The Best Italy Itinerary for First Timers: Gladiators, Gondolas & Gold


2 week italy itinerary


Discover the Best Cities in Italy


I’ve been to Italy many times and each time, the food tastes better, the sights get more impressive and I fall in love just a little bit more. Since Europe’s boot is quite a large country, I thought in today’s post I would share a classic itinerary focused on Italy’s most famous cities and beautiful places.

This is the route I followed on my first grand tour of Italy and what I think any first timer to Italy would love. It includes Italy’s trifecta of important cities: Rome, Milan and Florence with lots of beauty and romance thrown in!


The Best Italy Itinerary | Table of Contents

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italy in 10 days itinerary
7 day italy itinerary





10 Day Italy Itinerary


Days: 1-3: Rome

Rome is my favorite city in Italy. I know a lot of people visit the first time are overwhelmed by the noise, the chaos and the inefficiency but I love the history of the Roman Empire and it is a beautiful capital to me!

From the Vatican enclave and St. Peter’s Basilica to the crumbling Colosseum and bright Sistine Chapel – there is SO much to see and do in Rome. After all, this was once the cradle of civilization itself.

I took Latin for many years in school; did you know that Romans called outsiders “Barbarians” because they didn’t speak Latin or Greek and therefore everything sounded like “bar bar bar” Ha.


Top Sights & Attractions in Rome:

  • Colosseum & Roman Forum
  • Pantheon
  • Borghese Gallery & Gardens
  • Trevi Fountain & Spanish Steps

Don’t Miss: the Vatican Museum, Sistine Chapel & St. Peter’s Basilica (even if you’re not religious!). Get a Roma Pass if you have 3 days to save both headache and cash.




Where to Stay in Rome

Some people do in Rome in 1 day and are happy to get out of the exhilarating, but exhausting city. Personally, I recommend 3 nights to truly explore, especially if you like grand architecture, culture and/or are religious.

Rome is sprawling but visitors will want to concentrate themselves in the Ancient city center, where classical sights like the Colosseum, Forum and Pantheon are located. Religious pilgrims will look to the Vatican City neighborhood, west of the Tiber. If you just want to shop and stroll, stay in North Rome by the Spanish steps and trendy boutique area.


Recommended Hotel: Hotel Artemide 

We love this hotel's location, minutes from Termini, Rome's main train station, and Viz Nazionale, a main thoroughfare. It's walking distance to all the top sights – Trevi Fountain, Spanish Steps, Pantheon, Colosseum, you name it and the rooms are clean, comfortable and nicely modernized.


Check prices: TripAdvisor




Days 4-5: Florence

Florence is the birthplace of Renaissance art and is the perfect city for art lovers. Everything Florentines touch is fabulous – from food to fashion to gelato!


Top Sights & Attractions in Florence:

  • Michelangelo's famous David statue at the Accademia
  • the Uffizi Gallery for Renaissance art. Buy a Firenze Card to skip the insane lines
  • The Duomo is beautiful too!

Don’t Miss: Florence is known for its gold and leather production so if you like to shop, this is a great place to pick up some high quality items.




Where to Stay in Florence

I recommend at minimum 2 nights. Luckily, accommodation in Florence can be good value if you’re traveling off season, since there’s lots of competition among hotels. I’d recommend staying in the center of town


Recommended Hotel: c-hotels Diplomat 

A great location to explore Florence, with all of the major attractions in walking distance. Rooms are comfortable but basic and there are lots of restaurants and stores in the vicinity!


Check prices: TripAdvisor




Day Trip to Pisa

Another great day trip is to add Pisa, if you have more than 10 days in Italy; say 2 weeks. I loved this touristy town with its leaning tower and it’s so close to Florence that it’d be a shame to miss it!




Days 6-7: Venice

Rick Steves calls Venice a “puddle of elegant decay” and… I can’t help but agree.

The first time I visited Venice, I was a teenager and I loved the city of a hundred islands, each connected by fancy bridges and romantic gondolas. The second and third time I visited… Venice was a nightmare – jam packed with tourists hoards and locals eager to make their annual salary from just 3 short months.

Love it or hate it, Venice is a must see. In the Middle Ages, Venetians were clever merchants bridging trade from West to East and a wealthy, powerful city state throughout the 17th and 18th centuries. Today, few Italians live in the actual old city, as it’s incredibly expensive and slowly sinking. 


Top Sights & Attractions in Venice:

  • Cruise the Grand Canal at sunset
  • Be serenaded on a gondola ride
  • Visit the Doge's Palace and St. Mark's Basilica in the main square
  • See lovebirds at Rialto Bridge

Don’t Miss: a day trip to the glass makers in Burano (or just a short glass demonstration) and a ride on a water taxi!




Where to Stay in Venice

I recommend 2 nights especially if it’s your first visit to Venice. The city is best explored in the early morning and evenings after the tour buses and day trippers have left.

I’m warning you now the city is a shock to the wallet. But, it’s the only place like it in the world, so just pay the premium and enjoy it! If you can, splurge on a romantic 5 star hotel for the experience of a lifetime.


Recommended Hotel: Paladio Hotel & Spa 

Paladio is the sister hotel to Bauer Palazzo, the luxurious 5 star hotel along Venice's Grand Canal where George and Amal Clooney were married. This sister property, right across the water on Giudecca island, makes for a still dramatic but more affordable stay.

It was designed by a great Renaissance architect and the stunning gardens and huge rooms filled with elegant antiques give it an Old World charm.

With excellent customer service and a quieter location from Venice's city center, Palladio Hotel is a beautiful oasis away from all the noise. As a bonus, the hotel provides free water taxi service to and from its sister hotel on the Grand Canal.


Check rates: TripAdvisor




Days 8-10: Milan

Milan is Italy’s industrious second city and the capital of Lombardy.

Known for its banking houses and glamorous fashion, Milan is a slick, commercial powerhouse in the north of Italy and one of the main reasons for post World War II Italy’s revival.

Every country has its own tale of town cities. In Italy, there’s the government and religious center in Rome while finance and capitalism take hold in Milan. A great Italian saying I loved goes something like “people go to Milan to sin and to Rome to ask for forgiveness”!


Top Sights & Attractions in Milan:

  • See the Duomo (Europe's 4th largest Church) and Piazza del Duomo
  • Walk through Galleria Vittorio Emanuele
  • Visit the Museo del Novocento
  • Listen to an opera at the world famous La Scala opera house
  • Explore the old fortress of the Dukes of Milan, Sforza Castle

Don’t Miss: the rooftop of the Duomo where you can daydream high above the city among the church’s spires. Just beware tickets are a nightmare – I recommend buying in advance or getting a guided tour.




Where to Stay in Milan

I recommend 3 days, 2 nights. Although the city is large, the metro station is quite good so you can get almost anywhere around town in 30 minutes thanks to easy subway access.


Recommended Hotel: Glam Hotel 

Centrally located, hip and affordable, Glam Milano is located right in the heart of the city opposite Central Station and the subway.

The excellent location makes it a great base for day trips or to explore all Milan. Rooms are newly renovated, modern and quiet with some that overlook the grand square.

I will say the service here isn't great. When we booked, dinner came with our room (oddly enough) but we tried it one night and it was terrible – just skip it. There are lots of great restaurants around the hotel.

Go to Da Oscar for incredible pasta and especially pasta carbonara. It's a cozy restaurant, filled with locals, about 20 minutes from the hotel. Best meal we had in Milan and the portions are huge!

Book rooms:

Check rates: TripAdvisor




Days 11-14: Lake Como & Cinque Terre


Day Trips from Milan

If you have 14 days in Italy and can explore more, I would definitely recommend adding on the idyllic Italian Lakes region or the picturesque Italian fishing villages. I’ve done both and they’re very different.

Choose Lake Como and Lake Maggiore if you want to swim and shop; choose Cinque Terre if you want to hike, eat and sunbathe. Or add short trips to both if you can’t decide!

Lake Como is part of the Italian Lakes district near the Alps mountains. Both Como and Lake Maggiore are romantic throwbacks to the aristocratic old days. Idyllic, relaxing and glamorous!

Cinque Terre is the name of five picturesque fishing villages that line Italy’s northern coast. These are some of the prettiest places I’ve ever seen and worth even a quick day trip (but better if you can stay overnight). I have a whole series about visiting Cinque Terre here.

 Read more:  A Definitive Guide to Cinque Terre – Just In Time for Summer!




Planning a Trip to Italy

For Americans visiting Italy, there are 2 easy points of entry via flight: Rome or Milan. I would recommend booking an open jaw, arriving in 1 city and departing from the other to maximize the time you have.

There is so much to see and do in Italy that it would be a waste to backtrack just for an airport. I’ve written the sample Italy itinerary above starting from Rome but either works.




How much time to spend in Italy?

The itinerary I suggested is flexible, whether you have a tight 7 days or a leisurely 3 weeks.

Personally, I would recommend at least 10 days in Italy to explore leisurely but even better if you have 2 weeks! If you have 14 days in Italy, you can fit in some spectacular day trips.

For example, a day trip from Milan to Lake Como, the Italian Lakes region or Cinque Terre. Have more time? Add a day trip from Florence to Pisa and a day trip from Venice to the glass making islands of Murano and Burano.

For travelers who have been to Italy before and want to explore it’s small towns, I really loved my trip to Northern Italy. Italy was a nation of city states for much of its history so regional differences throughout the country can be quite distinct!

Northern Italy is known for excellent local cuisine so I have written a follow up post focusing on charming medieval towns and incredible Italian cuisine here.

 Read more:  7 Days in Northern Italy itinerary: Pastels, Prosciutto & Parmigiana


If I have the chance to explore more of Italy, I’d love to head down South and explore Positano, the Amalfi Coast and all the way to Sicily and Puglia! Also on my Italy bucket list? A road trip through the hill towns, spas and wine producers of Tuscany.

Below are some summary suggestions for various Italy itineraries.




Italy Itinerary 7 days

A classic itinerary to explore Italy’s rich history, museums and romance.

Days City Overnight
Days 1-2 Rome Rome
Day 3 Day trip to Assisi Florence
Days 4-5 Florence Florence
Days 6 Half day in Pisa Venice
Days 6-7 Venice Venice


Italy in 12 Days

The ultimate trip to Italy covering all of the country’s best sights, cities and attractions.

Days City Overnight
Days 1-3 Rome Rome
Days 4-5: Florence & Pisa Florence
Days 6-7: Venice Venice
Day 8: Padua & Verona Verona
Day 9: Bergamo Milan
Days 10-12: Milan Milan




Italy Itinerary 14 Days

A leisurely Italian vacation focused on beautiful places, lakes and the sea.

Days City Overnight
Days 1-3 Rome Rome
Days 4-5: Florence Florence
Days 6-7: Cinque Terre Cinque Terre
Days: 8-10: Milan Milan
Day 9 Isola Bella Lake Maggiore
Day 10-11 Lake Como Lake Maggiore
Day 12 Verona Venice
Days 13-14 Venice Venice


3 Weeks in Italy

If you have 3 weeks in Italy, why not extend your time in the North?

Check out the medieval town of Bergamo, with it’s Old City stacked on top of its modern day center or Parma, known for its cheese and prosciutto. Northern Italians know how to make the best food in Italy!

Other great additions to add to your Italy itinerary are Bologna, Varenna and Ravenna if you have more time.




Are you planning a trip to Italy? Let me know any questions in the comments below!


Visiting Italy – Trip Planning Checklist

There's so much to see and do in Italy that you can visit again and again and still discover new sights. I recommend concentrating on the big 4 cities (Rome, Venice, Milan & Florence) if it's your first time and then coming back to explore either Northern Italy or Southern Italy in more depth.

Go | Flight prices from the US to Italy are highly seasonal. You can set a fare alert here to be notified of discounts. Every fall & winter, I've seen great deals to Milan. One word of caution: avoid Alitalia at all costs!

Getting Around | A convenient way to explore Italy is via high speed train. You can search train schedules and book online here. Buy your tickets in advance to save on fares. Make sure to validate your ticket on the platform!

It also helps to speak a little Italian. Brush up on your Italian language skills with Rosetta Stone. You can take 10% off with promo code CJBT10.

Stay | Book hotels in advance to save, or check here for last minute deals. Many hotels in Italy are older so don't be surprised if even 5 star accommodation feels slightly dated. Opt for a room with a view instead of breakfast, as Italians don't eat breakfast in the same way Americans do and you'll probably be disappointed with their offering.

Alternatively, groups or budget travelers can check out Airbnb

Protect | Lastly, be sure to visit Italy with travel insurance. Whether you get injured and need to be hospitalized, your phone gets stolen, or a flight delay leaves you with nothing but the clothes on your back, travel insurance will help when you need it most.

A rail strike occurred during our trip, unexpectedly shutting down transportation for an entire day. Get a quote for your Italy trip here.


 You Might Also Enjoy: 


Italy Vacation Planning Articles

The First Timer's Guide to Italy: A Classic Itinerary

THIS is the Best Time to Visit Italy

What to Wear in Italy: A Packing Checklist


Northern Italy

The Most Beautiful Places in Northern Italy (that are still a secret!)

Headed to Northern Italy? Here's the Perfect 7 Day Itinerary

Exploring Bologna: Travel Guide

Quick Guides to: Bologna Day Trips & The Best Bologna Restaurants

Visiting Parma: The Center of Parma Ham & Cheese

7 Reasons to Explore Medieval Bergamo

Visiting Ravenna's Mosaics

Test Driving Fast Cars & Touring Car Museums in Italy's Motor Valley


Cinque Terre

Plan Your Trip: Travel Guide

How to Choose Which Village to Stay

A Blissful 3 Day Cinque Terre Itinerary

The Best Cinque Terre Airbnbs for Large Groups

Quick Guides: The Best RestaurantsPopular Hiking Trails

Inspiration: Photo Diary of the 5 Villages


The Italian Lakes

Exploring Lake Como: Travel Guide & Where to Stay

Quick Guides to: Varenna, Bellagio & Villa del Babianello

Visiting Lake Maggiore

Quick Guides to: Isola Bella & Villa Taranto

Discovering Hidden Lake Orta


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  1. terra
    April 19, 2018 / 8:19 am

    I think this is a great round-up of what to see in Italy. I did it in three weeks and hit most of what you mentioned here but there’s still so much to see! Guess I’ll just have to go back!

  2. Mike
    May 18, 2018 / 2:01 pm

    Fantastic post, great detail, and absolutely stunning photographs! Thanks for sharing your knowledge and for the Italy inspiration.

  3. Beatrix
    May 26, 2018 / 12:15 am

    I’m after a quick feedback on this itinerary for 3 weeks in Italy, still in planning stages, nothing booked yet other than flights into Venice and out of Rome.

    We will be travelling late this year with 4 kids (2 teens, 2 younger); we have exactly 19 days. We have never been to Italy before and would like a balance between seeing as much as possible without madly rushing around. We will be getting to and from places with public transport only.

    Here is what the plan looks like so far:

    Day1: Venice (arrive pm)

    Day 2: Venice

    Day 3: Venice

    Day 4: Verona all day, arrive Florence in evening

    Day 5: Florence

    Day 6: Florence

    Day 7: Florence

    Day 8: Maranello Ferrari museum day trip (this is a must)

    Day 9: Tuscany hilltop villages – ? hiring a private driver for the day or an organised tour

    Day 10: Pisa day trip

    Day 11: Massive Cinque Terre day trip from Florence

    Day 12: Early am train to Naples, spend afternoon in Pompeii; private shuttle to

    Day 13: Positano

    Day 14: Positano

    Day 15: Travel to Naples, archaeology museum, train to Rome in evening

    Day 16: Rome

    Day 17: Rome

    Day 18: Rome

    Day 19: Rome

    (fly out early day 20)

    What do you think? Am I cramming too much into this trip? Is it doable or would it be too stressful? I would have loved to also go to Lake Como, specifically Bellaggio, but have sadly cut this out… what would you change around in terms of time allocation and feasibility?

    Thank you so much for any feedback/ideas.

    • Sher
      May 26, 2018 / 1:11 pm

      Hi Beatrix – It’s an ambitious itinerary but similar to what I did for my first trip to Italy. I’ve been back to Italy several times, focusing on more local regions so I think it makes sense to cover a lot of ground on your first trip and then get an idea of any areas you’d love to revisit.

      If you were thinking about cutting out areas, I would suggest skipping your Tuscany day trip since you have about 5 heavy travel days in a row. Maybe swap the tuscany day trip with your cinque terre day, so that on day 11 you have a day of relaxation in Florence before your trip down south.

      Lake Como is lovely (I have a lot of posts on just northern italy since I went back to spend longer there) so you can save that for your next trip and fly into Milan, since I noticed you’re not covering Milan on this trip.

  4. Johanne Allard
    February 18, 2019 / 8:39 pm

    We will be in Italy 15 nights, the 2 first week of April 2019, we are arriving in Rome and returning home from Venise. So far we have booked 3 nights in Rome and 3 nights in Venise, we are still working the time in between. We want to see Florence, Tuscany and Cinque Terre.
    Should we ?:
    1- drive from Rome,visit Tuscany area, Cinque Terre then Florence, leaving the car in Florence and then taking the train to Venise, OR
    2- take the train from Rome to Florence, spending 3 nights, renting a car to visit the Tuscany area, going to Cinque Terre and driving to Venice.
    We are thinking 1 or 2 days in Cinque Terre.
    Any help would be greatly appreciated, Thank you

    • Sher
      February 18, 2019 / 10:22 pm

      Hi Johanne – you’re hitting up some of the best places in Italy! Both options sound great. There’s not much space for cars or parking in CT though.

  5. Ingrid
    November 21, 2019 / 6:13 pm

    Hi! I love the info. We will be going to Italy next year and spending 12 days (not counting travel days). We are flying in and out of Rome because we once again got a great deal. My husband and I did Rome this year (with one day trip to Florence) and loved it. This time we are going with friends that never been to Italy. We definitely want to spend time in Rome because they never been and we liked it. But would love to venture out a bit. Do you have any suggestion of itineraries in and out of Rome. I don’t want to get too crazy and add too much stuff/travel within cities.

    January 24, 2020 / 8:40 pm

    I love your content! super helpful! Do you have any on Hawaii?

    • Sher
      January 25, 2020 / 3:56 pm

      Hi Carolina – ah thanks for the nice comment! unfortunately, not yet but hoping to soon :)

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