Our Travel Guide: BOSTON **updated** - Kailee Wright
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Our Travel Guide: BOSTON **updated**

kailee wright boston tour guide

my top + pants + shoes + hat  ||  joe’s similar tee + hat + shorts + sandals

Let’s talk all things BOSTON!! It is such a beautiful city and full of so many fun things to do, see, and of course EAT! I shared some of our favorite things we did a couple years ago when Joe + I went for my birthday, and now that we just got back from taking Hudson there for his solo trip, we’ve got even more!!! So keep reading below to check out a few details on our favorites as well as a HUGE list of eats + things to do from all of your amazing recommendations!

kailee wright boston tour guide

When Joe + I went we were first timers and all about the tourist experience. Our first full day, we rented some bikes and rode along the Freedom Trail and LOVED it. It was so pretty! I highly recommend the bikes to see things more quickly. They also had a hop on hop off trolley a few of you suggested, so that would make it easier with kids too! That night we ate dinner at the HIGHLY recommended by you guys Boston Burger, and it DID NOT DISAPPOINT. Oh my gosh, it was so delicious. Joe got the Mac + Cheese burger and it was to die for.

After dinner we headed over to Fenway Park for a Red Sox game, and it was hands down my favorite part of the trip. The atmosphere there is incredible. Even if you aren’t a huge baseball fan like us, I think you would love it. Just the whole crowd breaking in to Sweet Caroline, ah it is was honestly so so fun. For sure the funnest game I’ve ever been to. I highly recommend it. We hit up Mike’s Pastry that night too and ordered like 10 different things to share.

kailee wright boston tour guide

kailee wright boston tour guide

joe’s tee + shorts + shoes  ||  similar cardigan + jeans + hat + sunglasses

Our second day we walked around North End and had so much fun. There is always something going on around you, and we loved all the street entertainment. We had lunch at Reginas Pizza (also highly suggested and SO AMAZING). Then we headed over to do a whale tour. Also most of the places there guarantee you will see whales, and if you don’t they give you a lifetime ticket to come back in 5, 10 or 50 years and try again! It was so cool to see the city from the ocean view and the whales so up close. We ate dinner at Top of the Hub which is on top of the prudential building, and of course had amazing view of the city.

And for our last day the boys hit up another game at Fenway while us girls took your advice and went shopping on Newbury Street. So many fun options and of course even more delicious food. Honestly we wish we could’ve stayed longer to see and eat all the things! Because as you’ll see below you had lots of great suggestions!

kailee wright boston tour guide

. . . 

Boston Trip best recommendations

This time around when we took Hudson for his Solo trip was much more laid back. So he was in charge of the itinerary and wasn’t really interested in doing your typical touristy things. Of course we hit up 2 Red Sox Games which were again so much fun! We went to a fun local park and ate the yummiest food (details below). One of the funnest things we did was go cart racing just outside Boston. Totally worth the little it of drive and so so fun! We also went sailing which we all LOVED! It is so beautiful and quiet/peaceful. Highly recommend!

Boston Trip best recommendations

Speaking of recommendations, below is a giant list of all your amazing recommendations for both things to eat and to do! I made my own reviews next to a few for more details. So it should make planning your Boston getaway a breeze!

kailee wright boston tour guide


Boston Burger Co. ** Highly recommend! Joe got the Mac + Cheese Burger and it is incredible.

Regina’s Pizza North End ** One our favorites for sure! Such GOOD pizza!

Friendly Toast **This one was new to our trip with Hudson and amazing food! We were all obsessed!

Ocean Prime – Amazing steakhouse for more of an adult trip. You must order the Peanut Butter Pie too!

Mikes Pastry – This is going to be an unpopular opinion, but personally for us this was a “do because its the touristy thing to do”, but we didn’t really love anything we tried. Don’t come at me!


Little Italy

Modern Pastry

Broccoli Salumeria

Big Daddy’s Pizza

Flour Bakery


South End Buttery

Limoncello Ristorante

Neptunes Fish Bar : best lobster roll


Tatte Bakery

Dolce Vita

Quincy Market

The Border Mexican

FoMu Ice Cream

Kane’s Donuts

Magnolia Bakery

The Grotto

Arya Trattoria

Cafe Luna

Omni Parker House – Original Boston Cream Pie

Citrus + Salt – coastal Mexican

Black Bird Donuts

Luke’s Lobster

Cafeteria Boston

Cafe Vittoria

Legal Seafood

kailee wright boston tour guide


Fenway Park – the funnest stadium and game I have ever been to! Even if you aren’t huge into baseball you will love it! You can also do a tour which I’m sure would be amazing!

Freedom Trail – Amazing way to get all the historical sites in. You can walk it, rent bikes, or do the hop on hop off trolley.

Faneuil Hall – yummy food, great Boston souvenirs

Supercharged Entertainment – This is where we rode the go- carts! It was SO SO much fun and we highly recommend!

Classic Harbor Line – So this is the company we did the sail boat tour from and really liked it. There were only about 8 others on the boat with you so you can move around and see a lot. It also is pretty affordable for a tour.

North End Park – My favorite place to just relax and people watch.

Quincy Market – GIANT food market with lots of different options


Boston Common’s – Main Park in the City

Beacon Hill – Fun to check out all the houses

USS Constitution – Free tour


Whale Watching

Science museum

MIT College Tour

Walden Pond

Arnold Arbetorum

Public Gardens – Ride the Swan Boats

Boston Tea Party Ship Tour

Boat Ride to Nantucket or Martha’s Vineyard

kailee wright boston tour guide

So as you can see, like always you guys came through with AMAZING recommendations! I wish I would’ve had a week or two to try everything you suggested. We can’t wait to go back and experience even more of beautiful Boston!

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