...and a sack to sleep in

A silk sleeping bag liner for staying in hostels and making rough, cheap sheets more comfortable
You can get a silk sleep sack for about $45.

Sleepsacks (thin sleeping bag liners) and when you need them for travel in Italy

Though handy for camping, couchsurfing, and even cheap hotels, sleep sacks are mostly for folks staying in hostels and rifugi (mountain huts).

Most hostels sill provide you with a pair of sheets and a blanket for your bed, but require that you use your own sleep sack. This is basically a sheet folded in half lengthwise and sewn across the bottom and most of the way up the long side—sort of like an ultra-thin sleeping bag.

However, note that you cannot use your own sleeping bag or a sleeping bag liner with a thick pile to it. This is because, from the hostel's point of view, Lord knows where you've been and for all the hostel know your bag is infested with bedbugs, which they'd rather you not introduce into their beds.

Buy a sleep sack before you go, or make one on your own using a basic cotton top sheet; just fold it in half the long way, sew across the bottom and 2/3 of the way up the side. If nothing else, your mom will be so proud you proved you actually figured out how to use the showing machine. Hostels will accept homemade sleep sacks as well as the store-bought kind.

My favorite: the silk sleep sack you can get from travel and camping outfitters like REI. It is dreamily comfortable and packs into a teensy roll about five inches long and two inches across (fully squishable for easier packing).

I always just toss this into my bag even if I don't plan on using hostels; I use it as a liner for my sleeping bag when camping, put it to good use when staying at particularly skeevy hotels, and for crashing on the sofas of friends. Should you arrive without a sleep sack, some hostels will sell you one on the spot.

Tips & links

Useful links & resources

GEAR, CLOTHES, & BAGS

Gear & clothing: REI.com, eBags.com, Backwoods.com, Travelsmith.com, LLBean.com , Magellans.com

Luggage: eBags.com, REI.com, Backwoods.com

Electronic converters: REI.com, Travelsmith.com

How to pack it all into a carry-on

Lay out everything you think you’ll need to take and consider the pile.
Put away any item that’s not really necessary.
Take what remains, pack half of it, and leave the rest at home—you won’t need it.

Pack for ultimate mobility, versatility, and necessity. Make travek an exercie in simplifying your material needs.

When in doubt, leave it at home. Whatever you forgot or discover on the road you need (sunscreen, bathing suit, sandals) you can also just buy it in Italy—and have a nifty extra souvenir of daily life to bring home (I often come home with odd, foreign brands of toothpaste).

Speaking of which: you shoudl have a little space in your pack for accumulating souvenirs.

If, as you travel, you find yourself running out of room, stop at any post office to ship home the personal items you've found you didn't need, or just before flying home, mail your dirty laundry to yourself. This way, you can carry your new purchases instead of entrusting them to the Italian postal system.

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How to tell if you've overpacked

If it doesn’t all fit in one carry-on sized bag plus a daypack, you have overpacked.
If you can't lift your bag over your head and hold it there for 10 seconds, you have overpacked.
If you can't shoulder your load and walk five times around the block without breaking a sweat, you have overpacked (and should probably also hit the gym—all the walking you'll do makes travel in Italy an aerobic workout and you need to be ready).

Trust me, you'll be thankful later when you easily shoulder you bag and zip off to your hotel while the guy who sat next to you on the plane gets a hernia just trying to get his luggage out of the airport.

Cardinal rules for travel clothing

Nothing white
Nothing that wrinkles
Clothes you can layer
Lots of pockets
Very few

Remember: Clothes take up the most room in your luggage, so be stingy with what you take. Take a maximum of 2–3 each of pants and shirts that can all mix and match toegther.

Believe me, it's easier to do a bit of laundry in your room every few nights than lug around a ton of extra clothing.

Only your immediate traveling companions will know you've been wearing the same outfit for the past three countries.

Socks, T-shirts, and underwear—the clothes that ripen quickly—are the easiest items to wash out and dry overnight.

Make sure you use a moneybelt

Keep your all valuables in a moneybelt: one of these large, flat, zippered pouched you wear under your clothes.

A moneybelt is like a wearable safe for your passport, credit cards, bank/ATM cards, driver's license, plane tickets, railpass, extra cash, and other important documents.

In your wallet, carry only a single day's spending money—maybe €40–€60. (Replenish this as needed from your stash in the moneybelt.) » more

Assorted packing tips

Some bags have zip-away straps and waist belts that convert the pack into a more respectable soft-sided suitcase for waltzing into your hotel lobby.
To keep the bulk of your bag under the carry-on requirements, layer any thick sweaters and coats and such to wear on the plane (you can strip down once seated).
Label your bag: Whatever sort of pack or suitcase you choose, be sure to put a slip of paper with your name, home address, and destination inside each piece of luggage as well as attaching a sturdy luggage tag with a concealed address window to the outside (some criminals peruse visible luggage tags at the airport, collecting the addresses of people leaving on vacation).
Get as many tiny travel locks you have zippered compartments on your pack and daypack. Make sure it is one of the special combination locks that have a red diamond-like symbol meaning they're TSA-friendly (baggage screeners carry a secret code and a special back-door key so they can open the lock if they feel the need to paw through your valuables and dirty undies).
Note that the TSA is considering once again will allow you carry small knives in your carry-on bag. However THIS RULE HAS NOT YET BEEN PUT INTO EFFECT (despite some early news reports to the contrary). For now, you will still need to pack any knife in your checked luggage. Here are the official TSA regulations.
Split up your stuff. If you're traveling with others and plan to check your luggage, distribute everybody's stuff throughout all the bags. Have your traveling companion pack some of your clothes and you pack some of his. That way, if the airline loses just one bag, both of you will have something to wear until it turns up.
Many bags come with zip-off daypacks, which is an excellent idea (or bring a small backpack). Keep in it your first-aid kit, sections of your guidebooks you stripped out for the day's use, tissue packs, water bottle, journal and pen, pocket knife, and umbrella.
Let's see. Besides a waterproof bathroom bag for the toiletries I think that's it.