Looking for the best places to eat in and around Boston? I’ve got you covered in my two favorite categories: dinner and brunch! Whether you’re in the mood for a fresh brew or want a 5-course Italian meal, these spots have you covered.

Boston Dinner Dates

1 | Trattoria il Panino, Boston’s North End

The first place I tried octopus and now I’m hooked. Their food is absolutely delectable. We sat in the side room and loved the ambiance. It was perfect for our Valentine’s Day dinner. Not to mention it’s prime location right in the heart of Boston’s North End. If you’re looking for mouthwatering Italian, bold red wines, and unique dishes then this is the spot for you!

Menu Picks:

Baby Octopus Affocato
Tortelli Panna e Prosciutto
Polla allo Valdostana
Mom’s Quattro Carni Ragu

2 | Strip by Strega, Boston’s Back Bay

Strip by Strega has a beautiful dining setting with two full bars and ample amounts of seating. The wait staff was all very kind when we went in and very attentive. I recommend making a reservation if you’re planning on going on the weekend or for a holiday. We went on a dinner date and loved every part of our experience from the exciting raw bar to the incredible dishes! If you have a sweet tooth the desserts are at the top of my restaurant recommendations list (that creme brulee).

Menu Picks:

Tuna Tartare
Bolognese
Chilean Sea Bass
Bone-In Filet

3 | Tonno Restaurant, Gloucester

Anywhere that has a yummy tuna tartare is a win in my book. I have been obsessed with the dish since last year and get it at every restaurant with it on the menu (it’s not that easy to find). All of the fish and other ingredients seem very fresh! I’ve enjoyed the variety of plates we’ve tried on our visits. The location is perfect for taking a day and strolling in the summer time. We enjoyed our dining experience both at the bar and at one of their tables. It’s very cozy and relaxed.

Menu Picks:

Tonno TarTare
Spaghetti Fra Diavlo
Scallops “la plancha”
Grilled Tonno Steak

4 | Lucky’s Lounge, Boston Waterfront

Hello, Frank Sinatra! We went into Lucky’s Lounge for the first time in excitement for the Frank Sinatra cover. We thoroughly enjoyed the show and went back AGAIN with family members (4 of them). We had a blast! All of the appetizers we shared were top notch and the dinner dishes we tried certainly didn’t disappoint. If you love live entertainment and a really unique setting this is the place for you. After that modern speakeasy style, my SO and I can’t get enough of this place!

Menu Picks:

Tater Tot Poutine
Fried Buffalo Brussel Sprouts
Lucky Burger
Buffalo Tender Mac & Cheese

5 | L’andana, Burlington

One of my #1 spots for a romantic meal. You pretty much have to make a reservation and I definitely recommend dressing nice! This restaurant is always packed and for good reason… their food is amazing! I told my SO that I need to have some sort of function here because they have a gorgeous private room in back. The steak was one of the best I’ve ever had and the other menu items weren’t far off. The dishes are what I would consider ‘different’ from other restaurants because they seem more high-end. A definite “must” if you’re celebrating a special occasion (or looking to pop the question).

Menu Picks:

Crisp Chicken Milanese
Swordfish
Tuscan Steak
Lamb Osso Bucco

Boston Brunch, Cafes & Diners

1 | Gaslight, Lynnfield & Boston

Gaslight is one of those spots that you want to return to again and again. I’ve never had the dinner there. Brunch? Phenomenal. My friend and I stop in here before we go shopping for the day and it’s so satisfying. Their portions are always exactly the right size and they have a very unique menu. The way the menu is set up for brunch is really helpful and, for the quality of food you get, the prices are where I would expect them to be. Gaslight is a definite YES for brunch! I can’t wait to try their lunch and dinner.

Menu Picks:

Prix Fixe – The Cinnamon Bun
Eggs Benedict
Rigatoni Bolognese
Smoked Salmon Toast

2 | Sugar Magnolias, Gloucester

I love taking a trip into to the Gloucester/Rockport area. It’s always a day well spent and fun for anyone traveling to or living in the area. Sugar Magnolia’s is the perfect choice for a tasty brunch (my favorite meal)! The hollandaise had just the right amount of flavor and the eggs were cooked perfect. I added bacon and eggs on and had a piping hot cup o’ joe. Service was fast and friendly! I managed to get our right around 10 and got the day going on a positive note.

Menu Picks:

Crab Cakes & Eggs
56 Hilltop
The Breakwater Omellette
Carrot Cake Pancakes

3 | Stephanie’s on Newbury, Boston

Stephanie’s On Newbury is one of my favorite brunch and lunch spots in Boston. Right on Newbury Street, you can grab a bite and spend the entire day without leaving the area. We had heard good things and were happy to not be disappointed. Our waitress was very friendly and checked on us the perfect amount of times during our meal. Sitting on the outdoor patio was a plus on the gorgeous day we had. This is a great spot to check out after a day of shopping in town. It is very relaxing and has good menu options.

Menu Picks:

Cinnamon Monkey Bread
Skillet Breakfast
Pecan Crusted Warm Goat Cheese Salad
Carnitas Scramble

4 | Caffe Nero, Boston

I love all of the Caffe Nero locations. They always have the perfect decor that makes you feel right at home. With books scattered around and that library feel, I could get blogs written and work done for hours without noticing the time go by. My favorite part, by far, is the atmosphere. Everyone seems to be genuinely relaxed, happy, and focused when they come to mingle or get work done. The lattes are spot on and the food is very appetizing. You may even make some new friends!

Menu Picks:

Espresso Con Panna
Cortado
Ham & Cheese Croissant
Prosciutto & Mascarpone Baguette

5 | Cibo Cafe and Bistro, Wakefield

The breakfast sandwiches are delicious. You can tell from the first bite that the egg and other ingredients were fresh. It didn’t fall apart when you bit into it or make a mess (which was perfect since I was on the road). They also have a drive through if you’re passing by but I recommend spending some time inside. The coffee is good and the atmosphere inside is delightful. My sandwich was worth 5 Stars on it’s own.

Menu Picks: