Tips and Logistics

Travel Dates

The most important tip is to avoid summer if at all possible.  (And if you still must, go very early in June.)  Italy's weather gets super hot and humid, many of the sites are outdoors, and air conditioning is rare.  Nonetheless, that is when the majority of tourists are there, so you will also encounter long lines and heavy competition for limited tickets.  If you can tolerate the cold, going in winter is great for the cheapest prices and lowest crowds, although any beaches or coastal cities will be a ghost town (with the exception of Venice).  So the very best time is spring or fall, whichever fits on your calendar better.  Spring has the advantage of everything blooming, although late October looks pretty when the leaves are changing colors and there's less pollen in the air.  

(It's inconsequential to planning, but don't forget to ask Google what time sunset will be on the dates you choose.  You'll want to know how early it gets dark and what time to visit an overlook for a photographic view.)

Flights

The very best way to save money is to be flexible with your travel dates if at all possible, and then wait patiently for an airfare sale.  You can either set flight alerts with various websites/apps or join a fare-discovery newsletter like Scott's Cheap Flights.  These sales come out of nowhere only a few times a year and can end within hours.  So be ready to pull the trigger immediately.  Americans have 24 hours to cancel a ticket purchase for free, so don't hesitate.  Any regular non-sale flight priced under $1,000 for basic economy is still a good deal from most airports, but a big sale can reduce that to $500.

Airports

Depending on your home airport, it may make sense to fly into one Italian airport and depart from another.  For example from Miami, it is always more efficient to fly non-stop round-trip to Rome and take a train from there to your first city.  But from JFK, you could fly directly into Venice, head south throughout your itinerary, and then out of Naples.  When comparing flights, be sure to look at the total travel time and check that your layovers are at least 2 hours long.  For Americans, a connection on the East coast is preferable to the unfamiliar mazes of Heathrow or Paris.  It's a real mess to get stuck overnight in the wrong country if there are any significant delays.  But sometimes you gotta do what you gotta do for a really good deal, even driving a few hours away from your home airport.  When running your search, use Google Flights because it can accept  multiple departure airports simultaneously for comparison, and set "Italy" as the destination to see the price all on one results page.  When it's time to book, Google Flights will take you directly to the airline as opposed to a third party online travel agency.

Hotels

The next biggest price factor within your control is your hotels.  Even the lowest budget places all over Italy ($50-100 per night) are more than satisfactory.  You may prefer a little more luxury, which of course is fine, but remember that you won't be spending much time in your room when Italy is waiting.  Just read the reviews online very thoroughly.  Make sure there's an elevator mentioned if you need one.

Location, location, location!  Chose hotels that are near the train stations or with easy transportation options to the train station.  Note the walking distance from the nearest metro station, bus stop, or ferry port.  Most aggregator search sites will let you sort by distance from a chosen address.  Staying on the outskirts will save you money, but you don't want to waste precious vacation time commuting.

Be prepared for strict limits on thermostats.  Italy's individual regions usually have inflexible rules about the dates that the heat can be used or that the air conditioner must be turned off.  (That's just a heads up, because there's not much you can do about it besides bringing your own fan.)

Trains

99% of the time, the best way to get around in mainland Italy is the train system.  It goes from city center to city center quickly, efficiently, and cheaply.  There are high speed trains or slower cheap trains, but your time is limited and usually more valuable than the small savings of the slow routes.  The cheapest seats on a fast train are much more comfortable than on an airplane.  They generally don't go on sale until around 3 months before the date you want to travel, costing about half as much at that time before slowly increasing in price each week.  For example, Rome to Florence may be $25 the day they go on sale, but $50 at the last minute.  You can still leave room for some spontaneity in your itinerary, but plan these journeys in advance.  Because you can't purchase train tickets as early as you're trying to make your itinerary, you can just search for the routes next week to see what times they depart.  Regional slow trains between smaller towns only go on sale about a month beforehand, the price is set, and there are no assigned seats.

One thing to note, there is no way to reserve seats only facing in a forward direction, because trains switch back and forth frequently and sometimes even in the middle of a journey.  If you get motion sick easily, book seats facing a travel companion and trade places when needed, but don't hesitate to ask a stranger to swap if necessary.  Most locals are very kind about this.

Heads up:  train tickets need to be "validated" right before getting on board either in the train company app or by stamping your paper ticket at little yellow machines on the wall in front of the platform.  A conductor will check your tickets during the journey and issue fines on the spot.

The easiest site to search for trains and make purchases all in one place is Omio.com, although I recommend booking directly on the train company's official website.  The Trenitalia app can give errors with the difference in time zones, so avoid making your purchases that way before arrival.  Trenitalia and Italo are the only two operators in the vast majority of Italy, so do not make a purchase from from any other site.

For the most comprehensive information about taking the trains in Italy, search the web for "The Man In Seat 61" to find all the details you could ever want.

Choose hotels near the train stations for the easiest experience with your luggage.  

Rental cars

The reasons not to rent a car are numerous.  You definitely don't need one unless you are visiting several rural locations.  Italy has extremely narrow streets, and only local residents are allowed to drive on the roads in the historical city centers, which is where all the sites are that you want to see.  So you'd have to find an elusive parking space on the outskirts, then walk or take a bus or taxi from there anyway.  I'm sure you've heard about crazy Italian drivers, but they're really only scary in the big cities.  Rental cars are quite expensive (especially if you can't drive a stick shift), and gas costs about 3x more per gallon.  Most people on most itineraries will save money and a lot of stress by just hiring a private driver or taxi if needed.  If you still decide to get a car, please do a little homework to learn the road signs, know exactly where the ZTL restriction areas are, and search Google Maps for public parking lots beforehand.

Luggage

Because you will be taking the trains, it is very important to pack the smallest, lightest luggage you possibly can.  The best advice is to bring only as much as you're willing to carry up a flight of stairs.  Google "minimalist packing" for tons of great suggestions.  Do a little research on the fabrics you choose to bring.  If you ever need to scrub clothes in the sink after a sweaty hike or a splattering from your spaghetti, be absolutely sure that they will drip dry overnight in high humidity.  It's also easy to find a laundromat if you want to just schedule that into your itinerary one evening.

Check out this Packing List for Italy.

City Navigation

To get from any point A to B within a city, all you need is Google Maps.  You can switch tabs between walking directions or public transportation (with exact timing even if the bus is running a few minutes behind).  Taxis are a bit more complicated with a different company operating in each city, and Uber is only present in a very few.  Don't get into a car with an Italian driver if it's avoidable unless you have a strong stomach.  When finalizing your itinerary, look up the travel time in between A and B beforehand, plus build in an extra 10-15 minutes when arriving on time is critical.  

In Venice, there are obviously no busses, and the expensive public transportation by water boat (called a vaporetto) isn't any faster than walking.  But there are an awful lot of stairs up and down over every single canal, so that may be a deciding factor for you.

Buying Site Tickets

To find the official website for any attraction, search for it on Google Maps and click on the link from there.  Nearly every website has an option to change the display language to English (although sometimes it's a little tricky to find that button), but your browser should translate just fine too.  Don’t purchase “skip the line” tickets from a third party reseller!  "The line" is to buy a ticket, so if you purchased one online from the official site, then you’ll already be skipping the line.  Always double check the opening days and hours on the official pages.

Many museums and archeological sites do not release tickets for sale until 1-2 months before the date you want to visit.  If you buy a ticket 6 months ahead from a third party for the Colosseum, for example, the company is literally betting that they will acquire them from the official site when that day comes.  Other places like the Uffizi museum sell tickets farther in advance, but you cannot change the entry time later if your itinerary ends up being altered.  So you have some decisions to make about these purchases, and only you know the timing and method that works best for you.  But do not wait until the day of to decide you want to spontaneously visit a popular attraction, because it's likely sold out.

Money

Italy is paradoxically both early adapters of the latest tech and also still prefers cash.  What that means is you can tap-to-pay with your phone or contactless credit card for purchases almost everywhere, but the vendor would usually rather have Euros from your wallet.  Whichever you prefer is going to serve you well, but always have the other available as a backup.  If you're buying a souvenir magnet or a Fanta for €2, they may have a minimum purchase required to use a card.  Or you might encounter a busy museum that only accepts cards to keep their lines moving faster.  A taxi may try to refuse to accept a card, so argue about it before getting in the car.

So you know that you'll need a credit card and to get cash somehow.  Many people are anxious about arriving in a foreign country without some local currency already in their hand, but it's no trouble finding a convenient ATM upon arrival.  You can order Euros from your local bank with a couple weeks' notice, but be aware that this incurs extra fees and/or a poor exchange rate.  The worst way to get cash is to bring bills from home and find a kiosk at the airport to swap it for Euros, because they charge the highest fees of all.  Avoid the "Euronet" ATMs often prominent in tourist-heavy spots.  You'll get the best bang for your buck by using your debit card (never credit card!) at a local bank's ATM.  It's typically the best possible currency exchange rate plus a small €3 fee.  (Your bank may also charge a small out-of-network fee.)  Go through your itinerary and calculate how much cash you may need and then only withdraw that amount.  You can always find another ATM later, which is preferable to carrying a large amount of cash that could get stolen.  If you have any private tours or private transfer drivers or other plans that will involve cash tips, be sure to break the large bills beforehand to have the exact amount ready.  Most cities have a tourist tax per person per night for lodgings, and those are often requested in cash when you check in.  €200 cash is usually enough for a 2-week trip. 

Credit cards require just a little research.  Usually only Visa and Mastercard are accepted in Italy, so don't bring your Discover or AMEX.  But most importantly, you need a card that has "no foreign transaction fee."  Google whether or not yours does, and apply for a new card if needed.  You don't want to pay the bank an extra 3-4% on every single thing you buy.  Most of the cards that earn travel rewards points are perfect.

(A note on pickpockets:  they usually hang out in crowded places where you're easily distracted, just like in every city on the planet.  Be street smart by keeping your wallet secure.  Extra zippers or snaps on pockets are a big plus.  Don't use your back pocket if possible.  Women need a purse they can wear crossbody, with an arm kept over it in crowds.  Security pouches that stay under your clothes are ideal.  Never put anything valuable in a backpack.)

Restaurants

You already know you'll eat well in Italy!  Here's a few tips.  If you're going between May and September, make reservations if possible.  Especially in the center of big cities that cater to tourists and in the tiny towns where there are few restaurants, a little pre-planning will go a long way.  You're more likely to find authentic places by checking Google Maps reviews from locals than by consulting other tourists on Trip Advisor.  Ideally you would avoid tourist traps by ignoring any place with a picture menu or a busker out front soliciting your business, but it's hard to find anything else in the middle of Venice.  The reality is that for most everywhere you're going, it's just good business practice for them to welcome people who don't speak Italian, and don't write a place off just because the host is friendly outside.  It's fantastic to find restaurants that have smaller seasonal menus without a dozen plus options for each course, but it's not a dealbreaker.  

Always eat the regional specialties!!!  That means don't order seafood in Florence or carbonara in Naples.  Sure, they'll probably be decent, but they won't amaze you like their best-practiced plates.  A quick Google search will tell you what each city does well, and always ask the waiter what they recommend.  First, please erase from your brain everything that Olive Garden has taught you to expect!

As a general rule, tipping is not customary.  There's not even a line to add it on your receipt.  However, a few tacky waiters in popular tourist areas can expect it as soon as they hear an American accent.  There is already a "coperto" cover fee added to your bill, so don't feel pressured to give anything more.  Still, leaving €2 on your table is never unwelcome.  Just remember that Italian waiters are intentionally very different than you might expect.  They don't hover or swing by just to check on you-- they don't want to interrupt you and your meal.  If you need their attention between courses, simply catch their eye and give a little wave.  They will not bring the bill until you ask, simply because they don't want to rush you.

Language

If you stay on the beaten path, you'll be fine without learning Italian.  Almost everyone that interacts with tourists will speak sufficient English.  But it's still helpful to learn a few basics.  Many people will recommend Duolingo, but it won't teach you the vocabulary that's most relevant for travel.  I'm a fan of using Quizlet for simple flashcards you can review for 5 minutes a day.  Just search for "travel Italian" or "most common Italian words" in that app.  I also have a short cheat sheet of Italian 101 pronunciation and vocabulary here.

Insurance

Side note, please always get travel insurance.  It costs up to 10% of your total trip expenses, but the best reason to use it isn't financial.  If any medical problems arise, trip insurance companies are an invaluable resource.  An Italian hospital will often require payment up front, which could potentially far exceed the limit on your credit card.  Or if you become severely ill while alone in your hotel room, travel insurance can find a doctor or pharmacy that comes to you.  Having someone to call is priceless when you don't know the steps to take.  Compare your options at insuremytrip.com

So, that's all the basics!  Now, on to the Suggested Itinerary...