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Everything you need to do (and when to do it) when planning your trip to Italy

There's a lot to do when planning a trip, and a helpful order in which to do things. I find that the one thing that keeps me up in the final few nights before a trip is not so much the excitement over the impending trip as it is going over and over (and over) in my head the list of things I still need to do. Simply writing this list down goes a long way to help keep it off my mind.

So, in the interest of helping us all sleep a little bit better, here is a step-by-step list of everything you need to do to get ready for your trip, starting with getting a passport (if you don't already have one) and booking your flights, hotels, tours, etc., then on to the final days of packing and preparation, and then the day of travel itself. Once you're on the plane, you're on your own. (Well, OK, here are a few tips to help make the trip more comfortable.)

This list is a bit obsessive in its detail, but it doesn't hurt to be reminded of the little things, the dumb things, and the overwhelmingly obvious things. In all honesty, I've left for the airport without my wallet several times and had to turn around. Once, not too long ago, I was riding in the car to the airport for 15 mintues before I realized I'd left my passport at home—and I travel for a living.

2–3 months before your flight - Get a passport. They say it takes six to eight weeks to get one (though it often arrives before that), so plan accordingly. If you already have a passport, be sure it's valid for at least six months beyond the date of return for your trip, as many countries won't let you in with a passport that's about to expire.
8–10 weeks before your flight - Starting looking into airfares. You don't want to book them just yet, just get a sense of what the going rate is so you can keep an eye out for deals—unless you run across a phenomenal fare (from the East Coast, anything under $500, including taxes, qualifies for early purchase; from the Midwest or West, anything under $700 to $800).
6–8 weeks before your flight - Buy your plane tickets. Now is the time to lock in the best price you can find and buy your pane tickets. Congratulations. The trip is real now.
3–8 weeks before your flight - Get guidebooks. Actually, you could get these later, but since the next step is booking hotels, you'll want the advice in the guidebooks on that.
3–8 weeks before your flight - Start booking places to stay. After you have your airfare locked in, feel free to start booking those key hotels (or hotel alternatives). If you're booking a longer-term stay like a villa or an apartment, do it as soon as your travel dates are locked in (i.e.: right after you've booked the airfare). Sure, you can wait a bit longer on hotels—or leave the trip more wide open to juggle your itinerary as you go. However, (a) it's always wise to book at least the first and the last nights, and (b) if there is a particular lodging you want to be sure you get, or are already comfortable with your itinerary, the sooner you book hotel rooms, the better your chances of getting your first or second choices (hotels that are cheap and central sell out quickly).
2–3 weeks before your flight - Start packing. Yes, do its this early. There are two reasons: (1) This way you won't end up frantically packing at the last minute, which always seems to take five times as long as you'd thought and keeps you up way past midnight. More practically, (2) you'll find there are specialty travel items you need (electrical converters, travel clothes, etc.) that will need to be ordered from a catalog ahead of time, and who wants to pay for rush delivery?
2–3 weeks before your flight - Look into tours. If you want to sign up in advance for a walking tour, guided daytrip excursion, something fun like gladiator lessons in Rome or a cooking class in Florence, or arrange for a private guide, go ahead and do it now.
1–2 weeks before your flight - Book entry times to key sights. There are some sights—like Leonardo da Vinci's Last Supper in Milan, the Leaning Tower of Pisa, and the Galleria Borghese in Rome—that sell out days, even weeks in advance. Book them now or risk not getting to enter them at all.

There are others—like the Colosseum in Rome; the Uffizi Galleries and Accademia (The David) in Florence; the Secret Itineraries tour of the Doge's Palace in Venice; the Scrovegni Chapel in Padua—that are wise to book ahead since they will save you up to an hour or two of waiting in entry lines once you're there.

Again, go ahead and book those first three (Leaning Tower, Last Supper, Galleria Borghese) now. For summer travel, I'd say also book at this point any of those others mentioned above you want to see, since entry times sell out fast in high season. At other times of year, if you prefer to keep a looser schedule, you can wait on booking any of the others until you're there; just try to do it at least two or three days ahead of time so you won't be disappointed.
2 nights before your flight - Finish packing. Seriously. Have everything in your bag and carry-on except your wallet and cellphone. Again, it will take longer than you expect, and this way you won't be up until 2am on the night before your flight. You'll be up until 2am on the night before the night before your flight. Trust me on this one.
Day before your flight - Prepare to leave. If you have note already done so, make your backup info sheets and leave copies where you need to. Call your credit card companies to let them know you'll be using the cards overseas (crucial if you don't want them to freeze the account when, from their point of view, you card suddenly starts acting suspiciously—like making large purchases in another country). Contact the post office to hold mail and put a hold on the newspaper delivery service. Make sure the neighborhood kid you hired to walk the dog and water the plants knows the difference. Check your flight times to make sure everything is still on track.
Four hours and five minutes before your flight - Re-check your flight times. Load the car or get to the curb to wait for your car service to the airport.
Four hours before your flight - Leave for the airport. This is assuming you live within about 30-60 mintues of the airport, and therefore budgeting an hour of travel time. I always aim to be at the airport three hours before my flight. Yes, that is way more time than they say necessary—technically, depending on the airline, you need to check in 60 or 90 minutes before your flight (and yes they can, and have done me, deny you boarding if you show up 59 minutes before).

Most people say to be at the airport two hours early. I say three (plus a generous amount of time to get there), because I've learned adding an extra hour does wonders for my stress levels—and air travel is ferociously stressful. That extra hour allows plenty of padding for delays, traffic, and long lines. I have, on any number of seperate occasions, spent more than an hour in (a) traffic, (b) check-in lines (I'm thinking of you, Delta terminal at JFK), and (c) security lines (Philly, often).

I've also waited half an hour for a car service to show up, and been to airports where it literally takes 20–30 minutes to walk to where you need to be. Now imagine if the stars of misfortune aligned and all of those happened at once. You'd miss my flight. If even only one or two happen—or there's, say, 15 minutes waiting for the car service, 30 minutes of traffic delay and a combined 45 minutes of waiting in airport lines. Suddenly, you're getting to the gate with barely enough time to hit the bathroom before boarding starts. Leave early, and you'll be happier. Just pack a good book and maybe a magazine or two to help kill time at the airport.
One hour before your flight - Be at the gate. By now, you should have already hit the shops for snacks and extra reading material, filled up the empty water bottle you brought with you through security, and visited the bathroom. Remove from your carry-on everything you actually want at your seat (as opposed to in the overhead—a book or magazines, snack, drink, gum, neck pillow, noise-cancelling headphones) and put those into a small plastic bag so you can just sling that into your seat when you get to your row, stuff your carry-on into the bin, and sit down quickly.

That's it. You're ready for your flight. Just crack open your book, and wait until you hear your row called. Try to get some sleep on the plane; I'll see you in Italy.

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