An Epic 2-Week Italy Road Trip Itinerary: Milan To The Amalfi Coast

For the past two summers, my boyfriend Andy and I have chosen countries in Europe to road trip through, taking our time to just enjoy the scenery and have adventures along the way.

Last year we explored the South of France, while this year we chose Italy, beginning in Venice and ending in the Amalfi Coast.

Our Italy Road Trip Route

Okay, so in reality we actually flew round-trip NYC -> Milan as flights to and from Milan seemed to be much more affordable than other cities. We didn’t really spend any time there, though, so for the intention of this post I won’t really be mentioning it.

As soon as we arrived into Milan we hopped on a pre-booked Trenitalia train to Venice.

After Venice we pre-booked an Italo train to Florence where we picked up a car and began our Italy road trip.

The full 2-week Italy road trip itinerary included Milan – Venice – Florence – Tuscany – Perugia – Amalfi Coast – Ischia.

Psst, Don’t forget to pin this Italy road trip guide for later!

Booking Ferries & Trains In Italy

For train and ferry travel we booked in advance, using Omio’s easy interface and reliable booking system.

We also found Omio often had cheaper prices than booking directly with TrenItalia and Italo.

Note: You’ll want to book in advance! The earlier you book your train and ferry tickets, the cheaper it will be.

For example, our train tickets from Milan to Venice were 60.80 Euros for two tickets (one-way) booked in advance.

When we arrived at the train station early from the airport and asked if we could switch our ticket to an earlier train, they said we would have had to pay the difference in price: 160 Euros.

Insane!

We were glad we booked early.

Renting A Car In Italy

Ugh. So the truth is we booked our car through Hertz.

I hate Hertz. I’ve had so many problems with them over the years, and their customer service just is not good.

Typically I’d book with Enterprise, but they didn’t have a car rental office in the city in Florence (only the airport).

We tried to book with EuropCar, but they didn’t have automatic cars in the city (only the airport).

In short, if you don’t mind renting from the airport — such as if you’re flying into Florence anyway — book with Enterprise. In my experience they are the best and have great customer service.

If you’re desperate for an automatic car in Florence and don’t want to trek to the airport, Hertz has what you need.

Here is another option that I sadly didn’t know existed before this trip:

Use a comparison site like Discover Cars.

You can save up to 70% on your rental just by comparing your options!

Use their widget here and try it out for yourself: 

Best Hotels In Italy

We booked almost all of our accommodation through Airbnb. You can stay in everything from gorgeous countryside wineries to historic palaces-turned-city hotels.

Accomodation Links: We loved all our accommodations aside for the Amalfi Coast, so I’m leaving that one out of the list.

• Milan Airbnb
• Venice Airbnb
• Florence Airbnb
• Montepulciano Airbnb (extra special!)
• Perugia Agritourismo (extra special!)
• Ischia Airbnb (extra special!)

Prefer hotels? Click here to search for the best hotels in Italy!

You can also use this map to search for local hotels and rentals:

Italy Road Trip Video

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Check out my entire Italy trip video above!

Italy Road Trip Highlights

Wow! Where to begin. There were so many amazing experiences to be had on the trip, from the wine travel to the scenic adventures. Here are 12 highlights from our journey — truly one of the best road trips we’ve ever done!

Quick tip: download these 6 amazing apps before your road trip.

Venice

1. A Floating Apertivo Hour

While we did the whole gondola thing — hey, you gotta! — we also booked a Canal & Aperitivo Experience with Urban Adventures.

Full disclosure:

I work with Urban Adventures in NYC as one of their guides, so when coming to Venice I reached out to their Italy manager and they set Andy and I up with this awesome experience.

We took a private water taxi down the Grand Canal and beyond, seeing everything from the city’s ancient palaces-turned-hotels to outer islands like Murano and Lido.

Along the journey we learned fun facts about the city — like that Venice invented the Aperol Spritz — while sipping Prosecco, munching on tasty finger sandwiches and clinking glasses with new friends.

While the gondola was fun, this felt like a much more local experience. It was definitely an Italy travel highlight, and would be a great social experience for those traveling solo in Italy too.

2. Explore The Art

For an inspiring afternoon, wander the sculpture gardens at Giardino Della Marinaressa (public park) — Carole Feuerman‘s sculptures were on view when we visited — before boarding a ~10-minute vaporetto (ferry taxi) to Murano.

Here you can drink an Aperol Spritz on the water before wandering the many Murano glass shops.

Within the stores, you’ll see gorgeous glass sculptures, jewelry, and housewares. Additionally, walking around the small island introduces you to giant al fresco glass works.

Burano is another island nearby — though a bit farther at about an hour away from Venice. Here the houses are in crazy bright colors, with the shops introducing you to artisanal lace products.

3. Lido Beach

While you can’t swim in the Grand Canal — both because there are so many boats and because it’s full of sewage — you can head less than 10 minutes by vaporetto to Lido Beach.

It’s about a 15-minute walk from the dock to the shell-gowned shoreline, with tons of gelato shops offering a snack for the stroll.

Once there, walk along the sand or jump in for a swim.

It’s seriously beautiful, not to mention their beach cafe serves tasty Aperol Spritz cocktails.

Can you tell what my favorite cocktail is?

Check out my full article on responsibly exploring the city for more things to do in Venice.

Florence

4. Take A Fresco Class

Sadly, the art of fresco in Florence is dying out. In fact, there are only three fresco artists left in the city, and you can take a workshop with one through Context Travel.

We had the pleasure of creating our own frescos with Dr. Alan Pascuzzi in his San Frediano studio.

The neighborhood is known for its artisan studios and introduced me to the city beyond the Duomo.

True fresco refers to applying natural pigments to freshly laid (wet) lime plaster.

There are no binders — like oil — in the paints, just water, and when the hues hit the limestone a chemical reaction takes place that leads to a truly lasting piece of art.

The tough part is having to complete your painting (and tempering!) before the plaster dries.

A truly creative race against time that leaves you with a deeper cultural appreciation and an authentic souvenir to take home!

This was one of a few great art experiences in Florence that we did!

5. Dinner In A Local Home

This was our second dinner through BonAppetour and as usual, it was a pleasure.

We opted for a traditional Tuscan dinner in the home of a local man named Andrea and his wife Giovanna, savoring a delectable spread.

On the menu: Tuscan tomato & bread salad (Panzanella), Tuscan onion soup (Carabaccia), spinach with baby squid in squid ink (Seppie al Nero con Spinaci) and cold chickpeas with tomato and sage (Ceci all’uccelletto) — all paired with wine of course. This meal made me seriously want to volunteer to do vineyard work in Italy and immerse myself in the vino culture!

We ended with a chestnut tart called Castagnaccio that’s typically eaten in mountain communities, paired with locally made dessert wine. Yum!

6. Wandering San Niccolo

We loved this Florence neighborhood! Walking around Florence we noticed a few recurring styles of street art.

One was the work of Blub, who painted small square portraits of cultural icons like Salvadore Dali and the Mona Lisa as scuba divers.

There was also Clet, who added stick figures in interesting situations to typical street signs.

Both of their studios are in San Niccolo — along with other Florentine artists — and you can purchase a creative gift.

7. Sips & Sculptures At Belvedere Fort

Okay, so there are MANY attractions offering a view over Florence. Andy and I first visited Boboli and Borelli gardens…and were unimpressed.

Maybe in other seasons there is a lot to see, but in late August there were not many flowers, especially after paying 10 Euros each to get in.

While wandering around the gardens, we stumbled upon Fort Belvedere next door, which was just 3 Euros each to get in.

Not only were the views stupendous, but the historic fort houses an indoor art museum and outdoor sculpture garden.

It’s pretty interesting to look out over a massive 79-foot skeleton with a Duomo backdrop.

Bonus:

The Aperol Spritz cocktails and pizza were delicious!

While TripAdvisor said it would be expensive, we thought $55.50 USD for two meals, two cocktails, and two coffees was very affordable, especially for what we got.

8. Drinks On Ponte Santa Trinita (Bridge)

Of course, the Ponte Vecchio is a must, though expect tons of tourists eating gelato and perusing the impressive amount of jewelry shops.

Once the sun goes down, grab a bottle of wine — might I suggest some Chianti — and head to the Santa Trinita Bridge.

It’s beautiful to see the reflections of buildings at night on the Arno River, and there are many people on the bridge also sharing some wine and taking in the peace.

Montepulciano (Tuscany)

9. Take A Scenic Bike Ride

If you’re active, I highly recommend a scenic bike ride with Cortona Wine Tours through the UNESCO World Heritage-listed Val d’ Orcia.

The valley is known for inspiring Renaissance painters and being landscaped in a way that led to locals living in harmony with nature.

You’ll cycle through cypress-lined paths, olive groves, medieval towns and endless rows of sangiovese, the predominant grape in the famed Vino Nobile di Montepulciano wine.

While challenging — it’s those steep rolling hills that make Tuscany so beautiful — it’s worth it for the views.

Bonus:

The 21-kilometer ride ends with a delicious farm-to-fork Podere Il Casale.

Clinking glasses of homemade wine while sharing plates of house-made pici (a local chickpea-flour pasta) and suckling pig laced with goat’s milk and ginger, the tastes and company were enhanced by a gorgeous aerial view of the valley.

If you’d prefer not to exert so much energy, Cortona Wine Tours also offers private wine tours by car, as well as Vespa tours, truffle hunting excursions and custom experiences.

Perugia (Umbria)

10. Stay At An Agriturismo (With Pets!)

While we stayed at some amazing accommodations, our favorite was Agriturismo La Fonte, a gorgeous farm stay accommodation in Perugia.

I was shocked to learn that not many Americans visit Umbria, skipping over it for the nearby Tuscany.

Which is a shame, because Umbria — known as the “green heart of Italy” — is so breathtakingly beautiful.

As soon as we drove onto the property and saw our apartment backed by endless rows of olive bushes and chestnut trees, we were in heaven.

Inside, a table showcased a spread of homemade and farm-sourced goodies:

Fresh eggs, lemon cake, tomatoes, olive oil, preserved eggplant and zucchini, jam, bread and a bottle of red wine — which quickly got poured into our glasses as we ducked out onto the patio to take in hillside views.

On property, we hiked, lounged by a pond, napped in hammocks, played with dogs and cats, swam in the pool, played ping pong and foosball, and just enjoyed the feeling of complete peace and quiet.

This is a must-stay in Italy! Also, if you’re looking for weekend getaways from Rome, Perugia is a popular option.

Amalfi Coast

11. Trek The “Path Of The Gods”

The 5-mile “Path Of The Gods” — also known as “Il Sentiero degli Dei” — sits beautifully embedded into the slopes of Monte Peruso.

It begins in Bomerano and ends in Positano, taking you along the hillside towns and ancient ruins.

According to The New York Times, the Path was “carved out by Greek settlers in the eighth century B.C. and was later used by those living in secluded monasteries.”

Not only are you traversing history, but the views over the sparkling Gulf of Salerno and of Naples as you wind your way up and down the terraced hillside are absolutely jaw-dropping.

What’s really neat is you have a view of chic Positano and its pastel-colored houses most of the time, so your eye is literally on the prize as you hike.

This was one of the most stunning, interesting hikes I’ve ever done.

Bonus: it’s free!

Naples

12. Have A Heavenly Island Getaway In Ischia

Just a 90-minute scenic ferry ride from Naples port sits Ischia, an island settled by the Greeks in 770 BC that’s shrouded in mythology.

In fact, it’s said that after an altercation with Zeus, a monster named Typheus was banished to live under the island, which is why it’s filled with volcanoes and thermal pools.

For the perfect itinerary stay in Ornella’s Airbnb in the island’s Campagnano neighborhood, a true slice of heaven on earth.

The accommodation has both a lush garden terrace and 360-degree rooftop, both offering gorgeous views of the medieval Aragonese Castle, the Gulf of Naples, and the adjacent islands of Procida and Vivara.

On the island also don’t miss a hike to the top of Mount Epomeo, the highest point on Ischia at 2,589 feet.

Follow the adventure with a wander through Sant’Angelo, a pastel-hued village full of artisan and clothing shops.

One favorite:

NaturIschia, where Andy and I sampled free tastings of local limoncello, locally-made liqueurs laced with melon and pistachio, and delicious chocolates filled with limoncello.

From there, walk down to the sandy Chiaia di Rose Beach, secluded Cava Grado Beach or the steamy Le Fumarole Beach.

Travel Insurance

While you hope everything runs smoothly, sometimes travel just doesn’t go according to plan.

This is why I recommend always purchasing travel insurance. The scary truth is it only takes one bad accident to lose everything — or be thankful you were covered.

Personally, I use SafetyWing, as they’ve got a large network, offer both short-term and long-term coverage (including limited coverage in your home country), are budget-friendly, and offer $250,000 worth of coverage with just one low overall deductible of $250.

Click here to price out travel insurance for your trip in just a few clicks.

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Italy Road Trip Travel Infographic