Many experienced sailors have told me that they have rented super yachts in the British Virgin Islands, in Tortola and in Europe. They flew there and had a blast for a week or month. One guy I know rented a sailing boat in Greece and sailed all around for 2 months around all the blue islands of Greece and Turkey. He had a blast.
You don't have to have a million bucks to have a great sailing trip. A big reason to rent also is that you rent it for a week and don't have to pay the mortgage or moorage fees on it after you leave!
Sounds great to me!
Check these guys out:
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