After planning a trip for a friend, we decided that the trip sounded amazing. So before we knew it, we’d booked the trip ourselves. We had 3 days to explore this beautiful city and pack in history, sight-seeing and lots of delicious food. Here’s our weekend guide to Boston.
Accommodation:
Hi Boston – We chose this spot for a few reasons: 1. Location 2. Availability 3. Part of the Hi Hostel family. We’d stayed at Hi New York and had an amazing experience, so we figured we’d give this one a try. We found out halfway through our trip that we were staying in a “green hostel”, which is basically a fancy way of saying they don’t want to pay for A/C. If you don’t mind shared space and very basic amenities, the location is excellent. We were a 5-minute walk from the red line, which took us everywhere we wanted to go.
Food:
Tatte Bakery and Cafe – Just down the street from our hostel, this quickly became one of our favorite morning spots. The baked goods were enormous and to die for. There are a few locations around the city, so make sure to stop by one of them for coffee and a baked good to go, or sit down and enjoy a lovely breakfast in their cafe.
Felipe’s Tacqueria by Harvard – my cousin took us to this spot after our tour of Harvard. It’s basically a fresher and tastier Chipotle. You choose ingredients as you go down the line, but it was probably some of the best Mexican food we’ve had in a while.
Quincy Market – not only is this a must-see stop on your Boston tour, it’s got every type of food you could possibly want. It’s perfect if you’re with a large group who can’t agree on what they’d like for lunch or if you just want to browse around. I grabbed a big cup of frozen yogurt while Lexa tried some gelato.
Sail Loft – We felt like it would be a crime to leave Boston without trying a seafood restaurant. The places we’d planned on trying were all closed by the time we arrived, but a guy on one of our busses mentioned this place. It had a homey feel, not too upscale. We were able to sit by the window and look out at the harbor; the servers were very pleasant too. We got large portions of food, but as Lexa learned, getting a lobster roll is pretty expensive.
Drink:
Black Rose: This was by far our favorite spot of our entire trip. We have never been to an Irish bar that was quite like this. There was a $10 cover each on a Saturday night, but it was well worth it. The place was packed, the Irish band was fantastic and the crowd was probably the most fun and engaged crowd we’ve ever been a part of. The drinks were decently priced, and you’ll be sure to find yourself out on the dance floor swaying to the beat or meeting a new dance partner.
Lookout Rooftop Bar: Located right off the water, the Lookout Rooftop Bar is the perfect place to start your evening. The drinks are a bit pricey and it gets packed on the weekends, so go early and be prepared to fight for a spot with a table. Here you’ll find a younger crowd looking to party and meet new people. This is a top location to view the Boston skyline and chat with friends while having a casual drink.
Modern Underground: We probably never would have found this speakeasy without the guidance of a local. Tucked under a cannoli shop in Little Italy, Modern boasts delicious drinks and a unique experience. Be prepared though, the basement space is small and gets packed on the weekends. The drinks were delicious (and boozy), so they didn’t feel overly priced at about $12-15. Just grab a cannoli, park at the bar and wait for your time to order.
Tours:
Freedom Trail tour: This history filled 2-hour walking tour is the perfect way to get the lay of the land in Boston. Your guide (dressed in character) will take you around to the most important sights in Boston and fill you with interesting stories of Boston’s origins. We recommend doing this first because it gave us a good overview, provided us with a background that we used for some of the other tours and allowed us to figure out what we wanted to spend the rest of our time visiting or re-visiting.
Boston’s Politically Incorrect North End food tour: We added this to our trip based on a recommendation from a friend, and it was probably one of our favorite activities. It’s a bit on the pricier side at around $70 per person (plus a tip), but it was well-worth every penny. Your guide is a sassy Italian man (Anthony) who grew up in Little Italy. He has genuine connections with most of the people who still live there and gave us a sense of which places were actually good vs. popular. The tour started off with a lot of history and less food, but we were definitely stuffed by the end.
Attractions:
Harvard (Free): You can’t visit Boston and not take a peak around Harvard. The grounds are open to walk around, so breathe in the smell of smart people and stroll around the beautiful campus. One thing we would recommend is spending a bit more time walking around stores. There are tons of cute bars, restaurants and shops to poke around, but we ran out of time before we had to head back for a tour.
Day trip to Salem: This is a fun one especially during Spooky Season. There’s a witch museum, tons of spooky stores, history tours and more. Make sure to plan ahead though because we couldn’t do a lot due to crowds. We also recommend planning transportation in advance because the bus you have to take only runs once an hour – it will take you significantly longer than you expect to get there.
