Many of your neighbors have already had the experience. Perhaps now it is your opportunity to charter your own personal yacht.
Bareboat chartering is availab throughout the world...prime locations would be the Caribbean, the Mediterranean and the Sout Pacific. A qualification resume wi be required on the yachtsman who will be "in charge" of the vessel. If the qualifications are questionable, you will be taken out for a test before the boat is left in your hands. If you fail, you will be offered a qualified captain with the proper credentials at an added fee or you can cancel, but, of course, you will not get complete refund. In any case, it wise to be sure one of your crew has the necessary qualifications. These qualifications are the ability to demonstrate proper boat handling under sail and power; and you should have minor navigational skills-the ability to read a chart to get in and out of harbors and inlet to be sure not to "hit the bricks." Putting a hole in someone's $300,000 yacht would ruin your whole day. Chartering in the Caribbean, although more popular in winter season, is still fun any time of the year and is far less crowded in late spring, summer and fall. The secluded harbors are empty. The local beachfront bars are deserted and the miles and miles of gorgeous beaches are your private oasis.
Most bareboat charter companies restrict the area that is available for you to cruise due to the necessity of servicing boats. Should problems arise, they cannot have you 100 miles down the island chain. However, the area that is allowed for cruising is more than adequate for a week or two of delightful sailing.
Should you desire, however, to be more adventurous and travel further down the island chain, you would then charter a crewed yacht. That option does cost more, but you don't have to be an experienced sailor nor do you have to do the cooking or cleaning up. Depending on the size of your boat, you could be living in the lap of luxury on one of the world's finest yachts.
Back to the rough and tumble existence in bareboating. Two couples can easily handle a boat to 50 feet in length. The charter section of most marine periodicals (Sail, Yachting, etc.) will have several listed charter companies as well as private owners
who charter through a service or with classified ads. The late summer and fall issues most often will have articles on charter cruising. They will give you an overview of the areas to sail in and the types of boats that are available.
I would recommend that whatever charter service you go with, you check their credentials and make sure they are financially sound, as many small charter companies have gone bankrupt, leaving customers without charters or refunds.
It has always been my opinion that going from point A to point B fast is a whole lot more fun than going slow, so performance should be one of the criteria in choosing your bareboat charter.
All charter companies can assist with provisioning and they all run a seminar prior to your leaving the dock on the handling of the equipment you have on your charter boat as well as the general area you will be sailing.
It would take many more pages to describe the areas where bareboat chartering is possible. The azure waters of the Caribbean, the ancient beauty of the Mediterranean, and the native magnificence of the South Pacific are but some of the areas to investigate. We leave this to your imagination. No matter what destination you choose to bareboat, your vacation will be remembered for a lifetime.