Travel To {Boston}

Last year around this time we were in Boston celebrating our 1st wedding anniversary (part 1, part 2, part 3, part 4). This wasn't our first time visiting Boston together as the first trip Billy ever went on with my family was to Cape Cod (with 30+ Whalens, seriously surprised I didn't scare him off!), but Boston is by far our favorite city to travel to. Which says a heck of a lot!

I've made the comment before that if I had to move but could pick a location, it would be Boston (I haven't been to San Fran, yet). No doubt in my mind. I have an aunt and uncle that live in Plymouth, 2 cousins that live in Lexington (and another city that I can't remember), and a friend that lives in Hingham. Therefore, I've been to Boston many times and each time surprisingly gets better and better! There is so much to do and you can't beat the history (which we love).

Today, I'd like to share some of my favorite things to do in Boston and do a little recap of our trip there last year. 

1. Newport Mansions:  full recap of our day-here

These mansions are actually in Newport, Rhode Island but I strongly recommend making the short drive to see these mansions. Billy still talks about how this was his favorite thing to do on a trip. The mansions are unreal and you truly won't understand how big they are (does 170,000 sq ft sound big to you?!) until you take a tour of them. They offer an audio tour and I don't think the experience would be the same if you skip that part. The audio tour takes you from room to room and shares so much history about the family who lived in the mansion, how they made their money, and all kinds of interesting facts. Try to get to the mansions as early in the day as you can so that you can tour multiple mansions (try to fit 3 in or more!) and then walk around the back of the mansions by the water afterwards. You really need a full day to fit in all there is to offer.

Also, make a trip into the city of Newport that is close by-it's filled with cute shops and restaurants. 

2. Whale Watch: full recap here

The best whale watching is in Boston. This is a must-do for our family since we love boat rides and my last name (maiden) is Whalen. We LOVE whales...duh. ;) If you have never gone on a whale watch, you are missing out. They are so much fun and are typically around $30.00-$40.00 per person for 4 hours. We normally leave on the boat from Plymouth because it's only a couple minutes away from my aunt and uncles house.

3. Downtown Boston and Freedom Trial: full recap here

There is an unlimited amount of things to do downtown, but you have to do the Freedom Trial if you've never done it before and enjoy history.

Some of my favorite locations include:

-Paul Revere's house
-Little Italy (on the North End)
-See the location of the Boston Massacre (literally an intersection)
-Quincy Market (can be very crowded)
-Eat at the Union Oyster House -oh.em.gee...so good. I'm hungry right this instant. 
-Charles St, Beacon Hill, and the Gardens: Charles St. has the best high end shopping....and now you don't need to wonder why it's my favorite street ;)
-Stop in the famous "Cheers" restaurant
-Old North Church

The freedom trial takes a couple hours, but you can kinda go as fast or slow as you'd like. You can take a guided tour or print out a map and just do it yourself. We've done it pretty quickly when we've been pressed for time, but if it's your first time and want the better experience I'd say do the guided tour!

4. Cape Cod & Martha's Vineyard: full recap here

Just gorgeous. I love the Cape. There are so many cities you can visit, but Chatham and Provincetown are two of my favorites. Provincetown is a good place to go if you want to see a lot of Cape Cod because it is the farthest town, and Chatham is the cutest town for upscale shopping and to enjoy lunch/dinner. 

Make sure to spend some time at Cape Cod's National Seashore which is 40 miles of beach, marshes, and ponds. 

5. Harvard: (sorry, no recap)

If you're interested in this college, it's worth a quick trip to take a stroll through campus and to look at the dorms/buildings.

6. Hingham: see recap here

This city isn't necessarily a must-see in Boston, but this is where we had our first wedding anniversary dinner celebration and it's one of my favorite cities in Boston, so I had to include it! 

Hingham is a cute city and has an upscale shopping center/restaurant area that is perfect for a night out. Our family recommended eating at Alma Nove - which is Chef Paul Wahlberg's restaurant (brother of actor Mark Wahlberg!). Holy cow! This restaurant is delicious and did not disappoint. You can sit down by the boat harbor while waiting for your table to be ready and it's beautiful. 

7. Fenway Park

For the baseball/sports fans-catch a Red Sox game here!

*Extra-8. Visit Erica who lives here! I'm sure she would be a great little tour guide. Unfortunately, last year we didn't get a chance to meet up with her but if/when we go back, we will definitely be hanging out with her. Love me some Erica.

....and don't forget to eat lots of LOBSTER AND CLAM CHOWDAH! ;)
Nom Nom Nom.

*UPDATE: If you want to see our recent 2 year anniversary trip featuring Lake Tahoe, Napa Valley, and soon San Francisco and Carmel--> go here to start reading!

Now, who wants to pay me to tour fun cities and then blog about it? Anyone out there? I would gladly accept (in a heartbeat).

So, tell me, have you visited Boston?

Do you love it as much as we do?

What is your favorite thing to do there?


  1. You may have just convinced me that this will be our fall trip this year. When did you guys go?! The weather looks like it was perfect! Thanks for being our little tour guide for the day...I think a new profession is calling your name...

  2. I've been to quite a few places in my life, Boston was probably one of my favorites. I loved it! I would definitely move there too :)

  3. I've never been to Boston (I'm a New Yorker I must pick a time to go when I don't care about my sports teams) but I have been to P-Town and The Cape. I loved it there! Have you ever had Purple Cow ice cream? Oh my heavens it is to die for and I can only find it at the cape. Great recap, you made even a NY'er want to visit bean town!

  4. not gonna lie...saw this and was like OMG OMG OMG ARE YOU COMING HERE!!!!????


    arent the mansions GORGEOUS!! Shalyn, DDHP, and Sabrina are coming here in October and I think I wanna take them down to Newport for a day!! ITS GORGEOUS GORGEOUS GORGEOUS and a photographers dream!!!

    Boston Massacre literally an intersection LOL! so true!!

    im just smiling so much seeing you at hingham shipyard cuz litereally im like FIVE MINS from there and its so cool seeing you guys here!

    makes me so happy how much you loved coming down here! love love love!!!!


    1. I would like to share this on social media. Visit train live status for rail info and cplt20official for IPL. So, keep up the good work.

  5. i think i need a new hat, i've been rocking that indians one for quite some time. love you

  6. I have never been to Boston but it's really high on my list of places! This is a great post, also all of your outfits are adorbs. Just btw :)

  7. I love boston!! It's probably one of my favorite places. I haven't been there in years, but I want to go again soon!

  8. I've been to Boston twice, and loved each and every minute of it. One of my favorite cities by far! And I have a picture almost identical to the one in front of Cheers. I'd live there in an instant.

  9. We've been talking about taking a trip to Boston and Salem in October, so this is SUPER helpful info! Do you know which months are best for whale watching?

  10. I'm originally from Cape Cod (I moved to Seattle a little over a month ago). You have made me so incredibly homesick!! Glad you enjoyed your time there :)

  11. I love that you love Boston so much! I hope that next time you make a trip here we can meet. And would you believe I've never been to Newport and it is on my to do list for asap! I really want to go Labor Day weekend so we shall see if I can make it happen.

  12. Looks like it was a great trip! I can't wait to go to Boston someday and no you are making me want to go sooner than later :)

  13. Ahhh, that looks like a blast! I've never been. Do you recommend a best time of year to visit?! I need to get some more East coast vacations in!!

  14. I post on The Nest and have since before we got married. One of my "Nestie Besties" live in Boston and in April I flew there to visit her. I loved Boston!! I loved Fenway Park--we did a tour of it and I loved it. I loved the historical part of the city, too. We went on the USS Constitution and it was amazing too. I can't wait to take Jon there!

    Hope you have a blast in Cali!! I'm ridiculously jealous!

  15. Haven't been to Boston but I'd sure love to go.

    In other news, I adore the tank top you're wearing in the very first picture. It's awesome.

  16. My husband's family lives in Boston so we visit frequently & I love it! Though I will say we did the Freedom Trail while visiting her sister & brother-in-law.... in November. A little too cold for it!

    And we vacation in Chatham every summer so loving your recap there!

  17. i've always wanted to visit boston/ the new england area! this makes me want to get to work on planning a trip. the newport mansions and chatham look beautiful.

  18. I do love boston, especially Martha's Vineyard, but I'm voting on San Fran. eeeeee :-)

  19. Reading this makes me want to go back! My now husband and I went when we were in HS for his family's reunion. I remember it being fabulous! My boss is getting married this December in the Boston Public Library. It is going to be fabulous!

  20. As a lover of Boston and a resident of Cape Cod, you def hit up all the hot spots!!! Boston is so much fun and home of the best team eva. Go SOX (well not this year lol). Glad to see you enjoyed yourself:)

  21. One of my friends from college lives in southie and we go up to visit her every year. I loved the harpoon brewery tour and even though it was winter, eating on the waterfront. it's such a great city.

  22. Yay Boston is my hometown!!! My husband and moved to NJ 2 1/2 years ago but we're moving back next spring! This makes me want to go now!!! Glad you had fun and ate lots of chowda! :)

  23. I've done 3 outta 7. Not too shabby I guess since I was only there once for 3 days. I want to go back so badly!! Your pictures are gorgeous :)

  24. my boyfriend is grew up in Attleboro so I recently went back to visit his family with him. This included a day trip to Boston! it's a beautiful city and I can't wait to go back more often!

  25. wow..so beautiful.when i will travel visit this city.thank for providing picture and information


  26. Katie! It was such a lovely experience to read your article. “There is so much to do and you can't beat the history” I totally agreed with you. I also visited there during my a href=http://www.getbustours.com/3day-boston-washington-baltimore-philly-york-tour.html/>boston new York Washington DC tour/a> with my family and had a remarkable journey. We visited numerous famous attractions included museums, landmarks, park, etc. but here I would love to share my experience relevant to historical spots. We had a fabulous walk in Freedom Trail which is one of most prominent landmark of this region. Boston Public Garden We had a good time all family members equally enjoyed. It is also one of historical sites and very entertaining too… your articles fresh my all memories as I just came back from my tour. Good job keep it up…..

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