It is always heart breaking to receive vintage items from some private suppliers that arrive with many broken pieces of glass.
Some suppliers pack the glass items incorrectly due to lack of knowledge - which we can accept and this article was written to assist those, others just by pure carelessness - they got their money and just couldn't care less about the delivery - those, I'm sad to say, go straight into our black book of banned suppliers.
We don't have a problem paying for the appropriate packing material, but careleness is unaceptable. But we support those that go the extra mile to make sure the risk of breakages is minimized.
An example of broken glass items we have received from a supplier in Lisbon, after we advised how we expected the items to be packed and carried packing material costs 
(Someone that we will not be buying from again)

Example of Wrong Type of Box (box too weak and old) and Material Used for Above Glasses (Only Used Newspaper) - This is a NO-NO!

This guide has been written to assist the normal man in the street on how to pack glasses safely, so that the risk of breakages is greatly reduced, especially for items like drinking glasses, glass jars and decanters.
Pre-Preparation
Choosing Boxes
Ûse a medium-sized box rather than a large box, which may get too heavy and awkward to move.
Example of the Correct Type of Thick Carboard Transport Box That Should be Used. 
Always choose a thick and firm corrugated cardboard box. 

A divided box with a cell pack inside is useful to protect glasses from getting in contact with each other. You can buy them already with those dividers, or you can make the dividers yourself by cutting cardboard from another box and making your own.

Example: you can use some corrugated cardboard, or just cut some pieces of cardboard from another box, high enough to protect the glass item size.
TIP: Before starting to pack the glasses, make sure the bottom is taped firmly shut.
Packing Materials
To pack fragile glass items, look for packing paper, kitchen paper or soft paper serviettes, bubble wrap, or another soft material—anything that can be easily wrapped around each glass or set of glasses safely as a wrap. Don’t forget to put some of the material inside the glass as well. Meaning provide a soft cushion for both outside and inside.
STEP BY STEP GUIDE
How to Pack Drinking Glasses
Glasses should be packed with the heaviest items on the bottom and the lightest items on top. Wrap every individual glass in packing paper or bubble wrap before securing it in the box. Additional packing material should be added below and above the wrapped glasses for extra cushion.


Preparing the Box
If you're using packing paper or a kitchen roll paper, crumple up enough sheets to cover the bottom of the box. Crumpling the paper will provide enough cushioning to protect the glasses from hitting the bottom, and it will protect the glasses if the box is accidentally dropped. If you're using bubble wrap or any type of soft material, make sure you have a thick enough layer on the bottom to protect the contents from bumps.
This supplier uses soft material to wrap the packed small boxes before puting into a larger box

Well wrapped boxes containing glasses is then packed into a larger transport box

Wrapping Big, Heavy Glasses
Always wrap and pack the biggest, heaviest glasses first. You'll be placing these on the bottom of the box with lighter glasses on top. Using a flat, clean surface, lay out your stack of paper or bubble wrap. Take one glass at a time and place it in one corner of the packing material at an angle. Start to roll the glass, and as it rolls, stuff the ends of the paper or paper towel into the opening of the glass. Wrap until the glass is completely covered.
Wrapping Stackable and Other Similar Glasses
Sort glasses into groups of similar sizes. Use scissors to cut packing paper or bubble wrap sheets in half for smaller items.
Box Up the First Layer
Now that your glass or glasses are wrapped, fold over the ends at the bottom of the glass, creating a nice tight package. You shouldn't be able to feel the glass's edges at this point. If you can, you may need to wrap another layer of paper depending on whether the glass has a handle or a large lip.
Fill the Box
Place the wrapped items in the box with large, heavy glasses on the bottom and lighter glasses on top. If you're using a box with dividers, they should slip easily into the small spaces. Add in a little packing material to help ensure a snug fit and prevent jostling when moving the box around. If there are no dividers, place the wrapped glasses neatly in rows. Use more packing paper or bubble wrap between each item to help prevent breakage. Make sure all sides of the box also has some packing material, not only the top and bottom.
This private supplier uses "pre-used" boxes that he collects from large retail stores (normally you can get those from Lidl or Continente or other major stores)
and wraps the glasses in soft material and bubble wrap

Wrapping Wine Glasses
Pack wine glasses by wrapping the stem first. Use half a sheet to wrap the stem, then place it on the stack of paper and start rolling the rest of the glass. This ensures that the most fragile part is well protected. Only wrap one stemmed glass at a time. These glasses should always be packed in the box last, leaving lots of room for extra cushioning at the top of the box.
Cushioning the Top
Leave room at the top of the box for packing material. Once the box is almost full, add crumpled packing paper or bubble wrap. Aim to add the same amount of packing material to the top as you added to the bottom. If you're using towels or other materials, ensure there is room for a thick layer of cushion on top.
Check and Seal the Box
Before you seal the box closed, gently shake it back and forth. You shouldn't be able to hear any glass clicking or feel much shifting of its contents. Once you're happy with the packing, seal the box closed with packing tape.
Mark the box as "Fragile: glassware" so that the couriers know to be careful when handling it.

TIP: For extra safety, you can pack that box, inside another bigger box that has protection foam or bubble wrap all around on the inside. Mark the outside box as "Fragile: glassware" so that the couriers know to be careful when handling it.