Can I pack carry-on for 7 months? Am I mad?

I have spent a stupid amount of time thinking about whether I can commit to only taking carry-on luggage for this trip. Hiking boots or trainers?  Can’t take both…or can I?

Two to three days of work travel?  Carry-on luggage only? No problem. I have mastered carry-on luggage for work travel. It’s all in the planning, which for me means a dedicated, coordinated section of my wardrobe (navy and black bases with cobalt blues for a pop of colour); and an always packed toilet bag containing travel sized toiletries permanently in my carry-on case ready to go.  This system minimises the packing and unpacking hassle and guarantees quick and painless entry and exit at airports. Plus I get the most ridiculous smug feeling about it – like my ability to pack light is somehow an indicator of being an excellent human!

I took my first extended trip with only carry-on luggage last year.  It was part work and part holiday, in Europe, late May, for 3 weeks.  I loved the freedom of easily navigating metro stairs and tossing my bag up onto overhead luggage racks in trains without having to ask for help or throwing my back out. I loved the security of being able to keep my luggage with me on ferries instead of dumping it amongst the piles of suitcases at the back of the boat.  I loved sailing through customs and knowing I was out the doors a solid 20 minutes before any of the suckers still standing at the baggage carousel. And yes, I loved being able to pull together multiple, perfectly respectable outfits out of my one little hybrid rollie with backpack straps.  Did I say smug again? Yep!

So now I’m weighing up (sorry, bad pun) doing it again.  But this time for 7 or 8 months, across multiple continents and climates.  I’m starting in high summer in Greece, will be hiking in the Dolomites in autumn, hitting London in early winter and hiking in Patagonia in December.  Yeah, that’s a challenging pack!  But with some careful planning and a willingness to do some swap outs along the way, I think I can do it.

My much-considered plan so far includes:

• An Osprey 40 litre Farpoint backpack.  My research suggests this is the pack of choice for travelling light, but not sacrificing the support of a decent pack harness. I’m still unsure about giving up wheels…watch this space and I will report back.
• A Pinnacle of Horror Crumpler bag for my personal items.  I’ll use it to carry my Surface Pro, DSLR camera, Kindle and other bits and pieces that would often go in a daypack.  The choice to go with a backpack as my main luggage means I needed a cross body bag instead of a daypack.  I think I’m going to love this – as long as I don’t over pack.
• Packing cubes. I’ve been using these for ages for my work travel. They really help to pack things down and keep your bag organised on the go. My plan is to use one for my summer gear and one for the winter, hiking gear that I want to take with me.
• A reduced size toiletries bag.  I bought an overly ambitious Macpack one, but I’ve had to go back and swap it for a larger one! I’m low maintenance, but I’m also not 20 anymore and need a few helping products!
• A small, light handbag to pack into the Crumpler.  For all those days and nights you want to walk about with minimal gear, no camera required.

What do you think? Am I on the right track? Can I make this happen? Any tips?