The Ultimate Packing List

Every item I myself pack for a trip to Italy
This is every single item I take when I travel to Italy. (Keep in mind I am actually wearing one set of clothes, including hat, belt, jacket, shoes, etc.). And it all fits into a carry-on sized bag and daypack (to prove it, see a picture of it all packed in the "How to pack it all into a carry-on" tip near the bottom of the page).

What to pack for a trip to Italy, how much to bring on your travels, and how to fit it all in a single carry-on bag with room left over for souvenirs

Below is the actual packing list I use (save the female-specific items) for any general, non-outdoorsy trip. Whether it's a six-night jaunt or a six-month research trip, I call up this page on my computer and tick off the boxes as I pack. Seriously. In fact, as I type this I am wearing the exact brand of convertible pants linked below Kühl Liberators), held up by the same hidden-zipper belt.

Travel clothing

2 pairs of pants (men/women)—Take quick-dry travel slacks (with secret pockets), not heavy, never-dry jeans; I always make one a pair of convertible pants (men/women) so I don't need to bring extra shorts.
1 pair of shorts (men/women) with pockets or convertible pants (men/women)—European adults don’t often wear shorts (& most churches won't let you in with bare knees), but they’re good for hiking and, for men, as swimsuits (women: buy a swimsuit there if you find you need one—a great souvenir!).
1 long skirt or travel dress—The skimpiness at which your respectability will be questioned varies with the country—and churches won't let you in if you're showing bare knees) so hedge your bets with something longish (knee-length at least).
4 pairs of underwear (men/women)—Get moisture-whicking, quick-drying travel briefs or boxers—not cotton; something you can wash in the sink and will dry overnight.
4 bras or camisoles
4 pairs of socks (men/women)—I wear Smartwool-type hiking socks—bulkier, yes, but great durability and foot-cushioning comfort; get a pair or two in black for dressy situations.

2 long-sleeve shirts (men/women)—Button-down collared shirts are respectable for all occasions; travel ones have hidden pockets, sunblock, and easy washability.
3 T-Shirts (men/women)—Wear under long sleeves so the easily washed T-shirt will soak up all the sweat. Get quick-drying tops, not cotton.
Sweater (men/women)—Warm and dressy (aim for pullovers, not sporty types). Or you can do a...
Jacket (men/women)—Only for fall to early spring (though a light rain jacket is always wise).
Wrap/Shawl—For covering bare shoulders (or improvising a below-knee skirt over shorts) to visit churches (it's a rule); also, for warmth on planes and cool evenings, and sun protection.
Long underwear (men/women)—Only for winter trips to colder climes.
Walking shoes (men/women)—Think: casual, sturdy, lightweight. Leather, not loud sneakers. No dress shoes, heels, flip-flops, or anything you can’t walk in all day for two weeks. (STURDY hiking or travel sandals [men/women] are also OK.)
Hat—An all-around brim offers sun protection and rain protection (also: stylish).
Belt—Those with a hidden zipper let you hide your passport photocopy and some emergency cash.

Cardinal rules for travel clothes

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

Remember: Clothes take up the most room in your bag, 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.

Don't dress down

Urban Europeans dress pretty snappily—not necessarily in the latest Armani suit, but well nonetheless.

While you should travel in whatever wardrobe makes you feel comfortable, you’ll probably be happier fitting in, so save the Bermuda shorts and sleeveless T-shirt for that trip to Hawaii.

Cover up in church

Even though Italian churches are filled with naked cherubs and frescoes of nudes (often being tortured in Hell), visitors have to cover up; bring a shawl or wrap to avoid the tissue-paper hospital gown freebies.Churches in Italy have a strict dress code.

From Rome’s St. Peter’s on down, most major churches WILL NOT LET YOU IN if your bare knees and/or bare shoulders are visible.

That means no shorts, no skirts above the knee, and no tank tops, sundresses, or other tops that bare your shoulders.

Pack accordingly.

(Hint: a silk shawl packs tiny, works as an emergency skirt or shoulder coverup, and doubles as an extra blanket during the plane ride.)

If all else fails, some churches hand out disposable shawls or smocks made out of heavy-duty tissue paper (see the picture above on the right, which I took in the cathedral of Pisa) —but do not count on this.

Bathroom kit

Toothbrush & small tube of toothpaste
Small soap & small shampoo—Bring the soap sliver from your bathtub to start; filch more from hotels as you go.
Razor & shaving cream—(Battery-op shavers are OK (electric razors just bring the hassle of electrical converters and adaptors).
Medicines—Prescriptions should be written in generic, chemical form (not brand name). Pill orginizers are handy.
Extra glasses/contacts— Count on losing them, and bring a hard glasses case. Also, bring enough saline solution to last (parts of the world sell it only in glass bottles).
First-aid kit—Take at least: a few Band-Aids, antiseptic ointment, moleskin (for blisters), aspirin, Dramamine or motion-sickness wristbands (I swear by Relief Bands, worth the outrageous price) hand lotion and lip balm (traveling promotes chapping), sunscreen, Pepto-Bismol (for indigestion and diarrhea; chewable, not liquid), and decongestant and antihistamines (for colds and unexpected allergies to local allergens).

Comb or flat brush
Laundry kit—To wash clothes on the go in your bathroom sink, you need travel detergent (biodegradable), a braided clothesline (the twists act as clothespins), and I suggest the truly remarkable stain eraser (perhaps I'm a slob, but I need them at least once per trip).
Towel—HG2G fans don't need to be told this, but a shammy-style camping towel or even small terrycloth towel is a lifesaver when confronted with Europe’s nonabsorbent, waffle-pressed jobbers.
Feminine hygiene products—You can buy tampons abroad, but take what you need with you, especially if you’re brand-loyal.
Condoms—US brands are safer.
Pocket-sized tissue packs—Invaluable for sudden spills, substitute napkins, bathroom emergencies, signaling surrender, and, if still clean enough, runny noses.

General bathroom kit tips

Minimize toiletries spillage disasters by storing everything in resealable plastic baggies.
Maximize the tiny space inside a bathroom bag/toiletry kit by using sample sizes and by decanting shampoo and detergent into small, screw-top plastic bottles—bonus, this makes them TSA safe.
I jumble together just enough pills—for pain, allergies, etc.—to last me into a single one of those plastic cylindars of travel-sized ibuprofen or Dramamine to make a personalized, pocket-sized pharmacy.
Keep all toiletries and cosmetics to a minimum. Perfume or cologne on the road become vain dead weights and spills waiting to happen (imagine everything in your bag drenched with Chanel no. 5).

Documents & Sundries

IN YOUR DAYPACK

Guidebooks and phrase books
Journal and pens—You won’t remember it all half as well as you imagine.
Camera—Bring extra batteries. Tote it in a purse or mild-mannered daypack, not a “steal-me” professional camera bag. I like a waterproof pocket cameras.
Memory Cards—Very expensive abroad (and you will fill them up fast!)
Tripod—I like the GorillaPod, with flexible legs so you you can wrap it around tree branches and other impromptu supports.
Tiny flashlight (I prefer a hands-free headlamp).
Tiny folding umbrella
Sunglasses
Cell phone —Only bother bringing yours if a tri– or quad-band world phone with AT&T or T-Mobile (on the GSM standard used in most of the world). Otherwise, rent a cellphone. » more
Swiss Army Knife or Leatherman/multitool—Most useful features: screwdriver/can opener, blade, corkscrew (for picnics), tweezers, scissors, nail file. Note: The TSA has been debating allowing small knives in carry-ons again—though HAS NOT YET changed the rules. For now, pack any knife in your checked luggage. (Official TSA regs)
Small bottle of water—Buy them as you go, but always have one. FOr the backcountry, or anywhere outside Europe and North America, carry a bottle with a built-in purifier or get a UV sterilizer.
Sunscreen
Bug spray—Most of Italy has yet to discover window screens, so insect repellent is handy. Also useful: After Bite for the itch.
Teensy binoculars—Maybe I'm getting old, but increasingly I find these useful for admiring distant frescoes, wildlife, landscapes, popes, etc.

IN YOUR MONEYBELT/WALLET

Moneybelt—The flat, under-the-clothes "safe" everybody hates to wear but is the best protection for your passport and other crucial documents.
Passport—You won't get very far without it.
Airline tickets—Crucial.
Wallet—But keep important stuff in the moneybelt.
Money—Credit cards, ATM bankcard, traveler’s checks, and cash (euros if you got 'em and some emergency dollars).
Driver’s license & International Driver’s Permit—Only if you plan to rent a car.

IN YOUR MAIN BAG

Luggage locks—Get enough for every zipper; make sure they're the kind approved for TSA use.
Sleep sack—An ultra-thin sleeping bag made of cotton or silk (sometimes called a "liner"); you need if you'll be camping or staying in hostels.
Travel alarm clock
Plug adaptors—For charging your digital camera, cell phone, etc. (Transfer to daypack for travel days, so you can charge in airports/train stations)
Chargers/cables—I carry all my plugs, cables, and adaptors in a small toiletry bag. (Transfer to daypack for travel days, so you can charge in airports/train stations.)
Pocket Sewing Kit—Trust me. Comes in handy.
Duct Tape—Ditto.
Address list—Friends appreciate postcards at the time more than a slide show afterward.

PLANE/TRAIN COMFORT

Neck pillow—For the plane; long train rides. Some prefer the all-around-the neck style to the old horseshoe collar (this nifty model also converts to a small rectangular pillow) to things like the shin-supporting J-Pillow, and the Travel Halo with its built-in eye mask.
Eye mask - Some love 'em; some don't. I find every bit of help sleeping helps.
Noise-canceling headphones—The one silly travel gadget I actually use (it makes flying less stressful, even if you don't sleep; also: way easier to hear the movie). There are tons of models. I currently rock a JVC HANC250—1/3 the price of Bose; just as good. Or go super low-tech with earplugs (sadly, I'm one of those people who cannot tolerate wearing them).
Book or tablet/e-reader—For long plane and train trips. If a tablet or e-Reader, load up on titles before you leave, or get one with WiFi (so you can download outside the U.S) or a Kindle 3G (which connects for free in 100 countries).

General "sundries" tips

Don’t forget to carry your most important documents—passport, plane tickets, railpass, traveler’s checks, driver’s license, and credit cards—in a moneybelt.
Carry your daily needs items in a small backpack or security purse (designed to foil pickpockets and purse snatchers).

OK, so I lied. I do often pack one more item: A laptop computer—but only because I have this strange job of "travel writer." (However, these days I can often get away with just using my iPhone or my Android tablet—I got a Google Nexus 7 for the great value and fact that T-Mobile LTE service works abroad—along with a pocket-sized collapsable keyboard.)

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.

Everything from the photo at the top of the page packed into a carry-on and a daypack (all the clothes are in that pale gray stuffsack).Pack for ultimate mobility, versatility, and necessity. Make travel an exercise 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 always simply buy it in Italy—and have a nifty extra souvenir of daily life to bring home. (I often return with odd, foreign brands of toothpaste.)

Speaking of which: you should leave 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.

» more

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.

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.