My husband and I drove from Kuwait to Medina and Makkah in March 2005 for Umrah. My husband talked me through the entire process while we did it, so I don't remember all the exact details (he would tell me what to say in Arabic and then translate it for me, but since I don't speak Arabic, it is hard to remember). I will stick to some of the practical things about Umrah.
In Medina, we got hotel rooms over looking the courtyard-type area around the Prophet's Mosque (we got rooms for about $30 US a night). In the area around the mosque, there are little shops that sell lots of different books on Islam in many languages. For women, there are only certain times of the day that you can go through the mosque to the men's side to see the place of the Prophet's home. Hire a taxi to take you around the city - we prayed in some of the oldest Mosques, including the mosque that is considered the "1st' mosque (I say considered, because it is in the exact place, but it has obviously been rebuilt, remodeled, and refurbished, so "it" is not the exact first mosque). I found many, many women who were willing to try to talk to me in the various mosques (again, blue eyes and pasty-white skin makes me stand out) - in one mosque, a group of ladies from Qatar even sent a little 5-year old boy over to translate from Arabic to English so they could talk to me!
In Makkah, take time to walk around all the Haram Mosque if possible - the architecture is magnificent, and even non-Muslims would appreciate the beauty of the building itself. Also, make sure (for Umrah) to take a taxi around Arafat and Mina and see the pillars. Also, it is great to tour both cities because it is amazing to see all this history and religon, but then just a block or 2 from the Haram Mosque there is KFC (Kentucky Fried Chicken), Hardees, and McDonald's! It is a fabulous mix of old and new!
Practical advice for both time in Medina and Makkah -
bring a supply of plastic bags and easy to slip off sandals. Put your sandals in the bag and tuck it under your arm - there are so many shoes lying around that it would be easy to lose yours (or, unfortunately, have yours "traded" by someone who needed better shoes).
Also, be very, very wary for all the street beggars (especially children) - I had so many children tugging and pulling on me that I nearly had a panic attack! They see my blue eyes and white skin and they know I am a foreigner. They also come running at you with scissors to cut your hair (and me, safety freak, is going crazy with all the little beggar kids, some as young as 3 or 4 years old, running in a big crowd of people with scissors!) - use one of the actual barbers. My husband got his hair cut by the barber, and the barber let him just borrow the scissors for a moment to pull a tuft of my hair out of my hijab to snip.
Smokers- when we went, there were signs everywhere in multiple languages speaking against smoking (using the verses from the Qu'ran about not injuring yourself and that the Prophet did not smoke) - even the hotel rooms, on the back of the doors with the emergency exit information, basically berated you for smoking at all since it is the cause of so many fires (again, quoting Qu'ran with their own statement).
If you have any questions, feel free to ask - I personally loved Saudi Arabia in general, and of course, had a very fulfilling Umrah!
Illalika!
Lana