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2-3 Months In England?

It can be difficult - and potentially harder by having longer.

One technique that has worked for us in the past has been setting a theme e.g. Mountain and city, or Tuscany taster, or by setting out in conceptual terms what appeals e.g. I want some history, some countryside, somewhere familiar and somewhere brand new.

For shorter stays it's easier to choose a key location that's a cornerstone of the trip, then radiate outwards on the map to find additional variants / areas of interest.

Looking at the above, one 'theme' option might be Southampton to Cornwall by coast and then back to London (?) inland. Maybe mixing up the stays by having 1-7 nights in each location on the way to Cornwall, then having 2-4 weeks there, before 1-7 night stays on the return eastwards. If happy to stay in B&B accommodation, there is often good value & availability.

Alternatively, with such a long period you could easily just say: "You write down your top 3 places that you absolutely want to visit, and I'll write down mine" compare the lists, and if they are all different, then that's your 6 x 2 weeks sorted. If there is agreement on any, or if any only really warrant a week, then you've got an additional location or two to fit in, but rather than resorting the 4th or 5th choices, see how the selected places fit together logistically and maybe there is an obvious stopping point (e.g. if you have Lincoln and Edinburgh, then York, Harrogate, North Yorks coast or Durham would be an obvious place to add). This might be a great way of doing it if you have too many possibilities, as it helps focus on what appeals the most.
 
Yes, one year we had the "walled cities tour" in England, another year it was all about one specific region. For 2018 if we arrive in Southampton it just makes sense to stay south of London. I'm thinking we would end our time in or near London so that we could easily fly to Italy. Other than that, I still have a lot of research to do!

If I were to find 2 great locations and negotiate a good rate for 4-6 weeks in each place that would be ideal. I'm thinking about Dorset or Wiltshire for one stay, then either E/W Sussex or Kent, OR Somerset and Gloustershire for the second stay of 4-6 weeks, thinking we might sneak in to Wales for a bit.
 
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Yes, one year we had the "walled cities tour" in England, another year it was all about one specific region. For 2018 if we arrive in Southampton it just makes sense to stay south of London. I'm thinking we would end our time in or near London so that we could easily fly to Italy. Other than that, I still have a lot of research to do!
Your post / challenge got me thinking, so I've added a new post in the Travel talk forum, asking forumites what techniques they use to do the initial shaping. I'm hoping we'll see some interesting / thought-provoking ideas!
 
I just put a deposit on a cruise from Miami to Southampton for April, 2018! I really, really want to do this! The deposit was only $50 per person, which is the reason I did it, plus the cabin is only $799, altho we will have to drive to Miami. Royal Caribbean will release their TA fares later in March, so maybe we can get a cruise out of Tampa! the Royal Caribbean cruise generally arrives in mid-May, which is 2 weeks later than the one we put a deposit on - April in England can be cold and rainy, so a later arrival is better!
 
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