The rooftop bar has a lively ambiance, so grab a mojito, margarita, or cerveza (and maybe a taco or two) while you enjoy the second stop on your Boston rooftop bar crawl!
Finally, it’s time to round out your (admittedly, pretty short) journey with a six-minute walk to Daedalus, which is ready and waiting for you with open doors until 2 am.
The restaurant and bar refers to itself as ‘Harvard Square’s Hidden Gem’ and serves up a pretty eclectic menu alongside their craft beer and cocktail list – so, if you’ve got the drunken munchies and are ready for a second dinner, you won’t go hungry here.
2. Back Bay Rooftop Bar Crawl Route
Walking Time: 19 minutes
Walking Distance: <1 mile
Bars Visited: The Rooftop, Globe Bar & Cafe, Earl’s Kitchen and Bar
The second route in Back Bay covers less than a mile and begins at The Rooftop, continues to the Globe Bar & Cafe, and then finishes at Earl’s Kitchen and Bar.
This Boston rooftop bar crawl is best for day drinking (ok, which one isn’t) because it starts with a sunny dip in the refreshing rooftop pool at the Revere Hotel. Non-guests have to pay a $20 to $30 entrance fee depending on the season and day of the week, but you can also enter after 5 pm for free.
After you’re done splashing around and have successfully gotten at least a little tipsy at the pool bar, it’s a quick 8-minute walk to your next stop at the Globe Bar & Cafe in Copley Square.
It only serves a limited menu of apps, salads, and sandwiches on the rooftop patio, but it has beer and cocktails, so who cares? Enjoy the sun and change of scenery before moving on to the third and final rooftop in this Back Bay bar crawl route.
Earl’s Kitchen and Bar is located in the Pudential Center (a Boston icon all on its own) and is a 12-minute walk from the Globe Bar & Cafe. It’s open til’ 2 am on Fridays and Saturdays and has late-night happy hour deals from 9 pm to close on Sunday through Thursday if you’re tackling this rooftop bar crawl on a weekday.
They also serve up drinks so big they recommend sharing them between four… but you could also just finish it all yourself and end your Boston rooftop bar crawl on a very drunk note instead 😉
3. South Boston Rooftop Bar Crawl Route
Walking Time: 16 minutes
Walking Distance: <1 mile
Bars Visited: Legal Harborside, Trillium Brewery, Sky Lounge Rooftop + Terrace, Lookout Rooftop and Bar
The third Boston rooftop bar crawl route on this list will take you to four rooftop bars in South Boston.
It begins with lunch or dinner at Legal Harborside and then continues to Trillium Brewery, Sky Lounge Rooftop + Terrace, and Lookout Rooftop and Bar.
Legal Seafood is a staple in Boston and somewhere we always ended up eating at during parent’s weekends or fancy nights out when I was a student at Boston College. It’s a bit pricey but definitely delicious, and their upper balcony is right on the water with gorgeous views of the harbor (hence the name) and the city stretching out beyond it.
After you eat (start your South Boston rooftop bar crawl early to take advantage of those sweet, sweet lunch deals) walk 12 minutes to the Trillium Brewery.
Maybe I’m a bad Bostonian, but Sam Adams just never really did it for me and I’m all about supporting the smaller craft breweries in the city.
Trillium has a lot of beers to sample – click here to see what’s currently on tap – and I’m especially intrigued by the Pot and Kettle oatmeal porter with coffee and vanilla. So, pay ’em a visit and wash down your fresh seafood with some craft beer under the sun – is there anything more Boston than that?
Next up, you’re heading right next door to the Sky Lounge and Terrace which has one of the best views of every rooftop on this list. However, that means it can also get a bit crowded in the evenings, so try to go early to make sure you get a spot and can snap a few pics with the stunning skyline views before you get too packed in.
Finally, it’s a quick 2-minute walk to your fourth and final stop on the South Boston rooftop bar crawl.
The Lookout Rooftop at the Envoy Hotel is right around the corner from the Sky Lounge and has the same sparkling city views, made even better with firepits to curl up around while soaking up a sunset over the harbor – so, sit back, relax, and enjoy the view.
Ready to go? Use Skyscanner to find the cheapest flights to Boston and explore accomodation like furnished apartments and unique stays on Airbnb or the top-rated hotels on Booking.com to plan the perfect night, weekend, or long-term stay in the city. Then, plan the rest of your trip with the US Series to go beyond Boston’s borders to cities like Portland, Detroit, Denver and more!
I’ve been traveling full-time for three years, these are the resources that make it happen:
➤ I exclusively use Airbnb for savings and security on long-term stays in furnished apartments.
➤ I use Booking.com for short-term stays in hostels and hotels on weekend trips.
➤ Upwork allowed me to take the leap to travel full-time because they make it so easy to find freelance clients in any field.
➤ The Superstar Blogging Travel Writing Course launched my travel writing career and helped me become a contributor at sites like Cincinnati Refined and International Living, and even get published in the Boston Globe.