We highly recommend consulting with your skipper on where to eat dinner, especially on the smaller islands. In Greece, dinners are a very important event for family and friends to get together. Dinners generally last many hours and include many courses of fresh Mediterranean dishes, usually accompanied by carafes of wine. Every island has unique local specialty dishes, which your captain will be happy to explain to you.
If you'd like to get to know your skipper/hostess a bit better, feel free to invite them to dinner on one of your first few evenings. They'll likely know the best off the beaten path restaurants and local menu items on each island. That being said, the skipper doesn't expect this at all and understands that every client has their own unique preference and personality.
You're welcome to dine at any time, but it is custom in Greece to eat later in the evening between 8-10pm.