Two More Sleeps

Overpacking, overplanning, and the seasons of life I never saw coming.

There are few things that get me more excited than anticipating a vacation. Almost any vacation, really… but especially the big ones. Trips to the beach. Traveling somewhere new. Or going basically anywhere with my family. I think I’ve been this way my whole life. The closer it gets, the more I think about how many more times I have to sleep before it’s finally here.

This year, I have more reason than usual to count.

We will have new family members on Anna Maria Island for the first time. My daughter and son-in-love (love, not law - law just sounds like a requirement and really doesn’t do them justice) have never been, and I cannot wait to watch them fall in love with the island the way the rest of us did. My son and his wife are already making plans for lunch dates, mini-golf, their own little agenda, and my daughter and son-in-love are doing the same. There’s something wonderful about watching people you love plan their own new version of a place you’ve been going to for years.

Our headcount upgrade has required a logistics upgrade to match. An eight-passenger golf cart for getting around the island. The biggest SUV I could find for airport runs. Four separate flights coming and going, for reasons that made sense to everyone individually, but in reality have created a small air traffic control situation that will no doubt throw us some curve balls.

Our growing family will also now require two beach tents instead of the one we’ve been using for years. I decided it was time for an upgrade and got two new tents because I didn’t want us to be those people with the mismatched beach tents. My kids think that’s a step too far? It makes perfect sense to me…

I have been packing and planning for over a week. I will not apologize for my overpacking. It is who I am; I made peace with it years ago. Thankfully, my airline status allows me three bags at 70 pounds each, and while I don’t always push it quite that far… I push further than most people would think is reasonable. I bring spices from home because resort towns charge a fortune for garlic powder you’ll use twice. I bring parchment paper and aluminum foil because I will need them, so I will pack them…70 lbs. I bring a first aid kit that would make a school nurse envious. The stories I could tell about all the times we have needed random medical supplies… My goal when I arrive is simple: not a single moment of wishing I’d packed something I didn’t. Overpacking is just preparation with commitment.

Despite all of the advanced planning I have tried to do, there is a wild card I cannot wait to see play out… the dinners. We plan for two dinners out, four dinners in and the last night we always order pizza in to allow plenty of time for packing, final beach walks, etc.

The original plan was that we would divide up into 4 teams of two. Each “team” would be responsible for planning, cooking, and cleaning up one dinner. Oh, the heated debates that have taken place over which team gets the easy stuff like tacos… Recently, however, my daughter, eight months pregnant and full of energetic ideas… has decided she wants to cook 80% of the meals. I feel sure she will have no issue finding more than enough “teams” willing to give up their cooking responsibilities, but I also feel sure that cooking the perfectly planned menus that she’s so beautifully designed in Canva isn’t going to sound so good after carrying that baby around all day at the beach. She feels certain she is up for it. We will see how it goes… regardless of how it lands, it will no doubt be amazing and fun, and everyone will get to eat.

This trip is the last one before everything changes again. As I think back over the many trips we have taken to Anna Maria Island, they were all very consistent… predictable (the kids might say almost boring). The memories actually blur together because so little changed from year to year. That type of consistency no longer exists; instead, it has been replaced with this new, ever-evolving family dynamic. Next year, there will be a baby on the beach. A whole new person to introduce to the island, and no doubt more new beach babies after that. Vacations that were once recalled by “that time we” did this thing or that thing will now be defined as “that was baby ____’s first trip.”

I am learning that the changing seasons of life are something you can’t actually prepare for.

I have always been an overpacker, overplanner, and overthinker. Despite that, this new season totally snuck up on me. If someone had told me during last year’s vacation what this year’s dynamic was going to be like, I never would have believed it. Not that it is not wonderful, and perfect and exciting because it is. But what it is not is predictable… predictability has left the family and I don’t think it’s coming back anytime soon.

I have two more sleeps before I get to find out just what this new adventure has in store for us.​​​​​​​​​​​​​​​​