Every broker has a default answer to "where should we go first?" Ours is the Ionian — and this exact loop from Lefkada, which we've sailed enough times to know where the bakery is in every harbour.
Day one is short on purpose: check-in never finishes before mid-afternoon, so we cross the two miles to Meganisi and anchor in Little Vathi. Day two rounds Meganisi's cliffs to Kastos, a one-village island where the evening entertainment is the sunset. Day three is the longest leg — about 20 miles south to Ithaca's Kioni, a horseshoe harbour that fills by 4 p.m., which is exactly why you leave Kastos after breakfast, not after lunch.
Day four crosses to Fiskardo on Kefalonia, the Ionian's dressiest harbour — book a quay-side table, it earns it. Day five turns north into Sivota's deep bay for the best swimming of the week, and day six closes the loop at Vlicho or Nidri on Lefkada, leaving a two-hour hop to the base on handover morning. No leg over four hours, wind on the beam most afternoons, shelter always within reach.
When to go: late June or September if you can. And one lesson learned the hard way — in the Ionian the wind arrives after lunch, so motor-sailors leave at 9 a.m. and sailors leave at noon. Be a sailor; the morning is for coffee and swimming anyway.