14 Days in Italy – Part 1 – Tips, Planning, & Itinerary Overview


Have you ever wanted to experience Italy for 14 days but didn’t know where to start and what to do?  What should you focus on?  How many days should you plan and what should you see?  Read on for one itinerary you won’t soon forget!

Typically when I plan and take roadtrips, my focus is on the US and Canada since that is where I have the most experience.  However, there are plenty of roadtrip adventures in other parts of the world and Italy is no exception!

First a few general tips to get out of the way.  Warning:  Long post ahead!

Getting Around

The cities of Italy are not very conducive to driving – it is much easier to walk and use public transportation.  Therefore, when planning a roadtrip in Italy, it’s best to save the driving for certain areas of the country where getting behind the wheel and experiencing the open road can be truly appreciated.  This itinerary takes that into account.

Booking Entrance Fees, Transportation, & Tours

Book as much as you can in advance online.  You’ll get discounts, avoid lines, and for some attractions (Leonardo’s The Last Supper), it’s the only way you’ll get to see them!  More details to come on this one.

Where to Stay

Italy has a wide variety of places to stay, from five star hotels to very basic hostels.  You can find most of the name brands, but I would recommend looking for places that are local and unique.  The star rating system

Italian Coast
Image courtesy of Viator.com

in Italy is mainly based on room size – not necessarily how nice a place is.  Many of the rooms in historic buildings can be small, but very cool to stay in.

Airbnb is another popular option that lets you experience a city or village like a local.   They can also be much lower priced and give you more space to stretch out.  Usually there is a kitchen (tired of restaurants?) and a laundry (pack fewer clothes!) which can come in handy on a 14 day trip.  So, just like any accommodation, read ads and reviews carefully and do a little homework on actual location, and enjoy!

When I’m taking a roadtrip, I rarely book a place for more than two nights.  I prefer to book along the route I’m going to take – even in the same city where sometimes I’ll book at one end and then the other.  However, sometimes it is convenient to have a hub and sometimes you can get a discount if you book for more than one night.  So, this is not a hard and fast rule, just a guideline I use.


Eat like a local, not a tourist.  Investigate what are the regional specialties for that area and seek out restaurants a block or two off the beaten path.  Most restaurants post their menus (hint:  translations=touristy) and prices outside and take a look at who is eating there before you go in.  And, btw, there is no ‘fettuccine alfredo’ or ‘spaghetti with meatballs’.  We’re talking real Italian food when you’re in Italy!  Oh, and ‘peperoni’ is peppers, not meat!!

Italian Menu
Image courtesy of shilpaahuja.com

Expect to drink only water or wine with your meal.  Cocktails, beers, teas, and spritzes are consumed before (aperitivi) and after (digestive) dinner.  Oh, and cappuccino is only a morning drink!  But espressos after meals is common!

Breakfast is a strong espresso and a sweet pastry.  Eggs are not a breakfast thing in Italy – however you could find an American restaurant that serves them if you’re desperate.  You can get something that resembles an ‘americana’ coffee where they add hot water to the espresso if you’re looking for your morning jolt in a bigger volume.

Also, eat when they eat.  Dinner is the evening entertainment.  It doesn’t start until after 8pm and it can last for hours.  Tide yourself over by enjoying aperitivo – before dinner drinks & appetizers – (cichetti if in Venice), then sit down, relax, and enjoy eating like the locals.

Things to Pack

If going in the summer, you may want to pack a personal fan.  Apparently, fans are not that popular in Italy and not everything is air conditioned.  A fan can help you get through in a pinch.  Especially if you’re staying in an Airbnb.

Shorts are for tourists.  And, they are not allowed in most churches.  Pack cotton or linen pants and capris or below the knee dresses and leave those shorts at home.  If you plan to wear sleeveless shirts, be sure to carry something to wear around your shoulders, a lightweight shawl or sweater, so that you don’t get suitcasesdenied entry into some of the churches.

Also, don’t wear flip-flops if you don’t want to be spotted as a tourist from a mile away.  Invest in some nice sandals and you’ll fit right in.

Don’t forget your travel adapters!  You can’t plug your US cords into Italian outlets, so if you want to charge your phone or other electronic devices, be sure you purchase and pack a high quality power adapter.

Bring along a refillable water bottle.  Water fountains are typically available and you can save a lot of money and avoid filling up landfills if you have a bottle to put it in.

Windproof travel umbrella and/or raingear.  Most of Italy is Mediterranean or subtropical and has a ‘rainy season’.  And, let’s face it, rain can happen at any time and it’s better to be prepared than not.  They don’t take up much room and can be the difference between joy and misery.

Some ‘dress up’ clothes and shoes.  The shoes should be practical (comfortable) and dark colored so that you aren’t just using up precious luggage space.  Dressing up for dinner is typical and expected in many restaurants.

The Itinerary Overview

Ok!  With that out of the way, let’s get on with the itinerary overview!  Note that this itinerary assumes you have not been to Italy before and that you want to be sure and hit the ‘must see’ spots.  It does not cover all of Italy and gives you plenty of opportunity to come back and enjoy other parts of this wonderful country.  Here is the high level overview.  We will dive into the details in subsequent posts.

A Note On Flying in

There are many places to fly into Italy from abroad.  Typically, I would recommend to fly into one city and depart from another.  However, I started planning this trip with the flying in and out already predetermined, so that is what is laid out here.  Note that you can easily modify this itinerary appropriately if you have other fly in/out ideas.

Day 1 & 2 – Bologna to Venice (stay two nights in Venice)

Fly into Bologna and take the 1.5 hour train ride to Venice, your first city to explore.  Venice is a great place to start your Italy vacation since you won’t have to worry about getting hit by careening vehicles while you are still in awe and starry eyed at the beautiful sites and the idea of really being here!

Image courtesy of telegraph.co.uk

While it is expensive, here is you will want to splurge.  Stay on the island so that you can enjoy the leisurely pace of the evening and morning hours to explore without all of the hustle of the day-trippers who swarm onto the island mid-morning to mid-afternoon.

If you look for travel advice on Venice, you will find this.  Wander the city and get lost.  You are on an island, so you can’t get too lost and you are never more than a 30 minute walk from the center.  There are signs to point you in the direction of the main attractions and you will get to experience so much more.

Day 3 – Venice to Milan

If you have more time, here is where you can hit the road and explore the beautiful lakes and dolomites

Milan Commons
Milan Commons – Image courtesy of Milan Tourism

regions of Italy.  However, we don’t, so hop on a 2.5 hour train ride to Milan and view the scenery from the

comfort of your seat.  The train to Cinque Terre goes through Milan anyway, so you may as well spend some time here.

Milan is a city of commerce and fashion (it is the home of Prada).  Here, you can enjoy the prestigious La Scala opera house and view Leonardo’s painting The Last Supper as well as luxury shopping.  Purchase a MilanoCard online which includes unlimited transportation, skip the lines, and discounts in the city.

Day 4 – Milan to Monterosso (Cinque Terre)

In the morning, take the 3 hour train ride to Monterosso, the northern most village of Cinque Terre.  Cinque Terre is a region of five coastal towns connected by walking trails and trains in northern Italy.  A lot of people visit the area as a day-trip, so spending the night here gives you the opportunity to take it slower and enjoy.  Book a night in one of the northern towns and explore the hikes, shops, and beaches in that area.

Cinque TerreDay 5 – In Cinque Terre to Riomaggiore

Spend day 5 continuing to discover and relax in the area.  Hike or take the slow moving train so that you end up in Riomaggiore for the night.  Cool off with a swim in the afternoon and enjoy a feast of local seafood in the evening.

Day 6 & 7 – Riomaggiore to Florence

The next morning, take the 1.25 hour train ride to Pisa and check out the leaning tower for a couple of hours.  If you want to take the time, go to the top and experience the views.  Then, hop on the train again

Image courtesy of travelchannel.com

for another 1.25 hour train ride to Florence.

Florence is known as the ‘birthplace of the renaissance’ and you can easily spend days here.  Most of the ‘must see’ sites surround the historic center which makes them easy to see.  Staying two nights will allow you visit them as well as some of the unique ‘off the beaten path’ treasures in the city.

Here is where you will rent a car before leaving town.  Tuscany and central Italy is a wonderful place for a roadtrip!

Day 8 – Florence to Siena

Hop in your rental car and head towards Siena on the Raccordo Autostradale Firenze – Siena.  You’ll want to stop at San Gimignano, a small walled town with it’s triangular square and medieval towers where you can enjoy a trip back in time and some lunch.  From there, head to Siena and explore the Piazza Del Duomo and climb the Torre del Mangia for a magnificent view of the city.  Stay overnight in Siena

Day 9 – drive Siena to Montepulciano to Rome

Retrieve your car and take this scenic drive from Siena to Montepulciano:

  1. Head southeast on SP438 to the village of Asciano and its 13th-century Romanesque-Gothic church
  2. Take scenic SP451 and stop at Abbazia di Monte Oliveto Maggiore, a Benedictine abbey with some excellent medieval art
  3. Continue on to Buonconvento, a pretty medieval village hidden behind ugly outskirts.
  4. Heading south on SR2, take Strada Provinciale del Brunello up to Montalcino, a walled village perched on a hilltop with a picture-perfect castle.
  5. Six miles south on SP55 is the Abbazia di Sant’Antimo, a medieval abby isolated amidst verdant
    Abbazia di Sant'Antimo
    Abbazia di Sant’Antimo – Image courtesy of travelingintuscany.com


  6. Continuing on SP55, head east on SS323 to Castiglione d’Orcia, a small town of cobbled streets huddled around an imposing fortress.
  7. From SS323, head north on SP2 and stop at Bagno Vignoni, a town with a square that is not a square, but a pool that bubbles with water from the hot springs below.
  8. Head east on SP53, then north on SP18 to Pienza, where Pope Pius II tried to turn the village into a model Renaissance city.
  9. From here, take SP146 to the classic hill town of Montepulciano and see the 16th century churches and palaces.
  10. You are now a 2.25 hour drive to Rome where you will park the car and spend the next four nights. Here you should return your rental car, keeping in mind you’ll want one again (or rent a Vespa!) for your final touristy day.

Day 10, 11, 12 – In Rome

You can’t visit Italy without exploring Rome.  Ok, you can, but why?  It’s been around for more than two thousand years and has historical significance around the world.  If you want a good overview of Rome,

Image courtesy of telegraph.uk.com

hop on public bus number 10 and take a ride.  Public transportation is your friend in the city.

Day 1 should involve the Palatine Hill, Colosseum, Roman Forum, Trevi Fountain, and the Pantheon.  Day 2 can be spent exploring the Rome’s neighborhoods like Campo dei Fiori, Trastevere, and Jewish Ghetto along with the Capitoline Hill Museums and Testaccio District.

On the 3rd day, you could visit the Ancient Appian Way, catacombs, Piazza Navona, or the Vatican.  Don’t forget to check out some quirky and off the beaten path places in an upcoming post.  On the final day, you can either stay in Rome or head out on a late 1.25 hour train to Naples and spend the night there to get a head start on Day 13.

Day 13 – Rome/Naples to Pompeii to Sorrento to Vietri Sul Mare – Amalfi Coast

If you’re not in Naples, take an early 1.25 hour train from Rome to Naples and then rent a car (or Vespa!).  Alternatively, you can book a private tour and driver at places like Simply Amalfi (and, no, I don’t get any commission for this!)  They get excellent reviews and you won’t have to navigate the narrow coastline roads yourself!

Drive from Naples and visit Pompeii before driving to the Punta Campanella at the tip of the Sorrento

Amalfi Coast
Image courtesy of cntraveler.com

Peninsula passing through the village of Sorrento.

Follow Via dei Campi to Sant’Agata sui Due Golfi for sweeping views over the Gulf of Naples to the north and the Gulf of Salerno to the south.  From here, take SS145 and SS163 to the cliffside village of pastel houses called Positano.

Farther along the coast, check out the Vallone di Furore, a dramatic gorge that opens up to the see near Marina di Praia.  Continuing on with stops at Amalfi, Ravello, and the beach at Maiori.  Visit the Abbazia di Santa Maria Olearia, a rock-cut abbey from the 10th century.

Finally, pass through Cetara to Vietri sul Mare with its famed ceramics on display all over town.  Here you will spend your last night in Italy unless you booked a tour, then you’re heading back to Naples.

Day 14 – Vietri Sul Mare to Naples to Bologna

On your final day, drive back to Naples if you’re not there already and take the 3.5 hour train ride back to Ferrari MuseumBologna for your flight home.

If you have time, check out the Ferrari factory and museum, just an hour away from Bologna.  You can even drive one!

That’s quite enough for this post.  Look for more details coming soon!

Are you looking for recommendations for your next road trip?  Or maybe a customized day-by-day itinerary?  We’d love to help!

As always, thanks for reading!

Kristi – aka The Trippy Tripster!

About Author

Kristi enjoys traveling and taking road trips to fully experience life. She loves to find local eateries, off the beaten path hidden gems, and the secrets to enjoying the journey.

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(8) Comments

  1. Life Hack Guide

    Awesome article! Your post on Italy is a very informative and detailed one. I have always seen pictures on the colorful village of Cinque Terre and is in my bucket list of the places I hope to visit one day. I love the pictures you included in your post, it made me almost want to book a flight ticket and fly there immediately. I will definitely bookmark your column so that I can refer to the details you have provided when I am planning on a trip to Italy. Thank you so much!

    1. Trippy Tripster

      Thanks for the comment and for reading my post!  I’m glad it will come in handy while planning your trip!  Stay in touch!

  2. JL

    Hi Kristi,
    Wow! This is such an awesome trip. I am a fan of Italian food, and even though, I have been to some Italian cities, I have never done a road trip over there, and this is such great proposal. It goes directly into my saved bookmarks 😉 I specially liked as well as all the useful tips you have included such as getting the tickets in advance for the busy tourist attractions, or that pepperoni are peppers and the cappuccino is a morning drink over there 🙂 When I was in Venice, I loved what you mentioned: wander the city and get lost. You absolutely discover many gems. Thanks for sharing!

    1. Trippy Tripster

      Hi JL!  It’s great that you can validate many of the ideas in my post.  I can’t wait to take a roadtrip there when I visit.  If you get a chance to do it, let me know!  Thanks!

  3. kumamonjeng

    I am planning to visit Italy in two years time and your blog is very details. It also tells where to use self drive and where not to and reason for it. I will need this as a guide when I depart in two years time.

    1. Trippy Tripster

      Thanks for reading! I’m glad you will find it helpful. Let me know what else you find or need as you plan your travels!

  4. Lori M

    Kristi, great article! Mark and I have had a trip to Italy on our bucket list and this is a great blueprint.

    1. Trippy Tripster

      Lori, Thanks! Italy is amazing! There is just so much to see and experience! Let me know if I can help! I love to research!

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