Easy to measure since ancient times are the angular diameters of sun
($0.53°$) and moon ($0.52°$), which happen to be nearly equal to each other.
This gives you
$$\frac{\text{diameter}_\text{sun}}{\text{distance}_\text{earth-sun}}
=0.53°\frac{2\pi}{360°}=0.0093 \tag{1}$$
$$\frac{\text{diameter}_\text{moon}}{\text{distance}_\text{earth-moon}}
=0.52°\frac{2\pi}{360°}=0.0090 \tag{2}$$
Historically, the next thing determined was the distance of the moon.
This was first done by measuring the parallax of the moon
(i.e. the apparent position difference of the moon
in the sky when viewed from two different
locations on earth at the same time).
(image from Lunar Parallax)
The difficult part here was to figure out how to do these
two observations at the same time even before choronometers
were invented.
When observing the moon from different continents
(i.e. separated by a distance $s$ of several $1000$ km)
you measure a parallax $\delta$ between $1°$ and $2°$,
which is easily detectable even without a telescope.
From this you can calculate the distance of the moon by
$\text{distance}=\frac{s}{\delta}\frac{360°}{2\pi}$
and get $$\text{distance}_\text{earth-moon}=380{,}000\text{ km}.$$
The parallax of the sun can be measured in the same way as above.
But it is much more difficult because the measured parallax
$\delta$ of the sun turns out to be much smaller
(between $0.002°$ and $0.005°$ when measured from different continents).
From this result you already see without any calculation
that the sun must be much further away than the moon.
When calculating the distance of the sun by
$\text{distance}=\frac{s}{\delta}\frac{360°}{2\pi}$
you get $$\text{distance}_\text{earth-sun}=150{,}000{,}000\text{ km}.$$
From these distances of moon and sun you can, by using (1) and (2),
calculate their diameters and find
$$\text{diameter}_\text{moon}=3{,}400\text{ km}$$
$$\text{diameter}_\text{sun}=1{,}400{,}000\text{ km}.$$