LOL - if you are a chronic overpacker, you'll think I'm nuts. For my family of four for a trip of 4-8 days, we pack a total of four 21-22" carryon bags and two personal items (that fit under the seats of the plane). Fully packed, each carryon weighs about 20-22 lbs.
EACH FAMILY MEMBER (DH, me, 11YO son and 9YO daughter) HAS - a single 21-22" carryon rolling bag, containing: (1) 2 pairs of sandals (1 hiking, 1 flip-flop); (2) 2 medium packing cubes containing 5 or 6 warm-weather outfits (shorts and top) with undergarments and socks, PJs, swimsuit and rashguard; (3) for me only, an ebags "Pack-it-Flat" toiletry kit with all of my non-liquid makeup items, the whole family's toiletry items and toothbrushes, razors, deodorant, combs, etc.; and (4) for me and DH only, 3-1-1 bags with liquid makeup items, moisturizer, primer, our preferred shampoo, toothpaste, sunscreen, shaving foam and a laundry detergent pod or two (if our visit is going to be longer than 4-5 days, which means we'll schedule a mid-week pool morning and do laundry). Additional items (packed in small packing cubes and spread between the kids' luggage, which due to the smaller size of their clothes are only 75% full after all of their clothes are packed) include cereal, granola bars and Pop Tarts for breakfast, powdered coffee creamer, hand sanitizing wipes, glow sticks, autograph books/pens, a packable beach bag, swim goggles, disposable rain ponchos, clothespins and a cloth laundry bag.
DH AND I EACH ALSO CARRY - a "personal item" for the plane (tote bag for me, backpack for him), containing our boarding passes, snacks for the flight, IDs, phones, electronics and chargers, earbuds, paperwork, everybody's sunglasses, MagicBands, a pair of shorts for ourselves and each of the kids to change into once we get to Florida. Tucked inside my tote bag is my "park bag," a tiny crossbody purse with all of the important stuff - ID, credit cards, etc..
TO TRAVEL, WE WEAR - all of our bulkiest clothing: sneakers, jeans, T-shirt and hoodie. We're usually flying down when it's cold at home and hot in Florida, so we change into shorts on arrival and don't need the jeans again until we fly home.