Trailer my boat from Poole to...somewhere France/Spain?

Looks like your set on S France, but if not then do look at Southern Brittany, and Gulf of Morbian (like Poole just 4 tiems bigger) and the Isles offshore like Belle Ile, just superb. For your needs suggest you base yourself at Le Crouesty. Nice modern Marina wtih petrol and diesel plus quaint shops for SWMBO etc and a host of harbours and islands to explore with 20 miles. The good news is we towed 3 tonnes of rib down there twice now and its only 2.5 hours from St Malo and an easy 50 mph drive. Have a look on Google earth.

Pete
 
There is. Takes you to Nice at the med end of the trip, probably other places too. Dunno about trailers. They drive the car on/off for you, you aren't allowed to do it yourself. It is VERY expensive, much more than the fuel for driving yourself
 
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