This is my goal for an upcoming two-week trip to the Caribbean (yay, yay, yay!) in December. Actually, packing and traveling light has been my goal for every trip I’ve ever taken thus far in my 42 years of life.

Sadly, I’ve yet to once succeed in this seemingly simple endeavor. Now factor in additional packing for my one-year-old, and I already feel destined to fail. Miserably.

The what-ifs are what get me every time. What if it’s cold? Better pack a sweatshirt (or three) and a jacket. What if it’s hot? Better pack 100 of the exact same tank tops in varying colors. What if I need running shoes? Better pack those along with the dress shoes and the several pairs of flip flops I already have shoved in the suitcase.

You see where this is going. Next thing I know, I have way too much stuff and I know I’m not going to wear it all, but I still bring it because… WHAT IF? (Insert a million different scenarios here.) See my dilemma? As much as I am mindful that this is the root of my packing problem, it will still be an issue. It is always an issue.

The good news is that this is a totally casual trip, so I won’t need to even consider bringing anything fancy. No meetings, no conventions, no formal outings. I mean, it’s the Caribbean for cryin’ out loud. Do I really need much more than a bikini (eh, a tankini these days…), sunscreen and one pair of flip flops?

Ideally, no: realistically, yes.

We’ve already mentioned the one-year-old and the vast assortment of distractions and contraptions I may need solely for the flight.(He’s never flown before, so I just don’t know what to expect. But that’s a topic for another blog post.)

Then there’s this thing of choosing a self-catering vacation, which we decided to do. No hotel for us. We’re renting a harbor villa for part of the time, and a house on another part of the island for the remainder of the time. This is a great option for us, it’s just that I’m already pondering which cooking spices I can’t live without and how I’m going today efficiently pack them. Daily vitamin container? Contact lens case?

See, I am already mentally packing more than just a swimsuit and flip flops. I can only imagine the realm of possibilities I will ultimately consider. Oh yes, friends, this is only the beginning of my fragmented thought process that will soon exponentially expand out of control.

I need help! I’m not too proud to beg.

I already “know” the basics: pack neutral colors with mix-and-match options, think layers, have a minimalist approach, yadda, yadda, yadda. I also realize that I can easily cut out my redundancies and be much improved. But I need more. That’s not enough for me. I need tangible, to-the-point recommendations that work. Hints, tricks, hacks, common-sense things; I need them all. I’m desperate.

This is where you come in. If you could share your most helpful tip(s) for packing and traveling light, I would be much obliged and eternally grateful. If you have some kid-friendly ideas, those would be super helpful as well.

I need to conquer this. I need to master this skill. But I already know that I can’t go it alone.

Ready, set, go! I’m open to as many suggestions as you are willing to give.