Boston Recap – Travel Diary

Last weekend, my fiance and I heading to Boston to spend a long weekend exploring the city. We met up with my brother and his girlfriend for an absolutely fantastic weekend. 


As soon as my plane landed, my fiance met me inside the airport. Whenever he picks me up at an airport, he always parks in a short-term parking lot and meets me inside, isn’t that adorable! Its just one of those little things that I love about him. Ok, enough mushy stuff onto the topic at hand, my Boston Recap. Armed with an iced coffee in-hand we headed off to our first afternoon exploring Boston. 

I’ll be breaking down the must-haves based on the neighborhood. Boston is distinguished by its many vibrant neighborhoods each with its own personality. 

First up, the North End aka Boston’s Little Italy. 

Boston’s North End – quaint neighborhood loaded with cafes, pastry shops, and tons of italian restaurants.


Neptune Oyster – Small, adorable seafood restaurant. Start of with a bottle of white wine, it pairs perfectly with the assortment of seafood options below.
What to Order:
Clam Chowder – This ranks as the best clam chowder i’ve had. 
A variety of oysters – This was my first time trying oysters and I did not hate them nor did I love them. I’m glad I tried them but will not be ordering them often (if ever again). 
Hot Lobster Roll – Stuffed with lobster smothered in warm, melted butter. One word: DIVINE.


Modern Pastry – Bakery known for their cannolis. Not as amazing as Mike’s but still a good cannoli. We got ours to-go and headed to the water to enjoy our pastries while relaxing on a bench overlooking the water.

Mike’s Pastry – Mike’s is a bakery that is well-known for their delicious cannolis. I tried the chocolate chip and the Amaretto and both were fantastic. Both cannolli’s are the best cannolis i’ve ever eaten!


the East End – another quaint neighborhood with tons of red brick brownstones, restaurants, and bars.

South End Buttery – I had one of the best gourmet breakfast sandwiches and home fries of my life at the South End Buttery. That is saying something since a good breakfast sandwich is my jam! The interior is bright with brick walls and dog portraits lining the walls. 

Historic District – another quaint neighborhood with tons of red brick brownstones, restaurants, and bars.

Faneuli Hall – great spot to do some shopping and grab some food.

Public Market – Go here hungry as everything is produced local. It all smells fantastic and looks even better. 

Harbourside – an up-and-coming neighborhood with  restaurants, breweries, and new condo buildings.

Harpoon Brewery –  Go, take the tour, and stay for the afternoon. One of the stops on the tour is their tasting room where you are given about 10 minutes to test as many samples as you like. It was a great way to try out Harpoon beers. My favorites are below. After the tour, we headed out to their main bar area with long, wooden tables and large windows. We brought Cards Against Humanity with us and stayed for a few rounds of Harpoon Beer.


Legal Harborside – Go for the view, stay for the drinks. Legal Harbourside is a beautiful restaurant with three floors of beautiful decor each with its own food niche. They have a great rooftop bar with to-die-for views.


Beacon Hill – Ridiculously quaint neighborhood with tons of red brick brownstones, trees, and bars. Go and just wonder through the streets. 

Things to Do: 


Urban Adventours Bike Tour – We went on the 10AM Boston Tour and had a fantastic time. I couldn’t recommend this tour more. Our tour was an 11 mile tour with various stops to soak in some history of the area. We started in the North End, headed to Cambridge, the financial district, the East End, the Historic District, Fenway, Harbourside, and then back to the North End. The trip was a great introduction to Boston while getting your history fix.

I just loved wondering the streets of the North End, the South End, and Beacon Hill. We stopped along the way whenever something caught our eye. Irish pubs, antique stores, hole-in-the-wall places, the Nespresso store. Boston is such a great walkable city, you can find the best places just walking.


What are your favorite places in Boston?