While we wait for the cool podcasts I have coming up next week, tell me about the time you went to Italy and help me plan what to do there with my kid before he runs off to college.
David - I'm from Italy, grew up in Rome. I understand the urge to see it all, but I would highly recommend focusing on just ONE (maybe two) regions. As in Latium, or Tuscany, Emilia Romagna, or Friuli-Venezia Giulia. Take the train, you will have a much better experience moving around towns than dealing with the stress of driving in Italy as an American (expect some delays at times but generally good, frequent, practical service). I'd also add that late June/early July gets hot in Rome so depending on your heat tolerance you might prefer being closer to the Alps (I personally love those temperatures but it's not everyone's cup of tea). Basically, resist the FOMO, know that Italy will likely remain exactly the same for a bit of time, and enjoy delving into the vast cultural richness of its regions. Buon viaggio.
You have already figured out what you need to do. It's this: "We could spend more time in Rome (which begs for an extended stay) and then just hang around Tuscany, eating and looking at old stuff and eating."
I am very excited on your behalf. You will all have a blast. That said, I have strong opinions on your potential itineraries.
Depending on how long you stay in Rome, you could add a few days on tail end in Dolomites. Hanging around Tuscany eating is, to my mind however, non-negotiable.
1) Dolomites over Venice.
Venice is fascinating and one-of-a-kind, sure, but it will be up to its eyeballs in tourists and the whole experience will just remind you generally of sea level rise and you'll see the vapors of their travel-related GHGs hovering over the heads of all the tourists jostling you in Piazza San Marco. Risk is high that frustration>>revelation if you go there in June. One cool thing about the Dolomites, aside from all the great hiking and vistas etc, is that the culture/language/cuisine is very Alpine, inflected by proximity to Austria/Bavaria/Switzerland etc, while also somehow still Italian. Bolzano is a good jumping off point.
2) Siena+Lucca over Cinque Terre+Florence.
I'm biased because I spent a semester living in Siena in college and had a sense while I was there, eating fantastic food and strolling the old city center and happening upon random banquets and musical parades in the streets held by the 17 contrade (neighborhoods), that 'This is it, life has peaked, it's all downhill from here.' Cinque Terre - while spectacular, we hiked it, good times were had - will, like Venice, be jammed with fellow tourists to the point of driving you to dive into the sea. And, as any Siena partisan will tell you, Siena is so much better than Florence. In every way. Skip Florence. Trust me. And like Siena, Lucca is a walled town on a more welcoming scale - good for an afternoon of flaneur-style wandering.
TLDR: Use Siena as a base for several days. Walk around and eat and look at art. Take half-day excursions to surrounding villages like Sam Gimignano and Monteriggioni and Castello Brolio, etc.
I'm so happy for your family that you get to take this amazing trip. I've been struggling a lot with balancing my love of travel and experiencing this miraculous gift of a world, with the fact that flying is actively contributing to its destruction. (Electric planes, come faster!) I've cut down on my flights a LOT, but am still in favor of flights for special, important occasions. Like your son going off to college!
All of that to say...I traveled to Italy as a teenager and loved Rome and Venice. But I think seeing the Dolomites would be absolutely incredible. So I'd be in favor of skipping Venice to spend more time in Tuscany and to see the Dolomites in person. Also, crazy trip change idea: What if you skipped Bologna and Venice to visit Lake Como and travel through the Italian Alps to the Dolomites? I'm a mountain girl so I may be biased, but if your sons love beautiful views, that could be a cool alternate route.
I also love your trip ethos - no matter where you go, it's going to be amazing! :)
Wiser and more experienced heads than mine have posted a lot of good advice here already, but I can't resist weighing in with a few points!
1) The Slow Food guide to Osterie and Locande was invaluable and took us to many truly wonderful restaurants. Not sure if it's up to date, but probably worth it even if there's not a recent edition.
2) A strong vote for visiting Bologna. Marvelous food, beautiful city, a joy to walk around.
3) Maybe this is obvious, but I'd recommend cars for places where you want to get out into the countryside or into nature and trains for getting between larger towns and cities. High speed trains are probably faster, and most definitely a more pleasant experience. (Though I found Italian drivers, while very forceful, surprisingly capable--less flakey than I'm used to stateside. Note that this is a statistically insignificant observation.)
4) I'd agree with those saying to cut Cinque Terre. Exploring Italian villages is one of the great pleasures of life, but the experience just a million times more agreeable if they're not overflowing with tourists.
5) Genoa is great, but probably not in the same league as your other destinations, and given your constraints might make sense to cut.
6) I'll unhelpfully recommend a couple other places: Ravenna was capital of the Roman empire for a while and has incredible architecture and art, including mosaics not unlike those of San Marco (if you miss Venice). Perugia, Arezzo, Gubbio are all magnificent hill-towns/cities, and close enough to your route that you might consider them. Val d'Aosta is a fantastic combination of numerous castles and alpine scenery.
1. Rome & Cinque Terre will be extremely hot and jam-packed with tourists in July. Dolomites less so.
2. I typically miss salads and vegetables on my travels through Italy. Vedura alla griglia can help.
3. We don't have ruins in the US, but we have mountains. Italian Alps have many cows and few trees or wildlife. They have rifugio with cold beers on mountain tops, though.
4. There are clear tourist walking corridors in Rome and other Italian cities. I didn't find them pleasant.
5. Renting one of the 4 person bicycles in Villa Borghese (top of the Spanish steps) and going up and down those hills seems like good family fun.
6. Going down into the Tiber is great for walks/festivals.
7. You will eat so much Gelato!
8. Venice is unlike any other place - the art part across the Ponte d' Accademia was funky (and quieter than St. Mark's square)
9. It seems like a good idea for an urbanist climate reporter to ride the fast, private trains. I rode Venice - Florence - Rome. To see the tunnels they've built is impressive. Seems like what high speed rail will look like in the US.
I've been freeloading on DR climate writing for a few years now. This article was enough to push me to subscribe to Volts, as your plans rang the memory bell quite loudly.
One of my best trips to Europe was a couple of weeks in Italy with my son after his graduation from high school. A sword lover since age 3, and a Latin student in high school, he was totally jazzed at the prospect of visiting Rome and whatever else we could fit on the agenda. So after starting with a few days in Rome, we moved on to Tarquinia (Etruscans), Orvieto (amazing fortress city on a massive butte), Montepulciano (another hilltop city), and Cortona (awesomely steep streets, and an excellent archeology museum), then back to Rome to fly home.
As to Rome: although the crowds in July are oppressive, certainly the Forum is amazing if you can tolerate the propinquity of the hoi polloi (I've always wanted to use that line ...). An early start lets you get in/out before it's too nuts.
If you are willing to deal with the crowds, try getting a private guide schooled in the classics. There are many ex-pats from England living in Rome, and some have married locals. Ours was recommended by a friend, was married to an inventor of train technology. She was friendly, had huge knowledge, and was a wonderful guide.
After the Forum, she took us to another few spots that were pretty magical, including the Baths of Caraculla (think steam heat engineering from 1800 years ago), walking on and talking about a Roman Road for an hour or so, then finishing with an aqueduct for a bit of hydration.
I'm about to do a walking vacation from Lucca to Siena. This has become my new favorite form of travel - to experience a new place at the speed that my feet can move me. This will be my first walking vacation with a teenager. I can't wait!
And, I share your dread of sending your baby into the world. My high school senior is about to fly the coop, and I'm already in mourning. I always figured by his age parenting would be a real chore, but that is not my experience. I am trying to be cool and excited for him (and me but that part is harder).
I dont always read your emails, but I am always grateful for your podcasts when I get to listening to them! I happened to read two recent emails, about your carpel tunnel (I am so sorry! Never type again and just speak to us and we will all be fine)… and ITALY.
I’m a painter, and Italy is Mecca. I’ve been there a dozen times, and will need the rest of my life (ever briefer) to keep looking and discovering. I’ll leave off talking about all of the art, since your eyes will glaze over, but just the briefest of looking tips:
Make reservations so you dont spend hours waiting on line for places like the Uffizi (and maybe you have to now, in the COVID era?). If you go to the Vatican museum, as soon as you enter head back to the Sistine Chapel, so you have the most time there with the fewest number of people (beat the crowd). Bring change to the churches so you can drop your coins into the little machines that turn the lights on the paintings (chapels, ceilings, etc). Don’t miss the French church in Rome (San Luigi dei Francesi) where the Caravaggios are. But any quick google will give you all the greatest art hits. Its endless. But maybe not the most important stuff for you and your family.
FOOD. Eat everything. Eat gelato at least once a day. The Italians go to gelato university. This is serious, incredible stuff. Go here in Florence, near Sante Croce: http://vivoli.it/en/home-2/. Really. Go here. This one.
I’m trying to keep this comment short, but if I get started on food… but I’ll make it easy. Go here in Modena: https://mercatoalbinelli.it/. Yep, make a special trip to Modena. Italians will tell you that Emilia-Romagna is the food capitol of their country. Modena is the jewel in the crown, and this market is where you can discover all of it. We would buy a little something, go outside, eat it, then reenter for the next something. I think we were there for four hours. And we usually look at art for 8 hour stretches with only a coffee break. (The Italians make excellent coffee, by the way).
In Venice in high season get up at the crack of dawn and walk through the city, from square to square before anyone is awake. You will be mostly alone and it is unbelievable. Honest. Do this. I've only been to Italy in the high season once, and this was a life saver. The only way to see and hear...
When we went to Italy recently we stayed in Montepulciano, did area hiking, and learned to make pasta at a small restaurant in town, and went to a few vineyards. It was a wonderful way to see and experience Tuscany.
We loved Venice but went in winter! A very different experience.
And Rome... go to Campo dei Fiori market in the morning. Grab a cappuccino for breakfast. Enjoy the start to the day!
We took a three-week trip to Italy in July of 2015 with our teenagers, ages 15 (boy) and 19 (girl) at the time. Our itinerary went like this: Venice — Varenna/Lake Como — Milan (1/2 day train layover mostly to see the newly restored cathedral) — Turin (for husband's 2-day conference) — central Tuscany — Amalfi Coast/Positano and Pompeii — Rome. I think you were right to jettison Milan and Turin as there are more interesting places. We avoided Florence on this trip because my husband and I had been before and our daughter was soon to return for a study abroad trip there, but I do believe it is a peak Italian experience that shouldn't be missed even though it might be crowded.
We took trains almost everywhere with two exceptions that we dealt with in different ways. We took a train from Turin to Arezzo in Tuscany where we rented a car to drive to our inn in the countryside and to tour around some of the smaller towns in central Tuscany. We wanted to go to Siena, but in the end our timing was bad and our visit coincided with their annual horse race when it was super crowded, so we didn't go. But we weren't disappointed with the smaller towns we visited like Montepulciano.
We continued south on the train and hired a driver with a van to take us from the station in Naples to our hotel in Positano on the Amalfi Coast, where towns are cliffside like in Cinque Terre and roads are narrow, winding, clogged, and often one-way. This service also took us to Pompeii on our way back to Naples to catch the train to Rome. I know you're not doing this part of Italy, but I mention it as something to look for to help you reach out-of-the-way spots if you decide not to rent a car. We found the trains to be a reliable and relaxing way to get between major destinations — any loss of time was definitely worth it for reduced stress. Driving in big Italian cities is notoriously difficult.
Looking back, two of our favorite activities involved experiences where we got to interact for a few hours with Italians. One was a personal walking tour of Venice with a native photographer named Marco Secchi (https://www.msecchi.com). He got us off the crowded main paths into quieter, picturesque spots and gave us advice on how best to use our cameras, which for most of us were our phones. He knew the history of the city well and had interesting perspectives on what is happening to it now. Since that time, he has expanded his business to include other cities now in your itinerary by hiring a few more photographers. Check it out the possibilities here: https://www.betterphotowalks.com
The second was a personal cooking class at a restaurant in Positano. Again, I know you're staying north of there, so I won't mention the restaurant, but I highly recommend looking for similar opportunities, as I'm sure they are available lots of places. It was one of the best meals we had as well as the most fun.
One last thought: It'll be warm, so always leave time in your schedule for gelato wherever you go! ;-)
I found it quite easy to avoid the tourist mayhem in Venice, it's a real city after all! And an incredible one at that.
I stayed on Via Giuseppe Garibaldi towards the east and I highly recommend a local restaurant called Il Paradiso Perduto in the Cannaregio neighborhood
We got a hotel in Sienna as a base for exploring Tuscany. We loved Sienna. You're biting off more than you can chew, I think. A narrower focus would leave you less exhausted at the end of the vacay. Two sites you don't mention are Assisi and Ravenna. My wife's and I are art nerds. Both of those have art works of world significance. Bon voyage!
I’d suggest Cinque Terre(the walking is incredible and there is plenty of pesto there. Luca is lovely, with curved streets and a walkway along the old wall. Good rail connection from the Cinque Terre. Florence for the art and architecture (though the heat and humidity are terrible) and Sienna just because. Rome is great, but takes a long time, so if you do it, you’ll need to leave other things out. The Dolomites are truly spectacular and you can do as much or as little as you want.
If you are in the Siena area, one thing you should do is have a picnic at dusk at the ruined abbey of San Galgano. The roof fell in about 500 years ago and only the walls survive. There is a little chapel and tourist shop but we were there at dusk and there was hardly anyone around. San Galgano is on route 441 just west of route 73 on the way to Massa Maritima.
David - I'm from Italy, grew up in Rome. I understand the urge to see it all, but I would highly recommend focusing on just ONE (maybe two) regions. As in Latium, or Tuscany, Emilia Romagna, or Friuli-Venezia Giulia. Take the train, you will have a much better experience moving around towns than dealing with the stress of driving in Italy as an American (expect some delays at times but generally good, frequent, practical service). I'd also add that late June/early July gets hot in Rome so depending on your heat tolerance you might prefer being closer to the Alps (I personally love those temperatures but it's not everyone's cup of tea). Basically, resist the FOMO, know that Italy will likely remain exactly the same for a bit of time, and enjoy delving into the vast cultural richness of its regions. Buon viaggio.
You have already figured out what you need to do. It's this: "We could spend more time in Rome (which begs for an extended stay) and then just hang around Tuscany, eating and looking at old stuff and eating."
I am very excited on your behalf. You will all have a blast. That said, I have strong opinions on your potential itineraries.
Depending on how long you stay in Rome, you could add a few days on tail end in Dolomites. Hanging around Tuscany eating is, to my mind however, non-negotiable.
1) Dolomites over Venice.
Venice is fascinating and one-of-a-kind, sure, but it will be up to its eyeballs in tourists and the whole experience will just remind you generally of sea level rise and you'll see the vapors of their travel-related GHGs hovering over the heads of all the tourists jostling you in Piazza San Marco. Risk is high that frustration>>revelation if you go there in June. One cool thing about the Dolomites, aside from all the great hiking and vistas etc, is that the culture/language/cuisine is very Alpine, inflected by proximity to Austria/Bavaria/Switzerland etc, while also somehow still Italian. Bolzano is a good jumping off point.
2) Siena+Lucca over Cinque Terre+Florence.
I'm biased because I spent a semester living in Siena in college and had a sense while I was there, eating fantastic food and strolling the old city center and happening upon random banquets and musical parades in the streets held by the 17 contrade (neighborhoods), that 'This is it, life has peaked, it's all downhill from here.' Cinque Terre - while spectacular, we hiked it, good times were had - will, like Venice, be jammed with fellow tourists to the point of driving you to dive into the sea. And, as any Siena partisan will tell you, Siena is so much better than Florence. In every way. Skip Florence. Trust me. And like Siena, Lucca is a walled town on a more welcoming scale - good for an afternoon of flaneur-style wandering.
TLDR: Use Siena as a base for several days. Walk around and eat and look at art. Take half-day excursions to surrounding villages like Sam Gimignano and Monteriggioni and Castello Brolio, etc.
3) Rome. Nuff said. It's Rome. Gotta see it.
It's gonna be great.
I'm so happy for your family that you get to take this amazing trip. I've been struggling a lot with balancing my love of travel and experiencing this miraculous gift of a world, with the fact that flying is actively contributing to its destruction. (Electric planes, come faster!) I've cut down on my flights a LOT, but am still in favor of flights for special, important occasions. Like your son going off to college!
All of that to say...I traveled to Italy as a teenager and loved Rome and Venice. But I think seeing the Dolomites would be absolutely incredible. So I'd be in favor of skipping Venice to spend more time in Tuscany and to see the Dolomites in person. Also, crazy trip change idea: What if you skipped Bologna and Venice to visit Lake Como and travel through the Italian Alps to the Dolomites? I'm a mountain girl so I may be biased, but if your sons love beautiful views, that could be a cool alternate route.
I also love your trip ethos - no matter where you go, it's going to be amazing! :)
Wiser and more experienced heads than mine have posted a lot of good advice here already, but I can't resist weighing in with a few points!
1) The Slow Food guide to Osterie and Locande was invaluable and took us to many truly wonderful restaurants. Not sure if it's up to date, but probably worth it even if there's not a recent edition.
2) A strong vote for visiting Bologna. Marvelous food, beautiful city, a joy to walk around.
3) Maybe this is obvious, but I'd recommend cars for places where you want to get out into the countryside or into nature and trains for getting between larger towns and cities. High speed trains are probably faster, and most definitely a more pleasant experience. (Though I found Italian drivers, while very forceful, surprisingly capable--less flakey than I'm used to stateside. Note that this is a statistically insignificant observation.)
4) I'd agree with those saying to cut Cinque Terre. Exploring Italian villages is one of the great pleasures of life, but the experience just a million times more agreeable if they're not overflowing with tourists.
5) Genoa is great, but probably not in the same league as your other destinations, and given your constraints might make sense to cut.
6) I'll unhelpfully recommend a couple other places: Ravenna was capital of the Roman empire for a while and has incredible architecture and art, including mosaics not unlike those of San Marco (if you miss Venice). Perugia, Arezzo, Gubbio are all magnificent hill-towns/cities, and close enough to your route that you might consider them. Val d'Aosta is a fantastic combination of numerous castles and alpine scenery.
Have a wonderful trip!
1. Rome & Cinque Terre will be extremely hot and jam-packed with tourists in July. Dolomites less so.
2. I typically miss salads and vegetables on my travels through Italy. Vedura alla griglia can help.
3. We don't have ruins in the US, but we have mountains. Italian Alps have many cows and few trees or wildlife. They have rifugio with cold beers on mountain tops, though.
4. There are clear tourist walking corridors in Rome and other Italian cities. I didn't find them pleasant.
5. Renting one of the 4 person bicycles in Villa Borghese (top of the Spanish steps) and going up and down those hills seems like good family fun.
6. Going down into the Tiber is great for walks/festivals.
7. You will eat so much Gelato!
8. Venice is unlike any other place - the art part across the Ponte d' Accademia was funky (and quieter than St. Mark's square)
9. It seems like a good idea for an urbanist climate reporter to ride the fast, private trains. I rode Venice - Florence - Rome. To see the tunnels they've built is impressive. Seems like what high speed rail will look like in the US.
I've been freeloading on DR climate writing for a few years now. This article was enough to push me to subscribe to Volts, as your plans rang the memory bell quite loudly.
One of my best trips to Europe was a couple of weeks in Italy with my son after his graduation from high school. A sword lover since age 3, and a Latin student in high school, he was totally jazzed at the prospect of visiting Rome and whatever else we could fit on the agenda. So after starting with a few days in Rome, we moved on to Tarquinia (Etruscans), Orvieto (amazing fortress city on a massive butte), Montepulciano (another hilltop city), and Cortona (awesomely steep streets, and an excellent archeology museum), then back to Rome to fly home.
As to Rome: although the crowds in July are oppressive, certainly the Forum is amazing if you can tolerate the propinquity of the hoi polloi (I've always wanted to use that line ...). An early start lets you get in/out before it's too nuts.
If you are willing to deal with the crowds, try getting a private guide schooled in the classics. There are many ex-pats from England living in Rome, and some have married locals. Ours was recommended by a friend, was married to an inventor of train technology. She was friendly, had huge knowledge, and was a wonderful guide.
After the Forum, she took us to another few spots that were pretty magical, including the Baths of Caraculla (think steam heat engineering from 1800 years ago), walking on and talking about a Roman Road for an hour or so, then finishing with an aqueduct for a bit of hydration.
Best of luck.
I'm about to do a walking vacation from Lucca to Siena. This has become my new favorite form of travel - to experience a new place at the speed that my feet can move me. This will be my first walking vacation with a teenager. I can't wait!
And, I share your dread of sending your baby into the world. My high school senior is about to fly the coop, and I'm already in mourning. I always figured by his age parenting would be a real chore, but that is not my experience. I am trying to be cool and excited for him (and me but that part is harder).
Dear Mr Volts
I dont always read your emails, but I am always grateful for your podcasts when I get to listening to them! I happened to read two recent emails, about your carpel tunnel (I am so sorry! Never type again and just speak to us and we will all be fine)… and ITALY.
I’m a painter, and Italy is Mecca. I’ve been there a dozen times, and will need the rest of my life (ever briefer) to keep looking and discovering. I’ll leave off talking about all of the art, since your eyes will glaze over, but just the briefest of looking tips:
Make reservations so you dont spend hours waiting on line for places like the Uffizi (and maybe you have to now, in the COVID era?). If you go to the Vatican museum, as soon as you enter head back to the Sistine Chapel, so you have the most time there with the fewest number of people (beat the crowd). Bring change to the churches so you can drop your coins into the little machines that turn the lights on the paintings (chapels, ceilings, etc). Don’t miss the French church in Rome (San Luigi dei Francesi) where the Caravaggios are. But any quick google will give you all the greatest art hits. Its endless. But maybe not the most important stuff for you and your family.
FOOD. Eat everything. Eat gelato at least once a day. The Italians go to gelato university. This is serious, incredible stuff. Go here in Florence, near Sante Croce: http://vivoli.it/en/home-2/. Really. Go here. This one.
I’m trying to keep this comment short, but if I get started on food… but I’ll make it easy. Go here in Modena: https://mercatoalbinelli.it/. Yep, make a special trip to Modena. Italians will tell you that Emilia-Romagna is the food capitol of their country. Modena is the jewel in the crown, and this market is where you can discover all of it. We would buy a little something, go outside, eat it, then reenter for the next something. I think we were there for four hours. And we usually look at art for 8 hour stretches with only a coffee break. (The Italians make excellent coffee, by the way).
In Venice in high season get up at the crack of dawn and walk through the city, from square to square before anyone is awake. You will be mostly alone and it is unbelievable. Honest. Do this. I've only been to Italy in the high season once, and this was a life saver. The only way to see and hear...
I wish you the most splendid trip.
When we went to Italy recently we stayed in Montepulciano, did area hiking, and learned to make pasta at a small restaurant in town, and went to a few vineyards. It was a wonderful way to see and experience Tuscany.
We loved Venice but went in winter! A very different experience.
And Rome... go to Campo dei Fiori market in the morning. Grab a cappuccino for breakfast. Enjoy the start to the day!
We took a three-week trip to Italy in July of 2015 with our teenagers, ages 15 (boy) and 19 (girl) at the time. Our itinerary went like this: Venice — Varenna/Lake Como — Milan (1/2 day train layover mostly to see the newly restored cathedral) — Turin (for husband's 2-day conference) — central Tuscany — Amalfi Coast/Positano and Pompeii — Rome. I think you were right to jettison Milan and Turin as there are more interesting places. We avoided Florence on this trip because my husband and I had been before and our daughter was soon to return for a study abroad trip there, but I do believe it is a peak Italian experience that shouldn't be missed even though it might be crowded.
We took trains almost everywhere with two exceptions that we dealt with in different ways. We took a train from Turin to Arezzo in Tuscany where we rented a car to drive to our inn in the countryside and to tour around some of the smaller towns in central Tuscany. We wanted to go to Siena, but in the end our timing was bad and our visit coincided with their annual horse race when it was super crowded, so we didn't go. But we weren't disappointed with the smaller towns we visited like Montepulciano.
We continued south on the train and hired a driver with a van to take us from the station in Naples to our hotel in Positano on the Amalfi Coast, where towns are cliffside like in Cinque Terre and roads are narrow, winding, clogged, and often one-way. This service also took us to Pompeii on our way back to Naples to catch the train to Rome. I know you're not doing this part of Italy, but I mention it as something to look for to help you reach out-of-the-way spots if you decide not to rent a car. We found the trains to be a reliable and relaxing way to get between major destinations — any loss of time was definitely worth it for reduced stress. Driving in big Italian cities is notoriously difficult.
Looking back, two of our favorite activities involved experiences where we got to interact for a few hours with Italians. One was a personal walking tour of Venice with a native photographer named Marco Secchi (https://www.msecchi.com). He got us off the crowded main paths into quieter, picturesque spots and gave us advice on how best to use our cameras, which for most of us were our phones. He knew the history of the city well and had interesting perspectives on what is happening to it now. Since that time, he has expanded his business to include other cities now in your itinerary by hiring a few more photographers. Check it out the possibilities here: https://www.betterphotowalks.com
The second was a personal cooking class at a restaurant in Positano. Again, I know you're staying north of there, so I won't mention the restaurant, but I highly recommend looking for similar opportunities, as I'm sure they are available lots of places. It was one of the best meals we had as well as the most fun.
One last thought: It'll be warm, so always leave time in your schedule for gelato wherever you go! ;-)
Incidentally, watch out for the cosplayers at the Coliseum, they are very aggressive about demanding tips for posing for photos.
Whatever you do, don't eliminate Florence from your itinerary!
I found it quite easy to avoid the tourist mayhem in Venice, it's a real city after all! And an incredible one at that.
I stayed on Via Giuseppe Garibaldi towards the east and I highly recommend a local restaurant called Il Paradiso Perduto in the Cannaregio neighborhood
We got a hotel in Sienna as a base for exploring Tuscany. We loved Sienna. You're biting off more than you can chew, I think. A narrower focus would leave you less exhausted at the end of the vacay. Two sites you don't mention are Assisi and Ravenna. My wife's and I are art nerds. Both of those have art works of world significance. Bon voyage!
I’d suggest Cinque Terre(the walking is incredible and there is plenty of pesto there. Luca is lovely, with curved streets and a walkway along the old wall. Good rail connection from the Cinque Terre. Florence for the art and architecture (though the heat and humidity are terrible) and Sienna just because. Rome is great, but takes a long time, so if you do it, you’ll need to leave other things out. The Dolomites are truly spectacular and you can do as much or as little as you want.
If you are in the Siena area, one thing you should do is have a picnic at dusk at the ruined abbey of San Galgano. The roof fell in about 500 years ago and only the walls survive. There is a little chapel and tourist shop but we were there at dusk and there was hardly anyone around. San Galgano is on route 441 just west of route 73 on the way to Massa Maritima.