Travel Guide: 3 Day Weekend In Boston

Hey Guys! I hope everyone is having a wonderful week so far! As you all know I went to Boston about two weeks ago and I wanted to share my three-day weekend itinerary with you guys. Boston feels likes a big city but with a small town charm feel. Here you will find amazing Italian food, quaint cobblestoned streets, delicious seafood, historical landmarks, and lets not forget good shopping.

Day 1


Tatte Bakery + Café: this quaint coffee shop offers breakfast, delicious pastries, and coffee. We went to the one located in Beacon Hill, where you’ll find cobblestone streets and some on the most gorgeous homes in Boston. I loved every street we went down.

Charles Street- here you’ll find cute boutiques, coffee shops, and restaurants.

Mike’s Pastry- Holy Cannoli!! The best cannoli I’ve ever tasted, I tried Pistachio but they have a ton of fillings to choose from. PS, their cookies and cheesecake are also worth every calorie.

Bodysuit: Here or Here /Denim Jacket: Madewell / Hat: Boston Baseball Cap

Boston Red Sox Game– You can’t come to Boston and not watch a baseball game. Plus, it’s the perfect excuse to eat a hot dog or pizza with an ice-cold beer. Make your way over to Bleacher Bar before of after the game, it’s a fun bar found behind the wall of the outfield.

Regina’s Pizza – the best authentic Italian pizza in the city!


Day 2

Freedom Trail- As one of the most historic cities in the United States, this 2.5- mile guided tour will take you through all the major sites and monuments.

Quincy Market– You can find just about anything to eat here, from Chinese food to Greek. When in Boston, try the lobster roll and clam chowder, I promise you won’t be disappointed

Green Dragon Tavern (oldest historic bar) / Bell In Hand Tavern (America’s oldest tavern)- both are on Marshall street in one of the oldest parts of Boston.


Day 3


Neptune Oysteria- Get there early because the wait time can be between 2-3 hours. The food here was delicious, the seafood was fresh, and the service was great.

Sunglasses: Ray Ban

Pier 6- Enjoy a drink while you take in the view. You can take a boat taxi from here to ReelHouse.

ReelHouse- You have to check out this waterfront restaurant! Here you’ll find great drinks, delicious food, and a gorgeous view of the skyline.

Envoy- This rooftop overlooks the Boston Harbor, the view is incredible and music.

Bova’s Bakery- Opened in 1932, you’ll find homemade cakes, cookies, bread, cannolis, and so much more.


Flour Bakery- two words, STICKY BUN!

Levi’s Shirt: Levi’s

Boston Public Library- This is the most beautiful library I’ve ever been in! We had tea at the Courtyard restaurant, the tea sandwiches are decedent, and the scones were to die for.


I hope this helps if your planning a trip to Boston soon! Xo, B!

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Hi, I would first like to welcome you to Windy Style! My name is Brenda, I am a lifestyle blogger born and raised in Chicago. Although I love my career as a Registered Nurse in the ICU, Windy Style was created with the everyday girl in mind. A place where I can share my endless passion and love for all things Fashion, Beauty, Fitness and Travel. Welcome to my world! I hope you find some inspiration and courage to try something new!

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