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 Italy itinerary when we vacationed during the winter months 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.
The first stop on our Italy itinerary was Rome
When booking our vacation in Italy it was important for us to experience the local culture so we decided to book our stay at Hotel Lirico in Rome. It’s a small Italian-run boutique hotel located 5 minutes from Termini Train Station next door to the Teatro dell’ Opera di Roma.
The entire staff was lovely. They served a simple and satisfying breakfast every morning of cappuccino and homemade pastries.
Our home base was 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 elevator up to your room.
When we were deciding our Italy itinerary, we considered staying at a hotel near the Trevi Fountain but we 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. Our hotel was quieter with occasional wafts of music coming 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 hop-on-hop-off buses. They 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 terrific production of La Traviata.
Highlights of our itinerary in Italy included tours of the Vatican and the Public Market at Mercato di Campo de’ Fiori with Walks of Italy and Cinecittà Film Studios, where Federico Fellini shot his films.
Restaurants in Rome are practically on every block and it’s hard to find a bad one.
Off to Tuscany
Next on our Italy itinerary after Rome to take a high-speed train to Florence. We knew we’d be back in Florence on our cruise so we didn’t book a hotel there.
Instead, 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 served an elegant breakfast buffet and also had a 5-star restaurant where we dined one evening.
Montecatini Terma and the surrounding areas are famous for their spas. We spent an afternoon and 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 spent part of a day there. It’s a completely walled in, well-preserved and fascinating to explore. We were there in winter, but during the summer you can rent bikes and ride around it.
The next day our hotel suggested we visit the hill town of Montecarlo di Lucca. I love the hill town experience even more than the big cities 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 the holidays while we were there.
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 up above it. We drove up instead.
Southern Tuscany – Siena and the Chianti wine region
We left Montecatini Terma and headed to Siena. On the way, we stopped at Greve in Chianti for lunch and then drove up to Castellina in Chianti, another charming hill town. A good way to avoid crowds in Tuscany, especially during the high season, is to visit the more obscure hill towns rather than the most popular ones. They all have fascinating histories.
We stayed at Hotel Italia in Siena. It’s another boutique hotel located just outside the Porta Camollia gate. The lobby is modern and decorated with kitschy photos of movie stars and vintage ads. The rooms, themselves, are more Tuscan with colorful tiles and furnishings.
The ladies at the desk were helpful and always friendly. We parked our car in a small gated parking lot in the back, and it was a quick walk to the old medieval city.
Siena is a fascinating and dark-walled city rich in history and intrigue. I was impressed by how clean and safe it was to walk around, especially at night. There weren’t any hustlers lurking around harassing tourists like we saw in Rome, Florence, and Pisa.
If you are visiting in the summer, you can enjoy 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 in Siena since the middle ages.
Cici is a type of pasta that the area around Siena is known for so the staff at our hotel recommended we try some at a restaurant called Trattoria FonteGiusta. Of course, you have to wash it down with locally grown Chianti because Siena is in the Chianti region of Italy.
On the way to Sorrento
Siena was hard to leave, but Sorrento was next on our Italy itinerary so we were back on the road again heading south.
Along the way, we stopped in Montepulciano, a larger and very vibrant hill town. After exploring for several hours, we had lunch at Caffè Poliziano, established in 1868 where we ordered homemade Tuscan soup and appetizers.
Throughout Tuscany, Pinocchios are everywhere. You can see them standing on rooftops or as statues on the streets. The author of the story, Carlo Collodi, was born in Florence.
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
After passing through Naples, we entered 3 long tunnels that were constructed to help ease traffic that led to the sea towns. But, once we got inside, we found ourselves stuck in a nasty traffic jam. We slowly chugged past several towns and were wondering if staying in Sorrento was a mistake.
However, once we arrived, we were pleased with how charming and romantic Sorrento is. Our mistake was driving during rush hour. There was also an Italian film festival in town causing some of the jam.
If you are vacationing in Southern Italy, Sorrento is a convenient area to base your stay. We spent 4 nights at Hotel Antiche Mura, another lovely boutique establishment. It sits on top of a deep crevice with an ancient mill at the bottom of it and is a block away from Piazza Tasso, the main square in downtown Sorrento.
Our room was large with a picturesque balcony view. The staff at the reception desk never hesitated to help us and staying there was a thoroughly enjoyable experience.
Partying like Fellini
As members of the film industry, we managed to snag free tickets to the Italian film festival Giornate Professionali Di Cinema that was in town.
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.
A private tour of the Amalfi Coast
No stay in Sorrento is complete without a drive along the Amalfi Coast. Rather than risk it ourselves, we booked Giuseppe from Sorrento Coast Drivers as our private driver. Before we headed to the coast, he suggested we stop at an olive oil factory he knew of just outside of town where we sampled various oils with crusty bread.
It rained off and on that day, but we didn’t mind and Giuseppe was a trooper through it all.
We stopped briefly at the seaside village of Positano. In the summer it’s crowded with tourists but because it was the off-season we had the town all to ourselves. A few shops were open so I bought a dress for our upcoming cruise and some lovely hand towels.
We continued along the coast to Amalfi and went inside its extraordinary cathedral. Its Baroque interior dates back to the 18th century and you can see glimpses of the original Romanesque church.
The altar is decorated with statues from ancient pulpits and the preserved head and bones of Saint Andrew are housed in the crypt.
Over the hill to Pompeii
There was a road closure after Amalfi, so we left the coast and drove through the mountains to Pompeii. It had rained sporadically throughout the day and completely dumped its load as we walked through the ruins.
That didn’t stop us or the others who were there that day. The rain made the ruins sparkle and look more mysterious. The only downside was it took a couple of days for my walking shoes to dry out.
Boarding the ship at the old Roman port
Our Italy itinerary on land was almost over as it was almost time to begin our Mediterranean cruise.
The day we left Sorrento, Giuseppe picked us up to take us to the Naples train station. He even walked us into the station to make sure we got on the right train. We truly appreciated that 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.
We took the high-speed train back to Rome and then boarded 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
The first port on our itinerary was Livorno in Northern Italy in Tuscany. The day included excursions to Florence and Pisa.
Florence’s Italian name is Firenze which is appropriate because it IS a “frenzy.” Even in winter, there are tons of tourists as well as all sorts of characters lingering about. I can’t imagine going there during the high season. It’s an incredible city but just make sure 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 meet the bus to Pisa.
Pisa’s main attraction is the Square of Miracles where you can visit the Leaning Tower, the Baptistry, and the Cathedral. However, just outside the entrance, you’ll see hustlers and souvenir vendors gathered to sell you whatever they have to offer. It reminded me of Tijuana.
Our guide pointed out a group of girl pickpockets that got all bent out of shape when they found out we had identified them.
The three monuments are well worth seeing once you’re safely inside the square.
Watch out for those selfie sticks
Selfie sticks were being hawked by hustlers almost everywhere in Italy but, especially in Rome, Florence, and Pisa.
We held out for a while but finally bought one. They take a little getting used to.
The weather was almost always comfortable while we were in Italy during November and December except for an occasional thundershower. That time of year is considered to be the rainy season but, for the most part, we stayed dry. Temperatures ranged between the high 50’s and low 60’s and we were fine wearing light windbreaker jackets most of the time.
When you’re ready to set your Italy itinerary we hope the links below give you inspiration
Italian-run 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 We were very impressed with the Food and Market tour and also the tour of the Vatican we took in Rome.
- 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. Maybe it can help you plan your next trip. Please leave a comment below.