Where to go in Italy your first time

If you need some ideas for where to go in Italy (or even inspiration/convincing for WHY you should go), you’re in the right spot!  Italy is an insane treasure trove of sights, food, wine and European culture that will take many trips to really, truly, experience. This post focuses on where to go in Italy for your first-time trip. You’ll see that I recommend some of the more major spots that you’ve undoubtedly heard of. I’ll get into that more in a second, but one thing to keep in mind is that I believe Italy should be visited multiple times over the course of a lifetime. I’ve gone twice for a total of 3 weeks spent in the country and still not covered all I want to see and do. Just like Italy itself, there is so much ground to cover on this subject so I’ll be updating the blog with more info soon about each city. 

The remainder of this post will:

  1. Provide inspiration and reasons for why I think you should visit Italy. If you’re already decided, this will just fuel the excitement!
  2.  Provide tips for where to go, how to approach sightseeing and itinerary ideas.
Florence Duomo
Duomo in Florence

First things first, why I think you should go to Italy:

  1. It is so interesting, historic and beautiful and you will recognize the historic landmarks which is extra cool when you see them in person (think standing in the Colosseum imagining Gladiator battles or Michelangelo’s actual frescos in the Vatican). It honestly almost seems like it’s not real life or Disney-like. But, it’s real! I kept having to pinch myself the first time I was there.
  2. In one country with easy train transport you can see coastal areas (such as Amalfi Coast or Cinque Terre), dreamy Tuscan cities, ancient Roman ruins and rolling hills and vineyards. Does it get any better than that?
  3. The food is amazing and approachable. You will recognize the food on the menu and it will be better versions of what you know. Sometimes it is intimidating to go to a restaurant where you don’t speak the language and aren’t familiar with the cuisine, but this isn’t an issue if you grew up familiar with Italian food. Seafood is also very fresh in the coastal areas, which is a bonus.
  4. Even though there can be a language barrier, if you are from the US you will recognize a lot of words since we have such a large Italian population, so it doesn’t feel so intimidating. (You know cappuccino, pasta, bolognese, caprese, pizza, etc.) If you’re new to international travel, this is a  bonus. Once you’re a seasoned international traveler, it’s less intimidating to be in these situations because you get more comfortable with how to navigate language barriers, but the first time, you may feel awkward so having some familiarity is nice.
  5. Wine is like table water out there. You just need to learn “vino.” You can remember that. 🙂
Florence Italy landscape
Florence, Italy

Where to go in Italy

I believe you should construct your first itinerary around seeing a few different regions of Italy to get a good “taste” (both figuratively and literally.) For the most part it is really easy to get around by train. Use Eurorail to book tickets between cities. I recommend booking the tickets in advance for peace of mind. You can usually book when you’re 60 days out from your travel date. The site is really user friendly. (Pro tip: Book the direct routes when possible vs. ones with stops.) Italy has different regions and they are all unique in their own ways.

You may receive different types of advice, but I really think that for a first trip, you should take some time to see the really iconic tourist sites. There’s something really insane (in a good way) about seeing some of these famous places with your own eyes. Yes, those iconic sights will be crowded and touristy, but I still think you should do it. You can go back a 2nd time (because now, you’ll be hooked!) and go more off the beaten path.

When to go

For Italy, I believe the best time to go is shoulder season, which is either mid-late September or late-May/June. Oct-April is their winter and the rainy season. July-August is oppressive heat, oppressive crowds and the highest prices. I’ve been to Italy during high season and it was extremely hot (sweating all damn day), but I also went in May and with my experience I really recommend shoulder season.

When traveling from the US, I would recommend no less than 10 days but 7 days at bare minimum. When you fly out there, you leap across a couple of time zones so you effectively lose a whole day and the way back also takes a full day out because the flights to the US leave in the morning. Ideal timeframe in my opinion is 12-14 days.

Venice Sunset Gondola
Golden Hour in Venice

My top city/region picks for a first trip: 


  • See top iconic sights such as the Colosseum, Trevi Fountain and Pantheon.  
  • Experience what the energy of a bustling European city feels like. (Watch for scooters when you cross the road!)
  • Visit Vatican City and see Michelangelo’s famous frescos.
  • Sit outside in a cafe sipping cappuccino, and watch how the Romans use the city as their living room. It’s an amazing vibe.


  • Get lost in a dreamy Tuscan city with pastel buildings and cobblestone streets.
  • Do day trips to nearby Tuscan towns and wine country, experiencing the rolling hills of Chianti. (With more time, take a 1-2 day trip to the picture-perfect Cinque Terre!)
  • Take in the famous sights of the Renaissance (such as the Duomo) and see the Statue of David up close and personal.
  • Eat and drink your way through the deliciousness of Tuscany. (Lasagna and baked spinach? Yes, please!)


  • See what it’s like to visit a city with roadways made of water.
  • Walk around with gelato and listen to live music with a sparkling city as your backdrop – you will definitely see people get swept up and start dancing! (Maybe it will be you.)
  • Experience Golden Hour like never before on a gondola ride. (Yes, it’s cheesy, but you have to do it.)
  • Eat seafood and drink wine in a Venetian alleyway under sparkling twinkle lights.

Amalfi Coast

  • Stay in Positano and experience the drama of a coastal town built up a seaside cliff.
  • Sip a limoncello under a striped umbrella with your favorite fancy beach wear.
  • Take a boat trip to the Island of Capri and take a swim in the beautiful aqua water.
  • Explore the neighboring areas of Amalfi, Ravello and Sorrento for a day out of a storybook.
Positano Amalfi Coast Italy
Positano, Amalfi Coast

Use tour guides! (but only good ones)

Italy is a great place to have local guides take you around and show you truly where to go in Italy. They’ll cover both the popular spots and best kept secrets. They’ll teach you about the amazing background of the places you’re visiting. BUT, do not find yourself on some large group tour with big tour busses. They are very common and not at all what I would recommend.

I had a guide named Stefano in Rome who was super fun and took us to all the iconic stuff during the day then let us in on a club to meet him at later that night (for funsies, not part of the tour) and saw a more “real” side of Rome. That’s the type of guide you want. (This was 12 years ago, so I unfortunately don’t know now how to get in touch with him).

It is really important that you do research to find the best SMALL GROUP walking tours and day trips. You will want a personal experience and ideally no more than 12-15 people in your group. I really believe an awesome guide can make or break your day. Plus, it is nice to have someone help you navigate a city you are not used to in a language you don’t speak.

There are guides that will center on historic places, food, wine trips, art, boat trips and sometimes a mix of all. Find topics that match your vibe. For example, a wine and food tour through Chianti can be a perfect way to spend a day in Tuscany and it will come with a driver to get you there. Or a boat trip to Capri could be the best way to see that part of the Amalfi Coast without a lot of hassle.

I recommend scouring TripAdvisor and going deep into forums to find the best tour guides. 

What to look for:
  • English-speaking (unless you are multi-lingual, of course)
  • Very small groups
  • Convenient pick-up times and options
  • Itineraries that really speak to your personality

Often, a good tour group will personalize a day just for you (usually a little more $$) so don’t be afraid to ask about that.

If you plan to check out Venice, take a read through my post for ideas specific to Venice. As I write about the other regions, I’ll update with more links.

Walls Rome Italy
Rome, Italy

Itinerary ideas

Here are some good itinerary ideas for where to go in Italy and how to tackle the trip logistics. You can take the train between cities. The only trickier one is getting to Positano because it is not directly on a train line. You may need to take the train from Florence to Salerno then take a ferry from Salerno to Positano. You can also go through to Naples and then connect to Sorrento. From Sorrento you can take a car or taxi to Positano. (That is the route you’d want to take going back to Rome.)

There is tons of information on this subject when you google it and it changes, so you’ll want the most up-to-date information. My advice is to ask your hotel/AirBNB host for help on this matter so they can get you current information. If you need some advice about when to choose an AirBNB vs. a hotel, check out my article on this hot topic. If this will be your first time using AirBNB, check out this article for tips on how to choose a good AirBNB host.

14 Day Italy Itinerary

  • Day 1: Travel Day
  • Day 2: Venice
  • Day 3: Venice
  • Day 4: Florence
  • Day 5: Florence
  • Day 6: Florence (day trip to Chianti and wine country)
  • Day 7: Florence (day trip to Siena and small Tuscan towns)
  • Day 8: Amalfi Coast (Positano)
  • Day 9: Amalfi Coast (Day trip to Capri)
  • Day 10: Amalfi Coast (Visit other Amalfi towns)
  • Day 11: Rome
  • Day 12: Rome (Vatican City)
  • Day 13: Rome
  • Day 14: Travel Day

10 Day Italy Itinerary (Option 1 – Amalfi Coast)

  • Day 1: Travel Day
  • Day 2: Florence
  • Day 3: Florence
  • Day 4: Florence (day trip to Chianti and wine country)
  • Day 5: Amalfi Coast (Positano)
  • Day 6: Amalfi Coast (Day trip to Capri)
  • Day 7: Rome
  • Day 8: Rome (Vatican City)
  • Day 9: Rome
  • Day 10: Travel Day

10 Day Italy Itinerary (Option 2 – Venice)

  • Day 1: Travel Day
  • Day 2: Venice
  • Day 3: Venice
  • Day 4: Florence
  • Day 5: Florence
  • Day 6: Florence (day trip to Chianti and wine country)
  • Day 7: Rome
  • Day 8: Rome (Vatican City)
  • Day 9: Rome
  • Day 10: Travel Day

And, that is my advice on where to go in Italy! Your first trip is truly one of the most amazing experience and something you’ll never forget. I hope you found this guide helpful. GOOD LUCK on planning and comment with any questions!


Colosseum Rome Italy
Colosseum in Rome
Cinque Terre Italy
Cinque Terre
Florence Duomo Italy
Duomo in Florence

Marissa is a travel consultant and digital marketing professional from Chicago, USA. Her business, Sips & Sojourn, specializes in helping busy people with full-time jobs travel more and travel better. Travel is Marissa's absolute passion but she believes you can hold down a successful career AND travel the globe. Marissa enjoys unique destinations, design hotels, sampling a culture's food and drink and meeting local guides focused on small, immersive experiences.

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