Watch my travel vlog on youtube

Boston, Massachusetts | Red Sox vs Yankees Game, Beacon Hill, Prudential Tower

I only got to spend 2 days in Boston which was decent but there is so much to do. Out of all of the big cities I’ve gotten to visit over the years, Boston has easily been the best one. It’s beautiful, I felt safe (safe enough to go here solo), and again… there is SO MUCH to do.

Keep in mind, I DON’T include travel days in my itineraries! :)

Getting around/stay

To my surprise, Boston is very walkable. I say surprise because where I’m from, people don’t walk the downtown area too much. A 15 minute walk in Salt Lake City would get you past some sketchy/abandoned buildings and a Starbucks. A 15 minute walk in Boston has a whole lot more to offer. Pretty much the entire first day we were there, we just walked. On that note, wear good walking shoes!! I’d still recommend having a rental car or looking into public transportation ahead of time for a few things I have in this itinerary.

When it comes to stay, I’ve said this once and I’ll say it again. I am the least informed when it comes to accommodation. My family stayed in an Airbnb that was in the middle of everywhere we were going… so it was in a random city in Massachusetts. Doesn’t help y’all for Boston. We did look and I will say that it is EXPENSIVE to stay in the city. At least it was at the time we were there. I’ve heard a lot of recommendations for staying in Beacon Hill which is absolutely beautiful, but it will run you $300 a night at the minimum.

DAY ONE

Public Gardens and Shopping + Optional Sunset Activity

The Perfect Itinerary

Grab Breakfast and Coffee From ‘Beacon Hill Books and Cafe’ (Reservations Highly Recommended) or ‘Cobblestones Eatery’

Recommendation: If weather allows, get your breakfast to go and picnic at the public gardens.

Stroll The Boston Public Gardens

Be sure to see the famous ‘Good Will Hunting’ bench.

If you’re anything like me and don’t love breakfast, stroll the gardens first, get some pictures, and do brunch at Cobblestones Eatery + grab coffee from Beacon Hill Cafe or Blank Street.

Shop Beacon Hill

Stores Don’t Open Until 10:30-11am
Beacon Hill Books and Cafe Has An Incardi Machine So Bring Those Quarters
Picturesque Spots Include Acorn Street and Rouvalis Flower Shop

Walk To Newbury Street and Grab Lunch From One Of The Local Spots

Shop Newbury Street

It’s A Mile Of Stores… On Both Sides
The Brandy Melville Is THE LARGEST Brandy I Have Ever Been To
Stop At Central Perk For The Fun Of It + Get Another Coffee If You Need One

Optional: Watch The Sunset From The Top Of The Prudential Tower | About $30 Per Person

Grab Dinner From ‘Earls Kitchen + Bar’ or ‘Ilona’

DAY TWO

Baseball Game/Free Day or Boston Tea Party Museum + Salem Witch Tour

If it’s baseball season and seeing the Red Sox interests you, then you have to go to a game. No baseball game will ever top a game at Fenway Park.

The Perfect Itinerary

Red Sox Baseball Game

The Team Store
Dels Frozen Lemonade
Hot Dogs and Italian Sausages

Games are either in the afternoon or at night and last a couple of hours. I’d also tell you to get there a bit early to experience the fans, stroll the team store, and see the stadium. Use whatever extra time you have for a free day or to just chill and relax!

If baseball isn’t your style don’t worry, I have an alternative.

Another Perfect Itinerary

Day Trip To Salem

A day trip to Salem is something I didn’t get to do personally, but I hope to when I eventually go back. I haven’t done a ton of research, but I was still able to make a flexible itinerary!

Visit The Hocus Pocus Locations

Max and Dani’s House
Allison’s House (Ropes Mansion)
Old Town Hall
Pioneer Village
Old Burial Hall
Salem Common

Grab Some Lunch

Shop Downtown Salem

Go On A Salem Witch Tour

Interested in Salem? Here’s another blog I found with more information!!

Salem, Massachusetts Travel Guide by Jasmine Jorges

DAY THREE

Art Museum and History

There are so many museums and historic places to see in and around Boston and unfortunately you will have to pick and choose. If you’re super into history, you could easily do 2 days of this.

The Perfect Itinerary

Boston Tea Party Museum | $26+

We didn’t do this museum, but I’ve heard it’s really fun for both adults and kids. Tickets do sell out, so I’d purchase them in advance.

Isabella Stewart Gardner Museum | $22 - Kids 17 and Under Are Free

Location Of The Largest Unsolved Art Heist
13 Works Were Stolen March 18, 1990
The Empty Frames Are Still In The Museum
The Courtyard Is Beautifully Detailed With Greenery

USS Constitution Museum | Free Entry

This is a part of the freedom trail located in Charleston, Massachusetts.
You can explore the navy yard which includes the visitors center, the museum, the USS Cassin Young, and the USS Constitution. To go onto the USS Constitution and I believe the USS Cassin Young, you do have to go through a security screening and those aged 18 and older have to provide a form of identification.

Walk The Freedom Trail

Guided tours are available, but you can also do a self-guided tour to walk at your own pace and make sure you get to see what you want. As I stated in the beginning, wear good walking shoes because you will be walking for a long time. This will take a few hours.
There are a lot of buildings you can go into to learn more about the history but most of them have admission fees.