Great Eastern Summer

The Great Eastern Summer

An itinerary and planning for “The Great Eastern Summer”, a trip of a lifetime, across three continents and over thirty countries.

With three months open for travel my friend Bill and I were set to do some serious exploring. We would start in Africa, go on safari and climb Mount Kilimanjaro, then venture into the Middle East to see world famous ruins and finally complete the trip by circling through Eastern Europe.

This ambitious plan would allow us to visit over thirty countries spanning three continents, see the major sights, and stay in ultra luxurious hotels.

The itinerary was roughly set before we left and all the major international tickets were purchased. We then had to fill in the blanks to see the highlights of each country.

This is our journey.

The summer could roughly be broken down into three parts

Part I – Eastern Africa

Itinerary Map

The start of the trip would bring us to Eastern Africa with a brief stop in Germany. We would start in Zanzibar, head through Tanzania to climb Kilimanjaro and see the big five on safari, then head north to Kenya and do another safari. Finally fly to Burundi and take buses northward up to Uganda through Rwanda.

Germany – Frankfurt
Tanzania – Zanzibar, Dar Es Salaam, Arusha, Mount Kilimanjaro, Serengeti National Park, Lake Manyara National Park, and Ngorongoro Conservation Area.
Kenya – Nairobi and Masai Mara National Park.
Burundi – Bujumbura
Rwanda – Kigali
Uganda – Kampala and Entebbe

Part II – Middle East

From Africa we would fly to London with a stop in Qatar for a birthday party of someone very close to me. Then we would head back towards the Middle East. The flight would start us in Cyprus then a hop over to Lebanon. From there we would fly to Aqaba, Jordan, then drive up to Amman and cross over the land border into Israel. Then I would leave the Middle East with a flight to Greece.

Qatar – Doha
Cyprus – Paphos, Limassol, and Larnaca
Lebanon – Beirut, Baalbek, and Anjar
Jordan – Amman, Aqaba, Wadi Rum, Petra, and Dead Sea
Israel – Jerusalem and Tel Aviv

Part III – Eastern Europe

The last part of the trip would be exploring Eastern Europe. We would start in Greece and continue north to Bulgaria, Macedonia, Kosovo, and Albania. Then cross over to Montenegro and Bosnia and Herzegovina. Continuing north is Croatia and then Italy where we would spend a week of relaxation in Sardinia.

From Italy, we would fly to the Baltics to start. Starting in Lithuania, we would drive around in a complete circle hitting every country in between (or so I thought) and ending up back in Lithuania to return the rental. Then continuing north to Latvia and Estonia. A ferry would bring me to Helsinki where I catch a flight home.

Lithuania – Kaunas and Vilnius
Poland – Warsaw, Auschwitz, and Krakow
Slovakia – Bratislava
Hungary – Budapest
Serbia – Belgrade
Romania – Bucharest and Brasov
Moldova – Chisinau and Transnistria
Ukraine – Odessa, Kiev and Chernobyl
Belarus – Minsk (FAIL)
Latvia – Riga
Estonia – Tallinn
Finland – Helsinki

All in all, we kept to the strict and very tight schedule and almost made it to every country and city according to plan. This trip would bring my country count up to 104 (if completed successfully) with a celebration of country 100 in Ukraine!

Belarus was the one country I needed a visa for which I didn’t check beforehand making a classic rookie traveler mistake and paying the price, a 15 hour drive around Belarus. But I’ll be back to visit in November!

Besides the highlights there were definitely some dangerous and extraordinary situations like almost dying on Kilimanjaro, prostitutes with AIDS in Uganda, gunfire near the Syrian border, intense security at the Tel Aviv airport, questioning in the back room at the Transnistria border, and spending six hours at the Poland border to exit Ukraine.

What an intense summer! Stay tuned for the in-depth story!


About David

Founder and writer at, David is on a mission to travel to every country in the world and has less than 10 countries left! He loves new adventures, unique cultures, historic landmarks, and luxurious hotels. Follow along as David shares a journey of a lifetime!