Two Week Italy Itinerary: From Coast to Country

Ciao Italy! This picturesque country, known for its rich history, delicious cuisine, and stunning landscapes, provides the perfect backdrop for creating unforgettable memories. In this blog post, i’ll guide you through everything you need to know for an enchanting trip that takes you through the charming cities of Milan, Tuscany, Sorrento, and Rome – with small stops in-between! I took this trip for my honeymoon and I couldn’t recommend it enough to anyone. Stay tuned for my two week in Italy cost breakdown post!

Table of Contents

• What to Bring
• Transportation in Italy
  • Trains
  • Rental Cars
  • Private Transfer
  • Scooter/Vespa
• Best Time of Year to Visit
• High-Level Itinerary
• Detailed Itinerary
  • Airfare

What to Bring

Here are a few things you may not think to bring aside from your standard toiletries, Italy is not underdeveloped, so you can buy some of these things there. However, coming prepared always relives stress during your vacation.

• Converter: they have different outlets than us and my husband and I each used one
• Packing cubes: were so essentially to packing 15+ outfits
• 1 carry-on, 1 large checked luggage: my husband fit all our things + souvenirs in these two
• Collapsible Water Bottle: We used this on day trips/while traveling often
• Crossbody: something cute but functional was so important, my husband also used one and said he found it very crucial to have
• Portable Charging: we kept this in our bags when we would go out for the day, planes & trains will have charger outlets available
• Medicine Organizer: Corner stores are not as available in some of the countryside cities/stays, so MAKE SURE to bring your own medicine for any relief (pain, stomach, cold)
• Sunscreen: you will get burnt, especially in south Italy in the summer, we did end up bringing a small one and buying a bigger one there
• Light Jacket, few pairs of pants: summers are warm and I wore linen pants occasionally and a jacket not many times

Transportation in Italy

Traveling in Italy is SO easy! While we were there we used: high-speed trains, rental cars, private transfers, trams, buses, scooters, and our two feet quite a bit.

Trains

Let’s start with trains as this is usually the hot topic. The trains in Italy are incredibly easy to navigate, affordable, well kept, and very reliable. We used Italo Tren, and I couldn’t recommend them enough. Their website is user-friendly and they are one of the two major train systems in Italy (the other is TrenItalia). I went with Italo based off reviews & recommendations.

Let’s be clear the answer is YES you should book your train tickets in advance. Why? because if you know which day you’re traveling, it makes no sense to not book it. Saves time while your traveling, eliminates stress & guessing the day of!

We took Italo trains: Milan→Tuscany, Tuscany→Naples, Naples→Rome. During the train rides you can pick from 4 ticket classes: Smart (Economy), Prima (Business Class), Club Executive (Executive Class), Salotto (First/Private Cabin). The prices on average will be around:  € 20,  € 30,  € 50,  € 80. The rates increase and decrease based on time of day & if its refundable. We mainly did Prima but did one trip in Club Executive, Prima is wonderful and plenty of luxe for the short trips. The crew does come around to provide you with drinks, treats, and small hot foods. It was all very yummy!

When you arrive at the train station, you have to wait until the terminal shows you the train station number it gets assigned. This typically happens 20 minutes before the trains departure time. The trains move quick and don’t wait for anyone so make sure to show up at least 30 minutes before you depart.

Rental Cars

We rented a car to drive around Tuscany, best decision ever! Some people will try to scare you, but driving in Italy is exactly like driving in a city in the USA. Roads are a bit more narrow and of course the road signs are different, but we managed to have a car for one week – free of accidents or getting lost. We used apple maps to get us around, though a lot of people prefer Google Maps, both worked fine! We got a Jeep Renegade which was plenty of room for just the two of us.

Private Transfer

We were on our honeymoon so a place that we splurged were in private transfers. This is when an individual or company sends a car to get you from point A to point B. The cars are typically higher end, I believe they were mostly Mercedes. You would use a private transfer in place of public transportation like Uber/Taxi, Bus, Tram etc. We used a private transfer to/from both Milan and Rome airports, to/from Naples train station to our stay in Sorrento (longer drive), and our stays in Milan & Rome. Prices range on average from $50-$100 one way depending on distance, company, vehicle size etc.

**Note: Uber is not used in Italy, they have an app called “free now” which is essentially an Uber for Taxis.

Scooter/Vespa

We did rent a vespa in Sorrento for 3 days! Gosh was this a whirlwind of fun and thrilling. Only my husband drove, I sat on the back and held onto him. In Sorrento, I would not recommend a rental car, the roads are made up of mostly one ways, are extremely curved, and generally chaotic. It didn’t rain while we were there (5 days), except for during the night, maybe twice, so we didn’t have to worry about getting caught. We used this to drive around the city of Sorrento (though its truly not needed) and to head down to Positano for a day trip. The trip to Positano was unbelievable. You scale the side of a mountain on a two-way road where you’re passing busses, cars, and other vespas. This drive is not for the weak (stomach haha – I did get a bit car sick but was fine). My husband says driving the Vespa was one of the highlights of the trip, it was truly a ton of fun and gave us so much additional freedom.

Best Time of Year to Visit

Embarking on a honeymoon journey through Italy in early June proved to be the perfect choice for us. With temperatures soaring, each destination we found ourselves thankful for the time of year we chose to visit. Our trip was from May 29 – June 13. Not only did we want to enjoy the beaches during our Honeymoon, but we also wanted to leave within a few days after our wedding, which worked out for us.

Some would say June is not the best time to go because of tourism but we didn’t find it to be terrible in most of the locations we visited. The most tourist-packed place we visited was Capri, it was definitely busy and not the most enjoyable part, but we still had a great time! As far as weather goes, we will be forever grateful for the wonderful weather we had. In Tuscany, a few of the days it would rain for about an hour around 5 p.m. In Sorrento, we didn’t experience any rain during the day! If I were to go again, I would possibly choose to visit mid to end of May to avoid tourism peak and still be able to enjoy the weather.

High-Level Itinerary

Detailed Itinerary

I am going to dive into our specific itinerary with restaurant recommendations and all the little details. Several friends & family have taken our itinerary, made it their own, and used it to explore the beautiful country of Italy in a holistic view.

Airfare

My husband and I flew Delta direct from JFK (NYC) → Milan, then back from Rome → JFK. Our flight in JFK departed around 7:30PM EST and was scheduled to land around 10AM CET. It’s said that doing an overnight flight from the USA to Europe avoids jetlag in the most natural way, IF you’re able to get some sleep on the flight. Upon arrival the Milan airport was nearly empty and there were only the people from our flight standing in the customs line.

Day One – Milan

While heading out of Milan Airport customs we were greeted by our driver holding up a sign with our name on it! We opted for the Private Transfer option when we booked our hotel to get us from the airport to the hotel.

Milan Hotel: The Street Milano Duomo – this hotel was very well kept, spacious rooms, very kind front desk staff, about a 2 minute walk from the Duomo and Galleria Vittorio Emanuele II. When we got back to our hotel we took about a 2/3 hour nap, this allowed us to feel fully recharged from attempting to sleep upright on the plane. In the late afternoon/evening some of the things we checked off our list were:

• Walked to Sforzesco Castle (15 minute walk)
• Explored the Brera Area – I would highly recommend, all of the business professionals hung out here after work to get dinner/apps with their coworkers.
• Had our first charcuterie experience at La Prosciutteria Milano – it was so delicious we ate here twice!
• Dinner: Nero 9 – it was delicious but accidentally ate a big pre-dinner meal
• Dessert: Baunilla

Day Two

This was a relaxed day in Milan spent freely exploring the city! It seems like Milan doesn’t get a good rep but we absolutely loved it and would definitely return.

• Breakfast at the Hotel – surprisingly delicious
• Check out all the shopping – hit up the brands made in Italy and make sure you take advantage of the VAT tax refund!
• Starbucks Reserve Roastery – this was really cool, especially seeing the ones in the US.
• Lunch: La Prosciutteria Milano – it truly was that delicious!
• Dinner: Pizza on the rooftop of our hotel with a bottle of wine

Day Three – Tuscany

Headed off to Tuscany! We were highly anticipating this area of the country and it did not disappoint us one bit! Starting off the day we called a taxi to get us to the train station where we picked up our Italo Tren! The train system in Italy is very advanced & easy to navigate.

Our train ride from Milan to Florence was about 2 hours, it was so smooth and fascinating as it was our first high speed train ride. When we arrived into the Florence train terminal, we headed to the car rental location which was at the Florence airport. We were warned about scammers near the terminal in Florence and there was a bit of that happening but it’s easy to ignore and keep moving. We took the city tram over to the airport, picked up our car and headed to our airbnb!

• Car rental: Avis Airport
• Airbnb: Bed & Breakfast in the countryside, a few miles south of San Gimignano / I would highly recommend this airbnb, we loved it!
• Dinner at our AirBnb’s fine-dining restaurant: Restaurant Zafferano – it was a bit pricey, unique foods, and was very highly rated!
• In the evening we popped up to San Gimignano to check it out & get some gelatto!
• Gelateria Dondoli is said to be the best gelatto in all of italy! It was surely yummy!

Day Four

Everyday we woke up in Tuscany we enjoyed our free Airbnb breakfast & hung out by the pool for a few hours.

• Full exploration day of the town of San Gimignano: we fell in love with this medieval looking town, the landscape, small shops, it all was incredible.

• Lunch: Tasty pasta bowls, this place was a local, family owned gem – called Osteria delle Catene

In the evening we decided to drive to The Mall Firenze which is a luxury outlet near Florence. This was about 40 minutes from our Airbnb, it was SO worth it. They have most of the big designers (especially all made in Italian: Prada, Gucci, Armani etc) at an extremely discounted price. If you’re into designer, make sure to make the trip. The two Gucci bags below were listed at $400 (smaller) & $600 (larger). I am sure these are older styles but it was still great prices for authentic luxury items.

• Headed back to San Gimignano for Dinner: La Biscondola. I would say this was our least favorite dinner spot, but nonetheless it tasted fine

Day Five

• Our typical breakfast and pool rotation
• Lunch at a little sandwich shop in San Gimignano called Forno Moderno: I would absolutely say this was the best pizza in Italy!
• The evening we drove over to the Chianti region for our winery tour (about 30 minutes)

The Winery was called Le Miccine Winery. It was an Airbnb experience and we adored this tour. It was very intimate, 8 people, and our host was very knowledgeable. The tour started with a walk around the grounds, how wine is made, then ended in a tasting tour. Of course, we had to get a package of wine sent back to our home in the US! We met a few people from Australia that when we told them we were from Scranton, PA, USA they freaked out because they didn’t think the place from “The Office” actually existed & they were huge fans! That was a really funny & cool experience we had.

• We headed back to San Gimignano to have dinner at Le Vecchie Mura. This was one of the best meals we had in Tuscany, we marked this as one of the best carbonara we had in Italy, and we had it many times!

Day Six

Ciao Siena! We took a day trip down to the beautiful Siena. This was around 40 minutes from our BnB. Another place we loved, it had beautiful architecture & great food.

• Hang out in the amphitheater area
• Buy tickets to the Siena Duomo, it was a must see!
• Lunch at: another incredible pasta restaurant, Osteria il Carroccio
• Explore all the little shops and allies

We headed back to our base in the evening and decided to venture around a grocery store. This was a fun experience! Their grocery stores are wildly affordable in Italy. We bought a few bottles of wine as souvenirs to take back home, you can’t beat the prices of what you find in their grocery stores. This place was called “Pam Superstore.”

• We ended the evening splitting a bottle of wine and enjoying some pizza from a local shop in San Gimignano. We made friends on the patio and hung out until the later evening.

Day Seven

One week down in Italy and we feel like we can live in this place forever. This day was probably our favorite day in Tuscany because it was the day of our cooking class. We found this Airbnb experience hosted by a woman named Katia. Another small group, I believe there was 6 of us. This cooking class taught you the joy of cooking from start to finish.

This takes place in her home, which overlooks the beautiful landscape of Tuscany. You start by hand making Pici pasta, something we loved so much we now do this at home. She teaches you about cheese tasting (which she was highly educated in). Then, our appetizer was bruschetta with capers, YUM! We made two different types of sauce, one red and one white. They were not traditional sauces, but wow did they taste delicious. As the protein, you make Saltimbocca, which again is something we are now obsessed with and make all the time. Of course, you are served with a red and white wine at dinner that she teaches you about. The host Katia, was incredibly kind, passionate, and so knowledgable! I would run back to this experience if given the chance.

Day Eight – Sorrento

Goodbye Toscana (Tuscany) – our favorite place in Italy! Today we embark on our journey to a little town off the shoulder of the Amalfi Coast, Sorrento.

• The trip day begins with taking the rental car back to Avis
• Hopping on the tram to head back to the train station, catching the train to Naples (2-3 hours)
• Private transfer vehicle from Naples train station to our Hotel in Sorrento
• Check into the Grand Hotel Riviera in Sorrento
• Dinner: Our roof top restaurant that overlooks the Mediterranean sea, a literal dream

This hotel was a bit of a splurge, but to be honest most places in or around the Amalfi coast are going to be on the pricey side. If we were to stay in Sorrento again I would absolutely stay here. Private beach, private pool, huge spread of free breakfast, incredible views, kind staff & it was very clean! This hotel is somewhat central to the downtown area, about a 10 minute walk.

I am going to be upfront with my opinion of the Amalfi Coast area… We truly enjoyed Sorrento as a base and would stay in this town again. However, not all the places feel authentic Italy and some feel very americanized. The landscape is gorgeous and i’m so happy we visited here but I wanted to preface with my opinions up front. And by the way, I don’t think you would ever catch me staying in Positano, i’ll get into that below!

Day Nine

A picture is definitely worth a thousand words and wow did this hotel take our breath away. Most hotels on the coast are positioned on-top of the rocks, and the beaches are built below. That was a photo of my husband hanging out in swim area with our hotel right above. Don’t worry, there is an elevator to get down!

The beach is a dock with tons of chairs and steps to get down into the water. If you don’t stay at a hotel that has a private beach (like this one) you will typically need to pay to go on the public access beaches in the area. Find a hotel with a beach if possible as the public access beaches are very crowded!

In the evening we wandered the town and ate at the famous Ristorante O’ Parrucchiano, under the lemon trees! For how popular this place was, the food was very good. Make SURE to make a reservation in advance. We really enjoyed this experience.

Day Ten

Every morning we had complimentary breakfast which overlooked the sea, it was so beautiful to start every morning like that. Today we had a private boat tour around Capri! We found a guy named Paolo, who owned Amazing Capri Tour. He has a boat that can accommodate a handful of people. His rates were very affordable for a private tour around the island, and surely this was the thing to do!

• After breakfast we took a public shuttle boat over to Capri, it was about 20 minutes
• Met Paolo at his spot in the Marina
• Took a three hour private boat tour around the island of capri
• Saw some coves, took a swim, saw the famous Faraglioni rocks and enjoyed listening to the rich history Paolo provided us with
• We even got to see Tommy Hilfiger’s yacht him and his family hang out on!

After the boat tour we walked around the island of Capri. There are many luxury shops, a chair lift, ice cream shops, and a gondola that goes up the mountain. We ate at il Geranio, a recommended restaurant I found in a Facebook group. The restaurant overlooked the rocks and had delicious food. I would suggest checking this place out!

Capri was a beautiful island but it was very busy compared to any other spot we had been. A bit too touristy for us, but we are happy we got to see it! We spent the afternoon and into the evening here then headed back to the mainland.

Day Eleven

• Our typical morning started with breakfast, delicious as it was every day
• Hung out by the beach & went out on the town
• Had lunch at Ristorante Fuoro, another small local gem – so yummy!!

My husband was envious of all the people on the scooters/vespas. We found a local place who rented them and decided to rent it for the remainder of our trip, it was an amazing decision! From here, we took a day trip down to Positano.

As mentioned above, we were not in awe over Positano but it was definitely a beautiful place to see. The drive to Positano was insane. You scale the side of a mountain on a narrow road for about 30 minutes. On a scooter, it feels like forever!

• Toured around the town and shops, everything was much more expensive in this town, it was very apparent this was a tourist destination
• Had dinner and snacks at Le Petit Murat Lounge Bar. We had fun here, live music, good drinks, fun atmosphere, kind people – what more can you ask for?
• Headed back to Sorrento in the evening

Day Twelve

A very relaxed day in Sorrento

• Breakfast & Beach
• Exploring the other sides of town with the Scooter
• Late lunch/dinner at Ristorante Terazza delle Sirene, one of the best Carbonara!
• The hotel we were staying at was having a wedding and the couple had fireworks on the water in the evening that we got to see! It was so magical

Day Thirteen

Goodbye Sorrento, Hello Roma!

• Private Transfer back to Naples train station
• <1 Hour Train to Rome
• Taxi from Rome train station to our Hotel
• Our Hotel was Hotel Delle Nazioni – less than 30 seconds from the Trevi Fountain
• Dinner at That’s Amore restaurant, another fabulous find!
• Walked around Rome, shopping, Spanish steps, Trevi Fountain

Day Fifteen

We chose to do the first Vatican City tour of the day. I believe we had to be at the Vatican for 7AM. Let me tell you, this was SO worth it. The Vatican gets insanely busy, every single day! The Vatican tour was put on by the company called “Walks Tour.” This was a small group – 15 of us. This allowed us to get to know the tour guide, ask questions, and have a very personalized experience. The Vatican tour was by far one of the highlights of our trip. The history was truly incredible, as was the architecture! The tour takes most of the day, approx 7am-2pm.

After our Vatican tour we walked around and saw some more land marks. We had our FAVORITE meal of our whole trip in Rome! The restaurant was called il Chianti Vineria! We got the cheese selection, cacio e pepe, and the beef & gravy dish. The savory flavors of this meal was unbelievably good!

Day Sixteen – Departure 🙁

We had our hotel arrange us a taxi for the early morning. Our flight departed around 10am. Make sure to get to the airport extra early so that you can take advantage of the VAT Tax refund which you have to do at the airport on your way out! We got back a TON of money (like $400) – so worth it!

Italy was so incredible to us. We had the trip of a lifetime and will remember this forever. We will be back to see more of northern Italy!