Step 1: Keep Your Handbag Safely Locked
A cheap way to replicate a very effected feature of these bags is to clip on a small carabiner onto the strap of your handbag. If your handbag zip has a loop, you can clip the loop through the carabiner (second photo). If it doesn't have a loop, you can add a keychain ring onto the zip pull (third photo), then clip that onto your carabiner.
This doesn't stop a determined mugger, but it will put off most of the opportunistic pick pockets. I even had one in Florence who tried to open my handbag and gave up when she couldn't open it on the first go.
Step 2: Have a Plane/train Pouch for Easy Boarding
Let's not be that person by having a train/plane pouch. Keep everything you normally need on a journey in a pouch. When you get to your seat, all have to do is pull out the pouch and you are done!
In my pouch I keep a inflatable pillow, a kindle, a notebook, a pen case and a charger for my phone and kindle. Since I've started doing this, getting onto a transport and settling down in my seat has become a breeze :)
Step 3: Carry a Retractable Cable Lock for Luggage on Trains
Step 4: Carry Two Wallets to Halve Any Loss
This way, if the worst should happen, and you lose the main wallet, you will at least have some cash on you to get back to your hotel, etc.
Step 5: Pick Luggage That Zips Up Fully
It reduces so much worry when you have to be on a busy metro that all your pockets are locked up and thus pickpockets would have a difficult time opening them without you noticing. It's a good deterrent to them and they will move onto someone who has easy opening pockets instead.
Step 6: Stick to 30 Litres for Luggage
We've all heard the traveler's tale about how the less luggage you carry, the happier you will be on your trip? Well, after 18 months of travelling around Europe, America and Asia, it seems that 30 litres is the happy number.
Why 30 litres? That's way less than most plane carry on restrictions right?
First of all, boarding a plane has become extremely stressful nowadays because there's simply not enough overhead compartment space to fit everyone's maxed-out-to-the-limit carry on suitcases. So everyone is fighting for that converted space. However, a 30 litre backpack will fit under most, and even the most budget, airline seats. No more fighting for the overhead space, no more queuing for hours just to be the first one on the plane. You can take your time getting on the plane and know that there'll be space for your stuff. (Some airlines will also offer priority boarding for those who do not need to put stuff in the overhead compartment.)
Second reason is if you end up a train or a bus that's absolutely packed with people and luggage, you can comfortably have your luggage on your lap for he journey without the weight of the pack killing you. A much more comfortable ride :)
Also, if you are planning to travel on trains in Europe, a 30 litre backpack will fit on most overhead luggage space, whereas anything bigger quite often won't.
if the thought of carrying only a 30 litre backpack freaks you out, have a look at the second photo. My backpack fits all that, plus a travel kettle, and enough space to put my handbag in when I need to. That's actually a quite a lot of stuff!