Background:
My wife and I have extensive experience on cruise ships of different companies and sizes in the Caribbean, Mediterranean and even ocean crossings. It is a matter of personal taste but we agree that the smaller the ship the better the experience and that puts Windstar at the top of our list. We have been on the 5,000 passenger giants where you are an anonymous part of a city at sea. With 280 passengers and 100 crew, the Windsurf almost feels like you are on a private yacht. Every single crew member treated us like we were the most important people on board and it was wonderful. We are sailors and our favourite curses in the Caribbean are chartering our own yachts. Second to that is the Island Windjammer cruises with real sailing yacht. Our last voyage was 12 passengers and 6 crew on a 90 foot sloop, but that requires a real love of sailing and it is expensive. Windstar cruises are the happy compromise. There is no real sailing sensation on a Windstar other than stirring music when sails are hoisted but the small size of the ship allows anchoring in remote locations that emulates the real sailboat experience. You also trade excitement and danger for luxury and pampering if you go Windstar.
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