You may be an experienced sailor with several years of sailing behind you and has all the right certificates in yachting. Even so, you may want to consider hiring a skipper and even a hostess for your next sailing holiday in the Mediterranean, Caribbean or other exotic places.
The great advantage of hiring a local skipper is that you can relax and just enjoy the voyage. The skipper is responsible for the boat when you are sailing and anchored. So you wouldt not have to stay up all night worrying if the anchor will hold or not. A skipper possess great local knowledge and will provide ideas and tips for places to visit - places that you may never even have heard about or would have been unable to find by yourself. The skipper can guide you to remote coves with great opportunities to experience the colorful fish and turtles while you snorkel in the crystal clear blue water and underwater caves. The skipper will also take you places where you can go ashore for exploration and perhaps see local ruins and other cultural attractions. He knows the local waters and thus the wind and weather conditions and knows how to set the most favorable course due to the current weather situation. Is the sailor dream still alive you and other interested participants can easily be allowed to help the skipper with various tasks during the voyage; steer the boat, help wheen mooring and other practical navigation tasks during the voyage. With a hired skipper your sailing vacation will be a combination of your own wishes and interests blended with the local knowledge of an experienced skipper.
His/her job is to serve light meals (therefore, do no expect big 3-course dinners), small refreshments, cleaning the saloon and stuff like that. His/her job is not to clean your cabins and make the beds. Before embarking on your journey the stewardess can join you going shopping, or you can order provisioning in advance and then the products will be on board at your arrival. You can order a provision list depending on what area you cruise. Part of the charm of a holiday abroad is to shop in the local supermarkets or visit local markets, but sometimes it can be an advantage to pre-order the heavy provisioning - such as drinking water, other beverages, etc.
Besides the cost of hiring the skipper, he must have his own cabin and food. You are not required to invite him to restaurants if you plan to eat out, but you must make sure that he gets fed. Make sure there is food in the fridge. However, sometimes the skipper have friends or acquaintances on the places you visit. In general skippers are very discreet and you are to decide how much you want to involve him. Also, if you choose to hire a hostess or stewardess, he/she should also have his/her own cabin and diet on same terms as the skipper. In most cases they do not share cabin.
Of course, hiring a skipper will increases the cost, but it will give you a very special sailing experience with focus on relaxation and unique experiences in places you probably would not have thought of going.