Went with the wife to Makkah and Madinah for the first 10 days of Ramadhan. We stayed in Makkah for the first 4.5 days (5 nights) at the Elaf Al Mashaer Hotel and then in Madinah for the second 4.5 days (4 nights) at the Rove Al Madinah Hotel. Both hotels we booked ourselves via the booking.com website. We flew via Saudi Airlines which we also booked ourselves direct from the saudia.com website. Car transfers we arranged with a Pakistani (not Arab thank God!) company called Al-Falah Transport Services (contact details in the comments) which was on point: good prices, good communication and good service overall. The visas we arranged with a London based company called Hassan Hajj Tours. Overall the total cost of the trip for two persons including everything (accommodation [£1500], flights [£1100], visas [£300], transfers [£200], food [£200]) except clothes and dates shopping was £3300.
In Makkah because of the heat and the crowds it's not so easy going back and forth between the Mosque and the hotel for each Salah. Thus the routine that we gravitated towards over the course of our stay was as follows:
- Fajr (4am) – we would go to the Mosque half an hour before the Adhan, pray and then make our way back to the hotel half an hour after Salah.
- Between Fajr and Dhuhr – this is when we would get our longest stretch of sleep.
- Dhuhr (12:30pm) and Asr (3:30pm) – we would make our way to the Mosque half an hour before Dhuhr, pray Dhuhr, hang around until Asr, pray Asr and then make our way back to the hotel half an hour after Salah.
- Between Asr and Maghrib – we would get some rest at the hotel, freshen up and pack our Iftaar snacks.
- Maghrib (7pm) – we would get to the Mosque (sometimes inside and sometimes outside) a few minutes before the Adhan and break our fast with dates, yoghurt drink and whatever other little goodies we had with us (croissants, Loacker wafers etc).
- Between Maghrib and Eisha – we would get in a Tawaf on the first floor. Sometimes we would do the first few circuits on the ground floor and then head up to the first floor when it got too busy and congested.
- Eisha (9pm) and Tarawih (9:30pm) – we would finish Tawaf before the Adhan, continue half a circuit more to the opposite side of the Mosque and then find a good spot to pray on the mats.
- Between Tarawih and Fajr – we would go to the third and fourth floors of the Clock Tower building to get some dinner and to purchase some snacks from Abraaj Hypermarket for the next day's Iftaar, then proceed to our hotel to do our social media browsing for the day and then on to the hotel's dining area for some pre-Fajr breakfast.
In Madinah it wasn't as strenuous as it was in Makkah to go back and forth between the hotel and the Mosque and so we tended to come and go between each Salah. Restaurants and takeaways close to the Mosque are in very short supply so we highly recommend arranging breakfast and dinner at your hotel if this is an option. Lastly, for clothes (Jubbas, Jilbabs etc) and dates shopping, Taibah Commercial Center outside the Mosque has plenty of options. You don't need to go anywhere else. There's a Bin Dawood supermarket in here also for you to stock up on snacks and fruits.