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Some comments in no particular order:

You will be in Jerusalem for Christmas and you have no accommodation booked? For obvious reasons it’s peak season, and you can’t just turn up and expect to find somewhere to stay, especially since you are looking for hostels – in other words cheap. This is true throughout the year, and multiply it by 10 at Christmas, when the place is heaving with tourists.

Your route is possible only on major highways. These roads are very busy, with buses and lorries rushing past. There are no pavements (sidewalks) except within towns. Just one of your days – at random – Metzokei Dragot to Masada is about 32 km. on a busy road. And repeat every day for 10 days? It doesn’t sound very appealing to me. Ten consecutive days, spending each night in a different place, you won’t have any time to see “notable places”.

You can buy bottled water in petrol stations that have convenience stores (which is about all you’ll find on your route). Otherwise, you could ask the locals – in inhabited locations – whether you can fill up at their tap.

The locals are likely to think you are off your rocker! No particular political problems relating to a 37-year-old male, though.

There are no restrictions on entering Sderot or anywhere else in Israel.

Here are two sites with lists of hostels. No personal recommendations for any of them. The Abraham Hostel in Jerusalem gets excellent reviews, but it was probably booked up months ago.
http://www.iyha.org.il/eng/
http://www.hostels-israel.com/index.asp

Bottom line, I don’t think you realise what the roads are like. You’ll be spending all your time trying not to get run over. It won’t be the least bit pleasurable. 30 km hiking on footpaths is a good day’s hike. On Road 90 along the Dead Sea – and others like it – it isn’t.

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Thanks for your response. Are there really major highways between Jenin and Nablus, or Nablus and Ramallah that have petrol stations with convenience stores? I can understand it for some of the legs, but i was under the impression that some of the legs would be quite rudimentary. How major is the route from Nazareth to Jenin?

Thanks for the links and comments regarding accommodation. Its a hurdle for sure.

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Sorry, I forgot to add that I don't know anything about the Palestinian stretch of your odyssey, except what I can see in a road atlas. And I'm looking now.

The only roads from Jenin to Nablus are very winding. I haven't a clue how much traffic there will be. Probably a lot less than in Israel, but that's all I can tell you. (And I can't go there to check whether there is a lot of traffic, or whether there are convenience stores!)

And something else, now I've looked at the map. Truthfully I know nothing about roads in rural areas under Palestinian Authority control, but you asked about the political situation. If there's anything about you that could lead someone to think that you might be a Jewish settler, you will likely be in for a hot time. Wearing a keffiyeh could help.

In all honesty, I think this is a somewhat deranged project!

Edited by: Shuffaluff

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Good advice with the Keffiyeh. Something i hadn't thought of and i will look into getting one. Having read your comments about the Israeli sections, i am now thinking of condensing the trip to just the legs from Nazareth to Jerusalem (maybe add a leg from Jerusalem to Bethlehem) and taking some time to take in the surroundings.

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I am planning on hiring a guide locally for the first 4 days. good
Would this be possible, and will i have any problems walking with a guide in these areas? http://no problem. see below
Can i cross from Israel to the West Bank just north of Jenin at Jalame still? yes, at the Gilboa-Jalame Crossing
Can i easily find some accommodation either hotel or hostel in those locations? yes, but book ahead
Can a 37 year old British male expect any problems due to the political situation in the region? no
Is drinkable water available en route? nothing reliable for a random walker although guide might know local springs
Are the locals likely to be friendly or hostile? once they know who you are- friendly
Any notable places to avoid? guide will know
Any notable places to definitely see? ["]
Any restrictions on entering Sderot considering its proximity to Gaza? none at all

I think your plan sounds very exciting .The route itself is definitely doable. There are rural areas between all the spots you mention and there is absolutely no need to walk on or near roads. You can walk either on marked hiking trails (where available) or along dirt roads/trails. Here is a list of walking guides you can use for the Israeli part of the route:
http://www.tiuli.com/guide_search.asp?lng=eng

It's best to use a Palestinian guide for the West Bank part of your trip.
I agree with Shuffaluff that you've probably calculated too many km p/day.

I can get into all the details of going on such a walk but it's better if you talk to a few guides first and then come back with more questions.

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amirico, doing it on dirt roads and trails will add considerably to the distance. Dirt roads and trails between Metzukei Dragot and Masada? (Assuming this part is still on the agenda, that is.) Highways, by their nature, are likely to be the shortest practical distance between two points, taking terrain into account. Hiking trails will inevitably be much longer.

OP has calculated his distances based on a road map.

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Shuffaluff,
I agree that in most cases following the roads would mean less km but I think neither of us sees the point of walking for a week along a highway breathing in the fumes.
As we also agree that even as is, the plan is a bit unrealistic, Old_Lady needs to either add more days (and walk on trails) or shorten the list of destinations.
Old_Lady, the best thing to do would be to contact the guide and decide together if you'd rather spend your time on one long stretch, combine several short walks, maybe try the Jesus Trail, Jerusalem Trail or a few segments of the Israel National Trail.

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Thanks for you inputs and advice. I have taken it on board and have no revised the trip to the following:

Day 1 Arrive Tel Aviv. Travel by train to Nazareth
Day 2 Walk Nazareth to Jenin 30km
Day 3 Walk Jenin to Nablus 40km
Day 4 Nablus to Ramallah 48km
Day 5 Ramallah to Jerusalem 26km
Day 6 Sightseeing in Jerusalem
Day 7 Jerusalem to Bethlehem 8km and sightseeing in Bethlehem
Day 8 Bethlehem to Hebron 38km
Day 9 Hebron to Metsadot Yehuda 35km then bus to Beer'sheba
Day 10 Bus from Beer'sheba to Ben Gurion Airport

Would you happen to know if there is public transport available from the border crossing at Metsadot Yehuda? Is that crossing still open?

Some of the legs are longer than i would have liked, but still achievable.

I plan on getting an arab israeli guide in Nazareth for the first leg, and then Palestinian guides for the other legs through the west bank.

I will also get a keffiyeh as suggested by Shuffaluff so i don't look like a Jewish settler.

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Here’s what I can add:

Travel by train to Nazareth: there is no train to Nazareth. Take the train to Lev Hamifratz (just after Haifa) and a bus from there to Nazareth. Frequent buses operated by a company called GB Tours.

Not sure how you get Ramallah to Jerusalem 26 km. It is only about 13 km by road – although we’ve already covered the “by road” topic. But maybe you have found a nice route on footpaths? Sorry, can’t help on this one.

The road from Metzadot Yehuda (road 316) goes south and then west through the Yatir forest (nice forest!). Bus 51 will take you from Metzadot Yehuda to Beersheva. Five buses a day: 06:50, 09:50, 14:05, 17:00, 20:20, 21:50. Times approximate as the bus starts in Kiryat Arba and could be late (or early!).

There is no direct bus from Beersheva to Ben-Gurion Airport. The easiest and fastest way is by train to Tel Aviv Hagana and change there for a train to the airport. There are direct trains from Beersheva to the airport at night: 00:51 and hourly until 04:51, taking 59 minutes.

What day of the week is Day 9? You say you are leaving Israel on January 2, which is a Sunday. If Day 9 is a Saturday, this won't work. There is no public transport on Saturdays, and the last bus from Metzadot Yehuda on a Friday is at 15:45. And if your day 9 is indeed a Friday, you won't be able to travel onwards from Beersheva - except by taxi - until after dark on Saturday.

Edited by: Shuffaluff to fix up stuff relating to days of the week!

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Oops, ignore what I wrote above about the days of the week. My mistake (forgot to change the page on my calendar, now it's December!!).

Of course January 2 is not a Sunday, it's a Wednesday. So no problem there. However, I note you arrive on December 22, which is really, truly and honestly a Saturday. You don’t say what time you arrive. There are no trains on Saturdays until after dark, the first one from the airport to Haifa being at 19:31. If you arrive considerably before that (Saturday morning) and don't want to wait for hours for the first train, you can take a shared taxi, operated by a company called Amal, to Haifa, which goes when it's full and will take you to anywhere in Haifa. Ask to be taken to Haifa Merkaz/Central railway station, where you can get the bus to Nazareth (these buses run frequently on Saturdays). On weekdays (including Sundays, which is a weekday here), the buses to Nazareth leave from Merkazit Hamifratz, next to the Lev Hamifratz railway station, and in addition pick up passengers Merkaz/Central station, among other places.

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Re the Palestinian part of your trip, there's no security issue involved as long as you do not dress like a settler - they're easy to spot as those living deep inside the West Bank wear specific, religious attire. People are used to seeing Westerners and are generally very friendly. Just make sure you do not dress like a settler in the most conservative areas.

The main issue in both Israel and Palestine will be that people drive like maniacs and do not necessarily expect to see someone walking along the road. Remain cautious at all times in order to avoid cars.

People in Palestine are not really used to seeing people walking or jogging and you're likely to be stared at with curiosity, especially from children. This also means you're likely to be invited for countless free meals and glasses of tea.

Hiking is slowly becoming an activity in Palestine thanks to a handful of Palestinian hikers and to the many expatriates living in Jerusalem or Ramallah who enjoy walking around. Finding a guide should not be a problem:

http://www.walkingpalestine.org/pages/homepage/walk-with-a-guide.php

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You'll have some long days, but the itinerary is doable if you're accustomed to 40+km days and have a good sense of direction and navigation.

I assume you've come across Abraham's Path and the Nativity Trail, long-distance north-south trails through Palestine. They are not marked, but there are local guides that know the way and I think you could get the GPS tracks. The Palestinian organization that developed the paths is Siraj, (http://sirajcenter.org ) located near Bethlehem. I would recommend getting in touch with them to hire a guide, get advice and see if you can get the GPS for the off-road route. They also have a system of homestay accommodations in many villages. They would also have a sense of what is happening on the ground, areas that might need to be avoided, etc.

You can enter at Jalame checkpoint, but in my experience the will not let you across by foot, so you might need to hitch a ride for 20m. to actually cross. For the route from Nazareth to Jalame, I would get an SPNI topographical map which shows all the marked trails in Israel (and there are a ton, over 10,000km of marked trails). You can connect a variety of trails to get close to the checkpoint (via Mt. Gilboa-- beautiful!) and then make your way by road to the checkpoint. I wish I had the map in front of me, I could give you a more specific route suggestions. The maps are only in Hebrew, but if you can read topography you can still utilize them. Click the bottom link on this page to download a translation of the legend/key on the Hebrew maps: http://jesustrail.com/route-maps/digital-paper-maps

I have walked much of the Nativity Trail route and it was very beautiful and remote, much better than walking down a paved road with traffic. I enjoyed the homestays as I got a better window into local culture (and very delicious home cooked food).

Edited by: yallah

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PS I think you'll have a hard time finding a local guide willing to walk such long days. They are more accustomed to doing 15km, 20 max.

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Old lady...did you do it? How was it?