I have backpacked through New Mexico for 11 days and traveled to Europe many times for trips ranging from a week to three months and the biggest tip I can give to new travelers is: pack light. Yes, we will have a hiking pack and an everything else pack (and technically a third 'laptop' bag) but imagine carrying all that. It's heavy, unwieldy, and short of a tacky Hawaiian shirt, you will be immediately identified as a tourist. With that identification, there is a whole host of nasty implications, but I'll get to that later.
First, back to packing light. Layers are the way to go, especially with the warm days and cold nights we'll be experiencing. The ORGT packing list is a good list that covers most of the situations we'll possibly experience and provides a good guide for the 'civilization' portion of the trip. Don't pack an additional jacket for the cities, wear the fleece/long shirt combo you packed for Croatia. Don't be afraid to wear clothing more than once before washing - everyone will smell just as bad and odds are, few people will even notice. This will minimize not only the amount of gear you're carrying but also help you easily adjust to changes in temperature such as transitioning from cool museums to walking around an outdoor market. Also keep in mind that darker shades can help hide dirt and slight stains better than whites and pastels.
The 'business casual' dress code of the city portions will help ensure everyone is appropriately dressed various activities around each city. If possible, avoid clothing with large logos and American flags (it can be a touchy symbol in some areas) and remember that most of the world tends to dress a little more conservatively than Americans in the summer. Religious areas (mosques, temples, and churches) and smaller towns especially merit a more decorous level of dress with shoulders covered and longer shorts - typically near knee length - than other, more modern areas. Keep in mind that we will be walking quite a bit so while flats with little support may look cute, your feet will not thank you.
With that being said, less is more. While we will be backpacking for a good portion, keep in mind that we will eventually re-enter civilization so you don't need to pack a 12 oz. bottle of shampoo/conditioner/lotion. If you run out of travel size anything, we'll be able to stop by a store and resupply. It'll be a fun cultural experience (popular fragrances can differ from country to country) and you'll get to avoid lugging a heavy bottle through three countries. (On the subject of toiletries, it should go without saying to not bring a hair dryer or straightener. While camping, everyone will be looking a tad rough (nothing a hat can't cover up) and while at the hostels, there will likely be hair dryers.)
Packing light can be difficult, especially considering the uncertainties of the trip (What's the weather like? How far will we be walking today?) but don't let uncertainty guide your packing. Pack tightly and well-organized as this will help you re-pack when we move from city to city. Ziploc bags help compress clothing and keep everything clean as well as minimizing wrinkles. Additionally, think in terms of what you can do without, what you can repurpose, and what can you buy there. This last tip refers mainly to toiletries but factor in what you're going to buy. Souvenirs take up space and could even be used while on the trip (I'm looking at you, t-shirts and hats).
So now, you have two well-packed bags and are ready to go. But what about keeping your bags safe? An unfortunate fact of traveling Europe is pickpockets and thieves. No matter what you wear, you will be easily identifiable as a tourist and that makes you a target. By all means, look at all the beautiful sites but keep one eye (and preferably a hand) on your bag. When sitting, loop your feet in the straps. Don't leave small items (cameras, phones, etc.) on tables even if you're sitting right there because they will 'walk' off. Keep money in a front pocket or in a money belt and avoid showing where you're storing money, especially how much money you have on you.
Thieves have various tricks to distract tourists and pickpocket them during the confusion. One common ploy is to have two or three people approach someone and ask for directions or give recommendations while another member of the group pickpockets the unsuspecting tourist. Other times someone will toss a ring or other valuable item in the path of a tourist and the thief will pickpocket the tourist as he or she stoops to pick it up. This isn't to scare you, but awareness can reduce your chances of losing personal (and sometimes expensive) items.
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