Italy Road Trip Itinerary: 2 Week Italy Itinerary

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I’m sure I can’t be the only one who feels that everyone on social media is traveling through Italy this summer. Well I definitely hopped on that trend and took off an epic 2 week Italy road trip with a few of my closest friends. 

This detailed guide will outline my entire Italian itinerary for my road trip, as well as everything you need to know about planning a perfect adventurous trip to Italy.

When to visit Italy? 

Italy is an amazing country to visit year round, however for this itinerary it is important to visit in the summer months, between June and September. You will find the best weather in July and August, but cheaper prices and less crowds if you choose to travel in September. Outside of these months, the hikes in the Dolomites will not be accessible, as the rifugios close. But more on that topic below!

While the warmer months are perfect for hiking in the Dolomites and swimming in the Mediterranean Sea, it goes without saying that these are incredibly busy months to travel. Italy is quite literally swarming with tourists during the summer.

I advise booking accommodations and car rentals at least a few months in advance to avoid disappointment. This is especially true if you are looking to rent an automatic car for your road trip. We even found that we needed a dinner reservation just about everywhere that we went due to the spike in tourism this summer, something that I rarely do when traveling. We were usually able to call same day to snag a reservation, but showing up without one proved to be difficult. 

Italian Road Trip Itinerary 

Days 1-4: Italian Dolomites

Days 5-6: Florence 

Days 7-8: Chianti (greater Tuscany region) 

Days 9-11: Amalfi Coast 

Day 12: Milan 

The Italian Dolomites (Days 1-4)

We started our two week Italian road trip in the Dolomites. If you’re read my blog before, then you know that the Italian Dolomites are one of my favorite places in the world. After my first visit in 2019, I was determined to visit again as soon as possible. I’ve previously outlined my perfect Dolomites road trip itinerary for hitting the region’s hot spots, but on this Italy road trip we chose a route with more hiking (and even some via ferratas). 

Day 1: Rifugio Firenze

After landing in Milan at the start of our adventure, we picked up our rental car and made the 4.5 hour drive to Santa Cristina, a small town just over from Ortisei. Here you you’ll find a small parking lot at the base of the Col Raiser gondola (parking is 10 EUR per day). You have the option of taking the Col Raiser gondola to the top of the mountain, or hiking up. After a long travel day we opted for the round trip gondola ticke.  However, I think a good option is to take the gondola up to avoid the 3 hour hike, and do the hike back down instead, which can accomplished in just over an hour from Rifugio Firenze. 

Col Raiser Gondola Details

Round trip gondola ticket: 25 EUR

One way gondola ticket: 16 EUR

Once at the top of the mountain, you’ll find yourself just a 25 minutes hike to your first stop, Rifugio Firenze. The path is relatively flat, and you’ll 360 degree views the entire way. Just like all of the rifugios on this list, I recommend booking ahead of time to secure a room. This is one of the few huts that actually has an online booking system.

The food at Rifugio Firenze is excellent, with an al a carte dinner option and a delicious breakfast buffet. 

Our time in the Puez Odle region was short but sweet, easily a highlight of our two week Italy road trip. While you could simply hang by the rifugio and enjoy the incredible views, you’ll find plenty of nearby hiking trails. I recommend the round trip hike from Rifugio Firenze to Seceda, which should take about 3 hours and could be accomplished before breakfast if you get an early start to the day. 

Day 2: Rifugio Rosetta 

In the morning we made our way back down the Col Raiser gondola after a few hours of exploring the nearby hiking trails and a delicious and hearty breakfast. Once at the car, we started our two hour drive to the small mountain town of Fiera di Primiero. This town will be the end of our 3 day hut-to-hut adventure, and where we picked up our via ferrata gear. I cannot stress enough that if you plan to conquer any technical trails with via ferratas, please make sure that you are equipped with the proper gear, including both a helmet and harness. 

Once we picked up our gear and parked the car, it was time to hop on the local bus to San Martino di Castrozza. It is just a 30 minute ride, but make sure to keep an eye on the bus timetable, as buses don’t always run super frequently. You can check the schedule online here. You can buy a ticket on board for 2 EUR, but make sure to have small change. 

The bus drops you off in the center of town, where it is just a quick walk to the foot of the Col Verde gondola. If you plan to follow our same route, you will just need to purchase a one-way ticket for 18 EUR, which includes both the Col Verde gondola and a second cable car that takes you up to the top. Bundle up, because you’ll gain a lot of elevation gain in the short ride to the top. Similar to Rifugio Firenze, today’s accommodation, Rifugio Rosetta, can be reached just a short flat walk from the top of the gondola. 

Col Verde Gondola Details

Round trip gondola ticket: 29 EUR

One way gondola ticket: 18 EUR

We had hoped to do an adventure hike to the top of Monte Rosetta, but were unfortunately met with zero visibility conditions on arrival. The stormy weather called for an afternoon in the hut of playing cards and warming up with local wine on tap and homemade flavored schnapps. 

The dinner at Rifugio Rosetta is delicious, but I would recommend adding some meat and cheese to the provided breakfast (or packing your own snacks) as you will need the extra energy for a long day of hiking ahead. Make sure to place any additional breakfast orders the night before. 

Day 3: Rifugio Pradidali

We were so excited to wake up on our second morning in the mountains to perfect weather conditions, after a stormy evening. There are a number of routes that you can take to get from Rifugio Rosetta to Rifugio Pradidali. The first route, which we did not take, takes just about 2 hours. The other route tacks on a summit of the Fradusta glacier, and quite a few extra hours. If you have the time, I definitely recommend taking the longer route as the views from the top of the glacier are absolutely incredible. We only passed a handful of people throughout our 7 hour hiking day, but the trail was well marked throughout with both signs and painted red and white markers. 

Make sure to pack plenty of water and snacks, and there is no where to refuel along the route. There is a quite a lot of both elevation gain and loss, with some loose rocks, so hiking poles are always a great option! 

The day is a long one, and we were sure happy to finally see a glimpse of Rifugio Pradidali in the distance at the end of the hike. Set high in the mountains, this small hut offers some of the most incredible sunset and sunrise views. Try to grab a table in the windowed section for amazing dinner views if possible. 

If you’re looking to fuel up, ask for their meat and cheese board! We managed to have 3 of these boards in under 24 hours. 

Day 4: Cant del Gal 

To be honest, I’m not entirely sure what my recommendations are for this day, other than to make sure you do a lot of research before embarking on this trail. Rather than heading straight to our hotel in Val Canali, Cant del Gal, which is just a 2 hour downhill hike straight from the rifugio, we decided to tackle a few via ferratas. After reading about a nearby loop from a travel blogger, and gathering more information from one of the employees at the hut, we attempted what was meant to be a 4-hour loop with two via ferratas. 

The route starts with a steep downhill climb into the valley, where you will need to watch your step, as there are many loose rocks. This section took us about 45 minutes, before we reached the point where it was time to clip into our first ferrata, Ferrata Porton. This was easily one of the most thrilling, but also crazy and terrifying things that i’ve done. It is definitely not for the faint of heart, or those who are afraid of heights.

We took Ferrata Porton very slowly, conquering the route in just under 2 hours. Right before the end of the ferrata there is a section where you will need to unclip and climb up a open rock field. Make sure that you follow the path that hugs the left hand side. 

After one more clipped in section, you’ll be back on a normal hiking trail as you make a steep climb from Forcella Porton to the summit where you’ll find absolutely gorgeous 360 views. 

Forcella Stephen Note

IMPORTANT: This is where things got a bit hairy for us. As we made our way from here to Forcella Stephen, the trail became incredibly steep and lacked all ropes. While we did see a view local hikers pass us going the other way, after studying the maps later, it seems likely that we ended up off our intended route. The route was well-marked with painted markers, but we were quite literally clinging to the side of the mountain, side stepping over 2 inch passes with a 4,000 ft drop and no opportunities to clip in for about 45 minutes. I would not advise taking this route, as it was not only one of the scariest things that I have done in my life, but also incredibly dangerous for amateur climbers such as myself. 

Once you reach the top of Forcella Stephen, you will begin your descend (now properly clipped in) with a steep but super fun climb back down to the rifugio. The route looped back to our rifugio 7 hours later, almost double the time we were expecting. 

After a much needed meat and cheese board and a few liters of water back at Rifugio Pradidali, we made our way downhill with the 2-hour descent straight to Cant del Gal. This is a gorgeous trail with incredible views throughout, ending with a stroll through the forest at the bottom of the mountain. We opted to stay at Cant del Gant, which is located right at the bottom of the mountain, rather that trying to coordinate a bus back into the town of Fiera di Primiero. The rooms are super comfy, and the included breakfast spread was one of the best that we had during our trip.

Things to know about staying at a rifugio in the Dolomites 

If you’re unfamiliar with rifugios, or refuges, they are simple mountain huts in the Italian Dolomite mountain range. Many offer full or half board options, and a simple bed in a private or dorm-style room. 

When visiting a rifugio it is important to bring your own sheet or sleeping bag, otherwise you will be required to buy one. I travelled with the Sea-to-Summit Sleeping Bag Liner which worked perfectly throughout our time in the Dolomites. You are also required to wear house shoes or slippers indoors, but these can usually be provided if you didn’t pack your own. 

Lastly, while some huts do accept cards, their connection is often not reliable. I recommend bringing enough cash to cover your stay during your Italy road trip. 

You can check out my guide on things to know when booking a rifugio. 

Florence (Days 5-6)

Day 5: Florence

After a quick stroll through the morning markets in Fiera di Primiero, and a dip in nearby Lago Schener, we started our 4.5 hour drive from the Dolomites to our next stop, Florence. I arrived in Florence on our Italy road trip with one big objective: to eat some of Italy’s best cuisine. 

We stayed right in the heart of the city at a super reasonably priced Airbnb. It was a bit of a tight squeeze for 4 people, but we knew we’d be out and about 90% of our stay in Florence.

First stop was obviously gelato – and Gelateria dei Neri did not disappoint.

For afternoon drinks we stopped at View on Art Rooftop Cocktail Bar, a rooftop bar with incredible views of the Duomo. This is a great way to experience the Duomo if you don’t plan on climbing the towers. I would have loved to stay for sunset, but we had lots to do and see with limited time in the city.

After our drinks at View on Art Rooftop Cocktail Bar, we made our way to the famous Ponte Vecchio. Its busy and chaotic, and yet absolutely charming at the same time. I guess some places are just famous for a reason.

For pre-dinner drinks, we snagged a table at Le Volpi e l’Uva, a wine bar located just over the river. I definitely recommend making a reservation, as it was absolutely packed even on a Monday evening.

Dinner was showstopper, as we dined at Osteria Cinghiale Bianco. This is another spot where a reservation is a must. We heard parties of 2 getting turned away all night, or being quoted 2-3 hour wait times. And I promise you, this is a meal that you won’t want to miss. I swear I still dream about the spaghetti with burrata daily. This was easily one of the best meals on our Italy road trip.

Our night ended with negronis at Caffe Letterario Le Murate, a converted prison that is now a lively bar with tons of outdoor seating in a courtyard.

Day 6: Florence 

We started our day at a local cafe, Dolce e Dolcezza for coffee and pastries before heading to breakfast number two, a sandwich from the famous All’antico Vinaio. Their meat-packed panini are delicious but massive. I recommend arriving right where they open at 10am to avoid a line, because with limited time in Florence you don’t have time to be standing around in line. We lucked out as there are two identical shops across the street from each other, one which had no line when we arrived. 

Next we made our way to the Piazzale Michelangelo and Forte San Miniato for panoramic views of the city. Both of these are famous sunset spots, with Forte San Miniato typically being less crowded. However, since storms were predicted for the evening, we took the opportunity to visit in the morning instead. If you have an open evening in your itinerary, I recommend grabbing a pizza or sandwich (and a bottle of wine of course) to-go and enjoying a sunset picnic with a view.

Our next stop of the day was at the Galleria Uffizi, an easy highlight of our two week Italian road trip. It is important to book your timed entry visit ahead of time, as tickets to sell out ahead of time. 

Evening in Florence

It wouldn’t be a trip planned by me if I didn’t scope out all of the natural wine bars in town. So pre-dinner drinks were at Vineria Sonora, a tiny bar with a not-so-tiny natural wine menu.

This was followed by a (very large) dinner at Acqua Al 2 and cheap drinks at The Box.

Chianti (Days 7-8)

Day 7: Chianti 

The drive from Florence to Chianti is a quick one – just about 45 minutes. After a long morning and breakfast in Florence, we started to make our way to Chianti. On our way to the airbnb we made a pitstop in Volpaia for lunch. I recommend making a reservation ahead of time at Bar Ucci for their delicious homemade pasta. We unfortunately didn’t have a reservation, so ended up eating at the sister restaurant across the way instead.

After lunch we made our way to our airbnb, Selvabella in Chianti. I cannot say enough positive things about staying at Selvabella in Chianti. Marta and Bernardo are unbelievably welcoming hosts. The property is absolutely gorgeous. And the cooking class is a must-do activity.

The cooking class, which lasted a solid 6 hours with endless food, was easily the highlight of our Italy road trip. We cooked multiple courses, including a Pappa al pomodoro, herb-encrusted pork, homemade pasta, a chocolate cake and more!

Day 8: Chianti 

The only thing that could possibly top our incredible cooking class is the amazing breakfast spread that we woke up to the next morning. Homemade individual flatbreads, rosemary and thyme panna cotta, fruit jams, parmesan eggs, and more! It was truly the best feast, and anyone staying at Selvabella in Chianti shouldn’t miss it.

We spent the rest of our time in Chianti exploring the nearby towns, including a vineyard tour at Il Vallone di Cecione, a local family-run vineyard. You can tour the vineyards, taste the delicious wines, and purchase a few bottles to-go.

For dinner we snagged a table at Ristorante Il Vescovino, a recommendation from our airbnb host Bernardo. The food is phenomenal and the sunset views are even better. Make sure to call ahead and reserve a table outside for the best views.

Amalfi Coast (Days 9-11)

Day 9: Naples & Amalfi Coast 

We started our morning early, rising with the sun. From Chianti it was about a 3 hour drive to Rome. Once in Rome we dropped off our car, and made our way to Naples by train. The fast train from Rome to Naples is just about 1 hour. After a long travel day we opted for the private transfer, rather than navigating to the coast via train and bus. We paid 160 EUR for 4 people in a private van for the 1.5 hour drive. Pricey, but worth it after a long day!

We checked into our airbnb in Praiano in time to enjoy a beautiful sunset. Praiano, located on the beautiful Amalfi Coast in Italy, is Positano’s sleepy sister. Just 15 minutes down the road from this bustling town, you’ll find the much quieter village of Praiano. With just 2,000 locals, and far less tourists, you’ll find some peace and quiet even during the busier summer months. You can check out my full guide to Praiano here.

Day 10: Amalfi Coast 

It is relatively easy to get around the Amalfi Coast, but it takes some time. There is a bus that leaves a few times a day between Praiano and Positano for just 1,20 EUR, but you can expect a very crowded bus in the high season.

I recommend taking a water taxi if you have it in your budget. A round trip water taxi between the two towns takes under 15 minutes and typically costs between 50-80 EUR round trip total for the group. We booked ours through Sharks. Most boats fit up to 6 people, but some fit as many as 8. You can pre-arrange your pick up time for a smooth ride back to Praiano.

With just one day to spend in Positano, we made our way straight to the beach to take in the iconic view. It’s funny, I wasn’t sure what to expect in Positano. It has been so over-hyped on social media that I was afraid that it wouldn’t live up to the hype. That said, it really is an incredible place – despite the crowds. If you’re looking for cheaper food options, I recommend heading uphill a bit further from the water.

For dinner we made our way back to Praiano and grabbed a delicious (and affordable) dinner at Che Bontà, followed by drinks up the road at Bar del Sole.

Day 11: Amalfi Coast 

For our final day on the Amalfi Coast we rented a private road to explore the coast line. After doing a bit of research we decided to book with La Boa, a boat that is operated out of Praiano. While it is not a cheap activity, it is absolutely worth it if it is in your budget. We paid 500 EUR for a 4 hour private boat along the Amalfi Coast, including soft drinks, beer, and prosecco.

Milan (Day 12) – the last day of our Italy road trip

Day 12: Milan

The last day of our trip was a long one. We started the morning in Praiano with a final early morning swim at Marina di Praia. From here we took a private transfer to Naples, followed by a 5 hour fast train from Naples to Milan.

We only had a few hours to explore Milan so we booked a super central airbnb, which we loved! Our evening included drinks at the fabulous natural wine bar, e/e enoteca naturale, followed by dinner in Navigli. Make sure to stop by the “world’s smallest bar,” Backdoor43.

Total Cost of our Italy Road Trip

We jam-packed a whole lot into our two week trip to Italy. From hiking in the Dolomites to wine tasting in Chianti to cruising on a private boat on the Amalfi Coast. This trip wasn’t exactly my usual budget-friendly adventure, but it was worth every penny.

Here is the breakdown by category:

• Lodging: $797.67
• Food/Drinks: $652.14
• Transportation: $572.64
• Activities: $362.94
• Shopping: $90.26

Visiting Italy? Here are some other articles to check out:

• Road Trip in the Dolomites
• A Guide to Hiking Seceda, Dolomites
• Hiking to Lago di Sorapis
• Visiting Lago di Braies

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