Let me start by saying we loved the food and service on the Windstar which is a 25 yr old 150 passenger sailboat/ship. Also, the excursions and guides are all well worth it. The newest ship is Wind Surf which is twice as big.
Sailboats usually like wind, but beware of the limitations on Windstar cruise. For starters, Windstar anchors offshore in many ports and the passengers must get on small tenders (42 passengers) to be ferried to the island. This is somewhat inconvenient and not real comfortable.The boast that Windstar is a smaller ship and can go where the big boats can't may be true in other parts of the world but not in the Greek isles and the Turkish ports of Kusadasi (Ephasus) and Bodrum. The actual fact is contrary. Dockage fees are based on the number of passengers. The big ships with 2,500 passengers get preference in ports and are often able to pull along side the dock while the smaller ships are forced to anchor offshore.
The brochure says that visits to Mykonos are "weather permitting". We arrived there in 35 knot wind. The small tenders took us ashore where we chose to spend a few hours on Delos, another smaller island that requires a large ferry (250 passengers) out of Mykonos. Delos is a terrific destination. However, when we got back to Mykonos, we were ordered back to the Windstar because they deemed the wind unsafe. As a result, we never saw Mykonos.