14 days in Great Britain

I think reversing your itinerary works best too ...

Day 1 Arrive Gatwick (stay in London)
Day 2 London (stay in London)
Day 3 London (stay in London)
Day 4 London (stay in London)
Day 5 Train to Edinburgh (stay in Edinburgh)
Day 6 Edinburgh (stay in Edinburgh)
Day 7 (pick up hire car), Highlands day trip (stay in Edinburgh)
Day 8 Durham, York (stay in York)
Day 9 York (stay in York)
Day 10 Caernarfon, Conwy (stay in Conwy)
Day 11 Blenheim Palace (stay in Chipping Campden)
Day 12 Stow-on-the -Wold, Chipping Campden (stay in Bath)
Day 13 Bath (stay in Bath)
Day 14 Wells, Glastonbury, Stonehenge (stay in Salisbury)
Day 15 Avebury, Windsor Castle, (return hire car), depart London at 17:00

I agree with Emma. Day 1 seems too full, too much driving. Day 3 sounds like too much to me. Glastonbury and Wells on the same day, yes, but adding Stonehenge as well would be too much for me. Driving from the Chipping Campden and touring 2 castles sounds like a lot. From day 6, your itinerary sounds much more workable.

How about reordering:
Day 1 - go to Edinburgh, spend 3 nights
Day 4 - train to Durham and train on to York
Day 5 - York
Day 6 - Train south and pick up rental car -- then do Blenheim, etc.
End in London

Advantages - you don't drive while jet-lagged. If you are only spending your time in York, not in the countryside, you don't need a car in York (and parking is a pain). Skip Wales, as you were only thinking about spending one night and it doesn't fit with the rest very well. By skipping Wales, you have one more day, which will make your southern England part more manageable.

Looking at David's itinerary, mine is essentially the same idea, but putting London at the end. (I like London at the end, so I have the energy to stay up late in London!)

If you haven't purchased plane tickets yet, buy Boston-Edinburgh. Then you don't have to worry about booking travel and worrying about missed connections. (Our last flight to Heathrow was 5 hours late...)

Echoing the sane advice above, don't plan to drive after a long-haul flight. You will be jetlagged and that impairs mental and motor skills akin to the effect of alcohol. Added to that, you'll be "backwards" in the car and on the road - driving on the "wrong" side of the road.

Thanks for the advice. I like the idea of heading directly to Edinburgh when we arrive and working our way south. Waiting to pick up a rental car until we leave York makes sense. I think we'll add a second night in Wales to make that stop worthwhile and take one from London as it's easier to get back to London to see what we missed than to get back to Wales. If we need to remove either Glastonbury or Wells which would you recommend?

Thanks
Anne

Don't drive after a long flight especially in England. I know someone who is spending time in jail for causing 2 deaths in a car accident from driving after a long flight in a country where the road is the opposite to North America.

My general impression is that you are trying to cover too much territory. Your stays are too short.

Day four is ridiculous, you plan to stay in Chippin gCampden for one night and see Blenheim Palace and the Cotswolds in one day!

Also, Day five, going all the way to Conwy in North Wales, staying one day. At least you have two days in York and three in Edinburgh, but somehow you plan a highlands trip!

I have been planning for a month in Wales and England for next year. I plan three nights in Bath. We go to Glastonbury and Wells as well. We plan six nights in Chipping Campden to see the Cotswolds, Oxford, Blenheim, and Stratford on Avon.

Consider, travel time, while driving (traffic can be brutal in the UK). You plan to go from Conwy to York after Day 5. How much time have you allotted for that trip? You might only have one full day in York, which is really not enough. Also, how much time did you allot for York to Edinburgn, stopping in Durham?