Do you have 9 full days? What time do you arrive and leave? If you arrive late stay in Lima and fly to Cusco the next morning. Go straight to Ollantaytambo (lower elevation). Explore the town, visit the ruins, walk up to the granaries. The next day Chinchero, Moray and the Maras salineras and late afternoon train to Aguas Calientes. The next day MP. Train back to Ollantaytambo. Minibus or taxi to Cusco. A day to explore Cusco. Then a day for Pisac and the ruins north of Cusco (Tambomachay to Sacsayhuaman). Then the south valley or a day hike. Fly back to Lima. 1-2 days Lima. Buy train tickets online (Peru Rail or Inca Rail). Buy MP tickets here:
http://www.machupicchu.gob.pe/
I recommend hiking up one of the mountains at MP: Huayna Picchu or MP Montana. We chose the latter. If you choose HP you should buy tickets soon as HP is popular and sells out.

..... depends on how you define 'safe' and what your home place is like. Firearms are restricted exclusively to Police and Military, in remote mountains places a small number of farmers might have a gun for dealing with vermin or predators foxes, large wild dogs etc. Generally, elderly people are afforded more respect and care.

The greatest dangers facing elderly people is traffic/road related injuries, Morocco doesn't have a good road safety record, it has improved in recent years with a Government sponsored road safety campaign. Railway travel is probably the safest mode of travel in Morocco, the railway network doesn't go farther than Marrakech though. Recently a high-speed service (Al Bourq) is available, a night-train/sleeper is also available.... see link for details...
http://www.oncf.ma/

Uneven and broken footpaths are common, high kerbs and a lack of ramps for wheelchairs and the lame can make for hard going. Muggings and bag-snatches are very rare, any bad behaviour on the streets can bring intervention and rebuke from passers-by. Street-policing numbers are high, in fact the numbers of plain-clothed police is high and these guys are almost invisible until needed.

I can say its a lot safer than Barcelona, Madrid, Rome or any big city in Italy, Paris or London.

The nearest place to Tokyo would be the Southern Alps. Train to Kofu and bus to the trailhead from there. But June is offseason. I don't know how many busses there are at that time. You can stay in mountain huts, but not cheap.

Yes, you should have no problems at all finding the station! Your greatest problem may be threading your way through throngs of other travelers with mountains of luggage. As you're walking, you might glimpse a large white Sheraton Hotel as you look out the windows, an that is over the TGV station.
If you haven't printed your train tickets already, you'll go down an escalator, and you'll see ticket agents. The office is divided into two sections; one is for travelers planning to go into Paris, and the other section is for people who want to travel to other destinations, and the line here is normally very short. There are also kiosks, but not all American credit cards can be used at those kiosks.
Finally, you'll need to validate ( "composter") your tickets in a yellow box that you'll see at the entrance to the platforms, which are just one level down fro the ticket office.

There is no motorized transport (and in fact, only a most rudimentary trail) over the mountains from Santo Domingo to the coast. There is a road from Bartolomo Maso down to the coast--it comes out more or less at the resort of Marea del Portillo, 15 km or so east of Pilon. But it's really not doable except in a 4x4, and even some taxi drivers with 4x4s won't atempt it.

I would suggest that you go to Santo Domingo, spend an overnight there and next morning do the easier hike to La Comandancia. Even going slowly you can get up there and back down to Santo Domingo in time for lunch. Then take a taxi from Santo Domingo to Yara, Manzanillo, & Pilon Pilon. I did this 18 months ago; did it in about 3 hrs and the fare was 90 CUC in a private taxi. Then I took another taxi from Pilon to Santiago, which I think was about the same--or less. Don't remember exactly. If you have a casa booked in Pilon, you can e-mail and ask them what a taxi to Santiago would cost and they can get back to you with a figure.

You would be familiar with the adage of 'find the right tools for the job', I assume.

Accordingly, if RS is your source of inspiration then you should really follow through and take your questions to the RS forum. You won't find any love for him here, as he represents everything that is the antithesis of the Lonely Planet philosophy. RS caters to fearful Americans who need hand-holding at every stage in crossing the US border and beyond, whereas the Lonely Planet philosophy is, for the most part, geared towards independent travellers who have found their own reasons for visiting places but who nonetheless appreciate a few local insights.

So accept that the comments you encounter here will not be sympathetic if you start from a base of zero insight yourself.

And you will get better advice if you offer an indication of your interests beyond The Beatles, and some indication of your travel budget and style.

By the way, if you are serious about The Beatles you would do better to visit Liverpool or Hamburg rather than to stand on a pedestrian crossing in suburban London or to visit a wax museum there.

Don't get me wrong, I actually think I would enjoy Rome more than Venice I'm just wondering if I could see enough in one day.

And right away we have an example of zero insight. You have this opinion before you have visited either city? They are entirely different experiences. I've been to Venice at least once a year for several years in a row and I continue to discover things there with each visit.

I have less experience of Rome, but I know enough to tell you that the Trevi fountain and the Spanish steps are NOT worth your time, despite the absolute hordes of RS fans who regard these as 'must see' sights and flock there for that reason alone. Do the reading to find your own reasons for visiting Rome or Venice -- there is plenty on online, and you need to match destinations to your interests.

I feel like my biggest places I want to go, don't require much time on my part. They just have important historical stuff that's a must see. This includes London.

This important historical stuff in each city is what? Each city on your list offers a lot to see, and much of this is spread over some distance. You need to allow for the travel time between the sights in each city as well as the travel time between each city.

If you can offer a list of things that you want to see in each place then people here can offer advice. On the other hand, if you have no such list then you are wasting everyone's time, including your own, in posting here.

There is a lot more to Munich than the Oktoberfest and a lot more than simply going there to drink beer, but if that is your only reason for visiting then cross that city off your list.

If London is a 'must see' beyond being your city of arrival and departure then that will already account for at least four days, including the days of arrival and departure. What can you hope to achieve in the remaining five days, allowing for the loss of the better part of a day with every change of city?

So perhaps take a train to Paris, spend two days there; then take a flight to Rome OR Venice, spend two days there; then fly back to London. But to make your time worthwhile in each place you will need a tighty-plotted plan of activities for each day. Without that, you will have wasted the time and money in making this trip.

Some further advice:

• https://www.lonelyplanet.com/england/london/travel-tips-and-articles/top-12-london-for-first-timers/40625c8c-8a11-5710-a052-1479d2767d82

• https://www.lonelyplanet.com/france/paris/travel-tips-and-articles/first-time-paris-top-tips-for-your-first-visit-to-the-city-of-light/40625c8c-8a11-5710-a052-1479d27612eb

• https://www.lonelyplanet.com/italy/rome/travel-tips-and-articles/first-time-rome-a-beginners-guide-to-the-eternal-city/40625c8c-8a11-5710-a052-1479d2763b51

Anatolian Side:

You may already have done this. Along Bosphorus the nest is Anadolu Hisari and as you know there are some hunting lodges along the way.

My walking tour recommendation is as follows if you haven’t done it:

a) Kadikoy Port
b) Haydarpasa Train Station and English Cemetary (not a fan of the cemetary but if you are interested in WW1 and who lost lives )
c) Marmara University- along Tibbiye Caddesi (means Medicinal Str, lots of first hospitals here)
d) Selimiye Fort (You cannot enter since its st Army HQ) and Cicekci District
e) Zeynep Kamil, Cinili Hammam, Kasimaga Fountain and Valide-i Atik Mosque Complex
f) Aziz Mahmud Hudai and Uskudar Mevlevi House (if interested in culture of rituals and spritituality)
g) Maiden ’s Tower
h) Semsipasa Mosque-Library
i) Uskudar Port
j) East Roman Cistern and Match factory, now theatre, along shore line north
k) Kuzguncuk, a small residential district with old wooden houses and small churces and mosques, can find some manti here
l) Fehmipasa Woods and Ozbekler Tekke (means you have done a circle back to Uskudar )