In this post, I’m sharing 3 Fall Road Trips to Take in Italy This Year. Fall is an incredible time of year to visit Italy, with the temperatures cooling down and the tourists thinning out. If you’ve been wanting to explore Italy hopefully this post inspires you to finally book the flights.
Italy has always been one of my favorite countries to explore. I spent over a month traversing the country on my first backpacking trip (back in 2014) and have since been back countless times. One of the things I love the most about Europe is how easy it is to get around with trains and public transportation, but if you want to get off the beaten path in Italy, you’ll probably still want to rent a car.
On my last trip to Rome and Corvaro, I rented a car through Discover Cars. Renting a car with Discover Cars was super easy and affordable and I’ve continued to use them ever since. They have no hidden costs and free cancellation up to 48 hours before your trip.
Discover Cars isn’t your typical booking platform. They negotiate prices with each car rental service that uses their platform which means they can offer you lower prices than you’ll find anywhere else. You can now explore with peace of mind.
Please note: This post contains affiliate links, meaning I may earn a commission if you make a purchase by clicking a link (at no extra cost to you). Thank you for supporting my blog!
Driving in Italy
Now, driving in Italy isn’t for the faint of heart. I’ve driven in many European countries (Ireland, Norway, Germany, Switzerland, Austria, Slovenia, Portugal, and Montenegro to name a few) and Italian drivers are some of the most aggressive I’ve encountered. They undertake, drive very fast and they aren’t afraid to let you know if they think you aren’t driving fast enough.
That being said, the roads are wide, well-maintained, and easy to navigate. If you’re a comfortable driver, you’ll be absolutely fine. (In other words, if my 65y/o grandpa who hadn’t driven a manual since he was 20 could do it, so can you!)
I would however stress the importance of having rental insurance on your car – something that’s easy to book with Discover Cars. This will give you peace of mind, especially when you’re exploring a smaller village or mountain town.
Pro tip: Rent a small car. I’m talking Fiat 500 small. You’re not in America anymore baby. You are going to want a little car that you can cruise around the villages in, without having to worry about parking, passing on tight roads, or squeezing down lanes originally built for horse and carriage.
Now you’re ready for my 3 fall road trips to take in Italy! Let’s dive in.
Table of Contents
- Overview of the 3 Fall Road Trips to Take in Italy
- Planning Your Fall Road Trips in Italy
- Itinerary One: Northern Italy & the Dolomites
- Itinerary Two: Central Italy (Tuscany Region)
- Itinerary Three: Southern Italy (Puglia Region)
- Italian road trip FAQs
- Packing for Italy in the Fall
Start Here!
You’ll likely notice that these itineraries tend to skip a lot of the main ‘tourist attractions’ and cities in Italy that most people rave about. That’s because I do not recommend driving in those areas. If you want to explore Rome, Florence, or Naples, you do not need a car. And you most definitely won’t need a car for Cinque Terre or Venice.
For any other travel around Italy, I recommend traveling by train.
If you would like to explore Rome, Florence, or Venice on your trip, I recommend giving yourself time to explore that city before renting your car. For example, you could fly into Rome, explore the ancient city before taking the train to Florence, and pick up your rental car after spending a few days around Florence. Or go south and pick up your rental car around Naples.
You could even fly into Venice, spend a few nights there, and then pick up your rental car to drive north.
Overview of my 3 Fall Road Trips in Italy
This post is a long one, your girl can really ramble on about the best things to do in Italy. So to make things easier for you – here is an overview of the 3 Fall Road Trips in Italy that I’ll be sharing with you in this guide.
Itinerary One: One Week in the Dolomites
You’ll spend this week hiking in the beautiful Dolomite mountains of Northern Italy. I’ll be sharing some bucket list accommodations for your trip, but another way to do this road trip would be with a campervan!
Dolomites Road Trip Itinerary Highlights:
- Lago di Braies
- Tre Cime di Lavaredo
- Seceda
- Alpe di Siusi
- Val di Funes
Your options for getting to the Dolomites include flying to Venice, Milan, Verona, or Innsbruck. For my road trip to the Dolomites, I flew into Venice and rented a car from there.
Itinerary Two: One Week in Tuscany
This week is going to be exploring the rolling hills and vineyards of Tuscany, one of my favorite regions of Italy. I absolutely love the landscape here – it’s unlike anything I’ve seen!
Tuscany Road Trip Itinerary Highlights:
- Pienza
- Bagni Vignoni
- Montepulciano
- Cortona
- Siena
- San Gimignano
For this road trip, it’ll be better to fly into Rome and pick up your rental car there! Then you’ll drive north to Florence with this road trip being your guide.
Itinerary Three: One Week in Puglia
Finally, you’ll have the chance to explore Puglia, the heel of Italy’s boot with this week-long itinerary through the south. I’ve decided to share this itinerary on the eastern side of Italy with you because the western side is already so popular – and it’s actually easier to explore by train.
Puglia Road Trip Itinerary Highlights:
- Polignano a Mare
- Monopoli
- Borgo Egnazia & Masseria San Paolo Grande
- Torre Sant’Andrea, Grotta della Poesia (Cave of Poetry) and Torre dell’Orso
- Ostuni
- Alberobello
- Matera
To explore Puglia, I would recommend flying into Bari Karol Wojtyla International Airport which is just a 2 hour and 45 minute flight from London.
Planning Your Italian Road Trip
When is the best time to visit Italy?
The best time to visit Italy is in the fall. I recommend planning your road trip between September and November. Because of where Italy is located, you’re still going to have great weather (especially in Puglia) but there will be fewer crowds and you can often get cheaper prices on car rentals and accommodation.
Fall is the best time to visit the Dolomites as well. September is the perfect time to visit the Dolomites because you’ll have mild weather and near-perfect hiking conditions. You should also start to see the leaves changing and the whole region becoming more stunning.
November in the Dolomites will start to be cold and you could have storms interrupt your hikes, but November in Tuscany and Puglia will mean better deals and way fewer crowds.
How much should you budget for your Italian road trip?
Italy tends to be a fairly affordable European destination, especially if you compare it to its neighboring countries of Austria and Switzerland (don’t get me started about the prices in Switzerland).
Our last rental car in Italy (mind you, we rented it at the height of summer) cost us €326.77 ($349.40). We rented the car for 8 days with a pickup and drop off in Rome, and since there were 3 of us, we got a midsized car instead of a mini. This price also included the full insurance with Discover Cars.
🏨 Accommodation
Around Italy, you should be able to get a decent private room with an ensuite bathroom for around €40-€70 per night. That’s around $45-78 USD per night. If you’re traveling alone, you can often find single rooms for slightly cheaper. And if you’re planning on staying in a hostel, a dorm room should cost you €20-€30 (around $22USD).
Midrange private rooms are going to cost more like €90+ per night and just keep an eye on things like school holidays and football matches – which will drive up the nightly prices in hotels and hostels.
Accommodation across Italy will be cheaper if you travel in the off-season, so don’t expect these estimates to be right if you plan your trip for the height of summer.
🍝 Food
Good food in Italy is incredibly cheap! That’s one thing that I love about this country. You can get a delicious, fresh homemade meal for around €10. Bakeries have cheap options for coffee and breakfast, you can usually get a pastry and coffee for less than €5, and ‘fancy’ restaurants should only cost around €25 per person.
When I was last in Rome, we had dinner for 5 in a nice restaurant with appetizers and wine for only €120. The one thing on your budget that you shouldn’t have to worry about in Italy is the food!
🍨 Gelato
Across Italy, gelato should never cost you more than €2-3 a scoop. In my experience, the more expensive the gelato, the more of a rip-off.
💃🏻 Activities
This is going to depend entirely on what kind of activities you want to do! For example, hiking in the Dolomites will cost you nothing but paragliding will cost around €125. Wine tasting in Tuscany will cost around €35-€50 per person. A cooking class in Alberobella will cost less than €30.
Gondolas and chair lifts in the Dolomites also tend to cost around €30 per day (especially the popular ones). If you know where you’re going to be exploring – I recommend buying a multiday chair lift pass to save money.
I would recommend booking your activities in advance as tours do tend to sell out. However, traveling in the shoulder season will give you the advantage of fewer people.
Italian Road Trip Itinerary One: The Dolomites
Autumn is an incredible time of year to be in the Dolomites. You’ll start to see the changing colors and avoid most summer and winter crowds. If you’re planning a week-long fall road trip to the Dolomites in Northern Italy, here is the itinerary that I would recommend:
Day 1: Arrive in Bolzano (the gateway to the Dolomites) and drive to Nova Levante/Welschnofen (stay for 1 night)
Explore the local markets of Bolzano (if you have a few extra days of your trip, this would be a beautiful place to spend them)
Day 2-3: Drive to Corvara in Alta Badia (stay for 2 nights)
But first, start your day with sunrise at Lago di Carezza, then drive to Obereggen, and hike to Oberholz Alpine hut for incredible food. Finally, drive one of the most beautiful drives of your trip to Corvara, the Passo Gardena.
Wake up early on day 3 (like 4 am early) and do the Via Ferrata hike to Gran Cir for sunrise.
Day 4: San Candido/Innichen (stay for 1 night)
On your way to San Candido stop to take in the iconic view of Seceda. To get to this view you’ll take the Seilbahn Seceda cable car from Ortisei (€32 return) or you can ride one way and hike back down (around 2 hours). Then drive 2 hours to Tre Cime di Lavaredo.
Day 5-6: Lago di Braies (stay 2 nights in Riscone)
Make sure to escape the crowds and take the picturesque 1-hour walk around Lago di Braies, another iconic point in the Dolomites. On your second day in Riscone, explore the Fanes National Park. No early mornings, just go at your own pace and enjoy your day.
Day 7: Make your way back to Bolzano
Watch one last sunrise over the Dolomites, this time the beautiful Alpe di Siusi before making your way back to Bolzano.
Additional tips for your road trip through the Dolomites: rent a small all-wheel-drive car as that will help you feel more comfortable exploring the mountain roads of the Dolomites. And be careful to avoid speeding – even when the locals are racing around you. This region is full of speed cameras.
Where to Stay in The Dolomites
Book Your Dolomites Activities:
Italian Road Trip Itinerary Two: Tuscany
Tuscany is truly beautiful all year long. It’s one of my favorite regions of Italy because of its rolling hills, green vineyards, and slow living. For this itinerary, you’ll start in Rome and end in Florence. If you need to start and end in Rome, just drive back to Rome from Florence. Here’s the 7-day Tuscany road trip itinerary that I recommend:
Day 1: Pienza – Bagni Vignoni
In Pienza, you’ll have a chance to enjoy some of the best wine and cheese Italy has to offer – already starting our Tuscany trip strong. Make sure to enjoy a Pecerino (one of my mother-in-law’s favorite wines) and do a cheese tasting at Podere Il Casale. Spend the afternoon at the thermal baths of Bagni Vignoni.
Day 2: Montepulciano
This is one of the cutest villages that you’ll explore on your Tuscan road trip. The ancient stone city and rolling green hills complement each other perfectly.
Day 3: Cortona
If you’ve ever seen Under the Tuscan Sun, you’ll want to stop in Cortona. It’s a beautiful Italian village that’s featured in the movie. You can even have a coffee right where Diana Lane sits to write her postcards in the movie.
Day 4: Siena
Siena is the largest of the hill towns that are scattered throughout this region. Almost every weekend during the summer there will be one festival or another happening, so make sure to check before you go! Visiting an Italian village during one of their many summer festivals is so much fun. There’s usually line dancing, cheap food and wine, and people dressed in traditional costumes!
Day 5: Stay overnight at a vineyard (Villa Bordoni, Greve)
If you have the budget, I recommend spending 1 night of your Tuscany road trip at a vineyard. Staying at the vineyard means you can do a full wine tasting and vineyard tour without having to worry about transportation home. You’ll also get a unique inside look into running a vineyard, that most day trippers don’t get!
Villa Bordoni in Greve has been on my bucket list forever. My first time in Florence I did a wine tasting here and absolutely fell in love. I’ve wanted to come back and stay ever since. It’s in the Chianti region which of course, means amazing wine – but Villa Bordoni is also well known for its incredible cuisine and beautiful pool.
Book your stay, I’ll be so jealous! And if you go in the off-season, it’s really affordable!
Day 6: San Gimignano to Florence
From Villa Bordoni you’ll have an hour’s drive to explore San Gimignano before finally making your way to Florence. San Gimignano is famous for its medieval towers and incredible gelato. Make sure to get a scoop from Gelateria Dondoli.
Day 7: Florence
There is so much to do in Florence, one day will definitely not be enough – so you can either return your car and spend a few days exploring, or cut a day from one of your other stops and stay in Florence longer. Either way, Florence is a beautiful city and you won’t run out of things to do.
As you can see, there’s a lot of ground to cover in Tuscany, so even a week-long Italian roadtrip won’t be enough. You’ll just have to come back.
Where to Stay in Tuscany
Find a hotel in Tuscany:
Book Your Tuscany Activities:
Italian Road Trip Itinerary Three: Puglia
Puglia is a beautiful and less traveled part of Italy. It’s still the region where locals take their summer holidays – but thanks to the power of social media, it’s becoming more popular. I recommend taking a road trip through Puglia in the fall, to avoid the summer crowds (and prices!). Here’s my dream week-long road trip to Puglia Itinerary:
Day 1: Arrival & Polignano a Mare (stay 2 nights)
Depending on what time you land, you might want to spend your first night in Bari. However, if you land early enough in the day, pick up your rental car and travel to Polignano a Mare. If you want to stay in a traditional Trullo, I highly recommend Trullammare. It’s a perfect base for your first couple of stops in Puglia.
Day 2: Monopoli
Monopoli is another gorgeous coastal town in Puglia, and it’s only a further 15 minutes down the road from Polignano a Mare which means it’s only another 8 minutes down the road from Trullammare if you decide to stay there. Here you’ll find beautiful beaches with iconic blue and white umbrellas! You can spend your morning exploring the city center and your afternoon relaxing by the beach.
Day 3-5: Ostuni (spend 3 nights here)
To save yourself from having to pack up and check out every day, Ostuni is a great base for the next few days of your Italian road trip through Puglia. Make sure to check out Borgo Egnazia & Masseria San Paolo Grande. You could also take a drive to Cisternino or Locorotondo which are both charming villages in the area.
Spend plenty of time exploring Ostuni, you’ll learn quickly why it’s the most popular village in this region. You could also hop in the car and venture south one day to Torre Sant’Andrea, Torre dell’Orso, and Grotta della Poesia. It’ll be a long day of driving but the views are definitely worth it.
Day 6: Alberobello
No trip to Puglia would be complete without a stop at the UNESCO World Heritage site of Alberobello. There are over 1,000 of the famous trulli here. It’s a site to see! If you can, try to sleep for the night in a traditional trulli.
Day 7: Matera
Matera is believed to be one of the oldest inhabited cities in the world! It has that classic old Italian feel to it – and it’s stunning. You can’t end your trip without a night here. You could also visit Alberobello on a day trip and spend two nights in Matera to end your trip.
Then unfortunately it’ll be time to head back to Bari, return your rental car, and fly home.
Where to Stay in Puglia
Book Your Puglia Activities
Italian Road Trip FAQs
Is it a safe destination for a solo female traveler?
In my experience, yes! Take normal precautions and when I’m traveling alone I never drive at night – but I’ve always felt safe traveling alone in Italy.
Should I get a SIM card?
Definitely! You are going to want to have Google Maps for each of these Fall Road Trips in Italy. It’ll save you from getting lost when you’re meandering through ancient villages. Just make sure that you download offline maps as a backup. You can get a cheap e-sim for Italy and Europe here.
eSims work with all phones and they mean you can be connected from the moment you land and pick up your rental car!
What currency do they use in Italy?
Across Italy, they use the Euro. Both cash and card are accepted in most places, but it’s always handy to have some cash on you, especially when you’re staying in smaller villages that are more off the beaten path.
Do I need a visa for Italy?
If you’re an American, you currently (as of September 2024) do not need a visa for the Schengen area. However, that is likely to change in 2025. Keep an eye on updates and make sure you’re prepared for your trip.
Packing for Italy in the Fall
Packing for Italy in the fall is going to vary wildly depending on which of these itineraries you pick! For the Dolomites, you’ll need hiking boots, poles, and layers because there will be chilly days and cold sunrise hikes.
For Tuscany, I would take lightweight flowy dresses to explore villages and vineyards in, along with a comfortable pair of sandals.
In Puglia, I would make sure to pack your bathing suits! The beaches and coastline are beautiful, plus you’ll probably stay in at least one hotel that has a pool.
5 Things to Pack for Your Fall Road Trips in Italy
Walking shoes. No matter how light I pack (and I usually pack very light), you’ll always catch me exploring in a comfortable pair of sneakers. My new favorites are my Vessi waterproof sneakers. These are great for exploring cobblestone streets, light hiking, and running.
Small, powerful camera. Trust me, Italy is beautiful and you are going to want to take a lot of photos. You’ll fill your phone storage in just one day! As nice as phone cameras are these days, nothing beats having a real camera in hand to capture these beautiful moments. This little camera always lives in my purse, I love it for photos and videos. Make sure everything is backed up and protected with this tiny external hard drive.
A reusable water bottle. Another thing I never travel without is my reusable water bottle. I love this one because it has various lids – which means I can use the same bottle for iced coffees and smoothies.
Entertainment for long travel days. It’s usually 50/50 if I’m going to get motion-sick on a long bus or ferry ride. Luckily, I always travel with motion sickness drops and tablets so that I can spend long journeys reading. My Kindle has explored more countries than most American adults! I love using the Libby App to borrow Kindle books even while I’m abroad.
Quick dry towel. I never travel without my quick dry towel. It’ll come in handy for quick beach pit stops, dodgy accommodation, or stays in hostels. There has never been a trip where I’ve thought I didn’t need it – but there have been plenty of trips where I didn’t bring it and instantly regretted that. It’s so small as well, you’ll hardly notice it in your bag.
Europe Travel Essentials
I usually spend between 2-6 months a year in Europe and have been to Italy countless times. It’s one of my favorite countries in the world and I hope one day to call Italy home! Here are some of the top travel essentials that I always recommend for Europe and Italy.
Flights: Find the most affordable flight deals on Kiwi. Don’t overpay for flights – let Kiwi do the hard work of finding cheap flights for you.
Credit Cards: I’ve started using the Capital One Venture Card and I couldn’t recommend it more. You get unlimited lounge access, TSA or Global Entry, $300 travel credit, $50-$100 experience credit, car rental insurance and so much more. Learn more and apply here.
Travel Insurance: I never travel without travel insurance! As a full-time digital nomad, I highly recommend SafetyWing. Learn more and get insured here.
Accommodation: Find the best Italy hotel deals on Booking. I’ve used Booking to book most of my accommodation for years. They always have the best prices and the widest ranges of available properties.
eSims: I used to get physical sims every time I went to a new country. Now, I keep my UK SIM in all the time and instead get eSims for the length of my trip. That means no more wasting time in airports or getting ripped off! You can start using your phone from the moment you land.
If you made it this far, thank you! Enjoy one of my Fall Road Trips in Italy. One of my favorite countries in the world! Where will you go first?
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