The Great Britain Roadtrip Conundrum

As to football don't right off the Championship ,you can be near certain to get tickets to any game and several clubs historically are " top league" ones.
You could trade that long Conway Newcastle day by stopping off at Tan Hill Inn and that would allow several hours in the hugely scenic Dales.

From Tan Hill there's a massive scenic route through Upper Teesdale with it's waterfalls ,the high high moors of the north Pennines ,England's highest market town at Alston and then the south Tyne down to Hadrian's wall

Not a bad plan, but you will find traveling by car in the UK, especially near any large cities will be slow.

We did a four week drive tour of England and South Wales in 2017 and planned most days to drive no more than two hours. Your plan has several days that likely involve much more driving than that.

Still, you plan a full day in the Cotswolds (we did two days there to see the Cotswolds).

we stayed at the Volunteer Inn at Chipping Campden. Also, you have one full day in York, which is way not enough. You will spend at least 3 hours just seeing the magnificent minster (Cathedral). Be sure to walk the ancient walls, visit the Railway Museum and the old streets of the city.

Wales is loaded with castles on both sides of the Wales-England border. Tintern Abbey is worth a visit. Conway will take about 3-4 hours to see.

Beware driving far on the M25 ring road around London, it is one huge parking lot much of the time.

Be sure to have a navigation system on your car and get an automatic. This will reduce the stress of driving on the left.

I might consider it in reverse so you're not hopping off a plane and driving. Don't underestimate how groggy you may be, plus unfamiliar roads, signs and driving on the left.

I haven't gone to a game yet, but from my experience in looking for tickets, you'll likely have better luck in the smaller locations. I'll be curious how successful you'll be getting tickets for Chelsea and how much they'll cost.

I'll be curious how successful you'll be getting tickets for Chelsea and how much they'll cost.

Hospitality tickets may be your only legitimate option. Remember reselling EPL tickets is illegal (yes, that’s right, Illegal ) so if you go that route you may get fleeced and nobody will be able to help.

Please don’t get off a plane jet lagged then try to drive anywhere in an unfamiliar car on busy roads.

Would it cost more to drop the car in York rather than driving it back down to Heathrow? It will probably take at least 4 hours to drive to Heathrow, and you'll still not be where you want to be, which is downtown London. The train from York to London (Kings Cross) takes just about 2 hours. You might be able to organize your sightseeing in and around York so you don't need the car the last day you're in the area, which might save on rental fees.

I think it would be better to get the match tickets and then finalise the route. Teams only play at home every other week so you’ll be very lucky to find Chelsea are playing on one of the 3 days you’re in London. Likewise on the other day you have set aside for seeing a match. Is that day a Saturday as that’s when most games are played and you have the best chance of getting tickets for something?

At a minimum, consider dropping the car in York and take the 2 hour train to London - not worth wasting time going back to LHR just to drop the car. A revised itinerary might be to start in London, train to York, pick up car, do your road trip in reverse, drop the car in Oxford (close to Cotswolds), then train back to London for your final 2 days + match. It's an adjustment for a pedestrian to navigate traffic on the "wrong" side of the road, never mind driving, so starting in London would give you time to see how traffic works there.

Drop the car in York and take the train, otherwise you will have to navigate around the M25 parking lot to Heathrow, which is on the south side (opposite) of London.

Don't drive the same day you arrive after a transatlantic flight. Catch the train or coach to Oxford for the night and pick up the car the next morning and then do the Cotswolds.

Don't underestimate driving times. Distances may not look very far on a map but are going to take a lot longer to cover than you might expect. If using google maps, add 25% onto their driving times AND THEN ADD ON TIME FOR STOPS. Roads can be congested and slow moving traffic can add time onto journeys.

Several days involve long drives - Day 3 and Day 5 in particular. You don't say when you are coming in October but you are beginning to get short days. Sunset is around 6pm (and getting a few minutes earlier each night.) On dull cloudy days it is going to seem even shorter. You don't want to be driving aftr dark.

You have a lot of one night stops which is hard work. It also means you have limited time to see and do things each day as you have to get between two points.

You are trying to push a lot into 2 weeks and are going to end up seeing a lot through the windscreen.

You will find plenty of pubs for him but the two football matches may be more of a challenge...

I'll join the chorus about driving on arrival day, not a good idea at all, for yourselves and others on the road. This bus (aka coach) service will take you from LHR to Oxford with speed and ease. You can pick up the car there the next morning and head into the Cotswolds. And try to drop the car in York to take the train into London, as suggested above.

I like road trips and have done a lot in the US, but I think yours is too rushed. You'll be moving much more slowly than equivalent miles on US freeways. And there's so much to see beyond the windshield. I think day 5 is especially unrealistic. You write "I’ve dreamed of visiting England since I was 8, so there’s a lot I want to see but I also want to enjoy what I’m seeing." You're in your 20s, so hopefully you'll have many decades of future chances to see and enjoy all that England offers, not to mention other parts of the world.

There's also a glaring omission in your plan -- no scheduled time or place for that beer in a pub. Gotta work that in somehow, maybe more than once. ;-)

I’ll be somewhat contrarian here. I’m not sure what your driving skills are, how much sleep you can get on a plane, or your knowledge of road signs in the UK so I won’t comment there. My husband and I in our 20s rented a car at Gatwick our first trip ever to London/UK and had a blast. We did an ambitious schedule too. We drove all over southern England the day we landed. We repeated that in Italy, Spain, and France several times. We figured out by our mid 30s we really didn’t enjoy it anymore and we just couldn’t handle it. We always front loaded our trip because even in our 20s, it really got tiresome. I’m glad we took advantage of our youth. Doing local stuff has always been my favorite part of traveling. Visiting friends in York will probably be the highlight. Enjoy your trip! I hope it is as memorable as mine was.

Just be aware that your time in London may not coincide with days where there are any football fixtures or Chelsea maybe playing away. The fixtures for the 2023/4 season are not released until the 16th of July and then they are provisional until about 6 weeks in advance pending the confirmation of the televised matches. Also there is an international break between Oct the 9th and 17th where they will be no EPL and Championship matches played. That is putting aside how extremely difficult and expensive it is to get legit EPL tix.

Given you are in York a while, see if York City are at home. It will be pay on the gate - they play in the NL step 5 of professional footballwhich is a good standard and York being a former EPL get good gates. You could combine this with going to pub, a lot football fans go to the Maltings ahead of York home matches and normally it is a cracking atmosphere and will be a far more real experience.

The best villages in The Cotswolds (in my opinion) are Bourton-on-the-Water, Lower Slaughter, Chipping Campden and Broadway. If you are heading off towards NW Wales from here, to go all the way down to Tintern is going on a much longer route. Although Gloucester has a Cathedral (which I think was used in a Harry potter film), I would normally advise people not to bother with Gloucester.

To go through the Elan Valley and then through the mountains to Pantarfynach (Devil’s Bridge) and on to Aberystwyth involves some narrow roads. Click this link to Google Maps and go to street view by the old lead mines and you will see what I mean.

Hi, I just read this and, though I don't have any input on your itinerary, I want to put my comments about driving when you get into London.

Absolutely do it - you are in your 20's! I'm a 75 yr old retired woman and 3 years ago we landed in London and I drove to Oxford for 2 nights before continuing onto the Cotswold. Stopped in Oxford mainly because we wanted to see it and it actually turned out to be a great spot.

Get started on your adventure!

I'm on this site because I'm planning a North Wales, Cromwell, London trip in June and need some ideas.

Have fun