Milos sailing trips

I can't recommend one but I can assure you that if you don't find one in advance you won't have any trouble booking an excursion once you're there. There were at least a dozen on offer in the marina in the main town of Adamas. Ask at your hotel or in a travel office.

Julie, If you want the best advice, you need to share the key fact -- WHEN. July-August will be a lot busier than May-June or Sept... altho at those times, there also will be more boats available. Even in High season, I advise against advance booking. It is not like booking a bus or train ride -- sailing fun depends almost completely upon weather. If it's super-windy. sailboats are forced to drop sails for entire trip and just motor, no fun if what you want is SAIL. and of course, if it's rain, it's cancelled and you're all prepped for somethng that doesn't happen. The smart thing is when u are on Milos, get weather forecast for say, the next 2 days. Every evening after the boats return, they're lined up along the port. People stroll along before dinner & talk to the captains, get info about routes, food & drink, prices etc., and make their choice.

In high season, there are large "party boats" -- sometimes mainly motor -- that can have 30-40 people aboard, lots of beer etc. Other options include smaller sailboats (6 psgr max). Some of these go all around the island. The drawbacks of this, are, less time to stop for picnics &swims & if it's windy, sails drop & u just motor. We chose a large catamaran, Chrysovandu (cap.= 14... there were only 8 the day we went). It does a half-round, going as far as the fab caves at Kleftiko then returning. Stops for swims & lunch, under sail most of time despite windy May day. More recently a new catamaran outfit with good reviews is Polco Sailing. Several choices -- round-island and half-round ... how many swim-stops depends on season. (in high season, no backtracking; you end at a beach and vehicle takes u back to Adamas). Lots of info at online site but again... weather forecast is important.

I'm not even sure you can book them in advance, and there really is no need to. Go down to the harbor the evening before you want to do the trip, about 6:30 or 7 is when the boats are all returning. As they are unloading they have a person (with a big sign) standing in front of the boat selling trips for the following day. I actually just 'shopped around' the night before and then went down there about an hour before they were scheduled to go and bought my ticket. That was in July. But to be sure you can buy the ticket the evening before. I used Captain Yiangos.

Here's my trip report - https://andiamo.zenfolio.com/blog/2018/11/greek-island-hopping-2018-part-2-milos-sifnos-and-folegandros

They have half and whole day tours, I think the whole day ones are better. I was a bit worried I'd be bored but not at all.

Thanks for the information everyone, I appreciate it! Janet-we'll be there the end of June, just before high season starts.

Good timing -- it's after that chilly Milos water warms up a bit, and just before all of Europe arrives!