We will be spending 3 days in Crete and 3 days in Rhodes. I would like to take a day sail to surrounding islands. Any advice would be helpful.
Depending on when you plan to be there, from Crete you can take a daytrip to Santorini using the Hellenic Seaways FlyingCat. It's motorized. If you want a daytrip on a sailboat you won't be able to do it and return in one day. I have no current experience with Rhodes but looking at a map I see that Chalki is the closest island that might possibly be reached by charter from Rhodes. There's also a ferry from Rhodes Town to Chalki, but be aware that ferry schedules sometimes don't allow for a long stay, or even a same-day return. Once you're there you can ask in the local travel agencies for some other options.
Rhodes is about a couple hours away from Turkish coast, you can take a speed boat to marmaris for day trip.
We are coming to Crete from Santorini. We spend two nights in Crete than go to Rhodes for 3 nights and than off to Turkey. I was looking for a good day sail charter to see some of the small islands while we stay on Rhodes or Crete. I don't think we will have time while on Crete.
And honestly, because of the distance of any other island from Rhodes Town, I doubt you'll have time for a daysail to them on Rhodes. That does not mean you can't enjoy exploring the Rhodes coastline.
You can do a day trip from Rhodes to Symi by ferry, so it may be possible to do a day sail there. Do you have a hotel reservation in Rhodes? If so, they may be able to give you the name of a local travel agent who could help you sort this out.
A round trip from Rhodes to Symi is about 80 miles, not sure if you can do that in one day on a sailboat. I guess it would partially depend on the wind?
We will be spending 7 days in Crete in mid October . How long and expensive is the speed boat trip to Santorini that you mentioned. Any other suggestions?
The trip takes 2 hours and the one-way economy fare is €56 per person. If you want the daytrip with Land Excursion and a Guide the price is €120 per person. http://www.ferries.gr/hfd