I'm putting in some outdoor speakers. I there any trick to drilling from inside to the outside (or outside to inside) wall?

Looks like most of the cable holes were drilled from the outside in, as they were drilled through the brick grout and not the brick. I watched the cable guy a couple of years ago and he drilled from the inside out, and went though a brick.

I have always seen it drilled from the outside in, through a mortar joint. Be mindful of wall A/C wires usually ran down to outlets.

Can you go wireless?

I'd thought about wireless, but all the reviews talk about a background hiss and a lack of volume. I'll have a separate amp/receiver powering it.

I may try it through a mortar joint as suggested.

If your mounting on/under the eave, you may be able to run the wire through the soffit vent through the attic if you want a more hidden look.

They have a plastic sleeve at the box stores (cable speaker wire section)to use in the hole you drill, or you can use mortar colored caulk to seal the hole.

Thanks, I'll look for the plastic sleeve before I drill.

It'll be an in-ground speaker, so it won't be under an eave.

Really depends on you. If you want exact placement on inside or outside. I would try outside in but the problem then is aesthetically or practically it may not work as well so..... You could go up to the crawl space then outside and down the wall using raceway to cover your cable outside which may be another solution.

I would probably start inside out. Remove the base board and drill as low as possible to outside. Replace board and run cable between carpet and base. Again depends on your situation and equip location.

I moved a tv cable drilled from the outside in just measure twice before drilling.

I'd locate studs on the inside to be sure and miss them. Measure from a window on the inside, go outside and measure from same window and miss the stud. A hammer drill makes life much easier going through mortar or brick. After that a very long wood bit is what I'd transition to. Outside, in.

I have a wireless system from Bose that is Bluetooth compatible as well. Just pick up the sound dock when done and bring it inside. Great quality, but you will pay the price!

Rock, wall or ceiling speakers?

I have run Cat 5 data wire from outside to inside a few times. A typical masonry bit will go through mortar on a regular drill like butter, but not brick.

I happen to have a real long specialized drill bit that is for wood. What I did was first go through the mortar with a typical masonry bit. After getting just through the mortar I put this other bit on the drill and ran through the OSB. As soon as I felt it get through the OSB I reversed the drill to backwards so as not to bunch up the insulation inside the wall. When I went through the insulation with the drill in reverse and felt the sheetrock on the inside I switched the drill back to forwards and went through.

Then I removed this bit from the drill while still sticking through everything. Next I butted the CAT 5 against the tip of this drill bit and wrapped some good tape around the bit and wire. Then I gently pulled the wire through.