We sailed on the Wind Spirit from 2 Feb - 9 Feb from Bridgetown to Bridgetown. The itinerary was "Jewels of the Windward Isles".
As this was our first cruise ever I have no point of reference to compare anything against. Being on a small boat we did feel the swells, especially on the run from Barbados to St. Lucia where you are essentially in open ocean. Being on the bottom deck it was kind of neat to see the swells washing over your cabin portals.
The boat was smaller than my wife thought it would be. I don't think I had any preconceived notions on size. The cabin (120) was better than I anticipated. 188 sq ft is way bigger than I thought it would be. The finishings are great, linens first rate and there is tons of storage including a closet. The bathroom is extremely well designed and very functional and also has lots of storage space.
The staff are awesome. The service is unlike any I have encountered on any vacation. First rate somehow seems inadequate. Truly top notch. After one day all the staff, from the bar to cabin to wait staff, knew us (and everyone else) by first name. The were always quick to greet us by name whenever they saw us. I cannot say enough about them. They will do whatever they can to meet your needs and more. They made the cruise.
The food was really really good. Only once was my fish a tad over cooked. Other than that everything was excellent. The only short coming according to my wife was the lack of "healthy" muffins at breakfast. I was too busy eating eggs Benedict and fresh pastries to notice.
Dress code was very casual. I wore slacks/pants with a button up short sleeve shirt to supper. And shoes of course. The women wore everything from pants to dresses. Their footwear varied from high heels to flip flops. The other meals, shorts and sandals and any shirt were sufficient. I did see one older gent turned away at lunch when he tried to enter the restaurant in bare feet and no shirt lol.
On the subject of age, 50% were in their 60's and 70's, 35% in their 40's and 50's and the rest younger. A few older teens were with their parents.
Drinks were excellent! They were large and strong with top notch brands. We bought the beverage package. On a side note you don't need to buy this when you book. When you sign into the boat the bar manager is there with a drink menu to show you what is included if you opt to take the package at that time. The fridge and booze drawer in the cabin was very well stocked with first rate stuff.
Your laundry can be done piecemeal. On day one I gave all my shirts to our room steward and he had them pressed ($1.20/ea). The total is added to your bill.
My wife used the gym every day, which was quite well stocked considering the size. 2 treadmills, an elliptical machine, free weights and a high tech all in one weight machine (using cables).
The itinerary was a bit slow for us. Plus I found out that I am not fond of "sea days" lol. Though there are only 148 pax, they are all on the back deck at the same time. Because you are on a small boat, activities are limited. Something to keep in mind is that there is in fact a small deck area with loungers at the front of the boat that wasn't very populated.
Before we would ever cruise Windstar again, we would cruise on a big ship so we could compare the two experiences. Having said that I would have no hesitation in recommending Windstar to anyone contemplating the idea.