Italy Travel Itinerary: Fabulous Food, Friendly People, and Vivid Landscapes

This is the secret: you can’t go wrong. But if you want a first time ItalyTravel Itinerary then dive in because you found it.

I’m writing from Sicily right now and this is my 7th trip to Italy. Why do I go back every year?

Because You Can’t Do Italy in One Trip or Seven Trips.

Certainly if this is your first trip to Italy here’s what I recommend. And some hotel links where I have stayed too.

Italy Travel Itinerary: 14 Days, includes arrival/departure days to and from Italy

1. Rome 5 days Minimum
2. Day Trip to Florence, fast train gets you there in 75 minutes from Rome
3. Train from Rome Termini to Naples Train Station, regional tram to Sorrento
4. Sorrento 7 days, this is your home base
5. Amalfi Coast day trip to Capri
6. Amalfi Coast day trip to Ravello
7. Amalfi Coast day trip to Positano or Procida
8. Walking around Sorrento for 3 days – its magical
9. If you savor every moment in Italy you won’t get flustered with too much on your plate. And will enjoy your yummy food and wine and digest it better too, why? Because you won’t be in a hurry to do everything at once like you do at home. Myself included.

Plan your Italy Trip for Two to Three Weeks

Yes you can go to Italy for less time but you’ll wish you had more days. Italy is too thrilling to do in less than a week.

When to go to Italy? Visit in the Winter, all the details here.

Popular Destinations

Venice, Rome, Milan, and Florence will be crowded unless you go in the Winter so keep this in mind. Smaller towns will be less touristy and have better prices. For Example: Assisi, Spello, Bari, Puglia (in Winter), and Reggio di Calabria.

How to Get to Italy?

Fly into Rome or Milan and take the fast train from either of these vivid and intriguing cities so you can see the gorgeous landscapes as you travel. And its fun!

If you’re from the USA you may have taken Amtrak but trains in Italy are higher up on the food chain. They’re exquisite. Comfortable. And usually on schedule unless there’s a strike.

Trainline.com will answer all your questions or you can book through Omio.com. 

One thing to remember for First Timers to Italy: don’t do so many things you’re exhausted and can’t savor a gelato and espresso while people-watching in a gorgeous piazza and doing nothing. I’m going to get a gelato after I write this.

Flying to Europe

What is the best way to fly from your country to Europe? My advice is from the USA; I’ve taken FrenchBee Airlines. It’s a direct flight from San Francisco, Los Angeles, New York City, or Miami. I book one-way flights and it has cost from $850 to $950USD buying two one-way flights.

You would pay less buying a round trip ticket.

Why do I like it? You land in Paris at Orly Airport, and are connected with many ways to get into the center of Paris. Bus, tram, train, and taxi, take your pick. It’s easy. Download all your maps from Google Maps before you jet off from home as you won’t have wifi when you land.

Planning Your Europe Trip on Budget, Advice

Landing in Paris you could stay for a few days and then take a low cost flight to Italy. EasyJet, Ryanair, Transavia, Caribe, Volotea. But only take Carry-On luggage as you’ll end up paying big time if you take heavy bags. Don’t overpack.

Your Italy Itinerary may be overwhelming but this is because you’re trying to do too much.

Two weeks is a minimum, any less and you’ll feel shortchanged. I’ve visited for over four weeks every time and I never feel its too much. There is always some thing you haven’t seen yet.

And I love going back to places I’ve fallen in love with and this is why I’m on Sicily right now.

 

Italy Travel Itinerary First Time

This is an exquisite way to see Italy for the first time. Here’s what I suggest.

Visiting Rome, Florence, and Amalfi Coast. Why?

Rome is a must do city. The landmarks, food, and people are enchanting and you can easily walk to all the locations you need to see. Also you’re at the hub of transportation options so you can take the train from Rome Termini to get to Venice, Amalfi Coast, Lake Como or Sicily.

Florence: Day Trip from Rome

Taking the train to Florence to see the museums is a perfect day trip from Rome. You don’t have to lug your suitcase and you can focus on seeing the Uffizi and Accademia Galleries. But make reservations because you may not want to stand in line at 8AM when they open to buy a ticket. I did this and got in quickly but had to wait in bitter winds for 20 minutes at the front door until they opened. 

But if you arrive early in the morning there won’t be a crowd or selfie sticks to ruin your view of this stunning marble statue, take your time and savor every inch of it. The lighting is sublime.

Florence Hotel in the Historic Center

You’ll want to walk everywhere in Florence so stay in a central location, you can see the mid-range hotel in the link above. One thing is: tourists can be loud especially in the centers of towns so bring earplugs just in case. You’ll maybe not get an elevator to your room or a large shower. This is common and shouldn’t cause any alarm.

Things to Do in Florence: stroll, wine tastings, eating, museums, shopping, and food and wine tours. Read the reviews and enjoy your time in Tuscany!

Hotel in Sorrento

Do you wonder about where to stay on the Amalfi Coast? See the link above.

Certainly staying in a central location is important. And this is Sorrento. Buses and trains leave from here to the Amalfi Coast and to Naples and Rome so you’re covered. 

I stayed here with my photography retreat participants and we had a wonderful time exoloring the Amalfi Coast 

Day Trips from Sorrento or Naples

Being based in Sorrento you have the options of going by ferry to Capri, Procida, and Ischia from Spring to Fall. If you’re going in Winter, Capri is the main option. Or you can take a train to Pompei.

Do you want to go to Ravello? Amalfi or Positano? Take the passenger bus from the Sorrento train station. Don’t drive. The Amalfi Coast road is full of twists and hairpin curves. Watching the bus driver expertly drive this road is remarkable. I wouldn’t have believed it if I didn’t see it.

You can fly home from Naples or Rome, or take the train from Salerno or Naples south to Sicily.

You can also fly from Rome to Catania or Palermo. It takes an hour.

Apartment in Naples

This apartment was perfect, I walked from the Naples train station solo and found it to be a perfect spot for Naples. I could walk to the ferry, boating over to Procida or Ischia and the neighborhood was full of restaurants and shops but I slept well at night. Quiet.

Wished I had booked longer, lovely owner, fast communicator. 

If you have 3 weeks you could add on Puglia, Calabria in Southern Italy, or go to Sicily. But one week isn’t enough for Sicily. Why? If you take the train or bus and don’t rent a car you can be more leisurely in traveling around the island and savoring each place you visit.

This time I was in Siracusa for six nights and will be back next year for a month. The history, seafood, and people are captivating.

Or if you want to experience the Northern regions you could add the Dolomites and/or Venice.

One thing you might consider is going to a smaller town, Asissi, Spello, or the Umbria region.

You’ll start to notice this: the truth is you can’t do Italy in one trip. But you can come back. If this isn’t possible then the first itinerary is what you must consider as Rome is breathtaking and vivacious, Florence is bursting with art and history, and the Amalfi Coast gives you the stunning nature.

When to go to Italy?

Winter in Italy is when the crowds thin out. Southern Italy’s weather is mild and you’ll get sunny days with a few rainy days (or none)  but nothing like the cold of Northern Italy.

Also, I’m in Cefalu right now, my favorite beach town on Sicily and yesterday was 65F, tonight is 50F and it has rained once during my 10-day visit on Sicily but it cleared up by the next day.

One thing to be aware of: checking in and out of hotels and packing things isn’t a real vacation and you’ll end up exhausted. You’ll need a vacation from this vacation when you get home.

What you want to do is savor a glass of wine and watch a sunset over the Mediterranean Sea. And you’ll absolutely create a magical memory by doing this.

Ortigia Island, Siracusa, Sicily

So leave your speed behind and come to Italy so you can fall in love with life here.

Here’s what I’ve noticed about Italy and Sicily: people take time to talk with one another and move slowly. Learning how to wait in a grocery line while the cashier catches up with a shopper ahead of me for a few moments is good for strengthening your patience.

Impatience is my worst fault so this is a good one for me to work with. And now I’m not tapping my toes for things to get going like I used to do in my first trip here.

And if you stay longer you’ll naturally start to try out some Italian words. Attempting to speak Italian without proper pronunciation I appreciate the ultra patient Sicilians helping me while I murder their language.

Sometimes I get corrected and other times locals just understand or smile at me. Often they help me with my new Italian words.

Your Italy Travel Itinerary

Just ask here in the comments or get in touch for a one-on-one deep dive consultation. Ciao Bella!