Bell services at the resorts will transfer your luggage to the new resort. A few other options are taking an uber or Minnie van to the next hotel. I had Bell Services transfer my luggage from Pop to the Boardwalk with no problems or issues. Luggage arrived by 3:00 pm, but I did bring a packable duffle bag with my medicine, bathing suit, and a few outfits to have with me when the room was ready, before the lugagge arrived. I brought the small duffle/back pack on the skyliner from pop to the boardwalk and walked around crescent lake. I used my transfer day as a resort day and it worked out well. I did bring my luggage to Bell Services by 9am for the transfer and tipped well. I also used a Minnie Van when transfering from Pop to Swan Reserve. It was no problem to bring my carry on lugagge with me -- but it was helpful to pack light for the trip, which sometime is difficult for a Disney vacation. Have fun!