Sailing for a Change

A gorgeous Saturday in Boston Harbor played host this past weekend to the 9th annual Flip Flop Regatta. Each year, The ALLY Foundation and friends organizes this weekend of sailing and partying to raise awareness for a very important cause.

This year, we were kindly invited to enjoy the regatta from a very special spot, aboard the boat carrying The ALLY Foundation founders and Ally’s family and friends.

Our day started in the Constitution Marina where we boarded the 61 foot yacht, Makin’ Way.Flip Flop Regatta

Charlestown Marina

The spacious vessel featured a beautiful kitchen and living room as well as an upper deck, back deck, and bow deck, a bathroom, and more rooms below, which we did not see.


Flip Flop Regatta

As we drove out of Charlestown Harbor, we passed right by the place where the Flip Flop Regatta evening festivities would take place, decked out in ALLY Foundation pink and green.

Flip Flop Regatta

Flip Flop Regatta

In addition to enjoying a relaxing day on the water with gorgeous views, there was also an array of gourmet delights on board.


Chef and owner of Carmen ( a fabulous little restaurant in Boston’s North End, one of my favorites), Jeff Malloy, spent the afternoon whipping up delectable treats including grilled shrimp, clams with grilled garlic bread, sausage, meatball sandwiches and pasta salad.

Carmen, Boston

pasta salad

And there were also, of course, North End baked goods for that sweet tooth.

baked goods

The food was incredible, and it was made more impressive by the fact that the chef was cooking while standing on a rocking boat. There were some waves out there!

Sailing for a Change

Luckily, for the sailors, that also meant there was wind to bring them from the outer harbor back to Charlestown. 70 sail boats all vying to get across that finish line was quite the lovely sight.

Flip Flop Regatta

Our hosts were warm and wonderful, as always, and we spent the day meeting many interesting and fun new people. I am so grateful to have been a part of their day and will definitely be marking my calendar to attend the Flip Flop Regatta tent parties next year.

Did you have a fun weekend? Do anything special?

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Tags: Boston, events, Food, sailing, The ALLY Foundation

  1. Daisy’s avatar

    that boat is insane! and the chef from Carmen?!- what a treat!


  2. MelissaNibbles’s avatar

    The boat is amazing. Looks like a great day!


  3. Emily @ A Cambridge Story’s avatar

    Woah what a boat! Looks like an excellent day on the water!


  4. Eric King’s avatar

    Looks like a beautiful day from these amazing photos.


  5. Michelle’s avatar

    It looks a beautiful time! I did some retail therapy balanced by time in the office this weekend. Yours looks a lot more fun!


  6. Megan’s avatar

    What a great experience! And looks like a beautiful day to be out on a boat.

    I spent the weekend in Portsmouth with my mom and sister and bought my wedding dress!!


  7. Elizabeth’s avatar

    Good food and a beautiful day on the water, perfect!


  8. Erica’s avatar

    The Ally Foundation is such a great cause – sorry I missed it this year. Looks like your boat trip adventure was fantastic!


  9. Terri’s avatar

    What a wonderful cause! Glad you had a nice day. The food looks amazing…any relation to the chef?


  10. Melissa’s avatar

    meghan, it was lovely meeting you on the boat :) great pics! ~melissa


    1. traveleatlove’s avatar

      Thank you for your comment. It was great to meet you as well!


    2. Taryn’s avatar

      What a lovely day for a boat ride! Especially for such a good cause. I was stuck inside furniture shopping… which was successful, but not quite like taking in the beautiful outdoors.


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