Holiday Cookie Boxes

When I was growing up, my dad used to get this tray of cookies right around the holidays from someone at his office. He would bring it home and we would all go crazy digging into peanut butter buckeyes, sprinkle cookies, and adorable cutouts of Christmas trees. My sister and I still have fond memories of this cookie tray that would stay hidden in the freezer long after December for us to nibble on.

Baking is my love language no doubt. When I visit my sister, I cook and bake as much as possible, and before I leave I make sure to stock their freezer well. Once the pandemic hit, and I wasn’t able to travel to my family, I started mailing cookies. My sister gets Auntie cookies and my dad gets my biscottis. He now requests a regular shipment of biscottis delivered.

I originally saw this idea on Half Baked Harvest and then snagged these cookie tins on Target.

What’s Inside:

Auntie Cookies

These have become a signature family cookie. It’s Dorie Greenspans’s Vanilla Sablé recipe with sprinkles instead of sugar. I send these with Rainbow sprinkles usually, but for the holidays I did red and green sprinkles. You can easily pick these up at Amazon or Target.

Biscotti with Chocolate Chips

These have also become a family staple cookie. My dad LOVES them. I recently added dark chocolate chips to the recipe and they made them even better. One recipe makes a large number of cookies. Be prepared to share if you are one or two people at home. When I make these, the neighbors get some, dad gets some and I get some for my coffee.

Chocolate Covered Pretzels

To make something Gluten Free, I made chocolate covered pretzels with sprinkles. I melted the chocolate in the microwave, dipped, and sprinkled. It was super easy, but messy. It takes a good amount of time to dry completely so be patient.

Vosges Chocolate Toffee

Another Gluten-Free item. This one I did not make but ordered from a local spot in Chicago called Vosges. You can order them as they ship nationwide. The funny thing is, my family all text that they loved the toffee the most out of everything. Thanks, guys! The one thing I didn’t make 🙂

Sugar Cookies with Royal Icing

This is the sugar cookie recipe. It uses a LOT of butter, but it is the holidays after all. I had plenty of cookies from this one recipe. I had a request from my niece Emma for snowflake cookies since she lives in Florida. I also did Christmas trees and gingerbread men.

The Royal Icing can be so messy. Last year at my sister’s, I decided to use a squeeze bottle instead of a plastic piping bag and it made all the difference. I grabbed a bunch of these on Amazon earlier this year for salad dressing and I had extra to use for icing. For under $10 for 6, this will change everything.

Let me just say that the process seemed a bit overwhelming with no time off for the holidays due to my full-time jobs. But, I carved out time on a Sunday to make it happen because I was dedicated and this was important to me. I wanted a way for my family to all feel connected even though we were apart. Everyone got the same amount of cookies and types of cookies.

Wrapping and Packing Cookie Boxes

I ended up sending all my cookie boxes via UPS 2 Day shipping. It was expensive but I wanted them to arrive fresh and somewhat on time. I wrapped each type of cookie in a different bag with a twist tie. I am happy to report, they all arrived in one piece. I did add a little tissue to the tin to help with any available empty space so they wouldn’t move around. I did this with some not all.

I hope this inspires you to make your own family cookie boxes and start a new tradition for the holidays.

Do you have a favorite family cookie?

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