We spent three weeks in Italy visiting Rome, Tuscany, Sorrento, and the Amalfi Coast before taking a cruise of the Mediterranean. This post lays out our entire Italy vacation itinerary with resources at the end. It was an amazing trip and I wanted to share where we went, the boutique hotels we stayed at and the fabulous restaurants we ate at.
First stop on our Italy vacation itinerary: Rome
When booking our vacation in Italy it was important for us to experience the local culture so we decided to spend our 5 nights in Rome at the Italian run Hotel Lirico. It’s a tiny and charming hotel located 5 minutes from Termini Train Station and directly next door to the Teatro dell’ Opera di Roma.
The entire staff was lovely. They served a simple and satisfying breakfast every morning with a delicious cappuccino.
The hotel’s a quick walk to restaurants, trains, subways, and tour buses and was reasonably priced. You have to climb about 20 steps to reach the main lobby, which might be difficult if you have trouble walking, but once you check-in, you can take a small lift up to your room.
Before we left on our Italy vacation, we considered staying at a hotel near the Trevi Fountain but were glad we didn’t. The Trevi Fountain was scaffolded at the time we were there but the area was still filled with tourists and hustlers. Hotel Lirico is quieter with occasional wafts of music from the adjacent Opera house.
The Hop on Hop Off Bus and touring Rome
While we were in the Eternal City, we took advantage of riding the hop-on-hop-off buses. Their stops dropped us off within walking distance of the Colosseum, Roman Forum, Pantheon, Spanish Steps, Vatican and the Trevi Fountain.
We also found time to spend an evening at the Teatro Salone Margherita (an opera dinner theater circa 1898) where we enjoyed a sumptuous meal while watching a fabulous production of La Traviata. I loved our food and market tour with Walks of Italy and our tour of Cinecittà Film Studios, where Federico Fellini shot his films.
Other than one restaurant we went to that had fishy tasting swordfish, we struck gold every time we went out to eat. Restaurants in Rome are everywhere and it’s hard to find a bad one.
Off to Northern Tuscany and Montecatini Terma
For the next part of our vacation in Italy we took the high-speed train from Rome to Florence. We knew we’d be back in Florence on our cruise so we didn’t book a hotel there.
We rented a car from Sixt Car Rentals and drove to Montecatini Terme in Northern Tuscany where we spent 3 nights at the Ercolini E Savi Hotel. It is a chic boutique hotel located a half block from the main boulevard. They have an elegant and large breakfast buffet and a 5-star dinner restaurant where we dined one evening.
The area is famous for its spas so we booked massages at Grotta Giusti in nearby Monsummano Terma and swam in their refreshing natural mineral pool.
A side trip to Lucca and nearby hill towns
The medieval town of Lucca was a short distance away so we decided to spend a day there. It’s a completely walled in, well preserved and fascinating to explore.
The next day our hotel suggested we take a look at the hill town of Montecarlo di Lucca. I love the hill town experience much more than the big cities packed with tourists and we ended up visiting several. Since it was the off-season, the towns were quiet with very few visitors, making it easy to walk around, take pictures and talk to locals. They were just starting to decorate for holiday festivities.
We also explored the hill town of Montecatini Alto. During the high season, you can take a funicular straight up from Montecatini Terma to the older hill town. We drove up there instead.
Doug’s a cranky driver without GPS, so we solved that problem by uploading an app to our phone called Map Factor. You have to download all the maps first and it worked even when we were going through tunnels. The only glitch was that it didn’t always take an exact address. We named our GPS voice Emma because she had such a delightful English accent. It also took the stress off me as a navigator.
Southern Tuscany – Siena and the Chianti wine region
On our way to Siena, we stopped at Greve in Chianti for lunch and then drove up to Castellina in Chianti, another charming hill town. If you want to avoid too many tourists, consider visiting some of the more obscure hill towns rather than the most popular ones.
We spent 2 nights in Siena at Hotel Italia, located just outside the gates of the old city. The hotel lobby is modern and decorated with kitschy photos of movie stars and vintage ads. The rooms were more Tuscan with colorful tiles and furnishings.
The ladies at the desk were helpful and always friendly. We were able to park our car in a small gated parking lot in the back, which was convenient and it was a quick walk to the old city gates.
Siena is a fascinating and dark medieval city rich in history and drama. We were impressed by how clean and safe the old city was. There were no hustlers or gypsies lurking around that we could see harassing tourists as they did in Rome, Florence, and Pisa.
Students walked comfortably through the streets at night alone. (Not that I’d recommend doing that) If you are visiting in the summer you can see the famous Palio di Siena, which is a horse race that takes place at the Piazza del Campo on July 2 and August 16. It’s been a tradition since the middle ages.
Cici is a specific pasta associated with Siena and the ladies at the hotel recommended we try a restaurant called Trattoria FonteGiusta that offers it deliciously homemade. And when you are in the Chianti region it’s always best to wash it down with a rich glass of the local red grape.
On the way to Sorrento
Siena was hard to leave, but we were soon back in the car and on our way to Sorrento.
Throughout Tuscany, you’ll notice various Pinocchios standing on rooftops or as statues on the streets. He’s still a popular character.
It was a long drive to Sorrento but the roads throughout Italy are smooth and immaculate. Just be prepared to pay a toll on the main highways. We were impressed by how easy they were to drive.
The romantic village of Sorrento
The weather throughout Italy during November and December was almost always comfortable except for an occasional thundershower. It’s considered to be the rainy season but we were lucky. Temperatures ranged between high 50’s and low 60’s so we were able to wear light windbreaker jackets most of the time.
If you are going on a vacation to Italy the winter months are not only festive but there are way fewer crowds.
After passing through Naples, we entered 3 long tunnels that were constructed to help ease traffic to the sea towns beyond. But, once we made it through, we found ourselves stuck in a nasty traffic jam. We slowly chugged past several nondescript beach towns and were wondering if staying in Sorrento was a mistake.
But once we arrived, we were pleased to see how charming and romantic it really is. Apparently, we made the mistake of driving during rush hour and there was also an Italian film festival going on causing the jam.
When planning your Italy vacation in the South, Sorrento makes a perfect home base. We stayed for 4 nights at the Hotel Antiche Mura. The hotel sits on top of a deep ravine with an ancient mill down at the bottom.
It’s a stunning location a block from the main street. Our room was large and beautiful. The staff at the reception desk never hesitated to help us and we thoroughly enjoyed our suite with its picturesque balcony view.
Partying like Fellini
Doug was able to snag free tickets to the Italian film festival (Giornate Professionali Di Cinema) because he helped publish a magazine for movie camera operators.
This entitled us to attend several nightly parties and receptions, including a Fellini-inspired disco bash “Koch-Tail Party for Koch Media” at the underground Fauno Notte Club complete with Roman goddesses yielding grapes.
A private tour of the Amalfi Coast
Giuseppe from Sorrento Coast Drivers took us on a leisurely tour along the Amalfi Coast and our first stop was an olive oil factory outside of Sorrento.
It was raining off and on that day, but we didn’t mind and Giuseppe was a trooper through it all.
We briefly visited the lovely seaside village of Positano. It was the off-season and we practically had the town to ourselves. Still, a few shops were open and even though it’s started to rain, I bought a dress for our upcoming cruise and some Italian hand towels.
During the summer Positano is packed with visitors. It was wonderful to be able to wander through the streets without hardly anyone else in sight.
Afterward, we continued on to visit the cathedral and have a snack in the town of Amalfi, where we also visited its extraordinary cathedral. It has a Baroque interior that dates back to the 18th century that conceals the original Romanesque church.
The altar is decorated with statues from ancient pulpits. In its crypt, the preserved head and other bones of Saint Andrew are housed there.
Over the hill to Pompeii
There was a road closure after Amalfi, so we left the coast and drove through the mountains to visit Pompeii. It had rained sporadically throughout the day and completely dumped it’s load as we walked through the ruins.
It didn’t stop us or the few people that were there that day. In fact, it made the ruins sparkle and made them even more mysterious. The only downside was it took a couple of days for my walking shoes to dry out.
Giuseppe was calm as a cucumber and always had a smile on his face. If you happen to be in Sorrento and are looking for a driver who’s reasonably priced and reliable, please check him out. What a sweetheart! The day before our tour, Doug had driven to Naples to ditch the car. We were glad he did because driving the Amalfi Coast would have been a challenge, especially in the rain.
Leaving for our cruise and our trek to the old Roman port
On the day we left Sorrento, Giuseppe picked us up to take us to the Naples train station. He walked us into the station to make sure we got on the right train. We truly appreciated it because, in large cities like Rome and Naples, there are plenty of hucksters who are eager to help you find your train and exhort exorbitant tips.
From Naples, we headed back to Rome on the high-speed train and then took a local train to Civitavecchia to board The Cunard Queen Elizabeth. Civitavecchia is an ancient seaport that still has some of its original walls and towers. We arrived late and missed the crowds boarding the ship. To our glee, we were upgraded to a Queen’s Suite.
Back to Tuscany – Florence, and Pisa
Our first stop on the ship was to be our last stop in Italy on our vacation. The next day we landed in the port of Livorno.
Our itinerary for our cruise included excursions to Florence and Pisa. Florence’s Italian name is Firenze and I think it’s appropriately named because it is a “frenzy.” Even in winter, there are plenty of tourists, as well as hustlers everywhere. I can’t imagine going there during the high season. You definitely have to watch your purse.
Cruise excursions are always rushed, but we were able to see the main sites, including the Florence Cathedral and Ponte Vecchio, before hurrying to leave again for Pisa.
Pisa’s main attraction is the Square of Miracles. There you’ll find the Leaning Tower, the Baptistry, and the Cathedral. Just outside the square, hustlers and souvenir vendors abound. It almost reminded me of Tijuana. Our guide pointed out a group of girl pickpockets that became huffy and rude when they found out we had identified them.
The three monuments are spectacular once you’re safely inside the square and definitely worth seeing.
Watch out for those selfie sticks
While we were in Italy on vacation, Selfie sticks were being hawked by hustlers everywhere, especially in Rome, Florence, and Pisa. It’s a long stick with a holder for your cell phone at the end. A remote control syncs with your phone’s Bluetooth.
Press a button and take a picture of yourself with historic monuments in the background. They’re actually great to have but be careful not to get your eye poked out by a passing tourist who has one.
Book Your Italy Vacation Today Using the Resources Below:
Boutique hotels we stayed in
- Lirico Hotel – Via del Viminale, 31 – 00184 Roma +39 06 48906230
- Ercolini & Savi Hotel – Via S. Martino, 18 Montecatini Terma, Pistoia 51016 0572 70331
- Hotel Italia – Viale Cavour 67 Siena +39 0577 44248
- Hotel Antiche Mura – Via Fuorimura 7 – Piazza Tasso Sorrento, 80067
Schedule a walking tour
- Walks of Italy +39 069 480 4888 www.walksofitaly.com We were very impressed with both tours we took in Rome, the Food and Market Tour, and also the Vatican.
- Tours by Locals – Find a local guide to take you on a private and personalized tour.
Enjoy a mineral bath and spa experience
- Grotta Giusti Spa – Via Grotta Giusti, 1411 Monsummano Terma – massages, treatments or swim in thermal natural mineral spring waters.
How we got around in Italy
- Sixt Car Rentals – We picked up our car in Florence and drove it throughout Tuscany. Sixt is available in Europe as well as the United States.
- Big Bus Tours Rome – The hop-on-hop-off bus is the best way to get around in Rome and Big Bus Tours do an excellent job. You can get all around the city with narration, which makes it much more fun.
- Sorrento Coast Drivers – Our private Driver was Giuseppe Glielmo – We loved this guy! He’s a sweetie pie! If you are visiting Sorrento, Naples, or the Amalfi Coast, look him up. Via Lucia 24 Sorrento, 80067 +39 33361 32502
- Rail Europe – You can’t beat train travel in Europe to get around from place to place quickly. Plus, you get to see the countryside.
Favorite restaurants we ate in
- La Forchetta d’Oro – This was the first restaurant we had dinner at and it was spectacular. Small, local, hidden away and absolutely delicious.
- Ristorante Enoteca Giovanni – Via Giuseppe Garibaldi, 25, 51016 Montecatini Terme, +39 0572 71695. We ate Thanksgiving dinner at this restaurant but arrived too early (7:30 pm) and were told to come back around 9 pm. Italians don’t like it when you make them rush. The food was wonderful and we made friends with a U.S. Airman and his wife who were having Thanksgiving there too. (We didn’t eat turkey, though – LOL)
- La Cascina – Viale Giuseppe Verdi, 43, Montecatini Terma. 39.0572.78474. A beautiful and family-friendly restaurant with seating available in their outdoor patio and garden during the warm season.
- La Pecora Nera at the Ercolini & Savi Hotel – Elegant and a little more high-end but exquisite cuisine.
- Trattoria FonteGiusta – Via Camollia, 102, Siena 53100, 0577 40506. Our hotel recommended it and we ate there twice. Their homemade pici pasta is excellent.
- Caffe Poliziano Via di Voltaia del Corso, 27-29 Montepulciano, 53045, 0578 758615 A quaint and beautifully decorated Art Nouveau caffé with a spectacular view of the Tuscan wine region from its balcony. We had Tuscan soup and bruschetta. The cafe also has tasty looking pastries.
- Ristorante Il Convivio – Via Correale, 19 Sorrento 80067 081 877 3530 Owned by a man and his daughter. They had fresh whole fish that they would cook and then filet at the table. We had delicious homemade Scialatelli pasta (native to Sorrento) with fresh local fish. They don’t have a website but it’s well worth finding this wonderful restaurant.
- Ristorante Da Filippo – Located up in the hills of Sorrento, this restaurant is a local favorite and popular. They came and picked us up from our hotel because it’s hard to find. Excellent food.
- Ristorante Pizzeria Tasso – Via Correale, 11d Sorrento 80067 +39 081 878 5809
I hope you enjoyed our Italy vacation itinerary and that it helps you when you are planning your trip? Please leave a comment below.