Boston, MA is a bustling city no mater what time you visit, but if you have the opportunity to visit in the fall, you’ll notice a slowing down of sorts that can be experienced all over the city. The air is cooler, the lines are shorter, and overall, it’s my favorite time to visit Boston! Today, I’m excited to share my ultimate Boston City Guide – fall edition. 

Where to Eat, Sleep, and Play In Boston, MA

Where to Sleep

Choosing a hotel when visiting any city is as important as the restaurant reservations you’ve got to make. A great city hotel has a variety of things, but my most important ones are: comfortable rooms, location, and great customer service (oh and accessibility to the airport if I’m flying out!). In Boston, the Sheraton Boston Hotel is the one hotel you need to book your stay with.

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Staying at the Sheraton Boston Hotel is seriously effortless travel, from the moment you arrive to the moment you depart. It’s central location to pretty much everything makes it easy to get around whether you’re walking or driving. The fact that the rooms are fantastic is also a plus – incredibly clean, with all the amenities I could need. A Starbucks in the lobby seals the deal for me, because when I’m too lazy to make my own hotel room coffee (they provide Pike Place by Starbucks), walking downstairs is a cinch.

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For those of you that work out while traveling (I commend you), there’s a fitness center. If you’re more like me and like to treat yourself, the Green Tangerine Spa & Salon is the ideal spot to get a quick manicure or a deep tissue massage. And after your massage, nothing better than walking over to the Prudential Shopping Center for some window shopping – it’s connected to the hotel via the 2nd floor.

P.S. If you book a Club Level room, you’ll have Club Level privileges and the best one is the Club Lounge. It’s a spot on the 29th floor that serves up a continental breakfast, fresh fruit and beverages to grab 24/7, and evening hors d’oeuvres. It’s worth it, I promise.

P.P.S. If you’re Catholic like me, the Prudential Center has a small chapel, St. Francis Chapel, which I attend mass at whenever I’m visiting. It’s good to take a moment to be thankful.

What to Eat

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Boston is a foodie city, no matter where you turn. Each neighborhood sprinkled with its own persona, you will find incredible food all around.

Start your day by heading to the North End, where we have challenged ourselves to find the best cannoli in town. The North End, or Little Italy, is a neighborhood of Italian shops, restaurants, and storefronts that if you haven’t been to Italy, will make you feel like you have. The cannoli competition is between three pastry shops: Mike’s, Modern, and Maria’s. It’s a war between them and everyone has their favorite, but after tasting them all, we realized Maria’s has them both beat! The shell was thin and crispy, the filling light, chilled, and just the perfect amount of sweetness. It’s a fun way of exploring the North End in Boston – by eating cannoli!

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If you’re looking for a more heartier option to start your day, Tatte Bakery & Cafe in Beacon Hill is a short 20 minute walk from the Sheraton Boston Hotel and the brisk walk will get your ready to devour whatever Tatte has to offer. Whether it’s one of their croissants or you’d rather sit down to enjoy some shakshuka or avocado toast, this spot in Beacon Hill is a must.

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By noon, if you’ve had three cannoli and a croissant from Tatte, you might be feeling the jitters and need something of substance. That’s when you head to Thirst Juice Co. and fuel yourself with one of their offerings. This fall, they’ve introduced a green juice called “Fall Apple”, made of coconut milk, spinach, green apple, banana, house made pumpkin spice blend, and dates. It’s seriously like the PSL’s fitness-driven, health conscious cousin!

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I promise, there’s also food in Boston, not just sweets and drinks! And one of those restaurants is Trade. Located on Atlantic Avenue (we normally take a quick Uber from the Sheraton Boston Hotel here), Trade has become a favorite of ours after a couple of visits. Jody Adam, James Beard award-winner, and the chef/owner of Rialto in Cambridge, is the Chef and Co-Owner of Trade, with Cory Seeker as her Chef de Cuisine. Trade is a restaurant you can come for lunch or dinner, cocktails or dessert. It’s laid-back and modern, approachable and playful. Most importantly, the food is outrageously good, always! I’ll be writing a full post on Trade and it’s incredible fall offerings, but know that if you’re there this fall, you MUST order the ice cream sandwiches – they’ll change your life.

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Where to Play

Boston is a playground for adults and children alike and granted, most of the travel advice I’ll ever give will be food-focused, there are other things to do in Boston other than eat. It’s quite historical, I hear. The Boston Tea Party, the Midnight Ride of Paul Revere, The Great Molasses Flood – it all happened in Boston. It’s also home to the best sports teams in America – The Boston Red Sox, The New England Patriots, and the Boston Bruins. Oh and the Celtics, but no on really cares about the Celtics, do they?

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But let’s get back to food, where I’m urging you to visit Faneuil Hall and Quincy Market. Faneuil Hall is a market building built in 1742 & the site of historic speeches by Samuel Adams & Frederick Douglas. But it’s also where you can stroll and shop and eat your way around! It’s also the spot where I became a citizen last September 2015.

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Another food favorite, close to Quincy Market is the Boston Public Market, a year round indoor market that seems all local produce, fish, treats, breads, and so much more. The place you must stop is Red Apple Farm – they are frying up the best apple cider donuts ever. Order half a dozen mini ones and you’ll come back for more! And don’t forget to grab a jar of their apple butter – slather it on your morning toast and you’re ready to go.

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In conclusion, Boston in the fall is fantastic. I hear there are some incredible foliage tours that are also happening in the area worth looking into this season. But leave me in the city, where cannoli are a couple minutes away and clam chowder is a given.

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Disclaimer: I have an ongoing collaboration with the Sheraton Boston Hotel and my accommodations were paid for. My love for Boston is 100% my own. 

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