14-Day Italy Itinerary (Rome – Chianti -Florence – Venice – Milan)
Me and my wife went on our maiden trip to Italy in March-April 2019 for 14 days. We preferred traveling on a slow pace, taking in the sights while sparing some time to absorb the atmosphere. Our itinerary is mostly influenced by the local food and wine affair. We mostly walked, but used trains, trams and also drove in certain areas (Tuscany).
We flew Qatar Airways from Penang and landed in Rome, making our way to the Tuscan country of Chianti, spent a few nights in Florence where we did day trips to Cinque Terre and Pisa followed by Venice and departed from Milan. We read countless blogs and travel guides, watched plenty of YouTube videos to prep for this trip. It was time-consuming but it was definitely well worth it as we had one of our memorable experiences of our lives.
It is worth to note that we traveled with luggage, so we opt for premium accommodation closer to train stations for convenience. Also we booked premium class seats on intercity trains for a bit of privacy and extra security. Here is a transcript of our itinerary.
Day 1
- Arrival in Rome
- Train from Airport to Roma Termini (€8 per pax)
- Check-in Hotel: The Independent Hotel (6 mins walk from Roma Termini) – €298 for 2 nights
- Vatican Museum & Sistine Chapel Fast Track Entry (€46 for 2 pax) – Book via Klook Note: Vatican Museum is closed on Sundays
After visiting the Vatican Museum, we stumbled upon this cozy restaurant at the corner of the street 100m away called La Caravella. We had early dinner before heading back. Understandably the price is higher due to the proximity to major attraction site but it tastes good and we enjoyed our time.
Day 2
- Colloseum, Roman Forum and Palatine Hill Skip the Line (€28 for 2 pax) – Book via Klook
- Trevi Fountain
- Spanish Steps
- Galleria Alberto Sordi (Shopping)
We spent the last our dinner in Rome at Trattoria Cecio within walking distance from our hotel. Trattoria is an Italian-style eating establishment, less formal than a ristorante, but more formal than an osteria. Usually they are also less expensive compared to ristorante. Was surprised that they even produce their own wine. We were lucky to get a seat without reservation as the place is usually full to the brim. So reservations are recommended. Alternatively, you may try the food gallery at Roma Termini station with plenty of options to choose from.
Day 3
- Train from Roma Termini to Firenze SMN (€59.80 per pax)
- Train from Firenze SMN to Florence Airport (€15 per pax)
- Pick up car from rental Sixt (BMW Series 1 Auto – € 196.12 for 3 days) *Malaysians require an International Driving Permit (IDP). You can apply from JPJ at RM150 per year.
- Check-in: Salvadonica Agriturismo (€304 for 3 nights)
Salvadonica Agriturismo experience was certainly one of the highlights of our stay. Breathtaking views from our room and how can you not admire the Italian Cypress trees which epitomizes the Tuscan landscape. Read my Tripadvisor review.
The Tuscan countryside is less accessible by public transport, so it is recommended to rent a car if you wish to fully explore the area. If you decide to drive, it is advisable to rent a car from Florence airport as the city area is a no-drive zone for tourists. You may end up with a hefty fine! So check out local driving regulations before you decide to rent a car.
There was no need to venture out for dinner as they had an excellent restaurant on-site La Volpenera. This is where we had our breakfast too. We sampled authentic Tuscan cuisine, our favorite was the beef tagliata with black truffle, rabbit stew and black truffle pasta. When you are in center of Chianti Classico, you drink Chianti Classico!
Day 4
- Explore San Gimignano
San Gimignano is an Italian hill town in Tuscany, southwest of Florence about a 45-minute drive away. Encircled by 13th-century walls, its old town centers on Piazza della Cisterna, a triangular square lined with medieval houses. We had lunch at a restaurant located inside the La Cisterna Hotel, named Le Terrazze. The restaurant has the best view overlooking the towers. We had the opportunity to taste the local San Gimignano wine made from Vernaccia grape.
Day 5
- Explore Greve
- Winery visits: Antinori winery, Castello Di Gabbiano
Situated 20 minutes from Val de Pesa is the town of Greve in Chianti. It is the principal town in the Chianti wine district. Nothing much here, so we ended spending more time enjoying our lunch. The town and restaurant was quite deserted even though it was lunch time. It was a challenge to choose a place when almost all of them are empty, eventually we ended up at la Terrazza. Nothing spectacular here so we moved on.
Antinori nel Chianti Classico is quite renowned and one of the biggest wine producers in Italy. It is free to enter and visit its facility with futuristic architecture. We did not do the tour but went for the tasting room instead. The wines were expensive so did not buy any. We can easily find a good bottle of wine for much less elsewhere.
If you have time, I suggest you take a drive south to Val d’Orcia which is approximately 2 hours drive. It has one of the most stunning landscapes of the Tuscan countryside.
Day 6
- Return car and arrive at Florence
- Check in: Airbnb (€476 for 4 nights)
- Piazza del Duomo
- Piazza della Signoria
- The Uffizi Gallery (Optional)
- Ponte Vecchio
- Pitti Palace and Boboli Gardens
- Santo Spirito (Dinner)
After checking into our Airbnb, we had lunch at the nearby Ostaria Dei Centopoveri recommended by our host. It was just at the corner of our apartment and a very good deal indeed. For €10, you get two courses with water and 1/4 wine each. Coffee and dessert are an extra €1 and €3 only. Our most inexpensive meal in Italy by far.
After wondering around Florence and before we knew it, it was time for Aperitivo. Aperitivo is the Italian version of happy hour with pre-dinner drink accompanied by salty snacks. We stumbled upon Caffe Donnini 1894 right in the center of the Piazza della Repubblica. We noticed this place charged a bit higher than the others but they offered 3-tier canape so it was fully justified.
Day 7
- Accademia Gallery Skip the Line (Michelangelo’s David – €32 for 2 pax) – Book via Klook
- Piazza Santa Croce and the Basilica of Santa Croce
- Piazzale Michelangelo for the best view of Florence (Sunset view)
After visiting the Accademia Gallery, we settled for lunch at Il Bottegone next to the Duomo. We knew for sure that prices will be elevated but we can’t help admiring the Duomo and we enjoyed people watching. Food was not too bad which made the overall experience even more awesome!
Before leaving Florence, it is a must to head to Piazzale Michelangelo to catch a glimpse of the most spectacular sunset over Florence. On the way, you will go pass the Ponte Vecchio and a short climb over the steep hill. Order some drinks and chill by the Vip’s Bar for the most romantic experience.
Day 8
- Explore Cinque Terre
- Train from Firenze SMN – Cinque Terre (Riomaggiore – €39.50 per pax)
- Manarola
- Vernazza
- Monterosso
- Riomaggiore
- Corniglia
Cinque Terre simply means 5 villages, is a string of centuries-old seaside villages on the rugged Italian Riviera coastline. In each of the 5 towns, colorful houses and vineyards cling to steep terraces, harbors are filled with fishing boats and trattorias. It is recommended to buy the Cinque Terre pass, for unlimited train travel on the Levanto – Cinque Terre – La Spezia line and also complimentary access to toilets.
If you have limited time and want the best views, I suggest to visit Vernazza for lunch and Manarola for the amazing sunset.
The best place to chill and watch the sunset over the colorful houses is Nessun Dorma at Manarola. This place is especially packed so make your way there early to secure a seat to have an unobstructed view. They serve drinks and snacks only (bruschetta, meat and cheese platters). Don’t expect to order a pasta or pizza here. Oh ya, do take note of time if you are doing a day trip we had to rush to catch our train back to Florence. Check out the time for the last train.
Day 9
- Explore Pisa
- Train from Firenze SMN to Pisa Centrale (€17.20 per pax)
The leaning tower of Pisa needs no introduction and a day trip here should be on your bucket list if this is your first time to Italy. It is just over an hour’s train ride from Florence. We had lunch at Ristorante Il Toscano which was enjoyable but not over the top. We admired the toilet decor, wished we could have spent more time here 🙂
Day 10
- Train from Firenze SMN – Venezia S. Lucia (€59.80 per pax)
- Check-in: Airbnb (€598 for 3 nights)
- Explore Venice (Piazza San Marco, Saint Mark’s Basilica, Doge’s Palace, Bridge of Sighs, Rialto bridge, Grand Canal)
- Gondola ride (€80 for a 30 minute ride)
- For best sunset view of Rialto Bridge, go to Taverna Al Remer order an Apertivo to pair with Cicchetti and sit by the pier.
We stayed in a beautiful apartment in Venice. It had a complete kitchen and we could do our laundry after so many days on the road. The place is not too far from the action and there is a grocery store just nearby. Our host welcomed us at the pier, offered valuable tips and gave us a bottle of local Prosecco, which we loved. After so many days of eating out, we missed home-cooked food so my wife dished out amazing meals with her great culinary skills using local ingredients (Check out her cooking at Kelly’s Private Kitchen). She was ecstatic to find fresh chilies from the supermarket!
To tick off our bucketlist, we had to do the gondola ride. Private gondola rides costs €80 for a 30 minute ride. You may share the cost if you can find another willing couple as the boat can take a maximum of 4 passengers. I wouldn’t say it was one of our most enjoyable experiences but we had to do it since it was our first time. The gondolier cut our ride short by 15 minutes, we didn’t make a fuss and we were just glad to have taken the photos we wanted.
For the most romantic sunset views overlooking the Grand Canal and Rialto Bridge, head to Taverna Al Remer (read my TA review here). Our Airbnb host referred this secret hideout. We ordered Spritz and cicchetti (small snacks or side dishes, typically served in traditional “bàcari” in Venice) and made our way to the pier to enjoy the sunset. It was one of the most amazing experience!
Day 11
- Shopping at Noventa di Piave Designer Outlet (Prada, Gucci, Furla, Fendi, Coach, Polo Ralph Lauren, etc)
After so visiting so many attractions, we spared some time for a little bit of retail therapy. Noventa di Piave Designer Outlet is located an hour away from Venice by shuttle bus. We took much longer ~2 hours as we took the train and bus. It was worth it as we found great deals, plus we get tax refunds (22%) at the airport. Check out VAT refund rates across different countries in Europe.
Day 12
- Explore Burano (Recommended to skip the 3 island tours)
- Have lunch at Michelin-star restaurant Al Gatto Nero (They open at 12pm, we made our reservation when we arrived at the island and had some time to explore around). Read my TA review here.
Day 13
- Train from Venezia S. Lucia to Milano Centrale (€59.80 per pax)
- Check-in Hotel: Glam Milano Hotel (Ideal location – just across the Milano Centrale) – €370 for 2 nights
- Explore Chinatown
- Sempione Park
- Duomo di Milano
- La Galleria Vittorio Emanuele II
The Glam Milano Hotel is very strategically located, just 100m away from Milano Centrale and accessible to major attractions. The price we paid includes breakfast and dinner, so it was great value.
While you are in La Galleria Vittorio Emanuele II, check out Camparino in Galleria serving the popular Spritz drink. The Spritz is an Italian cocktail made using soda, Prosecco / sparkling white wine and usually Campari or Aperol making it the signature amber color. If you love people watching like us, this is the perfect place to do it.
Day 14
- Explore Milan
- Spend the evening at Navigli (Great place to hang out and people watching)
On our last evening in Milan, we checked out Navigli which is a vibrant area with pubs and restaurants lining along the canal. We ordered a bottle of wine and watched endless people walking by. Notice the tables are arranged facing outwards for the very purpose of people watching.
Day 15
- Depart Milan
This concludes my trip report to Italy. Hope you find this information useful and have a safe trip. If you have any questions, please write it down in the comment section and I will try my best to respond. Good luck!
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