From Magadan, Russia to Cape Point, South Africa.
Longest Roadtrip on Google Maps
This 24,000+ km journey is very difficult from a political and safety point of view. But possible. Certainly there are better nationalities to try this, such as Japanese, South African, Indian, to ease travel through the Middle East and parts of Africa.
Caveat: While it is possible to drive the entire route on the ground, it comes down to illegal border crossing or off-road desert travel in the Sahara to actually do this. It is recommended, while the border between Egypt and Sudan remains closed to ground traffic, to use the ferry between the two countries instead of figuring out how to drive across. Unless Darfur is really high on your go-to places.
You will NEED to start up north if you plan to go through Iran. You won't be able to enter Iran if you go through Israel first. But if you pass through Syria, you will be able to start at Cape Point and work your way north. Probably. You should take this as a long, but incompletely researched itinerary through Asia, the Middle East and Africa.
Far East Russia
Starting in late October for the first leg might be best, as the roads in Siberia can be impassible in the summer. Flying/shipping to Magadan (on Wikitravel) would be the first step.
There is a seasonal road (winter only) from the port of Magadan, Russia that goes west to Yakutsk. Kolyma Highway - Wikitravel. A very dangerous route where caravan travel is the only way to insure you don't die alongside a frozen road if you break down. From Magadan you can travel eastward, but only to local communities. - 2025km (about 4 days).
Ewan McGregor and Charley Boorman rode part of this stretch on motorcycles as part of their documentary series Long Way Round, in which they drove around the world. (Magadan was their easternmost point in Russia. From there they took a flight to Alaska.)
You can follow the M56 from Yakutsk south to Never and then west to Chita, this last stretch more or less along the Transiberian Railroad line. Be aware that in 2006 this road had the distinction of being called "the world road in the world" because if its state of disrepair. - total 2085 km
Your real crisis from here is the Zilov Gap. It is an essentially roadless region in Central Siberia. Most travel avoids it by using the Transiberian Railroad, which is the route that the Long Way Round used. Another endurance motorcycle trip, Mondo Enduro got bogged down trying to cross it and eventually gave up and took the train. It was later successfully crossed in 2001 by Terra Circa. You'll be most worried about the section between Never, where the M56 starts, and Chernyshevsk, from what I am reading. However, the roads into the region have been extended since then, so this may be navigable now.
From Chita, you drive southwest to Mongolia. I don't know the best place to cross from Russia to Mongolia, but it seems that the border towns of Kyakhta and Altanbulag might be a good place (727km from Chita.) The Long Way Round team crossed there.
[Total so far: 4,735km]
Mongolia
A detour all the way south to the capital Ulaanbaatar (on Wikitravel) (351km) might be in order to take the best roads west toward Kazakhstan. As the national capitol, it is really the starting point of travel in the country. You would be traveling west toward Mörön (on Wikitravel) and then reaching the border with Russia again near Tsagaannuur, 1,567km from Ulaanbaatar.
[Total so far: 1,918km + 4,735km]
Kazakhstan
You will actually need to travel another leg through Russia to get to Kazakhstan.
From Mongolia to Kulunda, Russia is 1.095km. From there you have 571km to the capital of Kazakhstan, Astana (on Wikitravel).
From here your course will diverge based on which countries you want to travel through later. You can go west around the north end of the Caspian sea and then south toward Georgia, Turkey, Syria, Jordan, Israel and then Egypt. Or you can go south, through Uzbekistan, and Turkmenistan, then west through Iran, Iraq, Jordan, Israel and then Egypt. Basically, you have to go through Iran or Syria.
South route
If you are headed to Tehran, then you will be driving from Astana to Tashkent, driving through the Kazark desert to reach the river valley of the Syr Darya and skirting around the Qizilqum Desert in South Kazahkstan. 1,767km to reach Uzbekistan's capital, Tashkent (on Wikitravel). You will be following the old Silk Road as you travel along Syr Darya and toward the mountains.
[Total so far: 3,433km + 1,918km + 4,735km]
West route
The Long Way Round team actually went south to the Syr Darya and then west to the Aral Sea (but in the opposite direction, since they started in London). But the shorter mileage is actually through North Kazahkstan, due west, then southwest toward the Caspian basin. Plus you will still find that Russian is a useful language since the Russian minority live in the north. You'll be skirting the border with Russia until Aktobe (skant details on Wikitravel), which is considered to technically be the most eastern part of Europe.
From there you head toward Atyrau on the Caspian, then back into Russia at Kotyaevka for a dash south to Georgia. This very long route takes 3,254km with the last portion being through the Caucasus Mountains over the Georgian Military Road to reach Tbilisi, the capital of Georgia. Even in winter, this should be passable.
[Total so far: 4,920km + 1,918km + 4,735km]
The Middle East
At this point, you are either in Tbilisi or Tashkent and are facing potentially difficult travels based on your nationality and the state of conflicts in the region. Russian is still a useful language at the start of this leg, for both locations, but that will change soon.
Turkmenistan has very difficult visa requirements and the police are omnipresent. Iran will not allow anyone into the country if they have any evidence of visiting Israel, including visiting bordering countries. In fact, just a visa or itinerary that results in you passing through Israel (as this road trip MUST DO to get to Africa) can prevent entry. The consulate knows how to use Google, so a planned trip such as this is bound to be discovered if you have posted it online. Beyond that U.S. (and some European) visitors will have to expect to be accompanied throughout their visit by an MFA-approved guide. Iraq too is known to be risky (less so than a decade ago) for Westerners; and the Iraq/Iran border might be a difficult exit.
Syria, of course, is in the middle of a civil war. Taking a loop around Syria through Kurdish Iraq is an alternative. Or running along the Mediterranean until you are south of Damascus, but that means crossing into Lebanon.
Assuming you can negotiate the visas, political hazards and avoid doing something that lands you in trouble, you will find that all of these regions are desert terrain punctuated by rugged mountains.
Iran route
From Tashkent you will head south a short 4 hours toward Samarkand, the heart of the Silk Road. The entire city center is a UNESCO heritage site. Continuing along irrigated river valleys, you will cross into Turkmenistan and the city of Türkmenabat, second largest in the country. Skipping the capital for once, you'll be driving straight southwest for the Iranian border, crossing at Serahs.
Throughout Iran you will be skirting various mountain ranges until you reach Tehran and its highly developed (and air polluted!) city. At 14 million people, it is one of the largest cities encountered on this trip. And the traffic while driving through the city will make all 14 million of them apparent. The journey here from Tashkent: 2,131km.
893km more will get you to Baghdad in Iraq. Expect an exit fee for Iran. (Note, I have no idea if this route is allowed. Driving in/out of Iran is normally done through Turkey or southern parts of Iran, according to travel guides I've read.) You will be crossing the Zagros mountains and travelling through sparsely populated terrain, other than the province capitals of Hamedan and Kermanshah.
In Iraq you will be passing through the capital Baghdad. This city is still listed as one of the most dangerous cities in the world. Overland travel throughout the country is not recommended due to regular violence. Wikitravel has the following statement about local travel: "The preferred method of transportation is helicopter. If helicopter transport is not available, use of a fully armoured car or Rhino (armoured bus) is recommended." You might drive up to Samarra and then back down to Ramadi to give Baghdad a wide berth, but these cities come with their own warnings too.
Driving out into the Syrian desert gives you a straight-shot at Jordan. The border crossing on Highway 10 is somewhat built up with military and refugee services, but there really aren't any services there. This is 570km from the capital.
Crossing the desert to Amman, Jordan is about 330km, which is where the other route connects to this path.
[Total so far: 3,924km + 3,433km + 1,918km + 4,735km]
Syria route
Finally you are leaving the winter lands behind. South of the Caucuses you will be in green valleys, below snowy mountains, moving into farmland as you head south in Georgia. Passing from the Georgian peopled region to the Armenian border province of Samtskhe-Javakheti, you'll be passing into Turkey just after the town of Kartsakhi, 197km.
Things become more harsh as you pass through the region of Eastern Anatola. It is 1,025km to wind your way southwest through mountainous Eastern Turkey, reaching the city of Kilis.
If things have not quieted down in Allepo, Homs and Damascus, (the shortest route), you will want to continue through Turkey until you get to the Mediterranean coast and skirt through Syria to Lebanon and then into Damascus. Or you can go into Armenia, then Turkey and down into the Kurdish province of Iraq. I'm going to assume that Syria is passable by the time this trip starts.
The border of Turkey to Damascus is 421km, most of it highway between major cities. Because of Israel's occupation of the Golan Heights, you'll need to once again travel to Amman, Jordan to be able to cross into Israel and continue. 117km to the border with Jordan at Daraa, then 85km to Amman.
[Total so far: 1,760km + 4,920km + 1,918km + 4,735km]
Israel and Egypt
At this point, you are bottle-necked. Only way across is to go from Israel, to Egypt and cross the Suez Canal.
You have either driven 13,333km around the north coast of the Caspian Sea and into Turkey, or you have gone 14,010km down the Silk Road and into Iran.
From the capital of Jordan, it is just 57km more to the crossing into the Israel-occupied West Bank over the Jordan River. An hour of driving through the West Bank will get you to Jerusalem, assuming there are currently no hostilities between the Palestinians and Israel. Returning to the danger zone, you enter the Gaza Strip near Kissufim (153km) and then head to the Rafah crossing into Egypt (on Wikitravel) (20km).
Driving across the northern part of Sinai, you get to Al Salam Bridge and across the Suez Canal in 216km, crossing desert the entire way.
From about this point we can follow Ewan McGregor and Charley Boorman again. They did a follow up on their Long Way Around series with another series called Long Way Down. In this show they drive from England down to Gibraltar, across Mediterranean Africa, then down through East Africa to reach Cape Town. Much the same as this path (although they wandered a bit on their journey south).
For you, things get easier thanks to the Cairo – Cape Town Highway (on Wikipedia) project. Except...crossing from Egypt to Sudan by road is prohibited. While the counties have fairly good relations, they are in the midst of a decades-long dispute as to where the borders lie in the area of the Hala'ib Triangle.
I really think you should break your "no water" rule at this point and take the ferry across Lake Nasser, the only crossing from Egypt to Sudan. All of the travel accounts and packaged tours use it. (Example: Fully guided, self-drive, 4x4, Cairo, Cape Town, national park, safari and this travel account: Cape Town to Cairo – and back again.
Your alternative is leaving the Nile, following the International Coastal Road to Libya, then roads into the heart of the Libyan Desert. At the end of that track, you will trek out off road across the desert. Apparently the local smugglers don't travel the direct route from Libya to Sudan. They cut through the SW corner of Egypt instead (Libya to Sudan border on Horizons Unlimited). Further, driving into Sudan without proper paperwork is possible with the right guide, but always a risky proposition. Not to mention that this is about a 1,500km detour.
I'm not even discussing the drive around Libya, down to Chad and through Darfur to get to Sudan...
So, accepting that a single ferry ride isn't so bad, I'll continue following the 990km drive along Suez and the Red Sea, with a cut over to the Nile at Safaga. But, you should read up on that ferry. It runs once a week and has limited space for vehicles (motorcycles would be fine) and from load to unload it takes 24 hours. Ferry Ride on Lake Nasser from Aswan to Wadi Halfa.
[Total from Jordan: 1,436km]
Sudan and Ethiopia
That Israeli stamp in your passport isn't going to be doing you any favors in Sudan. Hopefully you already have your (expensive) visa and travel papers arranged. Aren't you glad you didn't come into the country in the same manner as a smuggler?
Meanwhile, time to drive south. You know those epic dunes you see in movies? Well that is the terrain you will be driving through to get to Khartoum (on Wikitravel), the capital of Sudan. 961km
The road to Ethiopia is fairly safe, by African standards. Technically you don't even need the travel permit for this, but it might be recommended just to ease things with police. It is 574km to the border, where you can stop in the Ethiopian town of Metema.
To get to Addis Ababa you will need to climb into the Ethiopian highlands. While this will be a reprieve from the heat, the paved roads might be dangerous due to the mountainous terrain. Camping might be very chill, so be prepared. But the terrain will finally be green and lush again. 897km to reach the capital.
You will be driving through well populated lands around and south of the capital, but as your approach Kenya, terrain becomes more desert-like again. The border town of Moyale is 764km, all paved.
[Total from Jordan: 3,196km + 1,436km]
Kenya and Tanzania
Reports I have read list northern Kenya as very difficult going and requiring a 4x4. Unpaved, occasionally plagued by bandits, with arid and demanding terrain. The route which runs SSE skirts the Chalbi Desert, but this is still tough land. Conveys are the best way to avoid the bandits and recover from a breakdown. You will also be switching over to driving on the left side of the road for the rest of the trip.
It will be 869km before you reach Nairobi, south of the tall Mt. Kenya. You will be crossing the equator 2/3rds of the way there.
Nairobi (on Wikitravel) has its own hazards. Travel by day to avoid car-jacking (although reports say that increased police checkpoints have reduced this risk). Or you might just take the Eastern Bypass at Ruiru and avoid the major city altogether.
It is only 164km to the border with Tanzania, where you'll have a good view of Mt. Kilimanjaro.
Tanzania (very detailed entry on Wikitravel) has both a high plateau, featuring the Serengeti Plains and Mt. Kilimanjaro and the Great Rift (although you will be crossing the rift at a high point on the border with Zambia).. The shortest route following the highway does not pass through the capital of Dodoma (recently moved here from the coastal city of Dar es Salaam), although the detour isn't exceptionally large, but both the shortest route and the direct route to Dodoma are generally gravel roads, at times impassible.
The paved route through Moshi (at the base of Mt. Kilimanjaro) and southeast through Korogwe and Morogoro might be better, but for the sake of mileage, I will be adding up the shorter route through Singida and Mbeya. It is 1,121km to cross the entire country.
[Total from Jordan: 2,154km + 3,196km + 1,436km]
Zambia and Zimbabwe
It is 1,135km to cross Zambia (on Wikitravel), reaching the capital of Lusaka about a 100km before the border with Zimbabwe. But be aware that you are traveling during the rainy season. Very rainy. However since you are follow the paved Tanzam highway, one of the most major links in Africa, this shouldn't be too much of a problem.
You will be driving through what tourists call "True Africa". The best safaris, Victoria Falls (and malaria, yellow fever, 16%+ HIV infection rates...). The highway actually passes within two miles of the border with The Democratic Republic of Congo, but doesn't cross.
In Zimbabwe you will be traveling about 357km to the capital of Harare (on Wikitravel), smaller than some of the capitals you have been to. As a failed state, only just recovering from the economic collapse under Mugabe, fuel is very expensive and sometimes hard to come by, pot holes on the dilapidated roads are a serious danger and you will be traveling during the rainy season.
Another 584km will get you to Beitbridge and the border with South Africa.
[Total from Jordan: 2,076km + 2,154km + 3,196km + 1,436km]
South Africa
Apparently the back-up at the border crossing is enough to get media calls to reduce the bureaucracy. (Zimbabwe and South Africa Urged to End Border Crossing Nightmare) So expect a wait, although visa issues will be pretty minimal for most attempting this route. A quick 475km jaunt gets you to the capital Pretoria (on Wikitravel), followed quickly by Johannesburg. Northern parts of the country are severely poor, although traveling on the good highway will run you between the few rich cities in the north and down to the first world cities in the south.
You have a last stretch of 1,457km as you go southwest to Cape Town. From there you should technically head out to Cape Point, 69km more, if you want to be as geographically distance as possible.
[Total from Jordan: 1,992km + 2,076km + 2,154km + 3,196km + 1,436km = 10,854km]
Additional notes and tips
You might be able to avoid some of the border problems with duplicate passports. (How to Get a Duplicate U.S. Passport). Certainly you could travel this route from south to north if you had the Israeli stamp in one passport and you handed another one to the Iranian border patrol. I worry that a complete search would turn that up, however, making a situation suddenly MUCH worse. Two passports does help with sending them to different embassies to pre-arrange all of the travel visas, however.
In any case, you are going to need to read up on the visa requirements for each country on your route, which generally vary with your nationality (and possibly your mode of travel).
And as exhaustive as this is, don't take this as complete research. You will want to do a LOT more study. Find translators, fixers, guards and guides. Pre-arrange repair stops and/or replacement vehicles. This trip could easily take more than a year of preparation.
Totals
Distance: at least 24,187 kilometers (via Syria) or 24,884 kilometers (via Iran). 62% of the way around the circumference of Earth.
As-the-crow-flies distance between the most distant points: 15,585km
8 or 9 Eurasian/Middle East Countries (Russia, Mongolia, Kazakhstan, Jordan, Israel--and either Georgia, Turkey and Syria; or Uzbekistan, Turkmenistan, Iran and Iraq)
8 African Countries (Egypt, Sudan, Ethiopia, Kenya, Tanzania, Zambia, Zimbabwe, South Africa.)
In comparison, the two continuous segments of the Pan-American Highway (using the shortest route through the US) are 12,034km and 11,347km (ending before the ferry to the last stretch of Terra Del Fuego.)
Read other answers by
Todd Gardiner on Quora:
Travel: What is the best option to take a car by ferry from the US to Vancouver Island?
Travel: What are the best websites, services and apps for chronicling a trip?
What are the best conditions for hitchhiking?
Read more answers on Quora.