No the ship normally berths. i wud recommend a walk to the cable car, up to the tropical gardens if your looking for something to do, beautiful place, and the view of the ship is fantastic. we took some fab pictures from the cable car too. good value for money. theres a thousand year old olive tree up there also.
No With p&O you dock and they usually provide a free coach into the town center or you join the tour bus or catch a taxi?
Normally the ship docks but there have been occasions at Madeira when the port has been full and tenders have been used.
We travelled on Aurora to the Canaries last year, calling at Vigo, Gran Canaria, Tenerife & Madeira, and no tenders were used.
No the cruise ships normaly berth up in the harbour, a good site to see the live harbour is http://www.madeira-web.com/camera/cam-04.html , iuse it as my screen picture.
You can either walk into town or take taxi/shuttle.