I've done it. Each person carried a rolling carry on plus a backpack. I have to say - it was a LOT of stuff to lug through the airport and keep track of. And - I think I was grumpier because we did have free checked bags - but DH hates waiting for luggage at the other end. That said, I would do it again. Especially if I have to pay to check my bag.
Usually we pack light anyway - 1 giant suitcase and one rolling carry-on for all 4 of us for trips from 7-12 days. This includes my pillow (hotel pillows give me a neckache). I do laundry every 4-5 days and while it takes a bit of time, I don't find it too big a deal.
My favourite packing light tips:
- roll clothes. I was shocked at this since I have always laid our clothes flat. Then one day I experimented - and its true, rolling (tightly) takes up less space.
- plan what you will wear. All our clothes are packed by outfit and because I am a detailed itinerary planner, I typically know what we will need to wear each day and pack accordingly (dryfit clothes on days we will get wet, etc)
- one set of swimwear is plenty. Just wash in the sink and dry after each use.
- use hotel-provided toiletries and supplies where possible and practical
- minimal shoes. I force myself to stick to the least amount of shoes possible (yes, this caused my heart to ache on my Europe trip - but I survived lol). For Disney, this means 2 pairs of sneakers and 1 pair of flip flops per person.
- no jeans. If space is tight, the jeans go. They take up more space and are heavier. We mostly wear yoga pants/nylon pants/shorts for all of us. Workout clothes are comfy, can handle rainy weather, and are perfect for long days at the parks.
Good luck!