2 Days in Boston: A weekend Guide

After spending a week traveling through the Northeast on a work trip, my itinerary ended in Boston. Having never visited the city, I had my husband fly up to meet me for a quick, jam-packed 2-day weekend. Boston is historic and charming, yet effortlessly cool. It is the perfect place for a girl’s weekend or a couple’s getaway. Here’s exactly how to spend 2 days in Boston without feeling rushed.

Day 1: Waterfront & Boston Tea

I arrived mid-morning to the Intercontinental Boston. I wanted a hotel centrally located to the waterfront. I booked the hotel through American Express travel and was able to get a room upgrade, early check-in in and a $100 credit to be used at the hotel. I was waiting for my husband to arrive and decided to head out and explore. My first stop…lobster roll for lunch.

  • James Hook & Co (waterfront)- This was a great stop for lunch and a literal 2-minute walk from the hotel. They have an indoor area and a food truck outside for ordering. I ordered a warm lobster roll and clam chowder. It was $$$ but worth it. The food was fresh and it was a great way to try a Boston classic.

Once my husband arrived, we headed out for our tour at the Boston Tea Party Museum

  • Boston Tea Party Museum- Another short 5-minute walk to the museum, and we checked in at the front. Tickets were $35 and I made reservations online. This was an interactive and fun show! I think it is a must-do when visiting Boston. You learned the history of the Boston Tea Party through a skit, and I even got to throw tea in the Boston Harbor!….. Huzzah!

We ended the night with dinner at 75 Chestnut and a walk around Beacon Hill.

Boston Harbor

Day 2: Historic Boston & Freedom Trail

The Freedom Trail was a must-see on my list of things in Boston. After room service for breakfast (courtesy of our $100 credit), we headed off to the Hop-on-Hop-Off Trolley that was going to act as our Uber for the day.

  • Old Town Trolley Tours- I reserved this excursion about a week before our trip. I knew we wanted to see a lot of the city, and we only had one full day. I researched the stops I knew we wanted to visit beforehand and mapped them out on the Old Town Trolley Tours. The key to a short vacation is having a plan! This allowed us to know exactly where we were going to stop and took out the guesswork.

Must-see stops:

  • Faneuil Hall - We started here. It was a 10-minute walk from the hotel

  • Historic North End - Stop here to see Paul Revere’s House (additional cost of $6)

    • Tons of great places for lunch in the North End

  • Old church North- Famous Paul Revere Church

  • Cheers Bar- Drive past. No need to go inside

  • Boston Commons- The George Washington statue

  • Copley Square/Trinity Church

Boston Commons


Later in the day, we left the Old Town Trolley and headed to Fenway Park. My husband is a huge baseball fan, and I indulged him in a walk around the outside stadium. There was a Yankees vs. Red Sox game going on, and the area was packed! We grabbed a drink at the bar and watched the game!

Dinner had us back in the North End at Bricco. The North End is extremely busy at night, and you must have reservations! Bricco is an Italian restaurant with amazing espresso martinis! I had to have two since one wasn’t enough!

We then ended the night on a Cannoli hunt. The North end has three cannoli legends…Mikes, Modern Pastry, & Bovas. There are many opinions on who has the best cannoli. We waited in the long line at Modern Pastry only to find out that I forgot my cash back at the hotel, and they do not take credit cards! We headed to Bovas, and it was much more my vibe. It is off the busy street, smaller, and has a traditional Italian vibe. It felt way less touristy. I got a traditional, pistachio, and chocolate chip!

Two days in Boston is just enough time to walk through history, eat lobster rolls, and debate the best cannoli in the North End. Huzzah to a perfectly planned weekend!

Links:

Intercontinental Boston- Boston Luxury Waterfront Hotel | InterContinental Boston

Old Town Trolley Tours- Hop On Hop Off Boston Tours with Old Town Trolley

Boston Tea Party Museum- Boston Tea Party Ships & Museum | #1 Best Patriotic Attraction

75 Chestnut- Home | 75 Chestnut in Boston, MA

Bricco- Gourmet Italian Cuisine and Cocktails in Boston, MA - Bricco Ristorante & Enoteca

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