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 don’t 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: Starting from Paros you can head in a westerly direction for the island of Sifnos, it is a 23 miles trip to the southern end of the island with good shelter from the meltemi in the bay of Plati Yialos. Other wise you can keep heading further north west to the bay of Vathi with its very sheltered bay and small tavernas, there is only a small pier to tie up to otherwise you have to anchor and use the dinghy. The main town is Kamares, which is still a little further north and does have a better variety of shops.
DAY 3: From Kamares in Sifnos, Serifos is only 10 miles, the only place to go really is Livadi which can get busy in the summer and some care is needed during the meltemi as there are strong gusts coming down the mountain, although very little swell.
DAY 4: After a night in Serifos it is time to head for Syros, you have a choice of Finikas on the west side of the island, or a slightly longer sail to Ermoupoli the capital of the Cyclades islands. With its larger shops and big town feel to it, care needs to be taken entering the harbour as there can be quiet a lot of traffic due to the shipyard.
DAY 5: 15 miles from Syros in an easterly direction lies Mykonos with its famous town that has appeared in countless films including "Shirley Valantine" and more recently the "Bourne Identity" to name but two. This is the tourist Mecca of Greece, there is now a new marina which has been built slightly out of town which has more facilities than the old pier in the main town used to. There are various anchorages around the south side of the island and also the small bays on the small island of Rinia and Delos close to Mykonos are worth visiting. Note that it is not permitted to stay over night on Delos without permission.
The night life is for you to discover on Mykonos, and there is lots of it so enjoy.
DAY 6: Hopefully a fast run down wind to the island of Naxos. Naxos with its long sea front in the main port has recently had a face-lift and is now a very nice clean harbour to spend a nice evening exploring the town.
DAY 7: This is you final sailing day, therefore you have to sail back to Parikia port. Depending on how much time you have on your last day you can sail inside the beautiful bay of Naoussa, on the north side of Paros. You can either take a swim at one of the sandy beaches or visit the town of Naoussa with its traditional fishing port and restaurants. Make sure to reach Parikia before dark.
DAY 8: Check out at 09:00
Find a sailing charter yacht to rent in the Cyclades