About this TourStarter Tour
After partnering together for an epic tour of Japan focused on the Gempei War, Geek Nation Tours partners again with History on Fire podcast host/university history professor Daniele Bolelli for an exploration of Daniele’s home country of Italy. Daniele will take us to explore some aspects of Italian history that are most dear to his heart. In the pre-tour, we’ll travel to the mountains where his step-grandfather operated as a partisan and even arrested Mussolini! Along the way, we’ll go on some gorgeous hikes, go on a boat tour of Lake Como and will eat some of the best Northern Italian cuisine available. We’ll also visit Daniele’s hometown of Milan, where his grandmother fought for the resistance. At the beginning of the tour, in Milan we’ll go see Leonardo Da Vinci’s uber-famous The Last Supper, the incredible castle in the middle of the city, and the architectural marvel that is Il Duomo. A visit to Piazzale Loreto, where the last dramatic chapter of Italian resistance took place, will give us a chance to shop in Corso Buenos Aires. Before leaving Milan, we’ll also dine by the Navigli (the waterways in one of the most beloved parts of the city), and come face to face with some works by one of history’s greatest painters – and by far Daniele’s favorite – Caravaggio.
After stopping in Bologna for a bite of the local cuisine, we’ll reach Florence to visit Palazzo Pitti, the Uffizi (home to many artistic masterpieces), and the Boboli Gardens. Of course, no visit to Florence is complete without a walk to Ponte Vecchio (the bridge on the Arno River) and a stop by Loggia dei Lanzi, where is located a sculpture by Benvenuto Cellini, the wildest Italian artist of all times. Cellini and Caravaggio were so intense that they make Tupac, Biggie and other hip-hop stars look moderate and restrained by comparison. And we’ll explore the weirdness of their lives throughout this whole tour.
While in Tuscany, we’ll visit a haunting abbey with no roof, the beautiful city of Siena and we’ll drink some of the best wine in the world right where it’s produced in Montalcino (also a much touted Daniele fav).
Castiglioncello is a sleepy seaside town that holds a special place in Daniele’s heart, so he’ll take us there and share its charm with us.
On our way south, we’ll stop where Caravaggio met his untimely demise. And then… it’s time to enter the ‘Eternal City!’ One could spend a month in Rome without seeing everything there is to see, but we’ll do our best to pack a lot in a few days. At the top of Castel Sant’ Angelo (where Cellini was imprisoned and where he also fought during the 1527 sack of Rome), we’ll catch a glimpse of most of Rome from above. And during a walk we’ll cross Piazza Navona, the most famous square in Rome, visit San Luigi dei Francesi (the church where two of Caravaggio’s renowned paintings are found), the Spanish Steps, the Pantheon and the Trevi Fountain. At Campo dei Fiori, we’ll see the spot where religious dissident Giordano Bruno was burned at the stake. And we’ll gorge on some great art at Galleria Borghese, Palazzo Barberini and the Vatican Museums. Dinner by the Tiber River will also be an experience to remember.
Note also that we will stop for many meals together along the way to regale the day’s victories and perhaps indulge in some drink!
Daniele Bolelli is a university history professor, author, martial artist and host of the incredible History on Fire podcast. History on Fire is the recipient of the iTunes ‘best new podcast of 2015’ and if you haven’t listened to his episodes on Caravaggio (ep 11, 12), Cellini (ep 99, 100), and his family’s WWII experience (ep 68 – My Grandma and Her Bombs: A Story of WWII, 69 – Capturing Mussolini… You can even try Sex in Ancient Rome If you want some thing more racy (and rather strange)), you really should! History on Fire offers is an exploration of the most intense times in the history of man. Through the podcast, Daniele hopes to inspire you with the examination of larger than life archetypal characters full of wisdom, bravery, passion who overcame the most extreme examples of adversity in human history.
Daniele’s better half, artist, martial artist, pro-MMA athlete, and History on Fire editor Sovannahry Em will also be on the tour. Sav also happens to be this tours artist 😊
Please remember that this is a once in a lifetime tour. While we might headed back to Italy one day to explore its rich history, this tour will not repeat 🙂
Optional Pre-Tour Add-on
Day 1 - Milan (Saturday, Jun. 14, 2025) / Pre-Tour: Milan
Today we will gather from all around the world to start our time-travelling adventure into Italy. When everyone has arrived, we will come together for our Welcome Dinner. Waste no time trying gelato!
Daniele's Take: Welcome to my hometown! This is where I grew up and lived until I was 18. This city is still home to most of my family and friends in Italy.
Overnight Location: Milan
Day 2 - Lake Como (Sunday, Jun. 15, 2025) / Pre-Tour: Dongo, & A Cruise on Lake Como
Time to go explore one of the most beautiful places in Northern Italy, Lake Como—where George Clooney has been living part-time for many years now! A lake cruise will give us a chance to enjoy the spectacular scenery from the water. We’ll also dive into some of the local history by visiting the End of the War Museum in Dongo, very close to where Italian partisans arrested Mussolini in 1945.
Daniele's Take: Can you believe my step-grandfather was the guy who commanded the partisans who arrested Mussolini? He’s the subject of episode 69 of History on Fire. I’ll tell you all about this story as we see the places where it happened.
Overnight Location: Lake Como
Day 3 - Gerola Alta (Monday, Jun. 16, 2025) / Pre-Tour: Gerola Alta
From Lake Como we travel to nearby mountains where partisans were fighting in the last days of WWII, and we’ll enjoy some mellow hiking in a natural setting that will take your breath away. The hiking may be needed as later we will stop by the Stella Alpina to eat local delicacies. As far as Northern Italian cuisine goes, Stella Alpina is the place to go! You have never tasted polenta like this.
Daniele's Take: I have spent quite a few summers in this area. We’ll see the house where my step grandfather hid at some point during WWII and the mountains where he fought. And the food… any time I know that I’ll visit Stella Alpina, I make a point of working out for days beforehand because I’ll definitely not restrain myself once I’m there :)
Overnight Location: Gerola Alta
Day 4 - Milan (Tuesday, Jun. 17, 2025) / Pre-Tour: One More Hike and Then to Milan
We will enjoy one last hike in the mountains before making our way back to Milan. That said, we will make a quick stop at the amazing Bottega Fratelli Ciapponi store to make sure we have some provisions for the trip! Once there we’ll join those arriving for the main tour. Milan is a pretty city so feel free to explore before we meet in the evening for our Welcome Dinner.
Daniele's Take: When I lived in Milan, I grew up in a less than glamorous part of town. Milan back then was considerably rougher than it is today. Investments done in the past decade or so have dramatically improved things, making Milan a prime tourist destination.
Overnight Location: Milan
Main Tour
Day 1 - Milan (Tuesday, Jun. 17, 2025) / Arrival Day - Milan!
Participants in the pre-tour will enjoy one last hike in the mountains before we make our way back to Milan. Geek Nation Tours will make sure you have instructions on how to find our hotel and where and when to join us for our Welcome Dinner. That said, Milan is a pretty city so feel free to explore!
Daniele's Take: As above :)
Overnight Location: Milan, Hotel TBA
Day 2 - Milan (Wednesday, Jun. 18, 2025) / Da Vinci's Last Supper, Caravaggio & Castello Sforzesco & Duomo di Milano
We begin the day by going to see one of the most famous paintings ever, Leonardo Da Vinci’s The Last Supper. The excitement continues with a visit to the incredible castle in the middle of the city (Castello Sforzesco). And we’ll wrap the day with a tour of the Duomo, Milan’s main church which is considered an iconic architectural marvel. We’ll make sure to get tickets to see the Duomo from the top, which is quite a sight.
Daniele's Take: I grew up going to the park next to Castello Sforzesco every day, and my first year of high school was in a building at the edge of the park. For the last few years of his life, my father lived a mile away from the Duomo. So, we’ll be seeing lots of sites that are rather central to my upbringing.
Overnight Location: Milan, Hotel TBA
Day 3 - Milan (Thursday, Jun. 19, 2025) / The Death of a Dictator, Pinacoteca Brera, Corso Buenos Aires & Navigli Flea Market
Our immersion in Italian art will continue with a visit to the Pinacoteca di Brera, one of the best collections of historical paintings in Italy. There, we’ll see works by Daniele’s favorite painter, Caravaggio (who grew up in Milan). Part of the program for the day includes also a visit to Piazzale Loreto, where Mussolini’s body was hung after his execution, symbolizing (in a rather gruesome way) the end of the fascist regime. We’ll lighten things up with a chance to shop in Corso Buenos Aires before we head to the Navigli for dinner. The Navigli are an old system of canals crossing part of Milan, and they are the site of a very lively night life.
Daniele's Take: More places that were part of my daily life. For a couple of years, I lived next to Piazzale Loreto, and my father lived close to the Navigli. And did I mention today we’ll see Caravaggio? To say that I’m fascinated with his life and work is a huge understatement.
Overnight Location: Milan, Hotel TBA
Day 4 - Florence (Friday, Jun. 20, 2025) / Florence & Caravaggio at the Palatine Gallery
We leave Milan for Florence, but we’ll make a quick stop in Bologna (the site of one of the oldest universities in the world) for a bite to eat. Once in Florence, we’ll visit Palazzo Pitti and take a walk around town.
Daniele's Take: Florence is packed with tourists but there are good reasons for it. It truly is one of Italy’s most interesting cities.
Overnight Location: Florence - Hotel TBA
Day 5 - Florence (Saturday, Jun. 21, 2025) / Uffizi Gallery, Ponte Vecchio & the Boboli Gardens
In the morning, we’ll start things with a visit the Uffizi, where we’ll have a chance to admire some of Caravaggio’s work along with the works of many other great artists. Speaking of artists, during a walk to Ponte Vecchio (the iconic bridge on the Arno River), we’ll stop by Loggia dei Lanzi. There, we’ll see ‘Perseus and Medusa’ a sculptor by Benvenuto Cellini, whose life is the subject of one of the most widely read biographies from the Renaissance. Cellini was a brilliant artist, but he was also insanely violent and more than a bit mentally deranged. We’ll discuss the story of his life and Caravaggio’s life throughout the trip, and in Florence we’ll get to see masterpieces by both. To wrap the day, we’ll relax in the scenic Boboli Gardens.
Daniele's Take: I love exploring the lives of Cellini and Caravaggio. Both of them were so over the top, so wild, and so dangerous that they defy stereotypes about sensitive, artistic types.
Overnight Location: Florence - Hotel TBA
Day 6 - Montalcino (Sunday, Jun. 22, 2025) / Siena, San Galgano Abby, Montalcino & Wine!
Today is a good day for wine lovers since we’ll spend the night in Montalcino, home of the world-famous Brunello di Montalcino, one of the greatest wines ever produced. Before that, we’ll stop in Siena to at least briefly explore this beautiful Tuscan city. Last but not least, we’ll stop at the San Galgano, site of an ancient abbey whose roof collapsed centuries ago, giving a haunting quality to the place.
Daniele's Take: Siena is a wonderful city, and San Galgano is such a unique site, but today I’m mostly excited about Montalcino. Did I mention how good the wine is?!?
Overnight Location: Montalcino - Hotel TBA
Day 7 - Castiglioncello (Monday, Jun. 23, 2025) / Necropoli di Sovana, Castiglioncello and Beaches!
For a different Tuscan experience, after a stop by an Etruscan necropolis, today we travel to the site where Daniele spent most of his summers as a teenager. Castiglioncello is a small town by the sea. It used to be a hotspot for Italian movie stars of the 1960s and 1970s. And it’s still a lovely place to visit.
Daniele's Take: I can’t wait to share with you a town that means so much to me.
Overnight Location: Castiglioncello - Hotel TBA
Day 8 - Castiglioncello (Tuesday, Jun. 24, 2025) / Campiglia Marittima & more Beach Time!
We’ll start our day by visiting a small medieval town called Campiglia Marittima. And for dinner we’ll treat ourselves to a fantastic family restaurant called Il Sigillo. In between, we’ll take it easy and leave time to go to the beach or relax in town.
Daniele's Take: Relaxing while listening to the waves before filling my stomach at Il Sigillo doesn’t sound like a bad plan at all.
Overnight Location: Castiglioncello - Hotel TBA
Day 9 - Rome (Wednesday, Jun. 25, 2025) / Porto Ercole & the Death of Caravaggio & a Walking Tour of Rome
Today, we say goodbye to Tuscany and make our way to Rome. It’s not a short trip and we’ll break it up with a short stop at Porto Ercole, the place where Caravaggio died. When we finally arrive in Rome, one of our first stops will be Castel Sant’ Angelo. At various points, the Castel has been a fortress, a prison, and the residency of the Pope. In 1527, from the walls of the castle, Benvenuto Cellini used his cannons to fight the imperial troops looting the city. A few years later, he ended up jailed there and staging a daring escape. For gamers among you, you may remember the Castle if you played Assassin’s Creed. But you don’t need to be a gamer to appreciate the incredible view of Rome you get from the top of the Castle. Right after this, we’ll gather in Rome’s most famous square, Piazza Navona. From there, it’s just a few steps to the church of San Luigi dei Francesi, where we’ll see the two Caravaggio paintings that launched him into stardom.
Daniele's Take: Back in 2013, I had one of the best days of my life walking in the very places we’ll visit today. I’m willing to bet we’ll have fun today.
Overnight Location: Rome - Hotel TBA
Day 10 - Rome (Thursday, Jun. 26, 2025) / Another Walking tour of Rome, More Caravaggio, the Pantheon and River Cruise Dinner on the Tiber
We’ll start our second day in Rome with a visit to Galleria Borghese, one of the best art collections in the city (and yes, more Caravaggio paintings). But this is just the appetizer. For the main course, we’ll see the ancient Roman Pantheon (a masterpiece of Roman architecture), the Spanish Steps, and the renowned Trevi fountain. Just a bit further is Campo dei Fiori, a popular square for modern Romans but also the site of the execution of famous religious dissident Giordano Bruno. Not far from here is also the place where Caravaggio dueled against Ranuccio Tommassoni, killing him and earning a death sentence. And for the end of the day, we’ll eat on a boat anchored on the Tiber River!
Daniele's Take: With so many beautiful places to visit today, I guarantee you won’t be bored.
Overnight Location: Rome - Hotel TBA
Day 11 - Rome (Friday, Jun. 27, 2025) / Rome again by foot -
Daniele's Take:
Overnight Location: Rome - Hotel TBA
Day 12 - Rome (Saturday, Jun. 28, 2025) / The Vatican Museums & Palazzo Barberini
Daniele's Take:
Overnight Location: Rome - Hotel TBA
Day 13 - Rome (Sunday, Jun. 29, 2025) / A Journey Home
All good things must end unfortunately, and today we rleave Rome and depart for home. The photos, memories and friendships you made on the tour are yours to keep forever!
Daniele's Take: Ah nuts! Time to go home...
Tour Notes
We get you reading straight away…
Osprey Publishing and Geek Nation Tours want to start you off right with our tours and thus will get you reading about the history we will be visiting. Each of our Signature Battlefield tours will see books on the subject bound for your bookshelves… Upon final payment of your tour …
NOTE: We do a load of walking this tour. Please note that we can walk as much as 8 kilometers a day in our attempt to show you as much of Italy as possible. Please keep this in mind. Further, there are steps in Italy …
NOTE: Attendance of special guests and celebrities is subject to change due to scheduling conflicts and conflicting professional or personal obligations.
NOTE: COVID-19 has changed both our geek and our real worlds. Some things may never be the same and others may not be able to be offered on our tours or will have to be altered in a new post Covid world. With that said, please understand that GNT is moving forward as if the disease is already conquered, but all tours are now subject to change.
What's Included
All accommodations, all motor coach and river transfers, Welcome & Farewell and most other Dinners, Breakfasts, most entry fees.
What's Not Included
Airfare, some local transport fares.
Don’t have a friend to get the double occupancy rate? That is what Geek Nation Tours does. Book as a double occupancy and we will match you up a roommate… This way you get the best of both worlds – someone to BS about the con with – and more cash to spend!
Covid & Inflation Pricing note: As we move into the post-Covid and into an era of rapid inflation there may well be price adjustments as we move forward. It has been postulated that the tourism industry as a whole will see many price increases. While GNT strives to give the best price along with the best service and experience, we may be forced to increase tour pricing in the future.
Additional Options
Want to do more in Italy? Geek Nation Tours can arrange hotel stays and other options for you. Just let us know what you have in mind and we will come up with a travel plan.
Non-Geek Spouse Argument
I mean…Italy! History, food, romance…
