Day Trip to Boston: What to See & Do

A few weeks ago, I had a conference on Wednesday- Thursday in Boston. My office bestie, Courtney, and I left Tuesday afternoon so we could do as much of the city as possible before the conference started at 4 pm.

If you find yourself in Boston for a day, here’s what you should see and do.

Best Boston Tours

The best way to see Boston and learn about its rich and crazy history is to do a tour or two. We did three tours in one day (we weren’t messing around). Here are the hits and the miss.

Best tour: Town Criers Freedom Trail Tour

Everything you read about visiting Boston says to do the Freedom Trail, which is a 2.5 mile walking tour of historically significant sites. After having done a tour, I believe a tour is the single best way to do the Trail. You would miss SO much information and story by doing it yourself.

We selected the Boston Town Criers tour because it had a 9:30 am tour, which was the earliest available on all the tour sites I researched. Moreover, it had excellent reviews, with an average of 4.5 stars. Our guide was knowledgeable, energetic and quirky.

 

 

Some of the highlights of the tour included Boston Common, the Grainery Gravesite, which is where Paul Revere, Samuel Adams and John Hancock were laid to rest, King’s Chapel, which contains a bell cast by Paul Revere, the site of the Boston Massacre and more.

Runner up: Haunted Boston Ghost Tour

At 8 pm, a small group of us went to Boston Common for a .5 mile, 90-minute haunted Boston ghost tour. This wasn’t a ghost hunting tour, but rather a tour about Boston history and the ghosts that supposedly haunt the area we walked. It was fascinating and added a lot of depth to the morning Town Crier tour, as there was a bit of overlap in terms of location. I especially was fascinated by the Boston witch trials and the hangings of innocent people that took place. A playground has been built on the spot where the hanging tree was — I don’t think I could let my kids play there. Too creepy! Our guide, Katie was a captivating storyteller and very knowledgeable about the city.

Skip: The Boston Ducks

Our cab driver advised that we do the Boston Ducks tour as a way to get on the water and see the city. We saw many stands selling tickets and decided that it would be a nice rest in the middle of our day (we went after lunch). The tickets were pricey ($40) and honestly, this tour was not worth it, especially if you do a walking tour. Our particular guide told bad jokes for 90 minutes, didn’t share enough history and the experience was a big let down. Moreover, the ticket seller said to arrive 30 minutes early, which was not necessary. We worked our afternoon around this tour and it simply didn’t deliver. Skip it.

Where to Eat in Boston

Boston is a foodie town, with no shortage of great restaurants. A few recommendations:

First off, you must go to Mike’s Pastry or Modern Pastry Shop, or both. Native Bostonians have strong opinions about which is better. Mike’s opens earlier, so Courtney and I went there first thing (8 am). We had the best cannolis ever!

We then stopped by Modern after lunch. Neither had lines, which probably was due to a midweek visit. (I have read the lines can be quite long). I had the best cannoli of my life from Mike’s, and it was my favorite. I loved its simplicity. Also, know that both places take cash only!

Eat Italian: We went to the North End, which was near the end of our Freedom Trail tour for lunch. It has more than 100 Italian restaurants. We chose Ristorante Fiore, which was delicious and affordable. (We found that many of the restaurants were not open for lunch.)

 

Two other popular restaurants are Sonsie and Stephanie’s on Newbury. Both iconic Boston restaurants have outdoor patios, a great vibe and are great dinner spots. If you only do one, my vote would be Stephanie’s.

The menu is more robust and frankly, I loved my meal a lot more there (I had their “famous” meatloaf.) If you can get to Newbury Street before 5 pm, many of the shops will still be open and you can do a little shopping too.

Other places to see

Trident Booksellers and Cafe

If you are a bookworm, you will love this store, which is chock full of both the latest titles and more unfamiliar ones. They also have hundreds of journals and a darling gift section. I could have stayed here for more than an hour. (Also, if you love books, check out my new bookish Instagram account, @BookSnobbery)

Quincy Market

For lots of shopping, both of local vendors and brands you love, Quincy Market offers something for everyone.

Boston Public Gardens

If I had a do over of our day, I would have skipped the duck boat tour mentioned above and gone to the Boston Public Gardens. With its famous swan boat rides and Make Way for Ducklings statues, I know this would have been a delightful stop. The boat rides are only open 10-4, so don’t wait until late in the day. (I think they should extend these hours during the warmer months!)

Boston Public Library

Another wonderful stop is the Boston Public Library. It’s truly might be the most spectacular library I have ever been in. I’ve never seen anything like it. Though I wasn’t able to stay long, it was worth taking a spin around some of the floors. I hear their map room is incredible.

It was a full, wonderful experience in Boston and I can’t wait to go back. What a magical city it is!

If you have been to Boston, what were your favorite spots?