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

kailee wright boston tour guide

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

As some of you may have seen, this past Friday was my birthday!! So to celebrate, Joe and I took a little couples trip out to Boston and it was SO MUCH FUN!! Neither one of us had ever been, so of course we reached out to you pros for all your best suggestions of must sees, dos, and most importantly eats, and like always you came through with SO many suggestions!! We only had a few days there so we were only able to do a few. But since I’ve had so many asking for the ideas, I thought I’d put together a list of what we did + loved, as well as alllll your suggestions too!!

kailee wright boston tour guide

joe’s tee + shorts + shoes  ||  my tee + jeans (+ similar) + shoes + sunglasses

Our first full day was Friday, so we rented some bikes and rode along the Freedom Trail and LOVED it. It was so pretty and I highly recommend the bikes to see more quickly. They also had a hop on hop off trolley thing 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.

kailee wright boston tour guide

my tee (similar, mine was from the ball park) + jeans + hat  ||  joe’s tee + shorts + hat

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, so I highly recommend it. We hit up Mike’s Pastry that night too and ordered like 10 different things to share and loved every single one.

kailee wright boston tour guide

kailee wright boston tour guide

joe’s tee + shorts + shoes  ||  my 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. 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.

kailee wright boston tour guide

joe’s tee + shorts + shoes  ||  my tee + jeans (+ similar) + shoes + sunglasses

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 Burger Co.

Regina’s Pizza

Mikes Pastry

Modern Pastry


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

Whale Watching

Arya Trattoria

Ocean Prime – amazing steakhouse and Peanut Butter Pie

The Friendly Toast

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


Faneuil Hall – yummy food, great Boston souvenirs

Fenway Park to see a Red Sox Game

Freedom Trail – take the hop on/off trolley to get to each place quicker

Duck Tour

Boston Children’s Museum

Newbury Street

Beacon Hill

Public Gardens – Ride the Swan Boats

Boston Tea Party Ship Tour

Hop on Hop Off Bus – Great way to see so much in a little bit of time

Boat Ride to Nantucket or Martha’s Vineyard

Walk Around the North End – best restaurants and so pretty


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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