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Scotland, England, France & Italy itinerary - thoughts please!

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Hi. My husband & I are planning the month of October for Scotland, England, France & Italy. We would appreciate your thoughts on the itinerary. I will have 2-3 extra days that I could place somewhere to spread it out if too tight or could add another city. Also would prefer to flip the whole itinerary to start in Italy and end in Scotland but concerned about weather in Scotland late October. Any ideas??

1. Melbourne, Australia to Manchester - arrive late afternoon - check in at Airport Hotel
2. Pick Up Hire Car - Visit Old Trafford and lunch with Manchester relatives. Travel to Carlisle late afternoon and stay overnight.
3. Carlisle to Fort William (View Jacobite Railway & Neptunes steps) overnight in FW
4. Steall Falls morning. Travel to Edinburgh afternoon via St Andrews (visit Golf Course) Overnight in Edinburgh
5. Overnight and sightseeing in Edinburgh
6. Edinburgh to Yorkshire. Visit Castle Howard. Overnight in Yorkshire To be confirmed where??
7. Yorkshire to Chatsworth and stay overnight at Hotel on Estate.
8. Chatsworth to Stratford Upon Avon - stay 2 nights with friends
9. Startford Upon Avon
10. Stratford to Portsmouth via Stonehenge. Drop Hire car off near Port Overnight in Portsmouth.
11. Visit HMS Victory in morning and then train to London in afternoon.London overnight for 7 nights at premier Inn Kings Cross.
12. London
13 London
14 London
15 London
16 London
17 London
18 London to Paris with Eurostar overnight in Paris for 3 nights
19 Paris sightseeing
20 Daytrip Train to Amiens - Villers Brettonaux from Paris
21 Train from Paris to Florence - all day trip with change over at Milan - overnight Florence
22 Overnight Florence
23 Day trip to Pisa - Overnight Florence
24 Florence to Rome - Train Overnight Rome
25 Rome sightseeing - overnight
26 Rome sigtseeing - overnight
27 Rome to Melbourne

Any feedback would be appreciated - especially the flipped version of this itinerary, extra city versus add extra days, Train trip from paris to Florence. Wish list for an extra place with the spare days would be Switzerland (Juangfrau region) or Venice.

We are in our 40's and are used to long periods of car travel.

Thank you

M

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