London, UK to Venice, Italy — The Orient Express

There are probably an infinite number of train routes you could use to get across Europe, and almost all of them would be cheaper than this

— the Orient Express has a hefty price tag of $3,300 per person one-way. But good god, is it a cool way to travel.

Venice to Istanbul, Turkey — Car

We won’t fudge the route with a car at any other portion of the trip, so bear with us, here — while you could easily take a train or a bus from Venice to Istanbul,

neither of those allow for the same flexibility, and flexibility is what you’ll want while crossing the Balkans. The region is physically stunning…

Istanbul to Cappadocia, Turkey — Bus

If you don’t want to take a detour south to Turkey’s Turquoise Coast, where you can add sailboat to your modes of transport for this trip, catch a night bus from Istanbul to Cappadocia for this leg of the trip.

Cappadocia to Tabriz, Iran — Bus

This part of the world is seldom visited by tourists these days because of its proximity to Syria and Iraq.

But the Caucuses are a beautiful part of the world, and the people are lovely — take a bus and take your time. This is an amazing spot for slow travel.

Jaisalmer, India, to Kerala, India — The Rickshaw Run

This is a bit of a detour, but it is one of the coolest detours you could possibly go.

Tour operators The Adventurists run a breakneck week-long race across India from Jaisalmer to Kerala in a rickety 3-wheeled auto rickshaw.

Kerala to Chennai, India — Train

Kerala is a favorite in India among travelers, and is one of the best spots in the country for eco-tourism (which might be a worthwhile cleanse after your rickshaw run).

Chennai to Yangon, Myanmar — Cruise

It’s time to take to the sea — most travelers are fairly cynical about luxury cruises, but they’re just going to beaches in the Caribbean.

You, instead, will be taking the Silversea Discoverer from Chennai to the Sundarbans Reserve, one of the last remaining homes of the endangered Bengal Tiger, to Bangladesh, and across the Bay of Bengal to Myanmar.

Yangon to Bangkok, Thailand — Bus and Cab

This is one of our more convoluted legs of the trip — check out the itinerary on the excellent trip-planning page, Rome2Rio.

Bangkok to Singapore — The Eastern & Oriental Express

If you wanted to skip the Orient Express in Europe, try the (slightly) cheaper Eastern & Oriental Express from Bangkok to Singapore

Singapore to Sydney, Australia — Freighter

If you don’t have time to island hop down to Australia, consider taking a luxury freighter. These are the freighters you’re thinking of — big box ships that deliver cargo to countries all over the world.

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