Valentine’s Day Dessert Box

I had so much fun making my Christmas cookie box this year I decided to make a Valentine’s Day dessert box!

While it might look like all fun and games, a lot of thought and planning goes into making a dessert box like this.

Let’s walk through the process together to make sure your Valentine’s Day dessert box turns out as amazing as possible!

Picking Out the Perfect Mix of Cookies

The key to making a stunning Valentine’s Day dessert box is all in the assortment of desserts. You want a variety of flavors, shapes, and colors.

Having a variety of flavors and textures is pretty self-explanatory! It keeps the cookie box interesting and makes sure there’s the perfect cookie for everyone.

In terms of shape, having different shapes and sizes is crucial. It not only gives the box an interesting, eye-catching look, but it also allows you to properly fill the box. A mixture of smaller and larger cookies lets you fill in all those little gaps and create a gorgeous-looking box.

It’s also a good idea to consider color. If you have all brown cookies, the box is going to look a bit lackluster. Incorporating some bright pops of color gives the box a stunning, seasonal look! This can be done by coloring the cookie dough or frosting, adding sprinkles, or picking a fun cookie design.

If you’re a Type A person like me, you can make a chart with pictures of the recipes you plan to bake to see what it’ll look like. It won’t look quite the same, but it’ll help you take a step back and see how all the cookies look together.

Below is my planning grid for this year’s cookie box. I had to fill in some photos of what I was envisioning, and I ended up making fewer desserts than I included in the grid because they wouldn’t all fit in my heart-shaped box. But you get the idea!

I did this with Canva (which I think you can use for free), but Microsoft PowerPoint, Paint or any program that lets you play around with pictures should work.

I decided the mini marbled heart cookies and the conversation heart macarons could be unique shapes, and the chocolate raspberry truffles and mini macarons would be small enough to fill in any open gaps.

Planning It All Out and Breaking Up the Process

Once you figure out which recipes you want to make, it’s time to figure out the timeline. This part can vary based on how many types of cookies you plan to make. However, I recommend breaking it up into phases and spreading the work over a few days.

It makes the process so much more enjoyable and reduces the stress around all that holiday baking! Because I was making 7 cookie recipes, I aimed to make them over 3 days and baked 2-3 types of cookies per day.

As you plan things out, it’s important to look through each recipe and see what the yield is. You also want to consider how many cookie boxes you want to make, and how many of each cookie you plan to include in each box before you start baking.

For example, if I want to make 6 dessert boxes and plan to include 8 raspberry truffles in each box, I’ll need 48 truffles. The recipe makes 25 truffles, so I’ll need to make a double batch when it comes time to make them.

Once you figure out how many batches of each dessert you’ll need, see if you can further batch your cookies to simplify the process.

For example, in my dessert box, the mini marbled hearts and the penguin cookies use the same base dough.

I made a double batch of dough to streamline things and it saved me some time!

My baking schedule went like this:

• Day 1: Mini Marbled Hearts, Penguin Cookies, Double Chocolate Cookies (batched together because the hearts & penguins use the same base dough recipe)
• Day 2: Conversation Heart Macarons and Raspberry Chocolate Truffles (paired the truffles with the macarons because they’re quick and easy and the macarons take a long time)
• Day 3: Raspberry Linzer Cookies and Red Velvet Crinkle Cookies (these were just the remaining cookies to be made!)

Making the Cookies in Advance & How to Store and Freeze Them

Before you start to stress about all the baking, remember that your baking days don’t have to be consecutive! I know plenty of people who make them over a couple of weekends to spread out the work.

With that in mind, storing the cookies properly so they taste nice and fresh when it’s time to assemble your dessert box is a must. You also want to make sure you have plenty of freezer space available if you want to make the cookies in advance.

An important factor here is that the recipes you chose can be made in advance and frozen. A majority of cookies can, but some can’t. It’s important to check that they can be frozen and to confirm how long they can be frozen for.

All the recipes I used to make my Valentine’s Day dessert box can be frozen for up to 2 weeks. However, I made them all about a week before I assembled my boxes.

I recommend freezing your cookies once they’ve fully cooled in an airtight container or freezer ziplock bag with parchment paper between the layers of cookies. If you have any delicate frosting decorations (like my cute little buttercream penguins!), freeze the cookies on a flat baking sheet before stacking them.

I was able to squeeze all my cookies into a few large airtight containers and freezer bags. Make sure you store any stronger flavored treats (like the raspberry chocolate truffles) separately in their own ziplock bags.

You also want to think about flavor if you combine different types of cookies in one container. Try to group similar flavors. For example, I stored the penguin cookies and double chocolate cookies together.

Ordering the Right Boxes

While the cookies are the star of the show, the box that they go in is important too! The size of the box that you need will vary based on how many cookies you make.

Because I made 7 types of cookies, I used these cute heart-shaped boxes. I liked these because they were sturdy and I loved their shape, but they were not cheap ($20 for 2 boxes!!).

If you make a similar number of desserts, I’d recommend getting an 8-inch square box. If you make fewer treats, I’d recommend using a cupcake box like this.

Most of these ship in a couple of days with Amazon Prime, but make sure you plan accordingly so that the boxes and any cute ribbons or bows you want to decorate them with arrive before you need them.

Assembling the Perfect Valentine’s Day Dessert Box

Now that we’ve figured out all the logistics, it’s time for the best part – assembling the boxes!!

If you’re making a larger box than mine, place a greaseproof cardboard cake board underneath the cookies to give the box support.

I also folded a large piece of white parchment paper into the box underneath the cookies to give it a cute, homemade look.

You might already know how you want to lay out the cookies, but my advice is to have fun with it!

Play around and shift the cookies until you feel happy with how they look. I like to start with the biggest cookies, followed by the smaller cookies. I also tried to space out the colors and cookies that had cute little faces.

You can also arrange cookies on their sides, tie up a stack of them with cute twine, or layer them at an angle to create more dimension.

The finishing touch is a fun ribbon or add a festive bow and a cute little tag!

How Far in Advance Can You Assemble Valentine’s Day Dessert Boxes?

While the cookies can be baked and frozen 2 weeks in advance, it can vary based on the treats you include.

For example, chocolate-dipped strawberries are typically only good for 2 days in the fridge. I recommend assembling your dessert box as close to when you plan to share them as possible.

Sadly most cardboard boxes aren’t airtight, and that means the treats will become stale as they sit out.

My general rule of thumb is that dessert boxes like this have a lifespan of about 2 days. Most of the cookies will still be okay after that, but they will start to dry out and lose flavor.

Another important factor that impacts the lifespan of a cookie box is whether you decorated any of the cookies with buttercream. Cookies with buttercream can only sit out at room temperature for 2 days before they start to spoil.

How to Ship Valentine’s Day Desserts

While the process and photos above are great for local deliveries, the process is quite a bit different if you want to ship the cookies.

It’s a good idea to stick with sturdy cookie recipes that can survive a few bumps. Remember to factor in ship time when making the cookies in advance so that they still taste fresh when they arrive.

To pack the cookies, try to group similar cookies in freezer ziplock bags. This is my preferred method because I think it keeps the cookies the freshest. You should be able to fit 2-4 types of cookies in each bag.

Or if you want a cuter presentation, you can also package each type of cookie in its own cellophane bag. Just be sure to seal the top of the bag really well to keep them fresh.

I highly getting some bubble wrap to line the inside of the box to protect the cookies as they ship. You can also fill in any space between the cookie bag with tissue paper or packing peanuts.

It’s also a nice touch to include a cute little card on top of the cookies.

In terms of the box you use to ship the cookies, I highly recommend using flat-rate USPS boxes. You can pick these up at the post office or order them online. They come in a variety of sizes, are nice and sturdy, and ship quickly. You can pick anywhere from overnight to a couple of days), and have a set price no matter how heavy the box is.

I usually opt for overnight shipping because some of my cookies are usually decorated with buttercream.

It’s best to get the boxes in advance and pack the cookies into them at home. That way you can carefully fill each box and tape it up really well before heading to the post office. It’s also a good idea to add a fragile label or write fragile on the box too!!

Then when you get to the post office, you can use the Kiosk to print the labels and drop off the boxes.

You can also overnight the cookies through UPS or FedEx, but I find it’s a lot more expensive.

This Year’s Cookie Assortment

While making 7 desserts was a bit ambitious and took me a few days to complete (especially because I’m 32 weeks pregnant), it was totally worth it in my opinion.

I love the combination of flavors, shapes, and colors!! Below are the recipes I used:

1. Penguin Cookies

2. Mini Marbled Heart Cookies

To make these I used half of the cookie dough from the penguin cookies (which is a chocolate version of my cream cheese cookie dough) and a 1-inch heart cookie cutter. They’re decorated with a batch of my royal icing which is linked in the recipe above.

I also added on some edible gold leaf for a little extra pizazz.

3. Raspberry Chocolate Truffles

4. Conversation Heart Macarons

5. Red Velvet Crinkle Cookies

6. Raspberry Linzer Cookies

7. Double Chocolate Cookies

Let Me Know What You Think!

I hope you found this post helpful and that your Valentine’s Day dessert box turns out amazing!! If you have any questions I didn’t cover above, please ask them in the comments section below.