Packing is one of those things that stumps most people. Packing for two months? Even worse.

I feel like I’ve gotten things down to a science by this point—particularly when going on a long trip—though I will admit I didn’t properly anticipate the fluctuation in weather we’d have over an eight-week period in Europe. It started with rain and cold in Barcelona, then gave way to sun and heat in Italy and Portugal, then was downright freezing (around 40 degrees) and pouring in Benelux. But most of you going on cruises are not going to experience such extremes in weather, as I venture to guess you will be gone one week to two, tops (and likely in one of two locals: the Caribbean or Alaska). So let’s talk about packing for your typical cruise shall we?

I always start with the shoes, which take up the most room. I’m a big fan of neutral-toned sandals that can be worn by day if needed but that go with everything by night. On this trip, I took two pair (both made by Sam Edelman), but you only need one for a shorter vacation.

I also took a pair of running shoes, and as those can be bulky, I’m loving the Merrell Barefoot Pace Glove that my sister gave me for Christmas. They fold up quite compactly in your bag if you don’t wear them on the plane (which I do). I also pack a pair of flip-flops (Havaianas) and a pair of TOMS, always.

Of course, taking closed-toed shoes means packing socks, so I stuff two pairs inside the shoes if packed (knowing that I can wash them in my sink if I wear them more that two or three times). My intimates all go folded up as small as possible in a gallon-sized Ziploc bag that is lain flat on top of everything else, that way I can find them immediately when I inevitably shower the second I get off that long plane ride and settled in my cabin. All of my toiletries are three ounces or less, packed in a see-through Ziploc and transported in my carry-on. That way, if my bag is lost by the airline (a common occurrence), at least I can brush my teeth.

But onto the good stuff: the clothing.

I’m a dress girl, as most of you know by now, so my suitcase is dominated by cotton frocks that fold up quite small, and once I have the majority of my necessities in the bag, I fill the excess space with a mix of short sundresses and maxi dresses. I recently interviewed celebrity stylist Petra Flannery—who styles Emma Stone, Mila Kunis and other starlets— for a Glamour feature, and she told me she hangs every outfit together on a hanger, wraps it in plastic then folds it over once in the bag to eliminate wrinkles. But most of us “normal” people don’t have the luxury of so much space, so I roll my clothes as tight as possible to save space and prevent wrinkles and then keep a small bottle of wrinkle release (which you can buy at Wal-Mart or Target) in my toiletries bag to fight wrinkles on-site. Works like a charm.

Prior to my departure, Before + Again asked if they could send me some clothes to try for my upcoming trip, I said “sure!” and so I had four new dresses to test out this trip.

I’d never heard of this company before they reached out to me, but it’s a cool concept: You pick the print you like and then you pick the style and fabric, and they make it for you. No two pieces are alike, which is pretty neat, no?

The best thing about these dresses is that they are lightweight and transition well from day to night. In other words, they’re casual enough to tool around port in but look nice enough to also go out to dinner.

I also pack a couple cardigans—usually one in a neutral tone and then go bold and pack something like yellow and cranberry that I can pretend match each ensemble—as it’s often cold at sea at night and even colder inside a cruise ship. On this cruise, I took a jean jacket and a hoodie, which you might not need in the Caribbean but which were crucial in late spring in Europe.

And though I loathe jeans, I pack a pair in the case of cold. And then, of course, a top or two to go with them. (This year, I’m loving Gap’s thin, colorful Tees that they offer in a rainbow of hues.)

This trip, too, I vowed to work out—something I never do on vacation—and I did: I made it to Zumba almost every day at sea. But don’t reserve too much space in your one suitcase for workout gear; one outfit will suffice, and you can re-wear it each time you hit the gym (you’re going to get sweaty anyway, right?).

Electronics are a whole other beast—for me, if checking a bag, then one carry-on is my camera bag, while the other is relegated to my laptop and Kindle—but everything I mentioned above should easily fit into a standard suitcase. I mean, I packed all of that and more in my Tumi to get me through eight weeks, and I hit the 50-pound weight limit exactly (try not to, though, if you can avoid it as you will be hauling that thing around for some time!). Personally, if I’m traveling for 10 days or less, I make it my mission to only take one rolling suitcase that is carry-on size to avoid checked bag fees and the possibility of the airline losing it.

Of course, my motto is always this: Leave something at home? Excuse to go shopping! And speaking of leaving things at home, forgo the heels, ladies, and also the excess accessories like handbags, scarves (aside from maybe one), etc. You think you’re going to use them, sure, but you’ll get on that ship and realize that less is more. You’re traveling; you’re not appearing in a fashion show!

Before + Again wanted to give a reader a dress of their choice, pending my approval of the brand (which I love! I genuinely do!), so if you want to throw your name in the hat, tell me the following:

What’s the one thing you never leave home without when going on a vacation?

I’ll pick one randomly selected winner at 5pm PST on Friday, June 28.

Update: Contest closed.