It has recently come to my attention that for my entire life I have been packing all wrong. My husband and I had our son 10 months ago and for our first road trip with our baby boy Logan I managed to fill, to the brim, an ENTIRE SUBURBAN. I packed everything baby related we owned. My son was three months old at the time and we were traveling to Massachusetts to visit family. I packed- a rock and play, a pack and play, a bassinet, the stroller attachment (just in case!), tons of books, stuffed animals, every item of clothing we had in his size and the next size (just in case!), warm weather clothes, cold weather clothes (I mean it was November, so ambiguous!) , white noise machine- you get the picture. Yet what did I pack for myself? Well, somehow I managed to forget to pack even one single shirt and absolutely zero underwear wound up in my suitcase. Just a few pairs of pants, a sports bra and a cardigan was unearthed in my bag that was otherwise filled with baby items. I ‘borrowed’ my mom’s clothes the whole week and ran to Saks for some new Hanky Panky’s.

Yes, this was an extreme case caused by baby brain maybe but looking back I really never nailed the whole packing thing. I have traveled a lot over the years and always thought about packing in more vague terms. Going to the South of France two years ago pre baby, I kept thinking flowy dresses and big sunglasses. I wound up wearing the same thing pretty much the entire time, a black flowy dress, with black sandals for nights out and a blue and white striped shirt with jeans and mustard Chloe flats for day. Only two outfits worked and we were there for two weeks! I always seemed to do the same thing, just pack a bunch of stuff that I like but when I arrived to my destination I realized almost immediately that half the things I packed didn’t fit properly, I didn’t bring the right shoes or even the right undergarments, I would bring a purse I loved but it went with absolutely nothing, and I never ever bring enough casual shirts.

Most of the items in my suitcase always go unused because while cute they are completely irrelevant. I was always all over the place because I never took the time to really think ahead. I would be buying books at the airport last minute because I forgot my kindle while remembering that the snorkel we have had stored in the entry closet for seven years is still in the entry closet and that we will have to buy yet another one. In most parts of my life I am extremely organized but packing, frustratingly, was never one of them.

Well, since that first road trip with our son, I have vowed to ACE this whole packing thing. I have become increasingly better with each trip as I started to understand the art of packing. We have flown to Palm Beach twice to visit my family and to Boston three more times by car. Having a baby and traveling means you need to think ahead and plan ahead, while staying organized without extraneous things holding you down.

This brings me to our upcoming trip, the one we have been waiting (and training) for. The big event this summer, Nantucket. We leave Saturday and will be staying for two weeks. We will be flying and staying in a home that we have rented. This trip will have a lot of moving parts. We have invited my mom and stepdad, my dad and stepmom, my in laws, and one of our closest friends to stay for varying nights. The second week my husband and I plan to relax on our own (yay!). So we have a baby, we will be having company and therefore entertaining, we will be having cookouts, date nights and beach days, I also scheduled a photoshoot a day when all of the grandparents will be there as our son approaches his first year (Christmas gift, check!).

To start tackling this I began by visualizing the whole trip from the moment I leave the house for the airport and just started jotting down what I need as I walk through the vacation. Just freeform at first. Then I used Emily Ley’s free printables to help organize these notes into actual lists. I use her printables often and find them helpful for my lists and planning for each week, I also have her planner and family binder. When choosing items off the packing list I have found it is easier to pick a theme for each trip. Anyone who knows me knows I looove a theme. So for Nantucket the theme is, obviously, American Summer. All outfits are various tones of red, white and blue with a little bit of beige. If it does not fit into the theme, it is out. This theme trickles over to the whole family, since I pack for them as well (yes, I pack for my husband, it is just easier that way). A theme just makes your mind clear and you can be very cutthroat i.e. a flamingo shirt? NO that is definitely Palm Beach not Nantucket and so on.

Three weeks before I put together and tried on all of my full outfits including bathing suits and cover-ups. Full outfits are to include, a shawl for cool nights, jewelry, undergarments, shoes, purse, hat. I sent out dry cleaning, brought in things for alterations, and did laundry. I also needed to consider the entertaining aspect. So I purchased cutesy summer cocktail napkins from Paper Source and some summer fun treats from Sunnylife, a couple games I came across at ABC home- Ridley’s charades and movie buff, as well as our good old standbys: Blokus, Backgammon and a deck of cards. I also made a family fun playlist for the ipod and brought small portable speakers.

My mom and step dad are kind enough to be driving to Nantucket from Boston via ferry. So we sent them them our luggage last week along with a baby Amazon order with all of Logan’s ‘stay fed and get clean essentials’ (a trick we have learned along the way). We have Petite Travelers in Nantucket baby proofing the house and setting up our baby items that we are renting through them, the crib, changing table, blackout blinds, gates, etc. We also rented beach chairs, beach stroller, beach toys, and a cooler from as well. They will even be stocking the fridge with some first night essentials.

Seems like I have it all under control, right?? Let’s hope so! Now that the packing is taken care of I need to start planning some activities for the family and put together some recipes and a grocery list to tackle the day after we arrive. Since our baby’s bedtime is still super early around 6:30-7 we will be spending many nights at the house grilling. So definitely need to plan ahead for that!

Petite Travelers  •  Emily Ley Printables

Some of the items in my suitcase and where to find them

Ridley’s Charades • Sunnylife Playing Cards •  Sunnylife Radio • Simplified Planner • Cocktail Napkins • Backgammon Set • Travel Jewelry Case • Carryall Beach bag • Ralph Lauren American Flag Sweater