Bear in mind that the sailing itineraries below are only proposal. You might have to alter your route due to weather conditions or even if the weather allows, maybe you or other members of the crew donít want to sail 4-6 hours everyday. Then you can skip couple of Cycladic islands and explore better the rest.
DAY 1: Check in at 17:00
DAY 2: From Parikia if you head north towards Naxos you can stop in at Naoussa for lunch or swim or even over night before heading in to Naxos the next day. Alternatively head south towards Despotiko bay just south of Antiparos and spend your first night at anchor in the bay and go to one of the small tavernas on the beach for your evening meal.
DAY 3: Head towards Iraklia, a small island just south of Naxos one of the "Little Cyclades" there is an excellent taverna half way up the street heading in to town.
DAY 4: Skhinousa is literally a small hop, about 3 miles away and also offers very quaint bays and hamlets.
Ano Koufonisi is also only about 10 miles away and is another nice island.
It is possible to spend a whole week just pottering around these small islands discovering beaches and bays and really not doing long distance sailing trips, highly recommended if sailing with small children.
DAY 5/6: Ios is the half way stage to going to Santorini and also offers a good place to stop and catch the ferry to Santorini if you want to cheat a bit, an excellent idea if the meltemi is blowing, Santorini can be a long slog up wind if the is "fresh".
Both the main town or the bay of Manganari offer good shelter from the north winds, the main town is about a 10 minute walk from the port and has some good restaurants and bars to visit, it is no longer the "party" island it was some years ago, and now caters for all ages.
DAY 6/7: Depending on which way you started you can either go to Naxos, Naoussa on Paros or Despotiko Bay for your last night and then head back to Parikia
DAY 8: Check out at 09:00