Adam Badat went Umrah in Ramadhan in 2018, here is some of his experience and advice:
TAWAF
Best time I found to do Tawaf was after Fajr. Even though it may be packed and slower, you have much more energy as you’ve just had Suhoor. The time we found the Mataaf the least packed (only by a bit) was between 10am-12pm in the morning as most people are sleeping and that when it starts to get baking hot.
SHOPPING AND FOOD
Between Taraweeh and Fajr you have quite a few hours so as easy as it is to go and spend that time shopping and munching try getting some Tawafs done then as well.
What we did and I’d recommend is wait until after Taraweeh to have a big munch. There’s not enough time between Maghrib and Esha to going to say the food court and order food and then get back in time for Esha and you don’t want to be rushing. Plus you don’t want to be going to the toilet mid Taraweeh (that is the WORST especially in those public toilets). Leave to get to Taraweeh as soon as possible because spaces get filled up quickly. Take some snacks with you and go for like a toilet/snack break after maghrib.
There’s quite a few fast food places to go to especially in Makkah but they tend to be packed after Esha it may take time to find a place to sit down and eat. We used to order from a Tiffin service where we ordered food around dhuhr time and would be delivered to our hotel after eisha. We found this much more convenient than waiting for ages to get food. For suhoor I’d recommend try getting this included with your hotel package.
LEAVING FOR THE MASJID EARLY
It really depends which hotel you’re staying at with regards to best time to leave for the Masjid. In Makkah it said on Google maps it should have taken 10mins to walk to the Masjid Al-Haram. In reality it took 30mins just because of the sheer amount of people that were there. So I’d say leave around 45 mins before Salah time but again this depends on which hotel you’re staying at.
PRAYING TARAWIH
The roof is amazing for Taraweeh but to be honest everywhere we prayed Taraweeh was great Alhamdulillah. There are Zam Zam taps located pretty much everywhere at Taraweeh time so it’s very easy to fill up bottles/cups if you need a quick break.
In Makkah, one thing is if there is a group of you going, try like set up base somewhere where there’s carpet and take turns doing Tawaaf etc. For example we always used to find a nice spot at Asr time and two of us would always stay with our prayer mats/bags whilst the others did Tawaaf and we’d always come back for Salah time. That way it’s also easier doing Tawaaf as you don’t have to carry your stuff with you as you can leave it with your group.
GENERAL ADVICE
Sunglasses are also ESSENTIAL for Zuhr time otherwise you get blinded by the marble.
Don’t over do it as well. The worst thing is overdoing it one day and feeling so exhausted and ill the next day not being able to do anything at all.

“We took these prayer mats with us”

“After fajr was proper peaceful subhanAllah”

“Madinah iftar was too niceee mashaAllah”

“They also serve some proper food at iftar in the courtyard bit in Madinah”

“There’s also pots of Kahwa/mint tea around at Iftar time if you’re a fan of that”