The Gondolier

The Italy Rules are my set of guidelines for the first-time and infrequent Italy traveler. I have traveled to, lived, and worked in Italy frequently over the past 20 years. In this time I evolved from a curious tourist to hardened, salty, veteran of the trials, travails, and pitfalls, of one of the world's most visited countries. One usually dreams of Italy for years before finally setting their foot into the proverbial boot. The dream usually crashes in much less time. This post is really for the traveler who has not been deep into the Amazon or climbed to base camps in Nepal. This post is for those of you who enjoy modern conveniences, large bathrooms, and the amenities of a comfortable Western life. For the most part, I am you. I love my big bed, my central heat and air, and my very fast wi-fi connection. However, Italy is reason enough for me forego these luxuries for a few weeks or months out of every year.

One of my dearest friends is half American and half German. He is the model of organization and efficiency. He said to me just the other night that one of the reasons he loves Italy is because it is chaos. Yes, he loved the chaos, and if you have any hope of really embracing la vita Italiana you'd better be ready to embrace chaos as well. I am 100% confident there will be detractors of my post, and let them come. The information I am going to share with you here is well won. I have been down many paths of serious consternation in Italy and if you listen to me, you can likely avoid most of these, and perhaps even enjoy a bit the ones you cannot avoid.

Now, without further ado, I give you, The Italy Rules:

1. Do NOT Over-Schedule - Italians typically accomplish about 4 things per day in their lives and have a damn fine time getting from 1 to 4. Do not attempt to do more than the locals do and you will be happy. Here is what an exceptional first 2 days in Italy look like: (this is not a derogatory comment about Italians, it is praise for the art of good living)

Day 1 - Arrive in Rome - Meet your guide (you will be 100% happier than you can imagine if you hire a personal guide) Check  in Hotel or Apt -   (away from sites at least 10 min walk)- Have long lunch - see 1 site - have cocktails - eat dinner

Day 2 - have good coffee outside of hotel and nowhere near any sites - go to first site of day (perhaps the Vatican) - have very long lunch - go to another site (maybe the Borghese gallery) - walk around eating gelato at a few places  or get another coffee - rest for a bit - have cocktails (called aperitivo and usually includes little snacks and is best taken out on some street-side cafe but not in Piazza Navona, or Campo dei Fiori - go over to Monti and enjoy a glass of wine at one of the many little wine bars in that hood) - have an evening stroll in your finest travel threads - eat a wonderful dinner at around 9 PM - you won't starve if you had a proper aperitivo , and you won't look like British granny arriving too early.

2. Do NOT Over-Travel - You may think you can do all of Italy in 2 weeks, but you cannot. You may think you must see all you can because you may not come back again to Italy. If you rush from town to town, hang around tourists and touristy places, and eat shitty tourist food you may indeed not ever come back. Here is my itinerary suggestion for the first-time Italy traveler.

2 Weeks - if you can't go for two weeks, go somewhere else and save Italy for when you can make a real commitment. Italy requires commitment

Arrive Rome - follow above plan...Rome is 4 days at a minimum including arrival day so let's say 5 in total counting departure day

Florence - Now, I don't love Florence, but there are things that must be seen and frankly, if I say skip it, I will get more hate mail than I care to read. Take the train from Rome and spend 2 nights in Florence. Make sure  to book any museums, churches, and  touristic sites in advance. I have no time to give you links to all this, and half the fun of travel is planning to me, so Google how to do it, and do it. Waiting in line sucks no matter where you are. Waiting in line on an expensive Italian vacation is a hell that would make Dante cringe. Hit a couple of great sites in Florence on Day 2 then get yourself a car and drive to...

Wine Country! - Real Tuscany happens in the hills. I would take 2-3 days to do Chianti (Radda and Panzano) - Montalcino and Pienza - San Gimignano - spend 1 day exploring each of these options (do not rush and make sure to eat well)

Bologna/Parma - go here and eat all the classics like Ravioli, Tortellini, Prosciutto, Parmigiano, and Balsamic - great towns, easy to drive in and out, and not nearly the number of foreign tourists (1-2 days)

Venice - I really love things about Venice but you MUST stay away from the central tourist areas - you MUST go to the islands (take the early ferries so you can get back to Venice by 2PM lunch and avoid paying for expensive island food) See the sites as early as they open, then wander around enjoying your day while the hordes crowd around eating shitty ice cream and wearing horrible clothes. Eat lots of seafood, drink loads of wine in the wine bars everyday before dinner. Stare at the wonders of water travel before flying home.

This is in my opinion an aggressive itinerary. Any more stuff than this and you will hate it. If you plan to return to Italy then just do Rome 6 days Florence 2 Siena 2 - Tuscan Wine Country 4 :-)

10 Things to Know and Myths busted

1. Pizza in Rome is an anytime meal (lunch and snack hours best). Pizza south of Rome is generally eaten only at dinner as the ovens are not fired up until evening. There are some Rome pizzerias that serve only at night but those serve whole round pizzas. The tasty square kind served throughout the day by the slice are fun to mix and match. Order by weight and eat on the go.

2. You do not have to order every course in a restaurant. Order what you want to eat. Be adventurous. Look around you and order things you see on the tables. Pointing works if your Italian is non-existent.

3. Breakfast in Italy is not hearty unless you are staying at a nice hotel or agriturismo. If you love breakfast (like me) buy some meat and cheese at the store and shove it down before leaving your hotel each day. Then order coffee and a pastry like everyone else. (you need not order food to enjoy a great coffee if you prefer to skip the sweets)

4. Do everything you can to make sure your own telephone works in Italy. Set up an international plan on your phone and get lots of texts and data. Getting an Italian phone can be done, but visits to the phone store wastes a ton of time. Use your US phone and budget the extra $100 bucks it may add to your bill

5. Pack lightly - Italy is a small country with lots of small spaces. I can offer suggestions how to pack if you ask me directly. However, for this piece I will simply say if you bring too much to Italy, you will hate yourself, and old ladies on public transportation will hate you! My travel friends and I compete on who can bring the least shit on a trip. It's a worthy competition.

6 Hire Guides - expats, especially ones with blogs about food, wine, and life in Italy are wonderful. I can suggest guides for many regions and a little investment will go a long way to your overall success as a first-time Italy traveler.

7. Plan heavily but be flexible - Do your research and have contingencies if something sucks. If you hate Rome, leave early. If you love Radda in Chianti and want to stay an extra day..stay! An old friend always said "never leave a good party hoping the next one might be better" if the place you are is stealing your heart, then let it be stolen.

8. Cab drivers in Rome suck...really bad! use the buses, the metro, and the trains. Walk if you can and have time (and you should). If you must use a cab make sure and ask them the fare in advance...which also sucks. Driving in Rome is also pure unadulterated hell and should be avoided.

9. Italians are not circus animals and they do not want to do tricks for you. Don't ask them to twirl pizza, throw pasta against a wall, or sing some fucking folk song for your listening pleasure. Keeping this in mind, Italians can be entitled, lazy, and intentionally vague. The fact is that all people are people and generally, people prefer to do things in their own way. Respect this and yourself. Don't give or take shit.

9. Try not to dress badly, but you do not have to wear a dress or suit everywhere. Italians frequently wear ugly clothes and have bad hair like we do, they just have their own ways to do it. Hipster glasses are standard and t-shirts are common among many. However, looking like an extra from Duck Dynasty is not cool. Somewhere between Mad Men, Anderson Cooper, and Honey boo-boo should suffice.

10. Don't spit, put your feet on things, go barefoot in public (or really ever outside of the beach). Do not flip anyone off, or try to buy anyone's attention in any way at a bar, restaurant, or airport counter.

These are the Italy Rules and you must abide by them. No matter what, you will have moments that are so sublime they will hardly be done justice by your memories, just as you will have days that will just suck. Italy is slow. Italians are less and less hopeful of their country, and the monuments are starting to decay faster than they can be repaired. I believe in all of this that Italy will have its generational renaissance and will continue to be one of the finest collections of art, people, and culture on the planet.

I look forward to your comments.