Boston Summer Giveaway

Enter for your chance to win a FREE Boston Summer Vacation! 


  • Just follow our Instagram and Facebook pages and use #mybostonsummer to share your favorite thing about summer in Boston and you will be entered to win!

  • We will announce the winner June 28th so make sure to enter before noon that day!

  • Already follow us? Comment on a friend's post for your chance to win!

  • Tip: Like our partners pages (listed in the slides below) for a better chance to win.


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*Subject to Availability. Transportation not included*

Featured Posts: 

  • catie_:There’s too many reasons I love Boston to choose just one! From the Pops on the Esplanade on 4th of July, to open Newbury, to sunsets on the Charles, to Fenway tours and Harbor tours, to delicious donuts and coffee, and local beers on the patio... to name a few! #mybostonsummer

  • 1_basic_dad: What is not to love? Game at Fenway, riding the T, walking the freedom trail. It's been 3 years since my last visit and I miss it.

  • idreamofjenn: Watching the Sunset by the Charles River 

  • mbcrowley: Always includes a duck tour with visitors, codzilla on the harbor for some laughs , lobster and ice cream bon bon’s at Legal and Shakespeare on the common ! Boston Rocks !

  • gileyde: I love walking on The Greenway. People, great music, different cultures. Boston makes me reborn each day during the summer time. Love..life....free spirit!!!

  • tinabellmodel: I used to take the T to Boston as often as I could from Braintree to Park St, go to Quincy Market for food, watch street performers at Faneuil Hall, walk through the Commons & the Gardens, Up Newbury St then people watch in Copley Square & head back. I’m embarrassed to say, I’ve lived in Boston for years and have never done a single thing on this list 🤭

  • ryan.s.spagnolo: There’s too much to love about Boston in the summer to pick just one. Whether it’s strolling down Newbury Street to shop, to visiting the historical sites in the North End, to taking to the water via the Harbor Islands and the Aquarium, to discovering new and interesting activities at SoWa or the Public Market. Not to mention, the various feast day festivals in August and Pride in June. All of these make #mybostonsummer great!

  • afaghfarhadi: Last and first time I was in Boston was in October and I really enjoyed it. Although it was a little cold to enjoy revere beach which I really liked I hope to visit there in summer and spend a sunny day at the revere beach and also try Boston cruise and maybe whale watching 🌹🌹

  • thegreatgatsbriella: The BEST part of Boston is now. As we finally drag ourselves out of the dark and dreary days of the forever lasting winter, my legs decide they may actually enjoy working out. I hustle past the Bunker Hill Monument, heading for Cambridge. A quick loop under the bridge and suddenly I’m greeted with a gentle breeze. Easing me and the sailboats along. I am so proud of myself, I’ve already made it four miles along the Charles! I catch a glimpse of the Citgo sign out of my peripheral, I hustle over the Mass Ave Bridge, onto the Esplanade. The ducklings follow their mothers lead, as I follow the Physician’s Assistant I want to look like down the runner’s path. I stop, is that a bird? No, it’s an owl. The Night Shift Owl. This is where my run ends because a delicious pint of Whirlpool awaits me. THAT is the best part of Boston.

  • dgalvis522: Nothing more fantastic in Boston during the summer than the following: 1) walk along the water in the morning. 2) The wonderful skyline view coming in from the south shore thru a boat! 3) Fenway Park!!!! 4) Good food and friends. 5) Playoffs! Riding the T. Seeing people take the duck tours and historic tours of Boston. City of Boston is just an amazing place to fall in love with. I moved here from Colombia and literally feel very much at home regardless the distance

  • paolopez1pao: Nothing feels more like summer than catching the sunset at the Envoy’s rooftop while you’re with friends, good music and a cup of rose! 💕

  • rhondakurbis: My fave thing about Boston is it’s citizens. You are friendly & helpful. My fave experience was when one of Boston’s finest stopped traffic & escorted me across the street

  • pamelahig#mybostonsummerlast year my and my friends have such a blast at the envoy rooftop, we literally were there every Sunday afternoon, and just recently heard about @chef.tatiana and @outlookkitchen and we have been there for brunch a couple of times this year! 100% recommended! Best view, great service and exclusive location! I absolutely love it