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Chris is right. Lyme Regis is an excellent place to stop.
Enjoy a pint of Palmer’s IPA while you’re there. My favourite pub was the Pilot Boat, absolutely basic but the beer came straight from the barrel. I’ve just checked and it’s been done up, unrecognisable but it still looks great!
You could also try West Bay, great for fish and chips (and Palmer’s)
You’ll need to plan for going around Portland. The inner route is by far the quickest but you’ll be very close to the shore all the way round. Check the tides before you set off.
Dartmouth is great as is Torquay. Our boat, Haston Dee, was moored on the River Dart when we bought her. We lived in the village of Dittisham and so we could row out to our mooring. Later we moved to Torquay – I got fed up with travelling to work from Dittisham – and we moored the boat in the Inner Harbour which dried out. Later on, the Harbour Board built new pontoons in the Outer Harbour – brilliant as we didn’t dry out.
Both Dartmouth and Torquay have yacht clubs a couple of minutes walk from the moorings. Torquay has the Royal Torbay and Dartmouth has the Dartmouth Yacht Club. It’s worth taking the ferry across to Kingswear where you’ll find the Royal Dart right on the water front.
Haston Dee is now in Malta so well travelled – we’ve had her for well over 30 years.
We now go to the Royal Malta Yacht Club which reminds we – our subs were due a week ago!