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Jordan and Israel

I am traveling to Jordan and Israel in the fall and i have heard that the border crossing between the two countries is a bit tricky and time consuming. I was wondering if we will have a problem crossing if we have a tour guide for Jordan who will leave us at the border and then another tour guide from Israel who will meet us on the other side.
The other concern that i have is regarding the holidays in Israel during October. It looks like Sukkot (Oct 9-16) is the biggest overlap with our trip. How difficult will it be to get around and will everything be closed for the first few days, including in TelAviv? Thanks for any input.

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Look at online experiences for 2 crossings where internationally recognized borders meet:

Northern @ Jordan River: Beit She'an, Israel, and Shaykh Husayn, Jordan.

Southern @ Red Sea: Eilat, Israel, and Aqaba, Jordan.

Ignore the Allenby Bridge experiences since this crossing is between Jordan and the occupied West Bank, and not at an internationally recognized border. It's not a normal border crossing and has extra steps. Visa for Jordan required in advance here traveling west to east.