Boston Travel Guide PT. 2 – Things To Do

June 18, 2018

– Boston Public Garden: You can walk through it pretty quickly, but it’s so beautiful and leads you to either Beacon Hill (one of my favorite neighborhoods of Boston – filled with brownstones and cute shops) and then it goes to Newbury St. which has endless shopping!

Beacon Hill: Walk around the quaint, lovely streets of Beacon Hill filled with historic brownstones and many shops/restaurants on Charles St. This is a must in my opinion!

Copley Square: I love visiting the Farmers market (every Tuesday and Friday). The Trinity Church (circa 1734) sits next to the tallest building in Boston – John Hancock Building. It’s really neat to see old and new architecture so close in proximity. Look for the reflection of the Trinity Church in the Hancock Building. Don’t forget to stop by the Boston Public Library!

The Boston Public Library: Right across from The Trinity Church and there’s free admission! Walk up the main stairs to see Bates Hall (great photo opp) and the Courtyard is stunning. This is the first free publicly supported municipal library in the US.

Newbury Street: The best shopping in Boston! It’s like a mini Fifth Ave. in NYC. It runs from the Boston Public Garden to Brookline Ave and is filled with shops/restaurants. I’d recommend doing Copley Square, Boston Public Library, Newbury St. all the same day because it’s all so close.

– My favorite drive is from Cambridge along the Charles River to Boston…if you are able to do this, I highly recommend it. It’s a beautiful view of Boston!

Charles River Esplanade: You can rent a canoe/kayak and enjoy city views along the water or take a riverboat tour! Or, if you’d prefer to be on land…walking/riding your bike along the Charles River is wonderful. Don’t forget to look for the MIT dome and the infamous Citgo sign near Fenway.

Fenway: Definitely recommend going to see the Boston Red Sox play at Fenway! You can also set up a tour of the baseball park.

Boston Public Market: a year-round market with lots of locally-sourced food options! You can take cooking classes as well. We love grabbing lunch and then heading to The Greenway to have a picnic. The market is also really close to The North End and Faneuil Hall if you wanted to check out those neighborhoods as well.

Eataly: an Italian marketplace and restaurants in the Prudential Center.

SoWa Market: Every Sunday, May through October 10am-4pm in the South End. The SoWa market is a farmers market, beer garden, food truck and art market! I love coming here with my family!

Boston Harbor Cruises Whale Watch: This is a great activity for anyone and everyone! Cody and I had a blast when we went and we were so close to the whales.

Harvard: You can walk around the beautiful campus (I think it makes you smarter just by being on campus) and then a few restaurants in the Harvard Square area I love: Little Donkey, Alden & Harlow, The Friendly Toast, Juliet

Arnold Arboretum of Harvard University: located in Jamaica Plain and Roslindale. It’s perfect for a picnic or grabbing a coffee and taking a walk/run. The Arnold Arboretum was designed by Frederick Olmstead, the same Landscape Architect who designed Central Park in NYC.

Spectacle Island: Rent a boat or take a water taxi to this island in the harbor. There are walking trails, areas for picnics, a lifeguarded swimming beach, and cafe.

Granite Links Driving Range: my favorite date night activity! There are amazing city views and a fun restaurant right by the driving range. Highly recommend!


Isabella Stewart Gardner Musem is SO beautiful. Even if you go just to get a photo of this:

Institute of Contemporary Art

Museum of Fine Arts

JFK Library

– Boston Children’s Museum


Freedom Trail: we never do the guided tour, but we always do this when friends are in town. You can make it kid-friendly or a pub-crawl 😉

It takes you around to all the historical places in Boston…like burial sites of our founding fathers, where the Boston Massacre happened, the first bars in the US, Paul Revere’s House, etc. Bring comfortable shoes! All you do is follow the brick path and it will take you to all these places. Here’s a map!

-Bars/restaurants to stop by during the Freedom Trail: Bell in Hand, Beantown Pub, any restaurants in the North End (where paul revere’s house is), and at the end of the trail you will be in Charlestown and I highly recommend Pier 6 for dinner (amazing views of the water/downtown). The Clam Chowder at Warren Tavern in Charlestown is my favorite (it’s a circa 1780 tavern where Paul Revere frequented and George Washington’s funeral speech was given).

Duck Tours

USS Constitution

Boston Tea Party Ships & Museum

– The Cheers bar





Olives & Grace

December Thieves

Patch NYC

Sault New England


Queen of Swords (Somerville)

Millay (coming soon to Boston!!)

Boston General Store

Forest Bound

Place and Gather

Cambridge Antique Market


Shake the Tree


Brookline Booksmith


Boston Public Library

Boston Children’s Museum

Boston Public Garden (swan boats)

Rose Kennedy Greenway (carousel)

Duck Tours

Science Museum

Boston Harbor Whale Watching Cruise

Franklin Park Zoo

Boston City Hall Plaza

The Freedom Trail

Boston Common Frog Pond (across from the Public Garden)