I’ve been twice and used Freeride Madeira both times. Great guides and a great place to ride. Booking was easy and they were very reliable on pickups etc.
They have a range of guides and they are all nice guys…
The island is great, very varied terrain and trails, uplift and a guide is almost essential though to get the most out of it. Pretty tech in places but great fun.
Food and drink pretty cheap
We booked a hotel / transfers ourselves and they just came and picked us up. Funchal is where the majority of stuff is and can often find pretty good deals (we got £200 off through jet2 holidays this time)
Have fun!