Can anyone help with my route?

There are some interesting stops on that list, not ones we see often. Do you have any particular reason for any of the stops e.g. family or friends locations?

Winchester to Torquay is an awkward journey by public transport. Likewise Blackpool to Leicester.

Gloucester is not a common destination and ordinarily I would every time recommend Bristol, unless you have a particular reason. You could be planning to use it as a base for the Cotswolds but it's not great for that. In any case I like to encourage visitors to look at other rural areas that are at least as pretty and much less crowded.

Blackpool was England's premier beach resort after the Second World War but has been in steady decline since we all discovered cheap flights to the Mediterranean. It still attracts plenty of visitors and I quite enjoy visiting but then I can cycle there from home. I can't see it being a great base to visit other areas in the vicinity - there are much better places for exploring the Ribble Valley and the Forest of Bowland for example.

Again Leicester is not often seen on visitors' plans unless you have a particular interest in Richard 111.

Thank you for your reply! On prior trips, I enjoyed London and Bath so I want to return there. I also want to see the Jurassic Coast because i like walks along the cliffs. Blackpool was recommended. Other than that, Im open to a route as long as I can get bus or train service easily. I can sign up for day tours to places I dont stay at. Moving every other day is challenging but I have accomplished it in Wales and Ireland so its not out of the question.

These are the places I have been in the area: London, Bath, Stratford upon avon, Chester, Liverpool, Edinburgh, Darlington, York, Cambridge, Leeds, Canterbury and Dover. I had limited time in each so not opposed to returning.

About 3 days to many for Blackpool, Carlisle might be a far more interesting stop and opens up doung the Settle n Carlise Railway ,englands finest.
The HUGE book shop with the cafe by the Cathedral is excellent

If you were going from Blackpool to Leicester the easiest (and cheapest) way is to catch one of the few Avanti trains each day to Birmingham New Street and change there for Leicester.

From Winchester to Torquay the easiest way would be to take a train back to Basingstoke, change there for Exeter on the South Western Railway route (rather than the better known Great Western route) then change at Exeter for a train bound for Paignton.

If choosing somewhere to stay in Torquay many of the hotels are actually around the coast at Babbacombe, a bus ride away, so check the address carefully. Personally if choosing to stay on the English Riviera I would prefer Paignton at the end of the line, or Brixham (a nearby fishing port)- frequent bus service from Paignton.

If staying at Blackpool then the nearby Lytham St Annes would be my preference, or maybe Fleetwood at the end of the tram line. By next April/May the hope is that the trams will be serving Blackpool North Station on a new extension.

At Gloucester one of the highlights is the Historic Docks- Britain's most inland port- where the River Severn meets the Gloucester and Sharpness Canal. I was talking to someone recently who reckoned that the City Centre away from the Docks was in a pretty run down state. I haven't been there recently so can only pass that on. But I think I would prefer Bristol as a place to stay- Gloucester is an easy day visit from there. Also an easier journey- either one change at Exeter St Davids or straight through on the morning Cross Country train. Also 2 National Express buses a day.

If you want to do the Jurassic Coast Weymouth is a better base- fast trains direct from Winchester to Weymouth, then trains straight from Weymouth to Bristol.

If you take up Richard's idea of Carlisle then you should take the coastal railway route from Lancaster to Carlisle via Barrow in Furness, Yes it'll take you nearly 3 hours longer than staying on Avanti up the main line, but a very scenic coastal route- sit on the left hand side of the train. A number of places round the line where you could break your journey.

My suggestion is a bit of a direction changer. I think you should consider the Rick Steves Best of Southern England Tour. I took it last April and absolutely loved it. It does much of what your are interested in and adds in Cornwall as well. No reason to book a lot of day trips, book one big trip. You could add in days before or after in London. You get so many added value features with this tour. A guide, logistics that make the most of every opportunity, and the opportunity to see just the types of places you said you are interested in.

It may not fit with what you are looking for, but I thought I would throw out the possibility for you to consider.

https://www.ricksteves.com/tours/england/southern-england

My very first time in England was on a Trafalgar tour and I didnt have enough time at any of the stops. I think going it on my own is the best way for now. Day tours also dont give a lot of time, but gives transport that is sometimes hard to find.

I discovered Bristol is a very good alternative to staying in Bath - cheaper and as good or better connections and an easy quick train trip into Bath.. I'm currently traveling in England and last week I couldn't find a room in Bath over the weekend for a reasonable price so I stayed just down the road in Bristol. I stayed in the IBIS hotel by the train station and found it very quick to get into Bath. As well, there is a bus stop just in front of the station where you can take a 90 minute bus to Glastonbury, spend a half day there, then catch the same bus later in the day going back and stop in Wells, see the cathedral, have supper there if you want, then catch the same bus again going back to Bristol. When I told the first driver my plan he sold me a 7 pound all day ticket. It all worked out nicely.

Greg, that is very good to know! Glad you found somewhere that worked out so well! Will definitely check that out.

I would totally second the idea of Bristol as a base over Bath. As well as the Weymouth train that would enable you to access the western part of the Jurassic coast (Bridport and Lyme Regis) through the X51/X53 bus from either historic Dorchester or Weymouth.
The X51 and X53 buses continue on to Axminster Railway Station (on the London Waterloo to Exeter line). By changing at Westbury you could do a great day trip from Bristol.
Axminster and Lyme Regis are the sort of quaint towns you are looking for.
And, if you are intent on going to Blackpool then there is an hourly direct train service from York. It takes a bit under 3 hours each way. By booking ahead you should get it for £15 each way. It's a service I often use. So a perfectly do-able day trip.

Blackpool is fun if you manage your expectations beforehand.

It's pretty grimy and derelict in places if you step a few streets back from the seafront. There's quite a few folks in Blackpool struggling with various aspects of life. If that doesn't bother you, getting into the spirit of the place is a fun day out. Candy floss, [cotton candy] fish and chips, going up the tower, the Illuminations, (the lights on the seafront are a big deal) the trams, the Pleasure Beach (theme park / funfair) are all big draws. You can even buy a burger for £1.

I haven't been in a few years, but my sister was there last year for the weekend. She had a nice time by all accounts.

Some may enjoy the Youtube channel "A Walk On the Wild Side", a local's view of Blackpool.

It's a bit grim in places, but the potential for fun is quite high if you approach it with an open mind.

Really like the suggestion of Bristol over Bath. Thank you! Not set in stone on any particular city but do want to return to Bath and see more things in London. Blackburn had been a suggestion and thanks for the information about it. I enjoyed Barry Island and Llandudno in Wales so maybe I will check it out.
I cant express how grateful I am for all the good advice. I know a few of you have helped me plan previous trips and you are angels. Happy travels!

Trivinow - Do you really mean Blackburn? Or do you mean Blackpool? I don't think I've ever seen Blackburn mentioned on a tourist itinerary before....

do you mean Blackpool?

I assumed the OP did mean Blackpool, in reference to my previous post. Blackburn is whole other matter :-)

Not even I would recommend Blackburn as a sensible base. But it does have some of the really best rural scenery just to the north in the Ribble Valley and Forest of Bowland. And a superb hotel and restaurant just outside the town boundary - Northcote.

Blackpool was in my original route only on a recommendation from a fellow traveler. As one of you mentioned it is a lengthy route from York, I will probably pass on it.

Decided to take the idea of several people and have picked three bases. London, Bristol and York. I had great luck finding affordable rooms in each and am all set except for planning excursions. Will do a few tours and some traveling just on my own. Thank you all so very much for your help! I couldnt do it without you.