Boston Itinerary: What to See, Eat, and Do

Looking for a Boston Itinerary with lots of fun things to do in Boston for adults? Sharing some of our favorite places to go in Boston including Beacon Hill, JFK Museum, Gillette Stadium, and more!

Luke and I enjoyed a great short trip to Boston a few years ago. We'd been there a few times before so, this time around, we focused on walking through neighborhoods and hitting as many of the "must-try" restaurants as we could.

If you are planning a trip, or eventually want to go to Boston, I've included a good 3 Days in Boston could look like. Plus, how to navigate the city and more.

Boston 3 Day Itinerary

I'm going to give you all the pretty pictures and what they are first and then, at the end, I'll break down all the restaurants and places by location (and give you a sample Boston itinerary).

Acorn Street is a must for Boston Sightseeing!

I'm sure you've seen this view a few hundred times, am I right? Acorn Street is just as beautiful in person as you would expect.

Exploring Beacon Hill

Beacon Hill was, by far, our favorite area to walk around in. I loved every street we went down.

We thought that it was such a cool place to go in Boston, that we went back for a few hours on the last day we were in Boston. There's just so much inspiration everywhere. This should definitely be on your must do's in Boston list.

Visit Isabella Stewart Gardner Museum

One of the things to do, that was mentioned frequently when I was researching places to go in Boston, was to visit the Isabella Stewart Gardner Museum.

Enjoy the Water Views in Boston

Pretty views and waterways were just everywhere. Luke went for a run one night and snapped the picture above. Isn't it gorgeous?

Fun Things to Do in Boston For Adults

Definitely shop on Newbury Street. It's cute and there are lots of restaurants and places to pop your head in.

After shopping for a bit, we wandered in to the Boston Public Library. Holy smokes, it was amazing!

Boston Public Library

Cannoli taste-testing is a fun activity to do in Boston!

Modern Pastry is a Boston staple, so we knew that we wanted to definitely try the cannoli's there.

If you want to have a lot of fun with comparing cannolis, then head around the corner and compare Modern Pastry to Mike's Pastry.

We weren't blow away by the cannoli but it was definitely a fun activity to do in Boston.

Visit Gillette Stadium

The whole point of going to Boston was to watch the Chiefs play the Patriots. It was such a fun game. GO CHIEFS! If you have a chance to visit the stadium for a game, definitely do it.

If you are visiting Gillette Stadium and are staying in Boston, here's what we found to be helpful.

Take the train, buy your tickets in advance but don't activate your tickets until you are in line at the train station.

Anyways, see a game if you can... it's always fun; especially if you are cheering on the opposite team in full gear and your team slaughters them. =)

Harpoon Brewery

We visited Harpoon Brewery on a Saturday around 11 and there was no one there when we first got there. We did the tour first and the went back out to the brew hall and it was PACKED! It has such a fun vibe. And, do yourself a favor and get the pretzels with the garlic parmesan butter (best thing ever)!

Tips for When you Visit Boston

A lot of Boston can be walked. We used the subway, Lyft and walked through the city. In our opinion, the subway wasn't cheap. In some cases, it was cheaper to use Lyft (and much faster). I'd definitely recommend buying a two day pass for the subway but plan to use Lyft quite a bit, too.

Boston 3 Days Itinerary

Minimize your travel time and combine your neighborhoods like this:

• Day 1: Downtown Boston + North End
• Day 2: South End + Fenway
• Day 3: Beacon Hill + Back Bay

One Day in Boston Itinerary

Explore the Beacon Hill neighborhood and then pick a museum or library to enjoy.

Fun Things to Do in Boston for Adults

What to do in Downtown Boston

• Boston Public Market - Not our favorite market but if you are in the area, it's worth a walk-through.
• Feneuil Hall Marketplace (stores, food, street performers, etc)
• 1630 - Cute store with vintage and local made products.

Things to do in the North End of Boston

• Modern Pastry Shop
• Shake the Tree - Very cute boutique shop (affordable prices on clothing, books and interior decor).
• Tenoch - Mexican (we liked the torta and the salsa verde on the enchiladas). Super casual interior/grab and take to a park. Location is between North End and the Waterfront. Could walk from here to Downtown Boston.

Things to do near South End, Boston, MA

• The Salty Pig - Nice outdoor area to sit and enjoy a few drinks.
• Toro Restaurant - Tapas (plus they had Tinto de Verrano which I fell in love with while we were in Spain). Good food, good drinks, cute place... go!

Things to do near Back Bay Boston, MA

• Boston Public Garden
• Newbury Street - shopping
• Gre.Co - Greek place on Newbury. Casual vibe (+ to go food) perfect for grabbing food while shopping.
• Boston Public Library
• Mike & Patty's - Breakfast sandwiches in a super small place but go and get "The Tasty."

Things to do in Beacon Hill Area in Boston

• Beacon Hill - Loved walking around here.
• Acorn Street
• Tatte Bakery and Cafe - Cute bakery with good baked goods.

Things to do Near Fenway in Boston, MA

• Tasty Burger - Greasy but good. Super casual (eat-in or take-out).
• Pavement Coffeehouse
• The Verb - Our hotel.
• Isabella Stewart Gardner Museum
• Thaitation - Just grabbed a Thai Iced Tea to-go but it was great!

Things to do around Washington Square in Boston, MA

• Barcelona Wine Bar (Brookline) - Cute restaurant. We went at mid-afternoon and got right in. I loved their wine flights and Sangria.

What to do in the Seaport area in Boston

• Harpoon Brewery - Amazing pretzels and fun atmosphere.

Outside of Boston

• JFK Museum
• Gillette Stadium

Where to stay in Boston, Massachusetts?

We stayed at The Verb and it was a pretty good location for everything (even running). Overall, we didn't love the hotel but there wasn't anything wrong with it either. It's a boutique hotel that's decorated in rock-n-roll so, if that's your thing... you should totally bookmark it. That's not my thing, so for me, it was just ok.

But, right down the street from the hotel, there was a cute coffee shop that we got coffee at every morning (or should I say, Luke got us coffee there every morning but the one time I walked with him). =)