Plan on departing first thing Sunday morning as it will take you a good while to check over the vessel and provision it first off. Change over day is manic at the best of times so don't figure on leaving early afternoon on Saturday. If you manage it then bonus.
Trogir to Vis is 30NM and will take the best part of 5 hrs at 6kts and is a full day sail on open seas which can get challenging if the wind
is up. If you manage to depart Sat afternoon then head
to Milna on Brac or Maslinica on Solta to break the journey.
Vis has some amazing military history
as it was Tito's base during the war and there is a small military cemetery at one end of Vis bay which has a monument to British soldiers and sailors who died there in WW2 and the Napoleonic campaigns.
Vis to Korcula is a long sail, 42NM, so again another full day and 7hrs at 6kts. If you want to go to Korcula island rather than the town then Vela Luka at the western end is an option and only 23NM. You have a town mooring
bouys and several restaurants in VL.
VL to Hvar is 18NM but I would recommend stopping in ACI Palmizana marina on the Pakleni Islands as Hvar Town harbour is uber busy and almost impossible to get into. There is a water
taxi from Palmizana to Hvar Town.
Hvar/Palmizana to Jelsa is 21NM so a good sail but not too long. Jelsa is a nice town to moor up in.
Jelsa to Maslinica is 30NM so another long day. Plus you talk about doing this on Friday but you will probably find you have to be back in Trogir on Friday night in order to change over on Saturday.
So you might want to rethink the plans based on 5 nights away and realistically do you want to be "racing" just to get somewhere at 6 or 7kts? Especially if the wind
is doing the usual and blowing from exactly where you want to sail to as you'll just end up motoring. To do what you suggest is virtually undoable to be honest unless you have a 41ft powerboat ;-)
September is a great time of year to sail Croatia
, the weather
is generally fine with good breezes, the sea is warm and everywhere is still lively but not too busy. Always check the weather as strong Jugo (SE) and Bura (NE) winds can come from nowhere. The Bura in particular can be dangerous in some bays so you do need to be very aware of the directions etc. Marinas
and town harbours will have forecasts plus you can get them on meteo.hr with excellent wind maps and Split Radio
broadcast the forecast
daily with an alert on Ch16.
Whatever you decide to do you will have a fun week of sailing but don't try to do too much. You can always come back next year and the year after and the year after that :-) I've been here 5 summers and am still finding new places to tie up, drop anchor
Hope that helps