This is what could happen:
Grab a few of your best best friends. One you love and could live with forever, one you could be attracted to maybe, one who's a little awkward, very honest, and sweet. They all love to laugh. Go somewhere with cool mornings, balmy days, and nights without too much light pollution. Somewhere with a beach, preferably, but failing that, excellent rows of tiny, independent shops and fabulous sidewalks.
This is what you pack: underwear, socks, flip flops, curling/straightening iron, blouses, t-shirts, jeans, skirts, a bikini or two, contact lens solution, glasses, brush or comb, sunblock, sunglasses, lotion, some nice shoes, toothbrush, toothpaste, nail clippers, a small bit of jewelry, makeup, and q-tips. Fortunately for you, the friend who is always prepared has packed a camera (which you always lament forgetting), aloe (because none of you remembers to wear sunblock), mouthwash (because sometimes you don't feel like brushing your teeth), and q-tips (because you thought you packed yours, but you really just dropped it beside your bag).
There is lots of sun. There is lots of sunkissing. Possibly sunmaking-out. Your shoulders are a touch burnt, but that's ok. You spend all of your time in a bikini. You buy a bunch of cheese while giggling at the grocery store (still in bikinis). A chevre, a nice manchego, a St. Andre, a Gruyere, some random semi-soft cheese, and somebody splurges on some sort of fruit conserve. There are about a million different types of crackers in the snack aisle and you pick the one with the funny name. There is a decent amount of cooking (apron over bikini). There are lots of late-night greasy food runs. You make lots of cocktails and drink them and share them and it's ok to fart because a.) it's always been ok to fart b.) fart noises are funny and c.) we're spending a lot of time together and you just can't hold it in the whole time, ok? It's picture time and you all make your best fart faces.
Boys hold a lot of possibility and excitement and they holler like they don't know any better but it turns out they're all boring know-it-alls and you go find an excellent local jewelry shop and each end up buying some earrings. They sparkle and glint and are a great deal. Every morning you wake up and slowly sip tea or coffee or mimosas or belinis. You see squirrels or geese or some other animal that congregates on the ground and everybody decides to chase them. You start out slowly walking toward them and they edge away. Then the chase moves faster and they start to run and make a bunch of noise as they get all flustered. They honk and chatter.
You all reveal something sad about your lives. You make scrambled eggs with Gruyere and everybody is quiet and contemplative but by the time the eggs are gone everybody has put the feeling somewhere else. Maybe it is in your stomach with the eggs.
The last morning everybody wakes up and has breakfast together for the last time for a long time. It's quiet because you've been together this whole time and you're thinking of the parts of your life the others can't relate to because they live so far away. Packing is slow-going. Everyone talks in soothing tones. You touch each others shoulders or backs a lot. Everyone's hands are soft and cool. In your throat are memories. In your chest is a hollow. You swallow the memories into this hollow. It is a bittersweet pill that makes your thighs sluggish and your brain unable to draw up words to say to everyone, so all you say is, "See you soon! Have a safe trip!" You get home and are glad for your own bed. You hope she stops dating that guy. You hope the other can find a new job. You dream that they are all nesting dolls. You dream you are the biggest one. You dream they can all fit inside. You dream that you crack open and they all roll out. You wake up and go back to your life.
EDIT: Totally forgot to put down a rule.
Rule: When you're on vacation, you should be able to wear whatever you want and eat whatever you want.