Pay for a group tour.

Whether it’s a day, a week, or more, traveling through Italy in an organized group tour — while certainly with its advantages — is a complete waste of money. Groups are large, lumbering hordes led by frazzled guides rushing through impersonal lectures punctuated by tired tour-guide jokes. Tour groups arrive at major attractions at the busiest times. I know I’ve hit an attraction right if I’m leaving as the tour buses are arriving.

Preferable alternatives to the dreaded group tour include:

  • Private tour with a local – Your day will be more of a conversation about history, politics, religion, and culture rather than a lecture. Plan the tour together, personalizing sights, eateries, activities, and pace.
  • Audioguides – Available online (often for free) or at the attraction for a nominal fee. In my experience, audioguides offer great value especially for solo travelers, but can be hit or miss in terms of entertainment value and are not conducive to small-group or family travel.
  • My personal favorite, “sidling” – First, find a tour group whose leader speaks your language. Second, sidle on up to the group — I recommend an oblique flanking maneuver near the guide — for a quick dose of knowledge as you eavesdrop. Listen discreetly for as long as you’d like, then move on at your own pace. Never worry, another tour group is usually nearby. Pro tip: Excessive sidling can generate a stern look from frazzled tour guides, so spread your sidling out amongst the groups. And don’t ask questions.
Rent a car without GPS.

Hey there, big spender, I see you rented a car in Italy. That must’ve cost a pretty penny, huh? Well, you made the right call. Getting away from the crowds in Italy is best done by car. While a great train system links the major mainland cities, much of sleepy, small-town Italy remains off the rail grid. Even if it’s just for a couple days, rent a car in Italy and go for the places furthest from an autostrada.

But the further you explore, the narrower the roads become, the less frequent the road signs appear, and the faster the drivers go. Be prepared with a GPS system that will suss out the best route, notify you of delays, and be an ever-present, British-accented companion.

Rent that car in a major city.

Well, crap, did I just say the roads were hectic and poorly marked in the countryside? Could they be worse in the city? Save money and a traffic-induced migraine by riding the train to a secondary city like Arezzo rather than Florence, or Viterbo rather than Rome, to pick up your car. Rates will be about the same, but your pickup and dropoff will be easier and faster. More time for sightseeing / wine drinking!

Stick to the major cities.

Italy’s major cities — Rome, Milan, Florence, Venice, etc — are cultural heavyweights and should be on your list. But plan a couple of days for venturing into the countryside. The most tourist-free locales and authentic encounters will happen away from the main event in places like rural Tuscany or Calabria.

Pick a country road or minor town, and go check it out. You’ll encounter cultural sights and rustic restaurants the guidebooks and guided tours can’t / won’t / don’t cover. In a country as densely populated and saturated with tourism as Italy is, it’s surprisingly easy to leave all that behind for a quiet glass of wine in an empty restaurant looking out over a sheep pasture.

Wake up after 6am.

Italy is ruthless to those who sleep in. Wake up early, grab a quick breakfast (you can make up for it at lunch — a far more satisfying meal in Italy), and get to your first sight before it opens. Finish your cappuccino and brioche while admiring the exterior of that amazing church / ruin / museum, then head inside just as the doors open.

Even if it’s only 15 minutes before the hordes invade, those precious minutes in a nearly empty Colosseum or Accademia or Duomo are what make a thoughtfully planned European trip so worthwhile. These early mornings — when security guards are still shuffling to their posts — are the moments you’ll recall long after you’ve returned home, not the afternoon spent sweating your way through throngs of tourists in the Sistine Chapel.

Buy expensive wine.

Everything’s expensive in Italy — hotels, restaurants, transportation. That is, everything except wine, glorious wine. The nectar of the gods can be had readily (it even comes in juice boxes) and affordably. Italy produces expensive wine, the qualities about which I’m sure some wine snob can erudiate, but five euros buys a damn fine bottle.

As price rises, quality does not necessarily correlate. Many higher-priced wines are trading on a brand, label, or — worst of all — a “tasting experience.” At restaurants, do it right by simply asking for the “vino della casa” in red or white. You’ll enjoy a lovely wine, and have plenty of money left over for an after-dinner gelato.

Fail to buy museum passes in advance.

Go ahead, play it fast and loose with the itinerary. You don’t want a reservation or expiration date dictating your travels, right? Well, I hope you like waiting in lines. And when it comes to long, hot, glacially advancing lines, nowhere does it better than Italy.

Most major attractions sell tickets online — do it! Some, like the Uffizi in Florence, even require it. A little foresight goes a long way in an overcrowded Italy. Case in point: After exiting St. Peter’s Basilica (where a monstrous line had developed — we arrived early to an empty St. Peter’s Square and strolled through security sans line) in Vatican City en route to the Vatican Museum, we slammed into a line snaking around the city wall for three blocks. We skipped the whole thing, going straight for the empty reservations entrance where a cheery security guard scanned the ticket I had printed at home weeks earlier, let us in, and informed us with a diabolical laugh that the wait was approaching four hours in the no-reservations line. Ouch.

Neglect the citywide museum passes.

Whether it’s Rome, Milan, Venice, or Florence, Italy’s all about the museum pass. Often good for free or discounted entrance to a plethora of local attractions as well as unlimited public transportation, Italy’s museum passes are a great value and time saver. Even if you don’t visit enough attractions to make it financially worthwhile, you’ll more than make up for it with ticket-less subway travel, line-skipping at major sights, and the ability to quickly pop into museums you’d otherwise bypass.

City passes can be purchased online and at tourist offices (TI) or tobacco outlets (tabacchi). Italy can be crowded and hectic, but a little planning ahead — like buying a museum pass — reduces stress and frees up more time for the important things, like lingering over a cheap bottle of wine.

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