Connecting transistors in series
A cascode amplifier is a kind of series connection where a common emitter stage drives a common base stage. Wikipedia shows a variant with multiple common base stages:
Yes that is possible but less trivial than placing them in parallel.
What you need is cascoding which is done like this:
simulate this circuit – Schematic created using CircuitLab
Qsw does the actual switching
Qcasc is for dividing the voltage between the transistors
I have used this kind of circuits where I need to switch 5.5 V but are limited to using (on-chip) transistors which can only withstand 2.7 V.