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Hi, Ihave cruised from Portland Harbour to Lulworth Cove. It is a fun cruise, and you do feel like you have ‘arrived’ when you get there, approx distance I believe was about 8 miles.
I have also sailed from Portland Harbour to Ringstead Bay, which is a lovely 5ish mile sail across Weymouth Bay, landing on a quiet beach (far less people than on Weymouth Beach, but no ice cream van).
So you have a few options. If just for an afternoon then Lulworth could well be a long hike, esp if you want to stop when you get there, or if the wind dies in the evening.
Also, there is a tide of (I recall) about 1 knot on the way to Lulworth, either with you or against you, which makes a difference, esp if both tide and wind are against you on the return journey.