A Perfect Family Vacation in Boston

There are precious few times in life when you can say that you took the vacation of a lifetime with your children. Fewer still when your lives are so utterly compromised with school, work and the daily monotony of life that even family meals are scarce. During a very brief and rare break from dental school, my husband was able to drive our family from New York City for a 4-day vacation in the beautiful city of Boston. One of the very best weekends to spend in Boston-a city rich with our country’s history-is precisely the weekend we stayed: Independence Day. This is a city I could live in.

We arrived at the Four Seasons Boston after a grueling 8-hour journey from Manhattan. Our kids happen to get extremely car sick and continued to do so throughout all eight hours-with no help from holiday traffic. When we walked into the lobby of the hotel, weary and relieved to finally have met our destination, the woman at the front desk immediately wheeled out a Radio Flyer wagon filled to the brim with stuffed animals. Jack and Zoe were invited to choose one for their very own: a gesture that not only warmly welcomed them into the new place, but one that made them completely forget about being sick for hours on end. Smiles abound, we were personally escorted to our double suite overlooking the Boston Commons. The room where we would be staying for three days and nights took our breath away. A crib had been set up in anticipation of our youngest’s arrival, while a full spread of fresh fruit was laid out for us along with a cookie decorating tray for the children. Sitting on the entrance table were seven envelopes: Our itinerary for each day and evening that we would be staying at the Four Seasons Boston, to be opened in order.

IMG_6350
IMG_6400
IMG_6366
IMG_6383
IMG_6381

This was just a taste of the journey that the hotel had in store for us. That evening we were invited to The Bristol Lounge, a luxurious and fantastic restaurant located on the first floor of the hotel. The children were given more stuffed animals, crayons and an activity book that kept them busy throughout the meal. We were impressed from beginning to end in culinary amazement, including the kid’s meals that boasted steamed vegetables and the best macaroni and cheese. Just before our dessert arrived, Jack and Zoe were invited by the chef to explore the kitchen. They came back to our table positively beaming in their own little chef’s hats.

We made it back to our room in time for the famed Four Seasons Boston’s Ice Cream Man’s scheduled visit. I couldn’t quite describe the kid’s delight if I tried, so suffice it to say they had the giggles for a solid hour after he left.
We went to sleep that night tucked snugly and happily into the fabulously comfortable beds, with bellies and hearts full of precious memories from even the first few hours on vacation.

IMG_9310
IMG_9314
IMG_6422
IMG_9318

The next morning, an incredible spread of food came for our breakfast: French toast, corned beef hash and eggs benedict paired with orange juice and a strong, excellent pot of coffee. We set out that day on a Boston Duck Tour to the Museum of Science, and quite possibly learned more in one afternoon than an entire course in American History. We ate dinner in the city’s popular Faneuil Hall of Quincy Market, danced to live music and treated ourselves to home made ice cream.
Day three in Boston started with yet another fantastic breakfast in our room, along with a mini duck hunt. The children’s book “Make Way For Ducklings” had been placed in our room for last night’s bedtime story in anticipation of our visit to the Boston Public Garden, where the story takes place. The kids were instructed to find two of Mrs. Mallards missing ducklings-which sent them into a tailspin of delight and frantic searching. Two little duckling Beanie Babies were retrieved and spent the rest of the day with us exploring the park and napped with the kids in the stroller while we checked out the Boston Chowder Festival.

IMG_7051
IMG_6438
IMG_6582
IMG_9322
IMG_6533
IMG_6607
IMG_6663
IMG_6641
IMG_6869

We returned to the hotel that afternoon and took a dip in their huge swimming pool. There were plenty of other children there, plus an attendant keeping an eye on everyone (a huge plus for traveling families). Upon our return to the hotel room, we found yet again a gorgeous cookie decorating spread, only this time with the Fourth of July theme-it being the eve of the holiday. We decorated cookies, put the children to bed and I soaked for a good 45 minutes in the tub in absolute peace. This might be the first time that my husband and I have spent three consecutive days stress and worry free in our entire marriage. There are no words for that kind of serenity, joy, and perspective.

IMG_7022
IMG_7041
IMG_7076
IMG_7139

Our last day at the Four Seasons began with another beautiful breakfast in our room. Chef Vosika’s Lemon Ricotta Pancakes have won their way into my memory and tummy-I cannot wait to go back for more. The kids opened their final gifts from the hotel: a bag full of Red Sox gear to help us celebrate their first experience at Fenway Park. We layered ourselves in red, white and blue and headed in a taxi to the big game, something I wasn’t leaving Boston without introducing my children to.

IMG_6724
IMG_7060
IMG_7059
IMG_7208
IMG_9363
IMG_9364

The days and nights that we spent at the Four Seasons Boston were some of the very best moments we have had as a family. The staff was beyond kind and accommodating, and our children were not only accepted into their luxury hotel, but they were welcomed with open arms.

IMG_7246
IMG_7161
IMG_7196

To this day, both of my kids-who are 4 and 3 respectively-have asked to go back to the “Boston hotel” on a near weekly basis. Truth be told, all four of us cannot wait to go back to create more beautiful family memories.

I covered our experinence at the Four Seasons Boston over on their blog as well, Have Family Will Travel. Head over here to read more!

I was not compensated for this post. Our accommodations at the Four Seasons Boston were covered in exchange for this review.

Join the Conversation

9 Comments

  • Lovely review…I too have stayed at the Four Season (Doheny, Beverly Hills) with my daughter and granddaughter. They could not be more accommodating. In a society which is getting more and more unfriendly to children it is so welcoming when a hotel can treat you to an experience that makes you want to return over and over.
    I love the Four Seasons and even try to make time to stay at the one in Chicago which is 30 minutes from my home just for some rest and relaxation.
    Definitely 2 Thumbs Up.


  • Do all guests with children get the same perks included with their room rate (ie teddy bears upon arrival, cookies in the room, ice cream man visit to the room, etc.), or does those cost extra?


  • Hi Jessica….I’ve been following your blog for a while now and really enjoy it. I was wondering the same thing as the commenter above. Is this lavish treatment standard at Four Seasons?


  • Ummm, your family is gorgeous. Boston isn’t high on my list currently, but I’ll keep this in mind because I’m sure I’ll get there eventually. 🙂


  • Thank you!!

    Sara and CK: I was very curious about this myself, but happy to learn that it is all very much a part of the standard package offerings at the Four Seasons Boston.

    The Kid-Kation package can be found on the website here: http://www.fourseasons.com/boston/rates_and_reservations/. The package starts at $445 and the wonderful news is that it includes half price off the 2nd room (if a second room is needed) as well as a $30 breakfast credit, in addition to all the other awesome inclusions as well (ie: the Ice Cream Man, cookie making, backpacks, toy cart, custom amenities, etc).

    Each Four Seasons is different, though, but I believe that most of them offer kid-friendly packages 🙂


  • I loved that you loved it here. Sometimes I lose appreciation for all that surrounds me in this city, but seeing it through someone else’s eyes helps reel me back in.


  • Wow. That final picture of your family is simply stunning. Glad ya’ll had a good time.


  • Please let me know if you’re looking for a author for your weblog. You have some really great articles and I think I would be a good asset. If you ever want to take some of the load off, I’d love to write some material for your blog in
    exchange for a link back to mine. Please send me an email if interested.

    Thank you!


  • It really does sound like you had the perfect family vacation in Boston! I loved looking at all of the great photos from your trip! What a beautiful family you have!

Follow @mommasgonecity on Instagram