Boston, Massachusetts – Mini Travel Guide

It’s crazy to think that I have never been to Boston even though I live SO freaking close. Jared and I decided to make a quick three-day trip down to the good ole’ Boston, Massachusetts for some exploring, good eats, and baseball games. We didn’t get to do as much as I had wanted to of course, but it’s safe to say I am now in love with this place and I already can’t wait to come back! However, for being there for as little as we were, I still think we accomplished A LOT…

Where We Stayed

Encore Boston Harbor Casino – 10/10 would recommend staying here. It’s close to pretty much everything. Jared and I are casino lovers, and I have been dying to go here! It was BEAUTIFUL, the rooms were so stylish, CLEAN, and decorated so nicely. Room tour can be found here. The casino area is strictly closed off to anyone under the age of 21, with tight security. However, kids are allowed in the hotel area and the dining outside of the casino. They have a huge club too that is always having special guests and events happening. There is also some beautiful luxury shopping inside the casino and I was eager to get in there but unfortunately it was closed on the days we were there. Darn! (I know Jared was soooo upset about that one.) With a few days to stay and a lot on our itinerary we didn’t spend too much time at the hotel, but I wouldn’t have minded if we did, it was super fun there!

Of course after any time of travel, I can always go for a good meal. They had a ton of food options to eat at Encore. We had arrived at an odd hour so it was a little too late for breakfast/lunch and not many things were open yet for dinner. So, we ate at a restaurant inside the casino area at On Deck which is American food and sports bar themed. It was a great vibe and Jared had this CRAZY milkshake (see picture below). It was a cool atmosphere but if I had to rate it I would probably give it a 6/10. It was good, but just regular sports bar food, nothing too fancy or out of the ordinary.

Jared and I also love to order room service, so we had to try their In Room Dining for breakfast. I had Eggs Benedict, my absolute favorite, and it was so freakin good. Unfortunately, because we were there during the week there wasn’t too much going on at the casino, however they had a TON of other food options to choose from. Below is a list of all the other restaurants located inside the casino. The coolest one, in my opinion, was the Mexican style food truck right in the middle of the casino. The few that I absolutely want to go back and try are the noodle bar, the steakhouse, and the cheese/wine tasting place.

Restaurants In Encore + Their Menus:

Things To Do

Boston Red Sox Game at Fenway Park – While this was the main reason we were here, it’s definitely a must-do on the list for anyone, especially if you’ve never been. We had tickets for two back-to-back games on Tuesday and Wednesday, and planned to explore as much of Boston in between. There’s a fun area that’s considered to be “inside the stadium” where they block off the road and there’s so much going on before the game. You can get snacks, drinks, get all of your Red Sox gear, and listen to live music all at once! It’s so much fun, I recommend showing up early and checking this out before heading to your seats.

For the second game, we sat on the Green Monster and this is a bucket list item for sure. It’s nearly a 38 foot wall, left of the field, with an incredible view of the stadium. (We definitely made it on TV too!) Beware if you sit here you will definitely have to pay close attention because it’s possible you can be hit with a ball. Fun fact – this MLB stadium is the oldest ballpark to date, and if you want a good stadium snack, be sure to walk all the way to the end of the stadium to get the classic baseball cap nachos – my absolute FAVORITE.

The Lawn on D – This is such a cool hang spot with live music, food + drinks, and games. Here’s where you will find those “Instagram Famous” Circle Swings. The Lawn On D is a 2.7-acre outdoor event space and there is always something going on. Unfortunately, they had a private event going on the day we had decided to go here. I WAS SO SAD – an Instagram girl has been let down! We Ubered all the way there only for them to not let us in, but I will totally be coming back here because it looks like a GREAT time. They have HUGE games and it really looked so fun. *Note they are only open from May – October.*

Rooftop Bars – There’s Lookout Rooftop and Bar and Rooftop @ Revere. We actually had planned to go to the Lookout but with a miscommunication with the Uber driver, funny enough, we ended up at Revere. It was definitely a cool spot to have some delicious drinks and of course snap some good Instagram photos. While Revere is closed for the winter, Lookout has the infamous igloos to lounge in during the colder season.

Shopping – There are endless places to shop in Boston! We stopped at one of the malls, Copley Place, and it was beautiful inside. This was a perfect spot for some luxury shopping. If it were up to me, I would have spent and entire day shopping in Boston but unfortunately for me, Jared is not that patient. But, it’s definitely something fun to to on a rainy day.

For Food and Drink..

Bricco – I was stunned with the great service and delicious Italian food. We sat outside to take in much as of the city as we could. We even had some live Italian music from local street artists which totally set the tone – I loved every second of it. We had a violin player and an accordion player play for us at our table while we ate. Food wise – for apps we had the Wellfleet Muscles, and Mozzarella di Bufala Caprese, both were astonishing. For our meals, Tortelli Pumpkin (me), and the Eggplant Bake (Jared) which I couldn’t get enough of. And for dessert, their perfectly made Crème Brûlée (I will never turn down a Crème Brûlée). I would highly recommend this place for some good Italian food.

jm Curley – This is a cocktail bar and steakhouse owned and run by one of Jared’s friends. This rustic themed bar is so fun and has such a great atmosphere. Totally totally recommend. The drinks were cute, fancy, and DELICIOUS. I had an Espresso Martini, the B&T (vodka, raspberry, lemon, and elderflower foam), and the Aperol Spritz (aperol, sparkling wine, and soda water) – all were up to par. For food we had the Roasted Garlic Hummus, Carolina Golden Wings, and the Buffalo Chicken Mac (A MUST HAVE). They are open seven days a week and serve food until close. They even have a nice private Steakhouse in the back, Bogie’s Place, that they just recently added.


Even though we drove into Boston, we Ubered everywhere. Everything is so fast paced here and they aren’t called “Massholes” for nothing, haha JUST KIDDING! But it definitely can get extremely stressful driving in such a busy area, so we stuck to letting the pros drive. Regardless, finding parking can be a pain and like in any city, so train or Uber/Lyft is your best bet. I couldn’t even imagine trying to find parking for the Red Sox game. It was more convenient to be dropped off right at the gate and walk right in. Also, a lot of things in the city are within walking distance from each other so walking or biking is a good option for the warmer seasons too!

When I Go Back…

While we were only there for a few days and tried to squish in everything we could, here is a bunch of things that are on my list to do when we go back:

Modern Pastry Shop – Although we were right near this (next to Bricco), we were so full from dinner we couldn’t fit it. We were recommended this place by a friend and EVERYONE was carrying boxes from here and it all looked so good and FRESH! This is a must do the next time we’re in the area.

The Boston Public Library – I heard this place is phenomenal and something cool to see and experience. I definitely want to check this out when we come back.

Isabella Stewart Gardner Museum – We tried to do this while we were here this time, but it didn’t end up working out. This is absolutely on my to do list for next time and in warm weather!

Eataly Marketplace – I’ve heard this was a great spot and the restaurant there, Terra, is perfect for brunch!

The Eliot Hotel – I’ve heard so many great things about this hotel and their ambiance. I totally want to check it out and see what it’s all about. I think it’s on the but pricier end but still would be cool to experience!

Selfie World – I know there are a few of these around the country but I think this might be the closest one to me. Of course what Instagram blogger girl wouldn’t want to check this out!? I am totally going here next time!

For just a short weekend getaway, we did as much as we possibly could in three days. I wish this trip had lasted longer because I was LOVING Boston. We’re not too far, so it’s safe to say I will definitely be coming back soon! If you have any other questions, feel free to send me a DM!

Be sure to follow me on Instagram for new blog post alerts, daily updates, outfits, travel posts, food spots, Instagram tips, and MORE!

With Love, 

Taylor Onze

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