Suggested Itinerary

These are the things everyone really should see.  Obviously you can customize your time differently, but trust that the highlights are famous for good reason.  If you want to also add some serious beach time in the south or mountain hiking days in the north, split the following recommendations across two trips.  Otherwise, knock all of this out at once, and then come back in the future as an experienced Italy traveler for a second trip more customized to your personal interests.

Itinerary overview

Now you're ready to hear what to include in your itinerary!  The classical Grand Tour of Italy refers to Venice, Florence, Rome, and Naples.  You can scratch the surface of each in 2 weeks, but you'll need to eliminate one if your trip is shorter than that.  Only suggest visit the Naples/Sorrento area if you will be there between late April and mid-October.  Outside of those months, the Amalfi Coast is mostly shut down, and there is very limited ferry service to Capri.  For all other months, replace that segment either with additional days in the other three cities, adding Bologna/Modena/Parma, or enjoying a little down time at a villa in Tuscany.

Outlining a 14-day trip covering the major highlights:

2 nights, 1.5 days VENICE
3 nights, 2.5 days FLORENCE
    includes a day trip to TUSCANY countryside
4 nights, 3.5 days ROME
    includes one day of personalized choices
4 nights, 3.5 days NAPLES
    includes CAPRI, POMPEII, and the AMALFI COAST

Itinerary order

The order of your itinerary may already be dictated by your flights, but otherwise I generally suggest traveling from north to south.  The north is a little more tourist-friendly to navigate and thus a bit easier to start with.  But psychologists say that we remember the end of our trips better than the beginning, so if there's something specific you're particularly looking forward to, you might want to save that for last.  For many, the food in the south is definitely the best part.  

It's strongly recommended to not plan anything exciting or expensive on the day your flight arrives.  You will definitely feel like a zombie and may even have encountered a delay that makes you miss it entirely.  And this applies the same for every time you change cities.  Don't plan to arrive in Florence from Venice in the late morning and then take an expensive food tour half an hour later for lunchtime.  Trains encounter delays too, although not very often, and it's a whole other conversation to discuss the possibility of a train strike.  (You can Google that and learn there are easy but slower ways around it.)  Since you'll probably be arriving before check in time at your hotel, most are happy to store your bags early, or you can search Google Maps for "luggage storage" to find several cheap options near the train stations.

Venice for 1.5 days

For your first half day in Venice, spend the afternoon strolling the separate island of Murano (and/or Burano).  This lets you enjoy the Venetian lagoon environment with smaller crowds, do some shopping, and simply experience a relaxed entry to this unique little corner of the world.  Google Maps will tell you how to get there by vaporetto boats from a starting point near your hotel.  Speaking of, if you're on a tight budget, you'll want to stay in the cheaper accommodations on the mainland in Mestre and ride the 5-minute train into Venice itself.  (The city charges a small entry fee for popular days, so Google whether that will apply on your dates.)

For your only full day here, a fun way to start is with the view from the bell tower in St Mark's square.  It has an elevator, and you can either pre-purchase the ticket online or simply walk up to the short line.  You definitely want to visit St Mark's basilica at 11:00am when they turn on the ceiling lights for only an hour.  Entry costs are low, but you should reserve a time online to skip the long line.  There are options to add on the church museum and treasury, but I wouldn't unless you are particularly interested in those details.  Rick Steves has a free audioguide for the basilica available on his website.  Then have a nice long lunch, as the Italians do.  This city is 90% tourists, so there's really no hidden authentic gems.  Look at reviews beforehand on Google Maps, check out their menus, and make a reservation anywhere that looks good nearby.  Eat the local specialties!  You will not find great pizza or carbonara in Venice.  Try the fresh seafood or duck ragu instead.  Always ask the waiter what they recommend!  Right after lunch, pencil in something chill, such as seeing the amazing La Fenice opera house.  Just have a plan so you aren't wandering around trying to figure out what to do if inspiration doesn't strike.  The last two things you need are taking a gondola ride and touring the Palazzo Ducale.  Gondolas cost more at sunset, but many people say it's worth it.  Or you could do it before the Palazzo, as long as it’s not immediately after that big lunch.  No need to reserve a gondola online-- they are a flat €90 per boat (up to 6 passengers) plus 10% tip, with a €20 surcharge after sunset.  There are plenty of them departing from tons of locations.  Moving away from St Mark's square and the Rialto bridge will help you avoid the longer lines there.  The Palazzo Ducale ticket should definitely be pre-purchased.  They have their own audioguide that's pretty good, and you'll enjoy the rooms a lot more if you have a clue what you're looking at.  Spend your last evening in Venice eating light like the locals do.  Google “cicchetti” and where to find them.

Florence for 2.5 days

The next morning, take the 2-hour train to Florence.  Have a good lunch on arrival.  The local specialty is medium-rare bistecca steak or a lasagna if you prefer.  There are also some Instagram-famous prosciutto sandwiches you may want to try, but you can find identical ones just down the street from those extremely long lines.  Take a "free walking tour" in the early afternoon.  The guides work just for tips, so they are usually quite talented.  It will help orient you to the city and review the important parts of its history.  Afterwards, visit the Medici chapel (if pre-purchased), the Bargello museum, or just do some shopping.  Ninety minutes before it closes, it's time to see Michelangelo's David in the Galleria dell'Accademia (pre-purchase the ticket) with the Rick Steves audioguide.  Then catch a bus to Piazzale Michelangelo in time for the sunset, and eat a sandwich from the cart there. 

For full day number one, you want a reservation for the very first entry time to the Uffizi museum.  If you're not pinching pennies, hire a tour guide for the best experience, but there are audioguides available.  This museum is the crown jewel of Florence.  Even if you are not usually a museum person, you just might be after visiting this one!  Next, visit Santa Croce church where all the famous Florentines are buried.  Have a big lunch.  Do a little shopping, or visit the Palazzo Vecchio (the Secret Passages tour is worth pre-purchasing).  Then it's time to tackle the Duomo.  It's mostly plain on the inside with the exception of the dome itself, but still worth seeing.  The baptistry recently reopened after restoration and should not be missed.  The hidden gem here is the short but very sweet duomo museum.  Near sunset time, you will want to climb either the Duomo itself or the bell tower.  The tower is less claustrophobic, almost identically tall, cheaper, and rewards you with a view of Florence that includes its most iconic landmark.

For your second full day in Florence, it's time for a day trip.  There are so many options!  Siena and San Gimignano are popular with tourists.  If you want to hike in Cinque Terre, it's an easy journey by train, although a very long day.  Another option is Pisa and Lucca for a more relaxed outing.  There are multiple private or group excursions to the countryside that focus on Chianti vineyards and wineries.  Ones that head south toward Val d'Orcia are the most scenic.  It's so hard to pick just one, but you will absolutely fall in love with Italy and come back again for more in the future.

Rome for 3.5 days

Next, it’s time for Rome.  Sleep in a little bit, then take the 1.5 hour train in time for lunch on arrival.  Try the carbonara and amatriciana pasta!  When you're done, walk from Piazza Navona, to the Pantheon (new $5 ticket required), Sant'Ignazio di Loyola (brief but amazing), Trevi Fountain (coin tossing mandatory), Spanish Steps (sitting now prohibited), and end with a short visit through the uncrowded Palazzo Massimo alle Terme museum.  Definitely pick up a gelato along the way.  One of the best parts about Rome is its metro system.  You can get from A to B a lot quicker than in other cities (thankfully, because it’s huge).  You don't have to worry about tickets, just tap your contactless credit card or smartphone to get on and off.  One great way to have a very mild adventure is to hop on the metro going in a random direction, get off anywhere outside of the city center, and ask the other locals exiting with you where you should eat dinner.  You are much more likely to find some authentic hole-in-the-wall place this way and gain a fun little story to tell. 

You now have three full days left in Rome, and you will need to shuffle these next suggestions depending on your dates.  For every site you want to visit in Italy, you need to check their opening days.  Often they are closed on Sundays, Mondays, or Tuesdays.  That is what will determine your itinerary schedule.  So here are my suggestions for your time:

The Colosseum opens at 8:30am, and that's the time slot you really want in order to avoid the worst of the sun.  For years, this site has been the most difficult ticket to get in the whole country.  There's literally an industry of professional scalpers who snap them up within the first second they go on sale and then resell them to tourists either with or without a tour guide.  It is worth making the attempt yourself to get tickets directly at the official source for half the price, but it requires waking up in the middle of the night and has a high likelihood of disappointment.  (This improved a bit last year, but not enough.)  With that in mind, you really do want that first entry time, and you definitely want a tour guide, making the markup expense 100% worth it.  There are tons of reputable companies on Viator, so just pick one with multiple reviews.  These tours are usually 2-3 hours and then leave you in the forum to explore more on your own.  When you're finished, have a light lunch anywhere nearby.  In the early afternoon, Le Domus Romane di Palazzo Valentini is very cool, and/or the Altare della Patria (take the elevator to the top).  My recommendation is to do this day on a Friday through Sunday so that you can also visit the Domus Aurea in the late afternoon.  It's amazing, and strict entry number limitations keep it from being completely mobbed on the tourist circuit.  For dinner, head to the Trastevere neighborhood (pronounced Trah-steh-veh-reh).  It's not really authentic anymore, but there's still good food in a very cute environment.

The next most important thing to see is Vatican City.  Trust me, you want the opening museum time of 8:00am before it is stuffed to the gills without sufficient air flow.  You can get a guided tour directly from the official website for a very reasonable price (but book early).  And you shouldn't even consider attempting to do this enormous place on your own.  The museum is also the only way to see the Sistine Chapel.  When that's finished, head to St Peter's basilica with Rick Steves' free audioguide.  Take the elevator to the roof if the line isn't too long.  Have a good lunch afterwards, then go back to your hotel and rest your brain for an hour or two unless you want to do some shopping.  In the late afternoon, it's time to visit the catacombs.  The very best one opened relatively recently and is off the more beaten path.  None of the catacombs are very close to the historical center, but this one is an easy tram ride from the main train station that lets you off right in front of the doors.  Marcellino e Pietro just needs an email to secure your reservation, which includes a 1-hour tour in English.  Then it's a great time for a sunset picnic in the aqueduct park if the weather is cooperative.  Take the bus to get there.  You will find no tourists here, only locals and some incredible picturesque ruins.

Use one full day in Rome to mix and match the following to your personal interests:

• art museums:  Borghese, Palazzo Doria Pamphilj, Capitolini, Villa Farnesina, Palazzo Colonna

• activities:  cooking class, Vespa tour, ghost tour, Torre Argentina cat sanctuary, DaVinci museum, opera or concert

• archeology:  baths of Caracalla, Stadio di Domiziano, San Clemente, Museo delle Mura, Castello Sant'Angelo

• nearby day trips:  Orvieto, Tivoli, Ostia Antica (especially if skipping Pompeii), Ostia beach

• (Here's a map of just these choices)

Naples/Sorrento for 3.5 days

Finally it's on to the Naples area.  This is a dense big city like New York.  People either love it or hate it, depending on their comfort zone.  The area immediately around the central train station looks a little sketchy, but you won’t need to step outside there.  If you're not comfortable staying in the city, no big deal.  A great alternative is suburban Sorrento, which you can get to either by train or ferry from Naples, and it's where most other tourists will be.  Wherever you're spending the night, I recommend doing these in Naples on arrival day:  ride the metro to Piazza Cavour, have lunch, pop in at Sansevero chapel (pre-purchase tickets), take the subterranean tour, check out the duomo treasury, and wander down Via dei Tribunali to find street food for dinner.  This city is where pizza was invented, and it's still superior to anywhere else!  If you don't order the classic margherita in Naples at least once, did you really visit Italy at all?

Spend the next day leisurely exploring Capri, although your wallet will get a workout.  Pre-purchase the last ferry back of the day, as it sells out early.  At the island, walk around the arrival dock and join a boat tour.  Add on the Blue Grotto if you're really interested, but that's a looong wait time for a 1-minute experience.  Take the bus to the town of Anacapri and ride the Solaro chairlift to the top of the mountain.  Pop into the unique little San Michele church after that.  And if you still want more of the incredible view rather than shopping, visit Villa San Michele too.

Next it's finally time for Pompeii.  It's not necessary to pre-purchase a ticket, but I very strongly recommend using a tour guide here.  To save money, you can buy your ticket at the gate and then join a cheap tour group right beside it with no reservation needed.  But for a truly amazing experience, hire a private guide beforehand. You'll spend 3 hours here, and it doesn't open until 9:00am.  Have lunch right outside the southeast gates for convenience.  Spend the rest of the afternoon at the archaeological museum in Naples where they display everything that was discovered in Pompeii.  Ideally, take your tour guide there with you, but an audio guide can also suffice.  Then eat more pizza in Naples just because you can.  All of these are easily reached by train from Naples or Sorrento.

On your last full day-- and remember we saved the best for last-- you're going to travel down the Amalfi Coast.  The ferry is the ideal way to do this, but you could also go by bus in the off-season, or hire a private driver for the day (around $400, and don't forget Dramamine).  Take the first ferry to Positano for the morning, then ferry to Amalfi for a late lunch.  From there, take the bus to and from Ravello, where you should visit Villa Cimbrone or Villa Ruffolo for the best views.  Back in Amalfi, take the last ferry to Salerno, which has a high-speed train direct to Naples or a slower train to Sorrento after a connection of a short walk in modern Pompei.

If you're not flying out of Naples airport on your last morning, then you'll need to head back to Rome (a 1-hour train ride) the night before your flight.  If you can squeeze in one extra day for this region, I highly recommend spending it in Paestum for the mozzarella dairy farms and the incredible Greek ruins.

Conclusion

So that's all the top into to get you started without getting bogged down in details.  It's definitely a slightly-exhausting trip.  Hopefully, this kind of full, whirlwind vacation doesn't discourage you from future visits back to Italy.  Because if you have seen all the top highlights already, you will never again have to wait in a long line or be faced with these kinds of crowds!  Next time, you can get off the beaten path and enjoy La Dolce Vita in the other beautiful regions and small towns of this endlessly fascinating country.

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