WHAT TO PACK

Take one good-sized suitcase per person and one knapsack or similar bag (See Additional Clothing Note below).  Plan to check the suitcase, which should not be too heavy to lift and should have enough extra room to bring back more stuff in.  Do not plan to take more than one bag per person on board.  If the plane is full you'll have to check one, and it may or may not accompany you to Italy.  

Added in 2004:  And worse and worse and worse.

(2006 NOTE:  Most airlines have reduced the size of the allowable bag.  The bags you bought specifically as carry-ons may not be allowed as airlines get worse and worse and worse and worse and worse.  [This sentence was first written in 2000.])

Nothing has changed.  We still have the best schedules and worst airlines in the civilized world.  The reason it was so much better in the 70's and 80's was that the prices were controlled by governments, resulting in fair profits.  But the airlines demanded deregulation, dreaming of the kinds of profits only utilities enjoy.  As a result, they're going broke, and your travel times have become the nightmare which starts a dream.  Until they charge fair prices again (and you're willing to pay a fair price adjusted for inflation) air travel will continue to be offensive.

(2008 NOTE:  Most airline are now charging extra for a second bag, with penalties for bags over 50 pounds.  Clearly, they don't want you to fly.)

Depending on where you begin, you're going to be in a plane from seven to thirteen hours.  
You're going to get a rental car and then travel to some other place, perhaps many miles away.  
You may be up as long as 36 hours between bedtimes.

The first thing you pack is deodorant.

STRONG DEODORANT

PERSONAL TOILETRIES:
Beside the usual, and deodorant, be certain you have antiseptic lotion or gel (not spray) for cuts, scrapes, and sunburn.
Bandages in various sizes
Small plastic baggies
Shoelaces
Adhesive tape for big scrapes and repairs to clothing
Electrical tape for repairs to luggage, autos, et al.
Laxative(s)

A NOTE ABOUT LAXATIVES:
Okay, this may sound tacky, but almost everyone who travels, because of time changes and not enough water, gets constipated.  In Italy, you're lucky; most of the hotels serve prunes and prune juice as part of the included breakfast.  That and liquids will serve you in good stead.  If you're in stores, you're looking for "prugne" or "prugne secche."

PERSONAL TOILETRIES(continued):
Kleenex because very few hotels have tissues available.
Toilet seat covers for women.   We highly recommend tucking a package in your purse so you have them with you wherever you go.  Probably most frequently used item with the exception of one's camera.
Prescription medicines.  If you're not taking them in their original bottles, get copies of prescriptions.

CLOTHING SUPPORT:
A few hangers, especially the kind that have clips for pants/skirts
Packets of Woolite.
Clothesline and clothespins (little bitty ones)
A few, gallon size vinyl bags, for undried laundry and other such.
Needle, thread, button or two, safety pins
Travel iron (be sure it's dual voltage).  Unlike American hotels, they aren't standard with housekeeping.  At the Aldrovandi in Rome our request was greeted with stunned silence, and an assurance the hotel was capable of such activity and it was beneath us even to ask.  (But it cost us $125 and took 3 days for a handful of stuff.  Pooh.)
Voltage transformer and adaptor plugs (generally in a simple kit)

CLOTHING:
Linen and linen blends.  Your clothes will wrinkle.  Italian laundromats that do the work for you will deliver them wrinkled.  The Italians are used to this.  Their clothes get wrinkled, and no one panics.  Look around you.  Plan on being wrinkled.  No one will care.  It's the fashion, and you'll be grateful it is.
Cargo pants.  After many trips to Italy Russ finally found the right pants for the trip at Old Navy.  We bought the tummy bags and money belts, since we read that wallets/money should not be kept in jacket or pants pockets; but the low, button-top side pockets of the cargo pants were perfect.  He could carry wallet, passport, even the digital camera in them without encumbrance while walking.  Now he won't wear anything else, even though the number of packs of small children who accost you with intent to rob in Granada Hills, California is very, very low.
Comfortable shoes.  You'd think this would be obvious.  Don't buy shoes for the trip unless you've worn them for at least a week straight before leaving.   Kaye bought very expensive walking sandals and it was the best purchase she made for the trip.
Unless you're packing two or three suitcases and have a maid, don't take wool suits, heels, furs.  Take several sweaters.  If it gets cold, you can wear one and women need to cover their shoulders to visit certain sites such as the Vatican.  
Take a "collapsible" raincoat.  If you need more than that, you're in Italy, land of great clothing.  It will be an excuse to buy something.
Pool/spa wear including a pool coverup and thongs since you will need to walk through the lobby and you will need to be covered.

ADDITIONAL CLOTHING NOTE:
Choose clothing that looks okay wrinkled AND/OR can be washed out at night and hung on your clothesline over the tub (and will dry in one night, which does not include men's cotton socks or underwear).  Plan to do as little laundry as possible.  Frankly, we'd rather take more clothes and and make them last the whole trip than have laundry done.  Whatever you do, don't have your hotel do them.  Kaye spent more to clean one of her dresses than she paid for it, and a handful of laundry in Rome was $125 to launder and took three days!  Local laundromats will do stuff for you, but it will all be dried on the highest setting.

Cell phone that works in Italy.  If you don't have a world phone already, rent a phone with the car.  (See Communications page.)

Pad, pen, pencil for the obvious reasons, writing down addresses, toting up expenses for Customs, but also for sketching architectural details you may want to copy back home when you remodel your bar.  The interiors of restaurants and hotels in Italy are often marvels of design and workmanship.
Small pillow (I know this sounds strange but the pillows in all the hotels we stayed in were very hard in most hotels.  We pack a small one for each of us.)
Small pocket calculator for computing all the tax you will owe on those purchases before you get to customs.

We have always been told to get a special form which lists our laptops, cameras, and other expensive electronic equipment, to prove we did not buy them abroad when we returned.  When we asked at Customs at the TWA terminal at JFK in 2000 the young woman seemed to know what it was, then led us through a labyrinthian series of halls to a back room where two other agents pawed through file drawers to find the form; then they argued about how to fill it out .  In 2002 and 2004 and 2005 Russ took cameras, laptops, you name it, and no one said a damned thing.  Obviously, it's no longer necessary, but it won't hurt to take a photocopy of your receipts.

Customs:  Upon our return we paid tax on the amount over $400 each that we had bought.  We were treated like crooks by a female agent who searched Kaye's purse for other receipts.  The only other person declaring anything was Italian, and they had his bags open.  Everyone else sailed through with, or so they were saying, nothing to declare.  Since then we have been called idiots by our friends.   In 2002 and 2004 and 2005 we weren't over our limits.  (No, really - we shipped stuff.)

DOES ANYONE DECLARE ANYTHING AT CUSTOMS ANYMORE?

FINALLY THE FEDS HAVE UPPED THE LIMIT TO $800!  
AND DON'T FORGET THAT FINE ART (NOT CRAFTS) HAS NO DUTY!

AND HOW COME FODORS.COM STILL HAS THE OLD NUMBER OF $400????  (Well, it did in 2005 - now it's just a flack site for books and anything else they can sell you.  It's practically impossible to find travel advice on it.  Yuk.)

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