We are doing a Trip to FL 12/14-12/31 including 3 nights at USO, 2 nights at our timeshare in Orlando 8 nights at WDW CBR, and ending with 4 nights at Daytona Beach. My idea is to pack only 5-6 outfits per person (we are a family of 4 Me DH DD14 and DS8) and to plan on doing laundry a few times. The problem is I have no idea what to pack Beyond bathing suits, shoes socks and underwear and PJs). Do I pack pants? Capris for the girls? Shorts? Do we need winter gear or will a zip up hoodie suffice at night/early morning? We are from MI so no strangers to cold but I have no idea how to pack appropriately for this trip!! I am trying to pack all our clothes into our individual carryons but we are checking one bag (mostly empty hopefully in order to have room for souvenirs on the way home but is also where I plan to pack toiletries in order to avoid the liquid rules for carry ons and random other crap like my husbands pillow he can’t travel without. How would you pack for this trip? Oh by the way it is a surprise for the kids they won’t know until we leave so I can’t ask their input.
We were there last year from 12/20 to 01/02. Mostly temperate weather until the last 4 or 5 nights when it became stinking cold out there and thennnnn the days were wet and cold too. Fortunately, we had warm outer wear w/ us since we traveled from NYC. DGD had a 20 minus down jacket that fits in a travel compression bag and a hoodie from Pandora that we bought as a holiday present; she wore both a few evenings. The man had a down lined fleece zip up, and I had treated self to a cashmere wrap just before the trip started-oh and nowwww DGD wants
my wrap so I told her when she gets her MBA she can have it

. Both adults were comfy with their cold weather gear.
As for your overall goal of packing? Totally doable from my POV. This is my packing list from last year's trip:
The man - 2 bathing trunks, 3 pairs of cargo shorts and 1 pair of chinos and one pair of jeans. 3 Tommy Bahama shirts, some solid, some prints. 2 or 3 polo shirts.
Furnishings for a week (AKA underwear) and 3 pairs of footwear: 2 pairs of sneakers with one pair being black leather and can be used as dress shoes. One pair of Velcro strap flip flops that work for the beach, general walking, and pool.
DGD aged 12 at the time of the trip:
5 bottoms. A mixture of solid shorts, leggings, and 1 skirt. All mostly dark in color. One pair of basketball shorts for sleeping and park wear .
7 shirts that do
not need to be ironed; she doesn't want to use an iron and neither do I. When wrinkles are apparent they were hung in the bathroom and hand stretched during a hot shower.
3 bathing suits. Two would have been fine but well you know....
Two simple dresses (also no need to iron) for church services and fancier restaurants. One was multi coloured from Lily Pulitzer and got a lot of play. The other functioned as both a bathing suit coverup(on sale for 5 bucks from Target's and made of a high denier t shirt mostly cotton fabric), park and restaurant wear.
Several bandanas in various colors although she wasn't adverse to borrowing my scarfs too.
Lingerie for 5 days. Hand wash nightly and go.
2 or maybe 3 pairs of socks- hand wash them nightly too.
One pair of sandals that functioned for "evening" and theme park/ water park use. They were actually flip flops with adornment changes to fit the occasion. 2 pairs of sneakers. One pair leather, the other, a mix of leather and fabric.
Me, a woman of a certain age, who has been dressing the same way for at least 20 years. I call it urban ready for anything, LOL.
4 days worth of lingerie; I hand wash nightly at home and on the road.
2 bathing suits.
5 mostly cotton t shirt dresses in various colors. Some with spaghetti straps, others with cap sleeves.
3 pairs of leggings; white, black and chocolate brown. Some are capri length, others, ankle.
A pair of yoga pants for sleeping and outdoor wear. Generally black or dark gray.
3 t shirts: white, black, and whatever fashion forward color that matches the rest of my wardrobe. One over sized t shirt for sleep and park wear.
As many colored coordinating accessories that will fit in my jewelry case. Scarves are thrown into any available space in anyone's luggage.
2 pairs of leather and fabric sneaker mules; one pair of fashion forward wedge sandals.
2-3 pairs of footies.
Generally two fold-able hats. It's just who I am.
Toiletries and makeup. Divided between the 3 airport carry-on bags. I do not duplicate items already given as hotel amenities unless someone has allergy concerns.
One wristlet pocketbook works for all occasions and fits everything I need: 2 credit cards, a govt issued ID, cellphone, and ephemera. Also makes going thru security faster.
I roll most all the clothing to make more space, and when needed, lay flat using tissue paper and plastic bags to prevent wrinkling.
I've packed Tide "balls" and vinegar for washing clothing but so far haven't used them at Disney's laundries. I find hand washing relaxing.
Everything fits easily in our 24"-25" spinners and wheeled luggage even when dirty clothing are packed in zip lock type bags. Push the air out and roll same as clean clothing.