I did a semi Anticlockwise in a Parker 235 in 2015 (Bucklers Hard to the Forth then the union canal to Glasgow, finally getting out at Troon).
We took it easy (only daylight sails, broken by trips home on the train for a week or two from Lowestoft and Grimsby).
I would say the trickiest bits were crossing the Thames Estuary (Ramsgate to Brightlingsea), and Wells to Grimsby, where we could not leave till late morning due to the tide, and got into Grimsby as the light was failing, narrowly failing to motor over a cable between a tug and a rig.
Lowestoft to Wells was also a long passage, we got to Wells a bit early for the tide, but the navigation was straightforward (keep turning left). If you are prepared to overnight and press on under engine if the winds are light, then it must be tempting to miss out Wells but Wells is a delightfull stop with god fish restaurants. Grimsby is a bit 'grim' (Hull would be nicer), but both Wells & Grimsby are the first stops after long stretches of inhospitable coast, and Grimsby is the cheapest place by far to leave a boat for a couple of weeks on the east coast.
My Favorite places to stop were
- Brightlingsea (excellent Curry),
- Southwold (pretty, good fish & chips at the harbour)
- Wells (good fish restaurants),
- Bridlington (just generally pleasant)
- Whitby (fish & chips again,nice walk to the abbey)
- Holy Isle (just a romantic spot)
- Eyemouth (first Scottish port, genuine fishing port which accommodates yachtsmen on a pontoon, good museums, good restaurants)
Reasonable were Lowestoft (use the yacht club basin), Sunderland (conevnient for petrol), Amble (nice small town, but very shallow not much in the way of places to eat), Ramsgate, Walton (very help ful guy gave us a lift in his Jag to get petrol).
Eastourne (too big, ) Dover, (Grotty, go to Weatherspoons, the only place with life) Grimsby (a walk into town, eat at a chinese, but convenient), and Scarborough could all be missed.
We had problems getting petrol at a lot of the marinas, if you are diesel this won't be a problem, although it may be 'pink'.
At the more disadvantaged places weatherspoons might be the best place to eat (their low prices mean that they are popular, and the food quality is pretty reasonable)
If you want to chicken out of going round the top or even the Caledonian, the Forth & Clyde canal is good, but you have to book ,Scottish canals provide help for the locks.
Hope this helps
PS to reinforce what someone else has said , I would be wary of too fixed a schedule. In certain places (Wells, the Thames estuary crossing), the tide governs .
Jim Hamilton
Sandy Lady