Trickiest harbours in the UK to sail to...

Only on LW springs.

Lots of quite easy ones quoted here already, if you really can sail.

But if for sailing to a berth with no engine, or no outboard or dinghy towing, then Porlock Weir in a SW wind must be the ultimate challenge. I could do it easily in a sailing dinghy, but you'd be tacking every 15 feet at the narrow bit. Or it could be done in a straight luff to windward in a very heavy boat but god help anyone already in the tiny pool if you did not get it dead right.

When it was a working harbour I'm sure boat were towed in and out with oars if needed. It was certainly raided by Vikings 1000 years ago who just possibly knew how to use oars as well as swords and axes.
 
Bristol would be hard work.
Not "would" but "is"��

It's not the manoeuvres but the tidal window. Very few refuges and hours of faster-than-boat tide. Too early at Avonmouth and you can swing on by and too late and you'll never get there!

Not tried it but the trick may be to hold up in Portishead pool and or use the counter eddy there.
 
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Not "would" but "is"��

It's not the manoeuvres but the tidal window. Very few refuges and hours of faster-than-boat tide. Too early at Avonmouth and you can swing on by and too late and you'll never get there! Not tried it but the trick may be to hold up in Portishead pool and or use the counter eddy there.

Getting as far as Pill on the River Avon not bad on a rising tide, and if tide is turning against you you can wait in Portishead Pool (The Hole) or anchor in the back eddy the next bay up. However the Avon has few anchoring spots so getting beyond Pill (Crockern Pill) a problem and its a deep sided valley so no wind unless its directly up or down the river at that particular bend. Even I have never attempted to get to the mooring at Chapel Pill by sail alone.

Boats used to tie up against the bank and wait next tide. Interesting with 10m tidal range. Much patience needed to get to Bristol and boats were usually assisted by towing from rowing boats from Pill. Many a boat went aground and quite few were wrecked or flooded.
 
Mayflower Marina in Plymouth - that tide takes you sideways entering that marina. A proper tricky marina to get in/out of, or you just go somewhere else in Plymouth like yacht haven or qab!
 
Whitby is tricky. There's a strong cross current as you enter, and the river Esk brings down debris from the country above Whitby. I managed the former, but just as I was congratulating myself on a safe entrance, a lump of wood brought down by the river caught the propeller and stopped the engine! Got onto a buoy and got a tow in, but not a good experience.
 
If say Salcombe has to be the trickiest by far. The harbour itself isn’t too bad but avoiding the harbourmasters launch as they home in on you for their I’ll gotten gains can be really challenging lol
 
Getting as far as Pill on the River Avon not bad on a rising tide, and if tide is turning against you you can wait in Portishead Pool (The Hole) or anchor in the back eddy the next bay up. However the Avon has few anchoring spots so getting beyond Pill (Crockern Pill) a problem and its a deep sided valley so no wind unless its directly up or down the river at that particular bend. Even I have never attempted to get to the mooring at Chapel Pill by sail alone.

Boats used to tie up against the bank and wait next tide. Interesting with 10m tidal range. Much patience needed to get to Bristol and boats were usually assisted by towing from rowing boats from Pill. Many a boat went aground and quite few were wrecked or flooded.

I have sailed to Bristol from Portishead (although I confess I had to put the engine on once I got to the Cumberland Basin as I had to hang around for 10 mins whilst they swung the bridge. The main challenge was the wind eddies around horseshoe bend. I should also note that it was on a 20foot trailer sailor which would easily dry out if I got it wrong.
 
I have sailed to Bristol from Portishead (although I confess I had to put the engine on once I got to the Cumberland Basin as I had to hang around for 10 mins whilst they swung the bridge. The main challenge was the wind eddies around horseshoe bend. I should also note that it was on a 20foot trailer sailor which would easily dry out if I got it wrong.

I take my hat off (or commiserate the insanity of) narrowboaters that use the Avon / Severn estuary to get from Bristol to Sharpness.
 
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