Hi Ellen:
I've been sailing since in teen in S. Fla. Got into bareboating via a Moorings owner 13years ago. Chartered as my own captain since 2010.
But I don't have a license, and neither do the other experienced couples we cruise with. So when we decided to expand our horizons we chartered with a local skipper. I looked into getting the license with the Collegate school, or ASA programs. But that still wouldn't solve the local knowledge issue.

Local skippers are like having your personal concierge cruising with you! He (we haven't had a she...yet) has the local knowledge and experience that helps take any of the apprehension about anchorages, restaurants, weather, etc. Their most valuable resource is the super-computer in his hand - now known as a smart-phone. (Gone are the days anybody uses a VHF!) They know the local areas like the proverbial back of their hand, but enjoy sharing their knowledge and expertise. They have let us help navigate, sail, helm, anchor, Med moor,and learn how to back into tight village quays and docks. We've found that a skipper will let you do as much as you'd like, Or just kick back, have another adult beverage and let him do the worrying! Personally, I like learning, and tried to do new stuff with the skipper by my side. And with him there, my wife and other crew were much more relaxed the entire trip.

Once tied off, he typically kind of disappeared, took care of the dock paperwork, had a coffee with friends, etc. One skipper appeared to have a girlfriend in every port! He learned what we liked about schedules, our likes and dislikes, and made the restaurant reservations at places that were perfect for us! Some nights he'd dine with us, others he'd get us to the restaurant, and then go off on his own. And many times the restaurants were not the typical closest tourist traps - but ones were he was welcome with open arms. Come morning, he'd be found ashore having coffee & waiting for us to rise and shine, or he'd sleep-in while we made the coffee and breakfast onboard.

We chartered in Greece from Athens a few years ago, and that was us in Hydra with the donkeys on the dock. That harbour was a total ZOO! No, not the dock, but getting in and getting a prime space. Skipper Greg had phoned ahead to a fellow skipper friend and timed our arrival just as the other cat was leaving. It was like finding a prime parking space in front of the football stadium right before kickoff - just as another left it empty. By late afternoon the boats were THREE deep - as there were two boats Med moored ahead of us. NO WAY could have we done that without a local skipper! Somebody fouled our anchor upon departure, but he showed his skill getting us free.

We chartered in Croatia last year, and had the same wonderful experience with a young fellow, recently graduated from a university that specialized in marine education. He was a mult-generational local. He had thought about getting on with giant shipping companies, but starting skippering locally and loved the opportunity working with fellow sailors, and hosting and showing the highlights of his home country.

Does that mean that I won't charter without a skipper? No. In areas where language isn't an issue, where we've been before, or can plan well enough in advance I can do well enough with our crew. But as we're sailing boats that are now getting close to $1,000,000 in value and we're not quite as young as we used to be, sailing with a skipper to new destinations is a great way to sail, learn, travel,and experience new destinations, while getting the the apprehension level way down!

We hope to sail Italy in 2021 - with a skipper! And if the Caribbean governments can get their act together, on our own again - without need of a skipper.

My two bits...fair winds