I took the Christmas 2015 voyage on Star Clipper through the leeward West Indies islands (St Maarten to St. Maarten) as a single traveler. There was no single supplement, which was a bonus. I’ve been a long time Windstar cruiser for over 20 years and, in my experience, the only difference between the two is that Clipper will give you a more authentic sailing, if that’s what you’re looking for. As someone who has lots of sailing experience, I have no problems with rocking and rolling but if you have a queasy stomach and easily prone to seasickness, you should be prepared for it, especially while sleeping and using the head. I found the passenger demographics between the typical Windstar passenger types very similar to that of Clipper (couples in their 40s -70s). There were more teens on this cruise, mostly due to the fact that it was over Christmas.
Here’s my key dislikes about Star Clipper:
-There’s no exercise room and no exercise equipment. If you want to workout while aboard, you’re hosed. Plan to go on excursions that require you to get a workout. Oh yes,they do post a daily workout in the center of the ship but just try stretching and exercising while the ship is listing steadily from side to side!
Small but efficient. Good storage. Kept very clean and neat.