If you have been thinking of taking a girls’ trip to Boston, I have so many ideas to share. We had the best time! You can cover so much in just one day, and a day is what we had. The first morning we explored the Mission Hill area which is delightfully walkable!

Before I go on about the Mission Hill area and how much we loved it, I can’t encourage you enough to stay in a VRBO or AirBNB in one of the many charming neighborhoods and literally embed yourself in the culture. Staying in a hotel is more about living that tourist life, and we were so much happier choosing to be a traveller instead. This allows you to avoid crowds and really experience the city more like someone who actually lives there.

We found the BEST coffee shop called Green Haus Coffee, and they also sold the healthiest looking green houseplants and succulents. It was incredibly charming. My friend and traveling companion would argue that Solid Ground Cafe made a better latte, and was just a few blocks away. On the same block as Green Haus, we discovered Milkweed, a breakfast cafe with a menu so captivating, it was as if someone took all of my breakfast favorites and compiled them all together. I ended up getting a bacon, egg, and cheese croissant which I devoured. All of these were just blocks away from our AirBNB. Also notable was Il Mondo Pizza, but we did not get to try them.

Mission Hill was an area lush with trees and beautiful wildflowers everywhere you looked. The brownstones gave you a vibe that you were on the set of any TV show or movie that might take place in a big city on the East coast. There were gorgeous views of the city as you trekked up and down the hilly streets. I lived in San Francisco for several years and this satisfied my craving for the feeling of living in a big city while also having a cozy neighborhood vibe. I’ve missed that so much.

While we were in the Mission Hill neighborhood, we strolled through a little park, and found a beautiful Catholic church called The Basilica and Shrine of Our Lady of Perpetual Help. Do yourself a favor and go inside that Catholic Church. It has had so many confessionals which fascinated me, and a shrine where you could light a votive candle to pray for someone. We also found a Walgreens that had an escalator. Our Walgreens doesn’t have an escalator! It’s the small, unexpected things I find that are the most memorable when I travel.

We waited for one of our friends to join us, and made our way to the Isabella Gardner Museum. On our way there, our GPS took us through the Wentworth Institute of Technology campus which was beautiful and so charming. There were fun chairs and hammocks strewn throughout the courtyard and we just enjoyed 15-20 minutes in the hammocks! It was so delightful!

Our friend Caryn, who we came to the Northeast area to visit, joined us at this point. I hope my girls enjoyed their day, because they entrusted me to navigate us and suggest things for us to do the rest of the time in Boston. I will say we walked SO, SO much we were all fatigued. We Uber’ed to our first destination, but then after that we walked everywhere and probably too much. I feel like if I had planned a little more thoughtfully we could have maximized our time better. There are hop on/hop off bus tours and other buses but these were all very pricey, so we opted to walk. In retrospect, I now realize that Boston is HUGE, and the places you want to go appear really close together on your map. In real life, they are pretty far apart. I am thankful I brought good walking shoes (I LOVE these), and that we checked the weather before packing. For that reason we packed lots of shorts, and sleeveless tops, and THANKFULLY we had lots of shade and cloud coverage and a nice breeze because we visited Boston during July when they were hitting record highs.

All of that said, we started off as a trio by visiting the Boston Public Library. Now that may sound like a strange place to have on your Boston itinerary, but it is extraordinary. This is a massive library, but what attracted me to it was seeing pictures of their gorgeous courtyard on several blog posts I read prior to the trip, AND there is a bar adjacent to the courtyard and a little restaurant/cafe. You can sit in at the bar, and enjoy some of the best tasting and beautifully crafted mixed drinks that I have ever tasted or seen, or enjoy in the beautiful courtyard at the tables they have around the perimeter. We only opted indoors because of the heat – it was just a little too warm for us.

After the library we strolled along Boylston Street which gives you those big city vibes and is rich with shopping and dining options. We walked about three minutes before arriving at Saltie Girl. Can I recommend Saltie Girl? I will say they were some of the most delicious bites I had while I was in Boston but also the smallest and most expensive. It is very posh! The three of us shared what we ordered so we found it to be enough food, but only because Caryn got the fish and chips which was more of a generous portion, as opposed to our salmon and yellowtail.

After leaving Saltie Girl, we found ourselves in a very bougie area of the city, on Newbury Street. We strolled past, Cartier, Armani, Rolex, and Tiffany and Co. At the end of Newbury, we discovered the park that was way high on my Boston bucket list – Boston Public Gardens. If I lived in Boston, I would walk and run here on the regular. The grounds are lovely. We stopped and enjoyed the shade of the trees and just being present and watching baby ducks swim in the pond. We crossed the little pedestrian bridge and debated taking a ride on the swan boats. The pond area was not shaded, and we were getting into the warmer part of the day, so we opted out of the boat ride and continued on to find the bar where everybody knows your name…Cheers.

The Cheers bar is RIGHT across the street from the Boston Public Garden which I wish I would have realized in hindsight. You could walk all the way through the Garden under tree cover in the shade and end up at Cheers. Instead, we walked to Boston Common and then down Beacon Street to get there which took a little longer, and was for sure hotter.

I had read before coming to Boston that the Cheers Bar is the exact same on the outside as it was during the show filming, but the inside is completely different. I expected to be disappointed for this reason, but once you’re inside, you’re relieved that they’ve added so much more seating and a Gift shop. This allowed us to be seated and get waited on faster. We found our seats upstairs where they had recreated the bar as it was on the set. I sat in “Frasier’s seat,” and had the possibly the BEST IPA I’ve ever had, Norm’s IPA. It was so, so good. We met a couple that sat beside us and were probably twenty years old than us. When we told him we were all 50 or about to be 50, the husband said, “no f’ing way!” very loudly! Ha!

After we left the Cheers bar, I realized we were very close to Acorn Street which is the most photographed street, and one of the most beautiful. It made Architectural Digest’s list of the most beautiful streets in America. It’s in the prestigious Beacon Hill neighborhood. The cobblestone street, window boxes and red brick homes are some of the most notable characteristics. We stumbled off and back on the Freedom Trail during this time.

If you are wondering why we didn’t opt to do more typical touristy/historical options, it is for a couple of reasons. One, my friend Caryn lives near the area and I figured she had done those things. I wanted us to all have a chance to do things we hadn’t done before. And two, I felt like I will come back here with my husband and girls and have a chance to do all of those things together it it would be new to us together. Three, I wanted to choose things that I would love to do in Boston that were adult friendly, because I never get to go to any bars or higher-end restaurants when we travel as a family. It’s expensive for a family of four to eat at a the fanciest Italian restaurant. But if it’s just me, it feels attainable and special.

That leads me to our pilgrimmage to Little Italy. We wanted to eat at a nice Italian restaurant for dinner, and also wanted a cannoli from Mike’s Cannoli. They ended up being on the same block! But we had lots of steps to get in before making it there.

We walked through some really cool areas and I wish I had taken more pictures of this part of our trip! I think I was feeling a bit haggard, hot and hungry at this point so taking photos just was not what I had on my mind.

We did stop off at North End Park which was the absolute coolest concept for a park, and much needed for our tired and weary legs! It has a long row of swings for you to swing on, and then sprinklers (think splash pad). I actually took off my shoes and walked through the sprinklers with the little toddlers. I have no shame and it felt so good!

We were very close to Little Italy at this point, but also Union Oyster House which was on my bucket list. I was very determined during our entire trip to locate raw oysters that cost less than $4 a dozen. Sadly I would be disappointed yet again when we arrived and I looked at their menu. If you are able to shell out the dough, I did read that they have the best raw oysters in Boston supposedly.

Once we arrived in Little Italy we actually went to Mike’s Pastry first. Our logic was that if we ate a big plate of pasta, we would be totally stuffed and talk ourselves out of even getting our cannoli. So we got the cannolis from Mike’s first, then made our way to what I researched and found to be the best Italian restaurant in Little Italy and that was Trattoria Il Panino.

So many things stand out to me now about this little restaurant looking back. The one you will notice almost right away is how it is packed full of tables. You are very (almost uncomforably) close to the tables next to you. It is therefore very loud in the restaurant. It is a lively environment which I appreciated. A lot of times Italian restaurants are so formal and quiet that you feel like the tables around you can hear your every word. So it is unique in that it is packed but also you are free to speak as you wish.

The second thing you will notice is that your meal is brought out in the skillet it was cooked in! Made to order, then not plated, but brought to you nice and hot in the pan. I have never experienced this! Let’s talk about our food. I had a gluten-free friend, and she loved her pasta! So often, gluten-free pasta dishes are tasteless or have an unpleasant texture. This was not the case! I also had a friend who got linguini with shrimp which looked amazing, and I had basically a fettucini that was to die for. We all could tell that the pasta was made in-house and everything was made from scratch. I am very particular about fettucini alfredo and only really like my husband’s (he is a classically trained chef). When I order it at a restaurant I’m always disappointed as it tastes like it was made from frozen. This is real deal! You will not find “fettucini alfredo” on the menu! What I ordered is called Cacio de Pepe on their menu – that is the closest thing I found to fettucini alfredo and it comes across as such, though not exactly.

That was our day and time spent in Boston! If you are planning a trip to Boston, and particularly a trip with girlfriends, I hope this has inspired you and given you some ideas of what you can do and how you can maximize your time there.