It’s happening! (3 days Israel)

I would definitely suggest a trip to Masada.

There is a lot of see in Jerusalem but the Old City is compact. You might want to sign up for a city tour. There are many of them with different themes. Some will take you to the sites you mention as well as a walking tour of the old city.

I took a couple of tours with Rent a Guide including a day trip to Masada and a city tour in Jerusalem. But there are other companies as well.

Ok so you think 2 days and one day at Masada is doable?

Maybe the itinerary can be like…

Day 1: Mount of Olives in the morning (iconic Jerusalem skyline photo spot), walk down towards Lions Gate and spend the day exploring the Old City Markets, eventually making my way to the Church of the Holy Sepulchre.

Day 2: Spend the morning seeing the Western Wall and Dome of the Rock first thing, and then walk the Northern Section of the City Ramparts from the Jafa Gate to the Lions Gate (should take about 2 hours for the walk).

Will there be time to see the Israel Museum and Oscar Schindler’s Grave between these 2 days?

Day 3: Masada Day Trip?

I would not consider Masada a must-see with only 3 days in J'lem, especially since you'll have been to the Dead Sea already.

Sunset's at 4.45 pm so you won't have that many hours of daylight to spend in the Old City. It's better not to wander around after dark unless you are in the most crowded parts. Check what hours you can visit the Temple Mount. It changes, depending on prayer times. It's often best to be there as early as possible. The security line can be long and slow. You can also take a guided underground tour of the Western Wall (book in advance). There are any number of interesting churches and a couple synagogues to visit. The Holy Sepulchre is an enormous patchwork. If you are really interested, find a private guide for a 2-hour tour. It's really hard to understand what you're seeing (or even see all of it) without at least a good guide book. One of my favorites is the Lutheran Church of the Redeemer, just a couple minutes' walk from the Holy Sepulchre. It's built in the style of the Crusader churches and there are excellent views from its tower. In the Jewish Quarter you can walk through the Cardo on an ancient Roman road, though today's shops are very upscale (i.e. expensive). There are also a couple of small museums that are interesting, like the Burnt House (from ancient times). You could easily spend all your time just exploring the Old City.

The Mount of Olives has nice views of the Old City. Take a bus or taxi up. Consider walking down. There are several very beautiful and interesting churches.

The Israel Museum is top-notch. It's open late on Tuesdays. One evening spend at the pedestrian mall in Ben Yehuda Street. There are lots of tourist shops (some have lovely handmade items that are fun to look at), cafes, kiosks, and often street performers. There's always a mix of tourists and locals for people-watching. It's a good place for dinner, lots of restaurants to choose from, or just eat street food, shwarma, falafel, fresh fruit smoothies and juices.

I've been several times and agree with Chani, Masada is not a must-do for a short stay. Also agree with her recommendations. Masada could be challenging walking/stairs for an older person (not sure how old your grandmother is).

Ok awesome! Yeah trying to fit in Masada kinda sounded exhausting. Plus with only 3 days, and with me just coming from Egypt and Jordan, I’ll probably appreciate not having to leave the city. This also frees up some time to see the Israel Museum and explore without working on a time crunch.

Also love the suggestions you guys! I’ll YouTube all of them and do some reading.

I forgot to mention the Armenian Quarter of the Old City which has good restaurants, beautiful pottery shops and a church you shouldn't miss.