A Weekend in Boston

Earlier this year I posted about my most recent trip to Boston. I talked about all of the things we did, things we ate and where we stayed. All in all, it was such a great trip and one of my favorites to look back on. I had always planned on sharing what I thought would make a fun weekend in Boston, but have been wanting to even more recently. With the increased time at home recently, I have been daydreaming of the day we will get to travel again and all of the wonderful places we will go.

My husband has never been to Boston, even though we drove right past it last year. I keep telling him how much I want to take him to this sweet city since it is one of my favorite places to visit. I wrote this itinerary with him in mind and what I would want him to see if we only had a couple of days.


Morning: Arrive in Boston and get settled into your hotel! Take a minute to unpack, drink some water and freshen up from your travel. Don’t forget you are on vacation and it is okay to take your time!

*Note: I stayed in an AirBNB during my last trip that was great, but I would love to try out some new hotels in the area. The Godfrey Hotel, Lenox Hotel and Boston Park Plaza all look like great options! Two of the three hotels are fairly close to Beacon Hill, which is one of my favorite areas of Boston.


12:00ish: Head to Beacon Hill (if you aren’t already staying there) and grab lunch at Figs by Todd English. It is a great little pizza place with wonderful food and an awesome vibe.  Their Caesar salad is delicious and you pretty much can’t go wrong with any of their pizzas. I particularly liked the fig & prosciutto pizza!

Afternoon: I like visiting new museums each time I got to a city, I would consider Boston no exception. So far I have visited the Harvard Natural History Museum, the New England Aquarium and the Paul Revere House. They were are super interesting and I enjoyed each trip. Two of the places I still have on my list are the Museum of Fine Arts and John F. Kennedy Museum. One of them would be my choice for my next trip!


Late Afternoon: Head back to your hotel, rest for a minute and get ready for a fun night out!

Evening:  It’s time for a Red Sox game! By far one of my favorite things I have done in Boston by far. Such a fun atmosphere and way to spend an evening. There are a bunch of bars right outside of the park, so consider getting there a bit early to grab a drink. Then pick up some food at the ballpark – nothing beats ballpark nachos, hotdogs and pretzels.


Mid-Morning: You have a big day ahead of you, so a delicious and hearty brunch is in order. Head to the waterfront for a fabulous brunch at State Street Provisions. If it is a nice day, I strongly suggest sitting outside! They have the cutest little patio to go along with their tasty menu. The eggs bene and breakfast sandwiches are quite delicious. After you have finished a yummy brunch, hop on the subway and head for Boston Common!


Mid-Day: You are now in Boston Common, which happens to be the start (or end, depending on how you look at it) of the Freedom Trail. Take the rest of the day to walk the freedom trail. The trail is only 2.5 miles long, but has 16 historic sites! The activity of the day is to way the freedom trail. There are so many great stops along the way, both planned and now. Some of my favorite planned stops were the Granary Burying Ground, Faneuil Hall, the Paul Revere House, USS Constitution and the Old North Church. I am a bit of a history nerd, so I get a bit excited about historic sites. By far my favorite unplanned stop was the street show outside of Faneuil Hall. It is definitely worth waiting around for! Doing the whole trail, while making stops can definitely take a while. Don’t be afraid to stop fro some lunch Union Oyster House, a sweet treat at Magnolia Bakery or  a snack at one of the kiosks inside of Faneuil Hall. This is also a great way to see so many Boston neighborhoods, so don’t miss taking advantage of that!


Late Afternoon: After a long afternoon, it is time to head back to your hotel and relax for a little bit. Maybe pick up a bottle of wine and some snacks and take some time for yourselves.

Evening: Now it’s time for a nice dinner out in Boston. One of my favorite restaurants, period, but definitely in Boston is Trattoria Il Panino. It has been featured in both of my previous Boston posts, because it is just that good. I will be forever grateful to the Boston Police Officer that pointed me in the right direction nearly four years ago. This place is amazing and the perfect place to have a wonderful night out. If you are not feeling too full after, consider heading down the street to Mike’s Pastry for a cannoli.

Trattoria Il Panino
Ravioli Porcini from Trattoria Il Panino

Late Evening: If you are not too tired from the day head to drinks at Lookout Rooftop and Bar. I will admit I have never been here, but it was on my list last time. I can’t think of a better way to end the night but to sit at a rooftop bar, looking out over a beautiful view, with a crisp glass of wine in my hand.


Morning: It’s your last day in Boston. I’m sure you’re sad to go at this point, but excited to make the most of your last day. Start off by getting some breakfast at Paramount Cafe. Right in the heart of Beacon Hill, this little place is always packed and worth the wait. They have pretty traditional breakfast, done really well and worth every minute you may wait. The breakfast potatoes may have been my favorite.

Late Morning: Spend some time after breakfast exploring Beacon Hill. There are so many cute little shops to pop into, everything from home decor to antiques to clothing. If you are needing a cup of coffee to keep you going, I strongly recommend Tatte Bakery and Cafe; the cutest little place with the best coffee and baked goods!


Midday: Spend the rest of your morning taking a stroll through Boston Common and the Public Gardens (they are right across the street from each other). Both are absolutely beautiful and the perfect way to spend an active morning. Personally, I think I like the Public Gardens a bit more. They are so lush, full of color and complete with a little pond right in the middle. I could spend hours walking through the park or sitting down and reading a book.


Afternoon: Sadly, your long weekend in Boston has come to an end. You’ve seen the sites and eaten some amazing food, but nothing is quite like home. It’s time to take a plane, train or automobile back home.

Boston is truly one of my favorite places to visit in the world. I love the history and culture of the city and never miss out on a visit. Hopefully you enjoy your trip to Boston as much as I have enjoyed mine. Until next time, friends… CML

2 thoughts on “A Weekend in Boston

  1. Thanks for sharing Catie 🙂 in the US I was only in New York and it was lovely, hope to return and visit also Boston 🙂 will save your article 🙂 all the best and greetings from Lisbon, PedroL


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