Conroy's 2nd Birthday Pirate Party

“Shiver me timbers,” my baby turned 2! This year we celebrated Conroy with a pirate party in our “backyard.” I put “backyard” in quotes because we live in an apartment complex and our backyard consists of a community grill and picnic area. It was the perfect August morning and we had the right amount of shade to mingle with friends and honor our little guy. 

OK, if you know me, you know I love party planning! It just makes me happy. I enjoy scrolling through Pinterest, brainstorming with my husband, and getting crafty weeks before the big day. Georgia is now four-and-a-half years old and I can happily say I have passed my love for party planning on to her. I feel like I just met a new best friend who LOVES to do exactly what I love to do. But it’s even better because she’s my kid! I can easily say planning this party was the most fun to date because we did it together.

I wanted to make sure Georgia was involved in all aspects, so we took full advantage of Conroy’s naps and started almost two months before the party. This gave us plenty of time. We’d work on a couple projects a week and fit them in whenever we had the time. Before having children I imagined crafting with my kids to be just like a crafternoon with my girlfriends. Let me put it bluntly – crafting with kids is NOT like crafting with your girlfriends!! But I promise you, if you change your mindset, it can be even more fun. And planning this party was just that… FUN!

The inspiration for Conroy’s birthday party this year came from the most amazing bathing suit I found at H&M. It was almost like a pirate costume. He wore it when we were on vacation at Disney and right after I took the photo I knew this would be the perfect 2nd birthday party. I mean he had his “shiver me timbers” down and was really great at his “arrrrgh”.


Obviously, the most suitable invitation for a pirate-themed birthday party is a treasure map! After a couple sketched ideas, we decided to make the map more conceptual and less realistic. We used elements from our “front yard” but arranged them artistically instead of accurately. Combined with a photo of Conroy in his pirate bathing suit, plus some creative writing, the invitation turned out to be even better than we imagined.    

I knew we would hand draw or paint the elements and then bring them into Photoshop. I put Georgia in charge of the components I knew she could get completely creative with and I drew the more detailed images. She painted the brown for the map itself and then she took full creative control of the water!

We used different shades of blue and added lots of glitter. After everything was dry I started scanning our art into the computer. She said, “Hey, mom, can I try?” I quickly replied, “Of course, you can!” Then the next thing I knew she was doing it all by herself! I was so impressed.

We love giving the party location a special name so we called it “BBQ Island.” We used a photo of Conroy in his pirate bathing suit and added all the text in Photoshop. To let our guests know they didn’t need to buy us gifts, we kept it playful and wrote, “No Gifts or You’ll Walk the Plank” on the back.

We chose blue envelopes and addressed them to all of our “buccaneer,” “matey,” and “captain” friends. Conroy joined the fun by being in charge of the postage stamps.

Georgia handled actually mailing the invites!

Once the invites were sent, the fun really began! Pinterest is full of great ideas for pirate parties. I spent a couple days pinning and then picked a few projects to make. A blissful trip to Hobby Lobby & Target sans kids really set the tone to fully enjoying this entire party planning process.


Currently, one of Conroy’s favorite things to do in life is walk across anything that slightly resembles a balance beam. When I saw this on Pinterest I knew we had to make it. We found some crates in my parents’ garage and used a scrap piece of wood for the plank. Everyone loved it.

We painted the “Walk the plank” sign in their driveway. This project is the perfect example of my theory on crafting with kids. It is so much fun. However, if you are at all slightly a perfectionist or enjoy being in control, doing crafts with kids can be a little tricky. Here’s what I’ve learned: take a deep breath and let them take the lead. While we were painting the sign, Georgia dunked the paintbrush in the paint and a huge drip completely covered some of the words I had painted. I told myself it was fine and asked her what else we should do. She suggested we paint the whole thing red. I loved this idea (and I was able to touch-up the wording by filling in the negative space with red). We did a little more Jackson Pollock dripping to make it cohesive and the sign turned out amazing.   It was very “pirate-y”!! And she was so proud!


I loved this craft. It was simple, modern, and a perfect summary of the party. I bought a cardboard #2 from Hobby Lobby along with some red craft paint. We covered a table with newspaper and painted it on my parent’s back deck. I love doing crafts outside!!


My mom is an excellent party planner and always up for a challenge. The moment I saw the Pirate Ship Fruit Bowl on Pinterest, I knew she’d create the perfect centerpiece for the party. In true Cathy Conroy form, she did a test run with the kids one weekend when they were on a camping trip. Georgia and Conroy loved helping and, of course, taste testing. 

The rest of the menu was pretty easy to figure out since we were having the party at the grills: BBQ food!! We decided to go with hot dogs and beef tenderloin. My husband Chad isn’t as much of a party planner as I am, but he sure knows how to entertain and really enjoys it. I think the only thing he kept talking about for the party was cooking a really good beef tenderloin, cutting it up, and a serving it off the cutting board so everyone could just grab a piece. He executed it perfectly and everyone raved about how good it was. We also had pasta salad and a veggie platter.


Oh, man, I really wung the cake! Two hours before the party started I still didn’t know how I was going to decorate the cake. We had already made cupcakes and decorated them with cute pirate flags, but I wanted a special cake. I kept thinking I was going to make his actual cake look like an open treasure chest full of gold and necklaces, but it was going to be too much work. At what seemed liked the eleventh hour, I thought, “I’ll just make it a closed treasure chest.” I used one of the gift boxes as inspiration and had it down in a half hour!


There are so many different options when it comes to dressing like a pirate. I bought several different hats and some eye patches, and made some telescopes out of paper towel rolls. And, of course, we ordered Tattly tattoos and had an adult help apply the tattoos. We ordered this setthis ship, and my mom & I wore these.

We put everything in a big bucket right by the entrance. As people arrived I let them choose something to wear and snapped a quick family photo. I love doing this, especially for years later when we can look back at everyone. Also, I feel like getting a family photo is pretty difficult to do in the busyness of life so making a point to do it is always a great idea.


For crafts we did our usual coloring book page with a photo of Conroy. This time I positioned him on a pirate ship. We put out pirate stickers in addition to the crayons for this party. I also found the great plastic stained glass set that included little paint buckets. Since many of his friends are Georgia’s friends, this was a great craft for four-year-olds.  

My Aunt MaryAnn from Florida came for the party and brought a simple pop-up tent for the kids to play in. They loved this. Any place that can be “just theirs” is a hit these days.

We also laid out a picnic blanket and a small Busy Zoo toy for the little ones who were just learning to walk. 

Since it was such a warm day, we also set up a water activity table.


Most of Conroy’s friends are 4 years old, even though he’s two, because the majority of his friends are Georgia’s friends and their younger siblings. I knew I wanted to do something special for the older kids. At this age, they completely understand an egg hunt and Hide & Seek is pretty much their favorite game so I figured they would totally love a pirate treasure hunt. I was right. We hid “treasure” puzzle pieces and handed out treasure maps. Each family had to find their piece of a puzzle and then work as a group to solve it and discover the picture! This was such a hit. I wrote a tutorial post for anyone who wants to create one for their next party.


What says birthday party more than a “piñata?” And I found the perfect treasure chest piñata at Hobby Lobby. It was the kind that has strings you pull instead of hitting it with a bat. But here’s the thing: we live in Brooklyn and NO ONE we know gives their children candy here. I am all about fun and, naturally, you think you must put candy in a piñata for it to be a good time. Then I thought: you know what?…I bet most of these kids don’t know candy is supposed to be inside so it’s not like they would be disappointed. So…I put clementines inside!! It was a huge hit!...with both the kids and the parents. And even our friends from the ‘burbs, who have mastered the candy collection after the piñata, is opened loved the clementines!! I was so happy because, honestly, that could have been a party foul for sure!


This is still one of my favorite memory keeping mementos. I love thinking of the different questions to reflect on the past year of Conroy’s life. I almost forgot to hand the quiz out this year because we were all having such a great time. Then, because it’s kinda what we are known, for someone said, “hey, did you do a quiz this year?” Grandpa again scored well and so did our good friends the Sterns!!

Overall, this whole party experience was ideal. I could tell Georgia loved making Conroy feel special. I could also tell Conroy liked having a party to celebrate him. For weeks after the party, he would look out our windows and say, “We had my birthday party there. We sang ‘Happy Birthday To You’ and I blew out the candles.”

As with every party we plan, it keeps getting easier and more fun. We have gotten the swing of having enough for the kids to do but not overscheduling it. We love that everyone had a wonderful time with all their friends…Georgia, Conroy, and us, too. When you have children you get to make a whole new group of friends. These people become part of your village. Celebrating with them, catching up, reminiscing, and making new memories is so important to us. We are grateful for everyone who came and spent the morning together.

We hope this inspires you in one way or another - whether it be crafting with your kids, new ways to enjoy party planning, or a fun game to play with your friends. We believe any event is a great excuse to have a little extra fun. We’d love to hear about your latest celebration!









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