Boston Travel Guide

I just spent the weekend in Boston with my husband and had so many of you reach out via Instagram to tell me that you love this city or that it’s on your list of places to go and asking me to share recommendations. I always love sharing recs for places that I’ve visited, so today I am sharing my Boston travel guide with you all. I’ve got my input on why you should visit and why we did, where to stay, where to eat and drink, and what to do! Plus, lots of unseen pictures from the trip to share with you all.

BOSTON TRAVEL GUIDE

WHY VISIT

I originally visited Boston this time ten years ago with my family. We started in Boston and made our way to Cape Cod, Plymouth, and Newport. Ever since, I’ve considered Boston to be such a fun and exciting city. My husband had a work conference Monday-Friday in Boston, so we figured that I’d fly up and we’d make a long weekend trip out of it. He had never visited and I was there so long ago that we thought it’d be so fun to explore the city together!

To me, Boston is such a charming city. The beautiful, classic style of so many of the buildings is amazing to see. Plus, it has so much history that is such an important part of our country. It’s so cool to see some of the oldest streets, restaurants, and buildings in the country. The homes are beautiful and it is a really fun city to visit! I also absolutely love all of the food. The fresh seafood right off the water is unbeatable.

WHERE TO STAY

We stayed at the Royal Sonesta Hotel. This hotel is just over the Charles river in Cambridge, which provides beautiful views of Boston and a bit of a quieter feel, which we loved. The location is great because you’re not far from anything you want to do in the heart of Boston and can still walk around as needed. You’re also close to everything there is to do in Cambridge!

The Royal Sonesta has over 400 newly renovated rooms divided into two towers. We were in a suite overlooking the water which was beautiful and had so much space! I saw some other standard rooms, which were also really spacious. The room my husband had stayed in during the week for work was SO much smaller and really cramped, so being not in the middle of the city center had it’s perks so we weren’t tripping over our luggage.

The hotel has a few restaurants including a coffee shop and bakery, which I always love having on site. I need my almond milk chai fix in the mornings and having a coffee shop right downstairs is always a pro! They also have an Italian restaurant called Dante and a bar and restaurant called Art Bar. We had appetizers and drinks here one night and loved it! You can sit outside and enjoy the view of the Charles river, or if it’s too cold you can sit inside. They also have a big breakfast available each morning if you’d rather do that instead of grabbing a coffee and a pastry. Plus, of course, room service! There are some amazing art pieces through the hotel, as the owners are one of the top private art collectors in the country, and the Art Bar has some really unique pieces as well, including Andy Warhol’s Campbell Soup dress.

When the weather is nice, you can borrow bikes from the hotel to ride around the river, which we will 100% due the next time we visit. They also have a really good size on site gym and an atrium style pool that is so neat! The staff at the hotel was so friendly and helpful throughout our stay and I would absolutely recommended the Royal Sonesta Boston as a place to stay for your visit to Boston.

WHERE TO EAT

• Neptune Oyster Bar: a must, but go early. We waited for like two hours here. We split some oysters and a hot oyster roll and fries + enjoyed some champagne at the raw bar. It’s by far the best lobster roll I’ve ever had. We enjoyed an appetizer and a few drinks across the street while we waited, but next time I think I’d go around 30 minutes before they open and hop in line.
• Giacomo’s: this is a classic Italian spot with locations in both the North and South ends. They are cash only with no reservations, so it’s recommended that you go early. We had plans to go here Friday night, but actually filled up on appetizers before so we didn’t. It is definitely on my list for next time, though!
• Beehive Restaurant: this is an adorable little brunch spot in the Southend! They have live jazz music going during brunch and everything we had was delicious.
• Union Oyster House: a must visit! I went here with my family last time I visited and we stopped in again to get out of the rain and have some drinks + a bowl of clam chowder. It’s the oldest restaurant still in business in America and it serves classic New England dishes. I can’t recall if they take reservations, but there is always a wait! You can grab a seat at the bar or the raw bar while waiting for your table though.
• Select Oyster Bar: we ate here on Saturday night and loved it. My only complaint would be that we made reservations and then were seated at the bar, but the food was all delicious and the service was good. We shared a ton of oysters and different small plates and every single thing was delicious.
• Tatte Bakery & Café: this is a cute little restaurant with baked goods and coffee with several locations throughout Boston and Cambridge. We went for breakfast on Sunday morning and split some pastries with our coffees. My husband got an egg sandwich and I got a salad for our meals, too.
• James Hook & Co: a classic seafood spot known for their cold lobster rolls and clam chowder. My husband went here earlier in the week and said it was delicious. You order at the counter and pay with cash, then find a table. It’s very highly rated and was recommended time and time again for classic Boston dishes.
• Barking Crab: I ate here during my last visit and it was recommended to me time and time again when going back this time. It has classic New England style food and is supposed to be amazing. They are supposed to have great lobster rolls, too and the seafood, particularly the crab, is as fresh as it comes.

I always have so many restaurants on my list for when I visit places, that I inevitably end up having so many leftovers for my next trip. So many restaurants, so little time. Below are all the places that I have on my list for our next visit!

• Coppa: this is a cozy Italian restaurant in the South end that has amazing reviews. I am 100% eating here next time I’m in Boston. The menu has a lot of small and mid-sized plates so that you can share a lot of items like tapas. I always love restaurants like that because I want to try so many different things. They are also supposed to have an amazing weekend brunch!
• Ostra: this is a more upscale, contemporary restaurant located in Boston’s Back Bay. They serve Mediterannean style, fresh seafood. were deciding between this and Select Oyster bar for our Saturday night dinner, and ultimately went with Select, but this is a must for me next time because I’ve heard so many great things!
• Yankee Lobster: this is a popular restaurant for classic New England seafood and was featured on the Food Network’s show, ‘Diners, Drive Ins, and Dives.’ It’s a cozy spot that will likely have a wait, but so many people say its absolutely worth it for their lobster rolls and fresh seafood!
• Tony’s Clam Shop: this is a seasonal restaurant with a big outdoor patio and water + Boston skyline views that is known for it’s fresh seafood and relaxed atmosphere.
• Terra: this restaurant is located on the third floor of Eataly and is supposed to be absolutely delicious, just like everything in Eataly is. We didn’t go here this time, but I definitely want to go next time I’m in Boston. I’m hoping hard that Dallas gets an Eataly one day, everything is seriously so darn good.
• Boston Sail Loft: this waterside restaurant has floor-to-ceiling windows with a view overlooking the water. They serve seafood staples and have a fun bar scene. This is a great place to get fresh seafood at a good price!
• Blackbird Donuts: this was recommended to me by a reader who lives in Boston. We didn’t make it here this time, but it’s definitely on my list for our next visit. Apparently the carrot raspberry and java berry donuts are to die for.

WHERE TO DRINK

• Drink: this is a speakeasy style bar without drink menus. You don’t need a password, but will likely wait to go in. You tell the bartenders what you like and they come up with custom cocktails for you. They have food + snacks inside if you need a late night snack, too.
• Alibi: located at The Liberty Hotel, this spot is a perfect post-dinner drink place that was recommended to me by one of you on Instagram. It used to be the ‘drunk tank’ for the Boston jail, so it’s dark and cozy inside. The walls are decorated with celebrity mug shots with info about their arrests and alleged ‘alibis’ from the nights they were arrested. We got a few espresso martinis and shared a tiramisu for dessert here on Saturday night after dinner. They also had a cool outdoor area, which would be really fun for warmer nights in the summer.
• Clink: this is another great cocktail spot at The Liberty Hotel featuring bars and cells from the Boston Jail. They supposedly have great food in addition to their fun nightlife atmosphere.
• Highball Lounge: this is a local favorite bar located on Tremont Street in Downtown Boston. They have craft cocktails and tons of games that you can play there while listening to their nightly DJs.
• Lucky’s Lounge: this is a Sinatra style lounge that had a line out the door one night when we went by. They serve up classic bar food and is said to be a local favorite for classic cocktails.

WHAT TO DO

• Red Sox game: you just have to go to Fenway if you’re in town during baseball season. Baseball fan or not, its iconic! I went to a game last time I was in town and my husband went to two earlier in the week before I arrived. I always think that baseball games are so fun and seeing Fenway is a definite bucket list item!
• Skywalk: this is towards the top of the Prudential Center building and provides 360 degee views of Boston. It’s a great way to go and get a sense of the city and see it from above. Tickets are $18/each for an adult.
• Top of the Hub: it was raining when we attempted to go to the Skywalk, so it wasn’t really worth it to see the view, so we came up to this lounge instead. It’s a restaurant and bar that gives you a similar view to the Skywalk, but you can eat and drink while you take it in. I’ve heard that the restaurant is actually really good, but as with many similar places, you’re also paying for the view!
• Brattle Book Shop: this is the cutest little used book shop that is half inside and half outside. They have a room on the third floor with really rare first edition books and it’s just a really cool stop if you find yourself out walking around Boston. My husband laughs that I am a book junkie, and I am, so I’m always down to explore a cute bookshop and see what I might find.
• Isabelle Stewart Gardner Museum: this is a beautiful museum with everything from a mansion courtyard you can see from tons of windows inside the museum, a book and gift shop inside, and a beautiful green house full of flowers. This was a perfect rainy day activity for us and the courtyard itself is worth the visit. It felt like being transported back in time or to somewhere else outside of Boston.
• Boston Public Library: oh, another place with books?! Yes. Even if you’re not planning to check any out, the inside of this library is stunning and totally worth a stop if you have time!
• Boston Public Garden & Boston Common: these parks are beautiful and are located in the midst of the city. I’d compare it to a feel of Central Park in NYC in that it’s in the middle of the city, but gives you this sense of escape from it. Even though the day we walked around here was pretty cool and raining on and off, it was packed.
• Beacon Hill: Just a short walk from the parks above, this is such a fun area to walk around. It’s full of tree lined streets with classic, historic Boston homes. I felt like every corner I turned was a picture perfect street or home.
• Acorn Street: when you’re in Beacon hill, make sure to go by and see this historic street. It is the oldest street in Boston or maybe even America? Its made up of like oversized pebbles and is really pretty. It’s no surprise that it is the most photographed street in Boston.
• Newbury Street: this is your place for shopping and great people watching. This street is full of amazing shops and boasts itself as Boston’s most enchanting street. There are so many cute cafes and restaurants, too.
• Freedom Trail: this is a two-and-a-half mile long trail that leads you through 16 historic sites important to the American Revolution as it began in Boston. I went through here the first time I visited Boston and I loved getting to see all the culture and history associated with each of the stops.
• Harvard Square: Walking around Cambridge is a must! Its so gorgeous and charming and seeing all the beautiful Harvard buildings is so cool. The campus is stunning and MIT’s campus nearby is also so cool to see. I had so much fun people watching here and guessing who is a student and potentially the next Zuckerburg versus who is just visiting and taking in the sites like we were.

If you’ve been to (or live in) Boston and have some recommendations that I might have missed, please let me know! I am always adding to my lists so I have more ideas for the next time I visit a city, so I’d love to know your favorites. I know this travel guide will help you all when visiting this fun city!!

In case you missed my other most recent travel guides, be sure to check out my Miami Travel Guide and my Santa Fe Travel Guide. I always like to save travel or city guides to my Pinterest boards about travel so I have them somewhere I can easily reference and search for them! You can see all of my travel posts here. I’ve been splitting up my travel posts into one with all of my recommendations and another recapping all of my outfits for you to shop in one place, so I’ll share my Boston Outfit Recap with you all later this week or next.

This is the last full week with kids at school before exams for me, so it’s a super busy week! I tried to work ahead as much as possible so I’d have a week full of posts for you all, but forgive me in advance if I’m short one or two. Travel always gives me a good outlook and makes me feel rejuvenated and ready to take on more challenges at home, so I’m glad I had a long, fun weekend before conquering the next few crazy weeks at work before my summer vacation. I hope that all of you had a wonderful weekend and that your weeks get off to a great start. XO

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As I mentioned, I’ll be sharing  a full recap of all outfits in the next week or so!

In the effort of full disclosure, I partnered with Royal Sonesta Boston to provide a review of my stay in exchange for our room and other complimentary amenities throughout the weekend. As always, all opinions are my own and I would never recommend something I do not truly love.