Can tenants drive/sail the boat when the boat is rented 'with captain/skipper'?

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Try your luck with the captain!

For rentals 'with captain', the owner (or the skipper) is the designated skipper.

If you wish to take the helm and perform certain navigation maneuvers if you are sailing on a sailboat, you need the captain's permission

If you rent a motor boat, they can also let you drive if you hold an adequate boat license.

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