Planning on a trip to Tuscany in 2026? I’d love to show you around my adopted hometown of Siena and discover the history of the Palio, learn about Renaissance wonders in Florence, or marvel at the towers of San Gimignano together. Check my availability here.

Please note that I am a city guide and not a travel agent or a driver, but I have contacts (scroll to the bottom of this page) who can help you plan the perfect Italian holiday and drive you where you need to go; I’ll meet you along the way!

Click here for tour ideas, here for some local events, or keep scrolling for videos, photos, and more…

🫒🫒🫒 Need Extra Virgin Olive Oil? Of course you do! Contact Dario Castagno or Claudia Cesa & they’ll ship Tuscany’s finest to you! 🫒🫒🫒

Check my availability here!

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Check my availability here! 〰️

Featured
Visit the Bottini of Siena!
Jan 28
Visit the Bottini of Siena!

How did Siena, a hill town with no river, provide water to citizens and visitors from the 11th century all the way to the 20th century? Find out with a special tour! Click on the image for more details.

Wine & Siena at Santa Maria della Scala
Jan 30
Wine & Siena at Santa Maria della Scala

Enjoy some vino and learn its history in Siena’s oldest hospital (wine is also medicinal, right?!)! https://wineandsiena.com

Giorno dell'Unità Nazionale (Anniversary of the Unification of Italy)
Feast Day of St Joseph, & Italian Father's Day!
Mar 19
Feast Day of St Joseph, & Italian Father's Day!

Wish all the Josephs and dads in your life a happy day! Click for more info (plus a link to a video I made a few years ago)!

Feast Day of the Annunciation (& Sienese New Year!)
Mar 25
Feast Day of the Annunciation (& Sienese New Year!)

What is the Annunciation and how is it celebrated? Click above to find out!

Spring Forward!
Mar 29
Spring Forward!

You know what to do!

Pasqua–Easter
Apr 5
Pasqua–Easter

Expect some shops and restaurants to be closed, but certainly more church services will be available!

Pasquetta (Easter Monday)
Apr 6
Pasquetta (Easter Monday)

Italians don’t have Good Friday off work, but Easter Monday is a national holiday (so book lunch ahead, as many will be out celebrating with friends!).

Giro della Contrada di Valdimontone
Apr 26
Giro della Contrada di Valdimontone

Patron Saint: The Madonna of Good Counsel. Click the image for more info!

St Catherine of Siena's Feast Day!
Apr 29
St Catherine of Siena's Feast Day!

This woman is the reason I’m in Siena! Click for more info.

Giro della Nobile Contrada dell'Oca
May 10
Giro della Nobile Contrada dell'Oca

Patron Saint: Catherine of Siena. Click the image for more info!

Giro della Contrada del Drago
May 31
Giro della Contrada del Drago

Patron Saint: Catherine of Siena. Click the image for more info!

Estrazione in Piazza del Campo for Palio 2 July!
May 31
Estrazione in Piazza del Campo for Palio 2 July!

Who will the Palio on 2 July 2024? Click for more details! • Onda 🐬 • Civetta 🦉 • Giraffa 🦒 • Leocorno 🦄 • Aquila 🦅 • Torre 🐘 • ? • ? • ? • ? •

Festa della Repubblica
Jun 2
Festa della Repubblica

In 1946, Italians voted for a republic over a monarchy, and the the modern nation of Italy was born! Click for more details.

Giro della Contrada Imperiale della Giraffa
Jun 7
Giro della Contrada Imperiale della Giraffa

Patron Saint: The Visitation of the Blessed Virgin Mary. Click image for more info!

Giro della Contrada Priora della Civetta
Jun 14
Giro della Contrada Priora della Civetta

Patron Saint: Anthony of Padua. Click image for more info!

For more local events, see the calendar here

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For more local events, see the calendar here 〰️

What a difference an hour can make! #siena #torredelmangia #piazzadelcampo #whenthefoglifts #sienaitalytours
What a difference an hour can make! #siena #torredelmangia #piazzadelcampo #whenthefoglifts #sienaitalytours
🎨Sometimes an art break is what we truly need, and January is the perfect time to do this in the Renaissance city. ⚜️ Festivities officially end on the 6th, and then you’ve got the place practically to yourself for a few weeks. No reservations
🎨Sometimes an art break is what we truly need, and January is the perfect time to do this in the Renaissance city. ⚜️ Festivities officially end on the 6th, and then you’ve got the place practically to yourself for a few weeks. No reservations? No problem! We didn’t even wait one minute to get our tickets to the Uffizi, and most rooms were practically empty.* 🖼️ It was also a great opportunity to catch up with dear friends, and even though we had snow just a few days before, check out that sun! ☀️ *There are always changes being made to the museum…the Botticelli rooms are now closed but the Birth of Venus and Primavera have been moved into another room on the 2nd floor for viewing, fear not! #florence #florenceinjanuary #galleriedegliuffizi #lowseason #sienaitalytours
📆 Every year I buy (and/or receive) new planners, and every year I abandon them and just end up using scrap paper 😅 2025 saw the introduction of the binder with a cheap and thin A5 paper. Will 2026 be any different? Thank goodness I also have Google Calendar to help! 🤓 #organization #disorganization #ineedasecretary #executivedysfunction #sienaitalytours
Not quite the same as in Massachusetts, but I still love any kind of snow!! ❄️ ☃️❄️ #siena #happynewyear #italiansnow #neveitaliana #sienaitalytours
Palazzo Strozzi always has fantastic exhibitions, and this one is no exception! Through 25 Jan you can delve into the world of Beato Angelico (then you can always enjoy his works in San Marco!). As is often the case with such important shows, many wo
Palazzo Strozzi always has fantastic exhibitions, and this one is no exception! Through 25 Jan you can delve into the world of Beato Angelico (then you can always enjoy his works in San Marco!). As is often the case with such important shows, many works were restored for the occasion, and altarpieces that haven’t been together in a century or more have been reunited for a short while. I thoroughly enjoyed the show, as I always appreciate a chance to get up close and personal with art (check out some of my favourite details in these photos!). Make sure to book your tickets in advance, especially if going on a weekend, and if it gets crowded with a tour group, just be patient. My friend and I would wait for the large guided groups to finish in one room and then we’d head back to what we couldn’t see before. Even with this going back and forth, we were in the museum for just under 2 hours, which really was the perfect amount of time. I hope you can go too! #beatoangelico #fraangelico #palazzostrozzi #firenze #artedelquattrocento #renaissance #15thcenturyflorence #sienaitalytours
There are few places I enjoy more than the Room of the Nine in the Palazzo Pubblico of Siena, especially when I have the whole place to myself with special clients! (No, I don’t have that much sway, but it’s low season 😅). After the rece
There are few places I enjoy more than the Room of the Nine in the Palazzo Pubblico of Siena, especially when I have the whole place to myself with special clients! (No, I don’t have that much sway, but it’s low season 😅). After the recent elections in the States, the messages in the frescoes resonate even more. “Love justice, you who rule the earth”. One must rule for the common good and not for one’s own interests. Ambrogio Lorenzetti illustrated the benefits of a good and just government, guided by wisdom, and the perils of tyranny when the leader rules with pride and justice is bound. What lessons can we learn from 14th-c Siena? ⚖️ #ambrogiolorenzetti #lasaladeinove #roomofthenine #palazzopubblicosiena #siena #goodgovernment #badgovernment #lovejusticeyouwhoruletheearth #diligiteiustitiamquiiudicatisterram #sienaitalytours
‼️Wed 29 Oct at 10pm/9pm ET on PBS!! 📺 It’s finally here! I had the distinct honour and pleasure of working with Impossible Factual when they were filming “CHASING THE PLAGUE” here in Siena. What a treat to be behind the scenes of
‼️Wed 29 Oct at 10pm/9pm ET on PBS!! 📺 It’s finally here! I had the distinct honour and pleasure of working with Impossible Factual when they were filming “CHASING THE PLAGUE” here in Siena. What a treat to be behind the scenes of this fascinating documentary! Please let me know what you think when you watch it! 🐀 #impossiblefactual @impossiblefactual #adamluria @adamluria #daisycarolath @daisycarolath #adeymusto @adeymusto #chasingtheplague #pbs #supportpublicbroadcasting #theblackdeath #siena #sienaitalytours
Morning office. #amiata #monteamiata #collisenesi #siena #tourguidelife #sienaitalytours
Morning office. #amiata #monteamiata #collisenesi #siena #tourguidelife #sienaitalytours
Current mood 🥰 #castiglionedellapescaia #sunset #maremmatoscana #sienaitalytours
Current mood 🥰 #castiglionedellapescaia #sunset #maremmatoscana #sienaitalytours
I’m still here! I’ve fallen woefully behind on social media, but I had a wonderful summer with a trip to France (will post pix soon!), England (family wedding and reunion with university friends!), and amazing tours with wonderful people.
I’m still here! I’ve fallen woefully behind on social media, but I had a wonderful summer with a trip to France (will post pix soon!), England (family wedding and reunion with university friends!), and amazing tours with wonderful people. Looking forward to meeting more of you!! #thankyou #tourguidelife #siena #sienaitalytours
What a difference an hour can make! #siena #torredelmangia #piazzadelcampo #whenthefoglifts #sienaitalytours 🎨Sometimes an art break is what we truly need, and January is the perfect time to do this in the Renaissance city. ⚜️ Festivities officially end on the 6th, and then you’ve got the place practically to yourself for a few weeks. No reservations
📆 Every year I buy (and/or receive) new planners, and every year I abandon them and just end up using scrap paper 😅 2025 saw the introduction of the binder with a cheap and thin A5 paper. Will 2026 be any different? Thank goodness I also have Googl
Not quite the same as in Massachusetts, but I still love any kind of snow!! ❄️ ☃️❄️ #siena #happynewyear #italiansnow #neveitaliana #sienaitalytours
Palazzo Strozzi always has fantastic exhibitions, and this one is no exception! Through 25 Jan you can delve into the world of Beato Angelico (then you can always enjoy his works in San Marco!). As is often the case with such important shows, many wo There are few places I enjoy more than the Room of the Nine in the Palazzo Pubblico of Siena, especially when I have the whole place to myself with special clients! (No, I don’t have that much sway, but it’s low season 😅). After the rece ‼️Wed 29 Oct at 10pm/9pm ET on PBS!! 📺 It’s finally here! I had the distinct honour and pleasure of working with Impossible Factual when they were filming “CHASING THE PLAGUE” here in Siena. What a treat to be behind the scenes of Morning office. #amiata #monteamiata #collisenesi #siena #tourguidelife #sienaitalytours Current mood 🥰 #castiglionedellapescaia #sunset #maremmatoscana #sienaitalytours I’m still here! I’ve fallen woefully behind on social media, but I had a wonderful summer with a trip to France (will post pix soon!), England (family wedding and reunion with university friends!), and amazing tours with wonderful people.

Some instagram fun! Click on an image to see the other photos in the post (you don’t need to have an account, but if you do, please follow me)!

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Join us as we talk about Venice, Florence, and Rome! For more videos and interviews, visit the Featured In page here!

Let’s go to Siena with with Rick (recorded Jan 2022)!

Passionate, prepared, and, as her college professor called her, “la Piperatissima”! A native English speaker fluent in Italian, Anna now calls Siena home.

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Well well well, what have we here? Looking for 2022 tours? Click here to check availability and to book your spot!

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In-person tours are back! Have a look here for some inspiration about what we can experience together!

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We loved everything about our too-short, 3-hour, personal tour with Anna-the-Americana: the Cathedral's remarkable pavement and façade...Catherine's thumb and head...But most of all we loved Anna's uniquely world-wise, funny and very high high-speed story-telling. We will do our very best to plan far-enough ahead to get on Anna's schedule again the next time we come to anyplace she offers to guide us through the long, rich history and artistic treasures of the region. Thank you, Anna!

— Charles & Marilyn

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