Canaries

Lava charters based in Arecife would give you a pleasant weeks sailing around Lanzarote with time to visit the small island of Graciosa and mebbe a night at anchor off Lobos, just north of Fuertaventura.

A charter from South Tenerife should get you a trip over to La Gomera and possibly El Hierro.

All Canary Island sailing is challenging between the islands, great if you are an experienced skipper.

Don't think anywhere does flotilla though.

Enjoy whatever you choose!
 
Did my Dazed Kipper with Canary Sail many years back. Can't speak to their flotillas, but the company itself was good to deal with.
Sailing in the Canaries if fun if you can handle going from force 3 to force 8 in a few boat lengths.
 
Accidentally entering the WAZ with the kite up is an interesting experience.

Did a few training courses out there a few years ago - great sailing and great fishing.
 
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