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Have Yourself a Day

One rooftop bar and brunch recommendation at a time

  • Writer's pictureJenna Kline

Have Yourself a Day in Boston

Updated: Sep 3, 2019

Boston, Massachusetts — a city filled with beautiful greenery, the proudest sports fans, a rich history and even richer cannolis.


Boston, MA

Brunch


North Street Grille

The North Street Grille is a staple among Boston locals. All I can say is come hungry because the portion sizes are huge and the options are extensive. If the long line doesn’t clue you in to how sought after this brunch experience is, then maybe the menu items might.


When you’re first seated, your table is brought over a warm loaf of banana bread sliced for the table. If you can’t get enough of this melt-in-your-mouth appetizer, I’d recommend ordering the banana bread french toast. The menu item is the same banana bread but also dipped in french toast batter. This dish is legitimately dessert for breakfast, so this meal should only be for those with an insane sweet tooth — and for those wearing very loose clothing.


I ordered an egg plate with homemade corned beef hash, which was both flavorful and delicious. The dish also comes with crispy homefries and toast. A dish that is next on my list to try at North Street Grille is the Chicken and Waffle Sliders, which includes cheddar, bacon, sriracha maple syrup and home fries.


Another popular dish is the restaurant's Boston Cream Pie pancakes, which are made with Bavarian cream and chocolate ganache. The restaurant's Instagram is filled with photos of this dessert-for-breakfast. Keep in mind, the ingredients and portions are not for the faint-of-heart or health nuts — but when in Boston, am I right?


Tatte Bakery

Tatte Bakery and Cafe

If your stomach hurts from just reading those menu items, I’d recommend going to Tatte Bakery and Cafe for brunch, which is my absolute favorite. There are a few locations around Boston, and you can’t go wrong with any establishment. The Tatte cafes have a bright and airy aesthetic, which includes a beautiful pastry window, a coffee bar and patterned floors (which makes for a great overhead shots of your brunch table).


The founder of Tatte grew up in Israel, and in doing so, many of the food and pastry offerings have a Mediterranean flair. The food menu items are freshly homemade every day, and you can truly tell in every bite you take.


Tatte offers an assortment of breakfast, tartines, shakshuka, sandwiches, salads, soups and bowls. With three types of shakshuka dishes to choose from, I opted for the traditional shakshuka, which is a North African dish of eggs poached in a tomato sauce with chili, bell peppers and onions spiced with cumin and topped with feta and parsley. This dish is served with a side of their homemade challah bread. The spices and flavors combination could not have been any more delectable. 


I’ve also had their prosciutto and fig panini for lunch, which consists of fig jam, melted brie, fontina cheese, prosciutto and sliced Bosc pear on homemade ciabatta. If this doesn’t scream “perfect summer sandwich,” I don’t know what does. Oh, and it was absolutely delicious!


Tatte’s pastries are almost too pretty to eat. Between breakfast pastries like croissants, puff pastries, roses and tea cakes, and desserts like cakes, tarts and galettes, Tatte’s pastry game is on another level. This spot is known for their high-quality ingredients combined with their bold flavor combinations and textures.


The Broadway

Hair of the dog is all I can say! If you’re looking for a boozy brunch that not only cures a hangover while providing enough substance to carry you over for the day ahead, The Broadway should be your spot. 


Their brunch menu items truly fit their “brunch so hard” motto. Whether it’s one of their breakfast sandwiches, a wood fired brunch pizza, a loaded burger or a veggie bowl (for those with major willpower), The Broadway is the move when alcohol is involved in the weekend plan.


The restaurant offers three types of punch bowls for a minimum of four people. The Broadway even has a Coffee and Donuts cocktail that is made of Jameson, Bailey’s, cold brew, simple syrup, milk and a daily donut skewer. With food and drinks so over-the-top, come ready to ready to party at The Broadway.


American Provisions

Perhaps underrated but worth its own post, American Provisions is a great stop for lunch if you’re living on the South Side. This no frills sandwich shop is everything you would want in a local neighborhood shop, from their hand-selected artisan cheeses and cured meats to their wine and craft beer selection. I opted for “The Pear ‘wich,” which is made of fig jam, brie, sliced pear and arugula on a ficelle, and I added prosciutto. Their fresh bread with everything seeds was soft and savory, and you could taste the quality of the ingredients in every bite. 


American Provisions also has a coffee bar, and they carry Oatly milk (which is tougher to come across in Boston than in NYC.) For those Bostonians who are reading this and have not been as exposed to this beautiful creation as many of us (which seems to be the case), head to this spot and order yourself a cold brew coffee with oat milk. Oh, and you are welcome.


 

Thinking Cup

Coffee


Thinking Cup

Having a go-to local coffee shop is necessary in any city, and in the city of Boston, Thinking Cup is one of the clear winners. With locations in Boston Common, North End and Back Bay, Thinking Cup is a widely popular coffee shop, serving the finest coffees, teas and freshly baked pastries.


With a cozy and welcoming ambience and really knowledgeable baristas, this coffee shop should definitely be a stop on your Boston visit. 



Cuppa Coffee

Cuppa Coffee

Apparently I cannot stay away from Australian cafes…


Cuppa Coffee is a lesser known coffee shop in Boston but a hidden gem, nonetheless. This Australian cafe offers an extensive range of coffees and teas, a variety of breakfast options as well as traditional Aussie food and treats. The espresso bar prides themselves on serving some of the best quality drinks accompanied by the best possible service.


Even though I opted for a cold brew with oat milk, I’ll be arriving much hungrier during my next visit. I'm looking forward to trying Cuppa Coffee's authentic Australian bites, which includes everything from The Great Aussie Pie to Tim Tams, to Lamingtons to ANZAC Cookies.



 

Activities

There are a ton of options for a daytime outing in Boston. With so much history and beautiful greenery in a compact city, I’d recommend exploring Boston by foot and hitting up all the major sites. 


Boston Public Market

For the foodies, head to Boston Public Market for a year-round, indoor marketplace with 35 New England-based vendors. The market is a bright, open, warm space that offers a variety of food and treats, including produce, fish, meat, gourmet snacks, vegan-specific dishes and more, which will satisfy all types of visitors. 


Boston Public Garden

Boston Public Garden

Another important stop during your afternoon exploring the city is the Boston Public Garden. Besides the fact that this is the first public botanical garden in America #history, it’s a large park situated right in the heart of Boston. It’s beautiful to visit and explore the Boston Public Garden in its beauty, especially during the changing seasons.


Newbury Street

For those who are more than fine pushing their suitcase weight to the limit, I’d recommend shopping in Newbury Street in the Back Bay area of Boston. Newbury Street is eight blocks filled with salons, boutiques and restaurants, making for the perfect rainy day activity.


Fenway Park

Fenway Park

To the sports fans out there, take time to explore Fenway Park. There are formal tours that are available for the die hard Red Sox fans, or you can also just explore the stadium on your own.


If you visit while in-season, I’d recommend going to a game. Besides being able to experience first-hand how many people actually enjoy baseball as a sport, you can get a chancet to wear cute Red Sox gear and snack on stadium food because #sportz.



Boston Public Library

Copley Square

To take in the history and charm of Boston, I’d recommend exploring Copley Square. Check out the Fairmont Copley Plaza, which is not only a luxurious and stunning hotel with over 100 years of history, but it is also the site of the “Tipton Hotel” in The Suite Life of Zack and Cody (priorities, am I right?).


Boston Public Library is also located within Copley Square, which was established in the mid-1800s. While there, check out Bates Hall to experience the iconic “reading room,” the courtyard for a stunning fountain and garden, and the Grand Staircase for its striking art and sculptures.


Another stop within Copley Square is Trinity Church, which was founded in the early 1700s, is an architecture-lover’s dream and is a must-see for visitors.


The Greenway

Walk along The Greenway to experience the meadows and gardens, which display unique water fountains, food trucks and a carousel. There are multiple sections within the park that are just so fun to roam and explore, so I’d recommend walking along The Greenway on a nice day. 


SoWa Open Market

On Sundays from May to October, head over to SoWa Open Market for Boston’s largest gathering of food, art and music. Over 175 vendors set up tents to offer unique crafts, jewelry, beverages, food and art, encouraging Bostonians and visitors to shop local. The best way to start a Sunday morning is with fresh air and sampling some of the best local food and drinks, while taking home some of the most unique treats from the New England area.


Drinks

The Barking Crab

The Barking Crab

For those looking for a day drinking spot, The Barking Crab is the move. Situated on the waterfront overlooking the Boston Harbor, The Barking Crab is a lively seafood joint that is the best weekend spot to drink with friends. Order pitchers of the Tea Party, which is a mix of Deep Eddy’s Peach Vodka, lemonade and iced tea — it's worth the sugar rush.


Trillium

Since I can’t explore a city without checking out a local brewery, I visited Trillium Brewing Company at their Fort Point location. The first floor is a taproom, the second floor is the dining area, and the third floor is the sought after roof terrace. Trillium is a great spot to catch up with friends, take in some nice weather and enjoy locally brewed beer.


 

Trattoria II Panino

Dinner


Trattoria Il Panino

You can’t travel to Boston without going to the North End and grabbing some delicious, authentic Italian food. With a romantic, intimate setting and both indoor and outdoor seating, Trattoria II Panino is perfect for any occasion.


I ordered the Gnocchi alla Sorrentina, which was some of the best quality homemade gnocchi I’ve ever had. Pairing one of their homemade pasta dishes with a glass of wine along with their cozy yet not-too-fancy setting truly makes for a perfect dinner experience. I'd highly recommend this spot for anyone visiting Boston, who is looking for an authentic Italian experience.


 

Desserts


J.P. Licks

If you’re in the mood for straight-up good quality ice cream, head to J.P. Licks. Committing to serving the local Boston neighborhood, the founders not only serve solely Kosher ice cream but they also offer a variety of flavors that specifically represent its many customers. For the non-dairy seekers who want to get in on the dessert fun of Boston, this shop offers a handful of non dairy options, where the smooth and flavorful non-dairy chocolate coconut was my favorite.


Mike's Pastry

Mike’s Pastry

If it’s your first time in Boston, heading to Mike’s Pastry is a must. Located in the North End, you can see people walking around the city carrying around Mike's Pastry's signature box with blue font with a string bow, showing off their treasured cannolis that they've definitely traveled to Boston for. I had the chocolate chip cannoli that definitely lived up to the pastry hype.


This shop is tradition for Bostonians and visitors alike. It's worth hitting up, even if it is a major tourist trap. I mean, it's popular for a reason!


The Cookie Monstah

The Cookie Monstah

This Boston-based food truck can be seen posted up all throughout Boston offering their “fresh batch, from scratch” cookies. Crafted from Callebaut chocolate, bourbon vanilla, and farm fresh butter, these cookies from The Cookie Monstah are crunchy on the outside and warm and gooey on the inside, making for the perfect, melt-in-your-mouth cookies.


I had the classic chocolate chunk cookie, but most people come for their famous ice cream sandwiches. Some of the most popular flavor combinations include “The Salty Dog,” which is comprised of salted caramel cookies and totally Turtle ice cream, and “The Peanut Butter Cup,” comprised of creamy peanut butter cookies and chocolate ice cream.


Bova’s Bakery

Bova’s Bakery, which is also in the North End, is my favorite cannoli spot. Their cannolis are made from scratch and filled with their homemade ricotta cream in multiple flavors. I ordered the chocolate chip cannoli, and the cannoli cream was just perfection.


This spot is famous for more than just its high-quality cannolis. In fact, the establishment was voted best tiramisu in the country, which I need to go back to try.

 

Hope this helps you plan your day in Boston. Feel free to send me recommendations on other spots to check out in the city!

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Feel free to leave me a message with any questions, comments, or suggestions for me to check out! Cannot wait to hear how you would plan a day in NYC.

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