Pienza might just be the prettiest tuscan town there is. Planned by Pope Pius II. in the 15th century (and - humble as he was - named after himself). And where else can you have perfect italian coffee/spritz in Via dell'amore with views on the beautiful tuscan hills? Montalcino isn't far from there, if you are into wine. Funnily enough, the Piccolomini family of which Pius II. was a member, still produces excellent Brunello there.
Ravenna was the last capital of the western Roman Empire and it has beautiful old churches and mosaics. It's kind of a dark horse pick, but I was very happy I was able to squeeze it in when I visited Italy years ago.
Modena, to visit the Motor valley (Ferrari, Lamborghini and many others), drive a Ferrari in the racetrack, and eat at the restaurant Francescana of Massimo Bottura, considered the best restaurant in the world 3 years out of last 10, and stay at his B&B. It’s very close to Bologna. I know Massimo and I own sport-cars. It would be a pleasure to host you here. If you like the idea, drop me a message at massimo@fahorro.biz
Go to the top of Vesuvius, 1hr by car South-East of Napoli, very close (obviously) to Herculaneum, etc. You can drive close to the top and it's a quick hike to the top. Look at the surroundings and ask yourself what would happen if it were to erupt (it's officially still active as far as I know.)
You'll probably see all the good sights in Sicily:
But make sure you hit up the church in the Piazza dei Normani in Palermo. That church has an amazing an eclectic blend of Latin, Byzantine, and Arab artistic influence. Yay for the mishmash!
The Carthaginian ruins at Motya is a hard to access spot, but very cool (there's a lot of room for debate about whether they were burning babies in those jars).
For Italy here are some hidden gems:
The Royal Palace of Caserta, which is the same as the Star Wars Naboo Palace.
The Tivoli Fountains at Villa D'Este outside of Rome.
Most importantly of interest for you Bryan would be Villa Torlonia, which has Mussolini's house and bunker, a museum, faux-ruins, and 20th century oddities.
Pisa is on your list, but I will say about it that I loved the cathedral there. It is also less crowded than it should be due to the stupid, leaning bell tower next door.
I particurarly like Civita di Bagnoregio, also known as "la città che muore" ("the dying town"), as it only has 12 residents now (according to Wikipedia), but still several residents. The natural sight around is nice, and if there's any area in Lazio where I would suggest to eat, it is precisely the Bolsena Lake area rather than the slightly overrated so called "Roman castles" in the South of Rome.
Alba and the surrounding hill towns of Babaresco, Seralunga, Barolo, Castiglione Falletto, . . . Stunningly beautiful, wonderful bike and hiking, a unique wine making culture, fantastic foods including but beyond all the white truffle rage. We've always found the people of these villages incredibly friendly and open.
You will find a much more 19th century 'bent' to this part of Italy and a more modern, experimental attitude throughout the still plentiful family owned vineyards.
I spend a lot of time in Italy and I know a lot of people in Napoli. Please feel free to contact with any specific questions about Napoli and environs. Napoli is disorderly and messy, and has some very rough looking people on the streets, but it's reputation for crime is completely undeserved and I've never had any problems there.
The most general advice I have is that for every very famous, crowded, tourist site, there is somewhere nearby that is much more pleasant and 95% as good. One example is to go to Ercolano instead of Pompeii.
I would highly recommend renting a car at some point to visit smaller towns that are not accessible by train. Driving outside the cities is easy. If you do this, you will be really glad you did.
I've never heard anything good about Pisa, you might want to reconsider visiting there.
The gelato is amazing, but educate yourself about how to identify the good gelaterias.
Neapolitan pizza absolutely lives up to its reputation, and probably offers the best price/quality of any food in the world. Gino Sorbillo, Decumani, Da Michele, and Starita are all fantastic. If you are in Vomero, Federico Gaurdascione's pizzeria is as good as any of those. All those places can be crowded, but if you go to lunch at noon (a reasonable time to eat lunch for Americans, but too early for Italians, you can usually get a seat without waiting.
Fried pizza might sound strange or bad, but please go to la Masardona and eat some. You won't regret it.
Eat seafood in Napoli.
I would be very happy to help you identify a good neighborhood to stay in in Napoli. I will be there from the 17th of June until the end of the month- it sounds like you will already be up north by then, but if you're around Napoli I'd be happy to meet with you.
Italy has a lot of little things (I.e. off the beaten path) everywhere. I would suggest renting bikes to explore any city you are in. You will stumble across small ruins, great cafes, great restaurants, and fun things to do. That said I would visit Pisa as a day excursion from Florence (a quick train ride). This guide, I believe was originally linked on MR, is excellent - you will find great gelato everywhere except Venice.
Pienza might just be the prettiest tuscan town there is. Planned by Pope Pius II. in the 15th century (and - humble as he was - named after himself). And where else can you have perfect italian coffee/spritz in Via dell'amore with views on the beautiful tuscan hills? Montalcino isn't far from there, if you are into wine. Funnily enough, the Piccolomini family of which Pius II. was a member, still produces excellent Brunello there.
Modena is gorgeous, as is the small city of Treviso.
Ravenna was the last capital of the western Roman Empire and it has beautiful old churches and mosaics. It's kind of a dark horse pick, but I was very happy I was able to squeeze it in when I visited Italy years ago.
Modena, to visit the Motor valley (Ferrari, Lamborghini and many others), drive a Ferrari in the racetrack, and eat at the restaurant Francescana of Massimo Bottura, considered the best restaurant in the world 3 years out of last 10, and stay at his B&B. It’s very close to Bologna. I know Massimo and I own sport-cars. It would be a pleasure to host you here. If you like the idea, drop me a message at massimo@fahorro.biz
IIRC, Serie D is officially an amateur soccer league, but with teams covering expenses that make it not so amateur for all. Group I of Serie D appears to be the group with Sicilian teams. The last regular season games are Sunday, May 22. https://us.soccerway.com/national/italy/serie-d/20212022/group-i/r65622/matches/
Go to the top of Vesuvius, 1hr by car South-East of Napoli, very close (obviously) to Herculaneum, etc. You can drive close to the top and it's a quick hike to the top. Look at the surroundings and ask yourself what would happen if it were to erupt (it's officially still active as far as I know.)
You'll probably see all the good sights in Sicily:
But make sure you hit up the church in the Piazza dei Normani in Palermo. That church has an amazing an eclectic blend of Latin, Byzantine, and Arab artistic influence. Yay for the mishmash!
The Carthaginian ruins at Motya is a hard to access spot, but very cool (there's a lot of room for debate about whether they were burning babies in those jars).
For Italy here are some hidden gems:
The Royal Palace of Caserta, which is the same as the Star Wars Naboo Palace.
The Tivoli Fountains at Villa D'Este outside of Rome.
Most importantly of interest for you Bryan would be Villa Torlonia, which has Mussolini's house and bunker, a museum, faux-ruins, and 20th century oddities.
Pisa is on your list, but I will say about it that I loved the cathedral there. It is also less crowded than it should be due to the stupid, leaning bell tower next door.
I particurarly like Civita di Bagnoregio, also known as "la città che muore" ("the dying town"), as it only has 12 residents now (according to Wikipedia), but still several residents. The natural sight around is nice, and if there's any area in Lazio where I would suggest to eat, it is precisely the Bolsena Lake area rather than the slightly overrated so called "Roman castles" in the South of Rome.
Alba and the surrounding hill towns of Babaresco, Seralunga, Barolo, Castiglione Falletto, . . . Stunningly beautiful, wonderful bike and hiking, a unique wine making culture, fantastic foods including but beyond all the white truffle rage. We've always found the people of these villages incredibly friendly and open.
You will find a much more 19th century 'bent' to this part of Italy and a more modern, experimental attitude throughout the still plentiful family owned vineyards.
I spend a lot of time in Italy and I know a lot of people in Napoli. Please feel free to contact with any specific questions about Napoli and environs. Napoli is disorderly and messy, and has some very rough looking people on the streets, but it's reputation for crime is completely undeserved and I've never had any problems there.
The most general advice I have is that for every very famous, crowded, tourist site, there is somewhere nearby that is much more pleasant and 95% as good. One example is to go to Ercolano instead of Pompeii.
I would highly recommend renting a car at some point to visit smaller towns that are not accessible by train. Driving outside the cities is easy. If you do this, you will be really glad you did.
I've never heard anything good about Pisa, you might want to reconsider visiting there.
The gelato is amazing, but educate yourself about how to identify the good gelaterias.
Neapolitan pizza absolutely lives up to its reputation, and probably offers the best price/quality of any food in the world. Gino Sorbillo, Decumani, Da Michele, and Starita are all fantastic. If you are in Vomero, Federico Gaurdascione's pizzeria is as good as any of those. All those places can be crowded, but if you go to lunch at noon (a reasonable time to eat lunch for Americans, but too early for Italians, you can usually get a seat without waiting.
Fried pizza might sound strange or bad, but please go to la Masardona and eat some. You won't regret it.
Eat seafood in Napoli.
I would be very happy to help you identify a good neighborhood to stay in in Napoli. I will be there from the 17th of June until the end of the month- it sounds like you will already be up north by then, but if you're around Napoli I'd be happy to meet with you.
Italy has a lot of little things (I.e. off the beaten path) everywhere. I would suggest renting bikes to explore any city you are in. You will stumble across small ruins, great cafes, great restaurants, and fun things to do. That said I would visit Pisa as a day excursion from Florence (a quick train ride). This guide, I believe was originally linked on MR, is excellent - you will find great gelato everywhere except Venice.
https://www.exurbe.com/tag/gelato/
Remnants of the Gustav Line and other field fortifications,if any, around Monte Casino.
Castel del Monte is fantastic, as is Monte Cassino.
In Florence, eat at La Buchetta https://labuchetta.com Lo Scudo https://www.loscudohospitality.com and 4 Leoni https://www.4leoni.it/?lang=en. Florence has great vendors for leather goods - authentic goods will have a stamp that certifies it was made in Italy, like the underside of a belt or backpack
Orvietto - off beaten track and stunning