Ultimate Two Week Itinerary in Italy

Ultimate Two Week Itinerary in Italy

We spent 19 charming days in Italy including stops in Venice, Bologna, Tuscany, Rome, Naples, Capri, the Almafi Coast and Matera. With such high expectations for Italian perfection we fought through the depressingly mediocre and came up with our ideal two-week vacation itinerary. Our journey brings you through a broad swath of culture and culinary delights.

Day 1-3: Venice

Exploring the streets of Venice
What's Groovy: Getting lost in the streets and aperitivos along the canal

It’s a known fact that Venice is full of tourists, so we were happy to stay in the quieter Cannaregio area at the Una Venezia hotel. Getting there was easy on the 15 Euro “B” line water taxi. If you're in the mood there are private taxis - expensive but a fully loaded experience! Our hotel was close to all of the tourist sights, but offered the tranquility found in the less travelled streets. The service was excellent with free tea and coffee throughout the day and free aperitivos from 6-8pm. Cold Prosecco on ice and tea sandwiches became part of our daily route before going out for dinner.

Stunning sunset from the Ponte dell'Accademia

The first recommendation you will usually see for Venice is to “get lost” in the streets, but it’s truly the best thing to do, especially on an empty stomach! There are many narrow streets and you are bound to find a hidden café with delicious cicchetti. Cicchetti are savoury small snacks usually served in bars or low key restaurants. My favourite was salami and artichoke on a slice of baguette and Ari’s was fig and prosciutto. Aperol Spritzes are claimed to have been invented in Venice and consist of an orange herbal liquor, Prosecco, and soda water. We had lots of them during our three nights there and the prices ranged from 3 Euros all the way to 12 Euros! You probably guessed that the 12 Euro Aperol spritz’s were found in St. Mark's Square, the famous piazza created in the ninth century. The cheaper Aperol spritzes were found in the less touristy areas and in bars that serve cicchetti.

Our favourite restaurant of the three nights and in all of Italy was Enoteca Ai Artisi. The restaurant was welcoming and the wait staff were friendly and enthusiastic. Our top dishes were the scallops, which were seared to perfection and the mussels, which came in a delicious broth. I never liked mussels before and thought I would try one of Ari’s. Game changer! I had four of them. There is not a lot of seating, so make sure you make a reservation in advance.

Day 4-8: Tuscany

Podere Felceto agriturismo in Panzano
What's Groovy: Staying at an Agriturismo overlooking the countryside, eating delicious Tuscan cuisine, and drinking Chianti Classico wine

We originally spent three nights in Tuscany and almost immediately wished we had planned for five nights in the rolling hills of the countryside.

It’s a breeze transferring from city to city on the train. We hopped off in Florence and grabbed a car rental to drive into the Tuscan hills. We booked our stay at an agriturismo with an Italian family near the town of Panzano in the Chianti region. An agriturismo is an authentic farmhouse that serves guests and it's a fantastic way to experience the nature while escaping bustling cities. We stayed at Podere Felceto, a tranquil organic live oil farm that sits on the side of a hill overlooking a tree laden valley. We were delighted to see a small bottle of Chianti wine, olive oil products, and a bag of fresh lavender awaiting us in our room. Our friendly host made restaurant suggestions for us in the town of Panzano and gladly called to book us in. We also pre-booked a homemade meal from our hosts at Podere Felceto for the third night of our stay. Their daughters who went to cooking school in Florence would be cooking it for us and it was a delight to stay in and not worry about having an extra glass of wine or shot of limoncello!

Chianti region

Staying in an agriturismo was one of our best “hotel/airbnb” experiences so far on our trip. It felt like staying in a gorgeous chateau, however it had a homey feel and the recommendations and history we received from the host family were stellar. It felt like we were living like locals!

Our first night we dined at Ristorante Oltre Il Giardino. Not a complaint to be had. We ordered papardelle pasta with a wild boar sauce, rooster, and pork ribs. We started with a glass of Prosecco and then ordered a glass of the 2013 Chianti Classico, which is known to be an extraordinary year for the region.

The second night we dined at Dario Cecchini's steakhouse Officina Della Bistecca. He is considered one of the most famous butchers in the world and his family has been in the butchery business for eight generations. We arrived 15 minutes early to a butcher shop filled with cheering tourists. Dario was blasting AC/DC Highway to Hell and chopping up meat with a huge cleaver. We were then invited through the back up to the top dining floor to a communal table where they brought you slab after slab of steak that was cooked on charcoal right in the same room. There were five varieties of cuts. My favourite was the beef tartare and Ari's was the bistecca florentina. Warning: if you only like your steak well done, make sure to let them know when you get there!

We also had time to take a winery tour at Castello di Verrazzano that came recommended by our host. The winery was formerly an estrucan and then roman settlement. It was the best wine tour we've ever been on. Our tour guide was passionate and we learned a lot about the history of the region and Chianti wines. You can easily book your tour online here. We wished we had a couple extra nights in Tuscany to explore the surrounding area and visit more wineries. We highly recommend at least five nights in the area!

Day 9: Naples

Sorbillo Pizza
What's Groovy: The best pizza in the world!

We chose Naples as our stopover along the way to the Almafi coast. It's easy to take a train from Florence and then rent a car for the journey to the Almafi region. Naples was a far cry from anything we had previously seen in Italy as it's one of the poorest cities in Europe. The only thing we knew of the city was that it's where the Italian mafia is from. Once we exited from the train station we was astonished by the shabby look of the central city and felt unsafe with strangers coming up uncomfortably close to our backpacks as we walked to our airbnb. The streets were narrow and locals drove their motorbikes very fast through crowds. It took some getting used to but ended up being ok for us.

There is an interesting charm to the city and we had the BEST PIZZA OF OUR LIVES at Sorbillo Pizza. Don't try anywhere else, just go, maybe twice! The pizzeria and its pizza maker, Gino Sorbillo, is the most famous in Naples. It's in the Michelin guide for its outstanding and tasty pizza. Ari is a pizza fanatic and it topped his list by far.

Naples is a great hub for trips to Pompeii and the Almafi Coast, but if it doesn't sound like your vibe you can take a 40-minute hydrofoil ferry from Naples to Sorrento on the Almafi Coast and pick up your rental car there.  If you choose this method, we recommend adding an additional day to fit in the luxurious island of Capri, which is a one hour ferry ride from Naples. From Capri it's only a 20-30 minute ferry ride to Sorrento to start your journey to the Almafi Coast!  

Read: How to take a day trip from Naples to Capri

Day 10-12: Almafi Coast

Positano from the water 
What's Groovy: Relaxing beachside in Positano and taking a boat trip along the coast

Driving to the Almafi Coast was not the peaceful scenic drive you see in magazines. The roads are small, windy, and filled with speedy locals and large tour busses trying to squeeze by! It's certainly manageable but not the slow rubbernecking coastline drive we imagined. We stayed an hour outside of Positano in the quiet village of Furore to escape the crowds. Perched on the cliff, our hotel Holidays Fico D'India was easy on the budget and the perfect simple escape with beautiful sea views. Just an 8-minute walk up the hill was our favourite restaurant on the Almafi coast, Bianca Zita Ristorante Enoteca. It has no menu but the waiter will tell you what is available that day. The fish they served was delicate and well portioned!

We took two day trips from our hotel. The first was a day trip to see the beautiful town of Positano and relax beachside. The next was to the town of Almafi where we rented a private boat with some friends to see the coast and Positano from the water. We rented a 39 foot boat and captain for four hours with the company Almafi Boats. They had great service and a reasonable cost considering the prices to rent boats from Positano. Our captain navigated down the coast where we saw beautiful hotels, beaches, caves and an entirely different perspective of the place. It was golden hour the whole afternoon and it was a delight to go for a quick swim. We played our music from the boat and brought aperitivos and Aperol Spritzes. Now that was relaxing!

Golden hour in the late afternoon at the Almafi Coast

Day 13-14: Matera

View of the old city from our Airbnb in Matera
What's Groovy: exploring one of the oldest continuously lived in cities in the world.

The hidden gem of our trip to Italy was Matera. The 9,000 year old city went from an ancient civilization to a poverty-stricken area and now to Europe's capital of culture and setting for Hollywood movies! The drive from Almafi to Matera was leisurely and took 3.5 hours.

We stayed at an airbnb located in the centre of the Sassi, which is a network of cave houses. It was another one of the best airbnb experiences we've ever had, especially since they had adorable cuddly cats. Outside of our apartment we had a marvellous view of the old city. As we sat on the patio and enjoyed our espresso our favourite cat of the three, Rufus, would always be there for some head scratches. Across the ravine you could also marvel at the natural caves, which were home to Neanderthals more than 50,000 years ago!

Natural caves in Matera

Each evening we sat along the streets at our favourite spot, Monkey Drink House, and sipped mojitos while people watching. There was a grocery store near by and we bought fresh Italian ingredients to make delicious pastas back at our airbnb.

From Matera, it's only a one hour drive to the Bari International airport where you can drop off your rental car and fly home or to your next destination!

Read: 5 Reasons You Should Visit Matera, Italy

Monkey Drink House

Our tour through the middle and southern regions of Italy was a great adventure and full of discovery. Unfortunately, Rome and Bologna did not make the list. The combination of city life in Venice, wilderness in Tuscany and scenery on the Almafi Coast make for a diverse itinerary that changes in pace allowing you to both recharge and also to fill your sense of adventure.  

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