Hi, We have sailed in Greece for many many years and have visited over 100 islands (see:
Greek islands we visited). Some thing about Greece:
1: perfect day trips from island to island
2: many many coves, little harbours and some marinas 8although we do not prefer to stay in marinas)
3: good winds, but during the summer season the famous Meltemi may blow for several days at 6-8bf in the Aegean. Areas as the Ionan and Dodecanes are less attacked by the Meltemi.
4. food is ok, but try to avoid tourist restaurants. especially on small islands, going to the only restaurant available is a good idea!!!
5: one may still find coves where one is all alone for the night!
6: during hight season especially in the Cyclades and Ionian sea it may become crowdy with lots of charters
7: small harbours are very cheap to stay, coves are free, this in contrast to for example Croatia, which is quite expensive
8: hardly bouys to stay on, but mostly good achor grounds
9: try the "Navily" app to see where you all can go to.
10: we just love it!!!!!!!!
Now Italy,
On the Adria (east) side ot Italy there are hardly islands (exept Trimeti Islands) and also hardly protected coves, so one has to stay in harbours or marinas.
South of Italy is not a charter area, so not crowded but also not many facilities
West Italy has several islands (Liparian islands, Ponza, Capri, Sizilie etc). The Liparian islands are vulcanic so anchoring is somewhat more difficult (steep waters).
Winds in summer are moderate.
The whole west Italian side is less cheap
In August the western area is crowded
Italy in general is more costly than Greece.
Croatia is the most expensive!
If you need more detailled information 8especially on Greece) just let me know.
Klazien