Exploring Boston: An In-Depth Tour with your Favorite Local

I love Boston. We all know I'm one of the most iconic locals here, and I love getting to share that with others. Going on almost 6 years living here, it's the best city on earth. Sorry NYC! And there's nothing I love more than hosting, so I wanted to share my favorite spots in Bean Town! I spent a weekend recently introducing it to one of my sister’s friends who just moved here, and it's always special for me to show it to others. After years of bringing my friends and family to my favorite spots, I’ve mastered out how to efficiently show my top places. I've perfected the best spots to hit in a time crunch of 1-2 days, despite the ability to make a Boston tour weeks long. Come along for the ride as I give you the 411 on my top things to see.

Beacon Hill: Tuxedos and Paul Revere

I usually begin in Beacon Hill as it’s my favorite place to shop, find makeup, get coffee, or grab a book. OR antique—if you’re into that. Personally, I’d rather eat glue than stare at an ancient dish, but to each their own. I always go to Credo Beauty right on the main strip- it has my favorite makeup brands, and the employees are super nice and helpful. (Read: they turn a blind eye when Charty tests out the expensive makeup on her entire face)

I then stop by Beacon Hill Books and Café, but only if the line isn’t out the door with tourists. It’s a beautiful bookstore and café, but not a huge place so make sure to plan when people won’t be on top of you. Covet thrift store is down the street a bit, and it has the best trendy clothes. They have upscale bags, jewelry, shoes (if you have a tiny, cute foot), so many jeans, tops, etc. They also have a location in the South End as well. It’s always a must when I’m down there! East Coast Ivy is my next shopping destination. The owner, Greta, has created the prettiest, girly boutique, with each piece being so unique. If you like to antique, Upstairs Downstairs Antiques is one of my mom’s favorites. I seriously think they know her by name! If you’re hungry or need a quick glass of wine- Figs is a great pizza place in the mix of all the shops. Tatte Bakery is also a few steps away for coffee or a treat. And before you leave Beacon Hill, make sure you check out Acorn Street for all your Instagram needs!

Back Bay: The Athletic, Beautiful People

I always walk back through the Public Garden to Newbury to finish off the shopping after Beacon Hill. I don’t love shopping in person, however there are so many cool places to pop into on Newbury. Between Nike, H&M, Glossier, Mejuri, etc you can’t go wrong. Just avoid Zara as it’s like the traveling circus every time I step a toe in there! Saltie Girl is always a delicious place to stop for oysters or a drink, and EVA is one of my newer fave restaurants. If you're a sushi person, Zuma is the best sushi in the world.

But, if you loop back around to Boylston Street, you’ll find a million bars and restaurants along with the Prudential Center. The Pru has great shopping, the VIEW 360-degree observation deck on top, as well as restaurants. Eataly is a classic, as is Back Bay Social for drinks! (I fell down their stairs once from being overserved) Earls in the Pru is amazing for cocktails on their rooftop or sushi inside in their cool lounges. If you meet Emily the hostess there, she is the best. She saved me from my 35-year-old hinge date who wore basketball shorts and slides. Uh yeah, I'll take a vodka on the rocks miss!

The North End/Government Center/Theater District

The North End is always the place to be for a great Italian dinner out or espresso martini. The pastries, pasta, wine, bartenders, and pastries are to die for. Get your cannoli at either Mikes or Modern Pastry, I’m a lover of both! Then, please finish your night off at Café Vittoria for the best espresso martini in the city. Lucca is my all-time favorite North End bar between the fun bartender, cocktails, and atmosphere (write in the bar book if you’re asked!). You really cannot go wrong with any restaurant for dinner, but for weekend brunch you must go to Strega. You’ll be twerking on the table to Ludacris with shots in no time. If you’re an oyster person, wait in line for Neptune Oyster. They’re a very tiny restaurant, with no reservations, but have the best oysters in the city. Mare is also good and very vibey. If you're a cigar person, Stanza Dei Sigari is a fun place to have a few. But be warned- the smell of smoke will linger on your clothes for at least 20 years.

The New England Aquarium is a perfect attraction for all ages—it doesn’t feel too touristy and is really cool whether you're 7 years old or on life support. It’s beautiful and the penguins are so cute. When you're at the aquarium, you’ll be down by the North End and Government Center. If you’re near the Boston Sail Loft- go! While the outside looks tiny, they have the best chowder in the city.

Government center is fun if you’re trying to go to Faneuil Hall, Margaritaville (personal fave), or be the annoying tourist. No offense of course. You can stop into the Paul Revere House if you're into history or the State buildings. Government Center has a strip of bars for the college kids too (remember my prime!) which include Hennesy’s, White Bull Tavern, Bell in Hand, etc. Moving downtown, Yvonne’s is a delicious place for dinner and cocktails, or a girl's night. And, if you go more toward Emerson and the Theater District, Carrie Nation Cocktail Club and Roxanne’s are amazing cocktail bars too. If you're a theater girly, there are always good off-Broadway shows playing in the theater district. I love catching a show with the touring groups off Broadway. (Make sure you get the canned wine or frozen rose to enhance your night!)

Fenway: Sports and Beer!

Fenway is a cool little place that I often only frequent in the summer for Red Sox Games or concerts. Am I a sports girl? No! But I do like a beer and a glizzy #gobbler. They have a lot of hidden treasures there... Offices, fitness studios, colleges, and more. Loretta's Last Call (for my country fans), Cask 'N Flagon, Bleachers, and the Bullpen are just a few of the iconic divey bars in that area. Grab a drink or 7 after a game and dance the night away baby!

Great restaurants and bars, and if you go deeper into the Fens, you'll find where all the museums are located. If you're interested, you can head over and find the Museum of Fine Arts- Boston or the Isabella Stewart Gardner Museum. I don't go crazy over old artifacts in a building; however, the Boston museums are must-sees. They're so cool and have great stories behind them.

Seaport: Can you drop $6k monthly on rent?

If you find yourself wandering over to Seaport…well good luck Charlie! No, but Seaport has a few great places, including Pink Taco for Mexican food, YOTEL Rooftop and Deck 12, and Ocean Prime just to name a few. The Nautilus Pier 4 is a fun little place for oysters and wine if you can get in. If you’re wanting good tequila and Mexican food, Lolita’s is the best. They also have a location in Back Bay that's much more vibey! Seaport is fun with Cisco Brewers in the summer and a ton of pop-up shops for unique gifts. If you’re into night clubs, The Grand and Scorpion Bar are fun! (Me having been once because I am a dive bar girl). I'm a Lucky's Bar girl, which is the basement bar in Seaport. If you're cultured, there is an amazing French Restaurant called Coquette. It's amazing and a must try! There are some cute scenery moments in Seaport too, like the Harborwalk or a sunset cruise in the summer.

The South End: Are you Artsy?

This brings us to the South End which is such a cute little treasure of Boss town. I admit I forget about it most times, but whenever I’m there it’s always so cute, artsy, and lively. Barcelona Wine Bar (also one in Brookline) is always delicious for Tapas and wine. Beehive for drinks, food, or a show is an amazing place too! SRV, Five Horses Tavern, or Shybird are classics of the South end for dinners too. Citrus and Salt for Mexican as well, make sure you don’t forget about this hidden treasure! And check out so many of the artsy happenings in the South End.

Southie: Do you party every night?

This brings us to Southie. Yeaaahhhh that part of Boston! With the beaches, college kids, hot guys, dogs, and bars. Now I’m low key scared of Southie, but one of my besties (Erin Gibbons-love you!) lives there so sometimes I stumble down to that part. Castle Island is such a beautiful walk, as are most of the streets/neighborhoods there. The easy beach access as well as young vibe of it is, I admit, a lot of fun. The bars are always hopping and exciting, especially Capo, Lincoln, Loco, and the Broadway. These bars are like hot tub time machines, meaning once you go in there's no telling when you'll return. Plus, it’s where all the beautiful people (men) are.

Boston Beaches: Summer Lovin'

One of my favorite things about Beantown is the accessibility of the city. It's so easy to drive up to Vermont to ski in the winter or go to the beach in the summer.

That being said, the Boston beaches are the way to go in the summer. I pack my cooler of booze and snacks, my book, and rip it up. I love going to Carson Beach, or to Winthrop, or Revere just to name a few. Pack your seltzers and sandwiches, and rot on the beach all day. Such a dream! If you go up to Gloucester beaches, make sure you buy a parking pass ahead of time.

Brighton/Brookline: Charty's Big Adventure

Finally, if you go back to my part of the city, Brighton and Brookline, I have a few personal beloveds. The Chestnut Hill and Brookline reservoirs are my safe havens. I love reading or walking at them. You can catch concerts easily at the Brighton Music Hall or Roadrunner as well. Obviously, Bar Cino is on my list as a fun post work drink or dinner spot. Cityside in Brighton is absolutely fire, despite being full of BC college kids most nights. Makes me feel young! Their brunch or dinners are so good. Café Landwer is also so special to me, because it was the first place my mom and I went when I moved to Boston! Their array of food and drink are to die for. If you’re into dive bars, The Last Drop in Brighton is the dirtiest, best place to rip it up. And if you meet Andrew the bouncer, name drop me! He is my bestie and is harboring a crush on me.

Whew. These are just a few of my favorites when I have family and friends visit me. There are so many different options and fun places to go, but you'll have to find a few favorites that you love. Whether you're a history nerd, outdoorsy person, etc. your favorites will definitely be different. I am so lucky to live in such an amazing city--I think about this all the time. It's just the most doable, clean, fun, and safe place. Boston is obviously tinier than other major cities, but there are so many hidden treasures. Make it your own!

Happy hunting!

-Charty