Pamela Haack's Strada Toscana

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Pamela Haack's Strada Toscana Join a trip or create a trip at a villa in Italy. BUONGIORNO! Our fresh itineraries were a hit, and our loyal guests were delighted.
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I’m Pamela Haack, and welcome to Strada Toscana, where we help curious travelers, creatives and experts to experience, explore and learn in an extraordinary place. After moving to Italy more than 15 years ago, I dreamed big, took a leap of faith and created Strada Toscana. In the beginning we were a boutique tour company, offering off-the-beaten-path tours for small groups of travelers. But over t

he years my vision grew more focused and my mission became more clear: to offer a uniquely special PLACE where creatives and intimate groups can meet, travel, learn and explore, as they immerse themselves in the beauty of Italy, and of life. WHAT We Do

We create and customize workshops, retreats, weddings and private trips – all based at a 17th century villa. The villa is reserved exclusively for your group, and we customize your stay with any number of private excursions or insider experiences. Over the years we’ve explored the countryside, befriending local Italians who are eager to create and host insider experiences and activities for you, their special guest. This network of local connections is our heartbeat. ❤️

Because our team is based in both the U.S.A. and Italy, we’re able to seamlessly gather your requests, then make it all come together.

It’s been a fabulous week with a delightful group of mixed media artists. From inspiring lessons in the studio with Eliz...
13/09/2024

It’s been a fabulous week with a delightful group of mixed media artists. From inspiring lessons in the studio with Elizabeth St. Hilaire to making cantucci and hunting for truffles, the days have been full and wonderful!

What a gorgeous evening to welcome Elizabeth St. Hilaire and her first group this fall. The next days will be a whirlwin...
09/09/2024

What a gorgeous evening to welcome Elizabeth St. Hilaire and her first group this fall. The next days will be a whirlwind of mixed media experiences that are nothing less than inspiring - and super fun! Here’s to the magical days ahead! ☀️😊

What a phenomenal week its been with the amazing Kathleen Clemons and her delightful group of photographers. Spending ti...
05/09/2024

What a phenomenal week its been with the amazing Kathleen Clemons and her delightful group of photographers. Spending time with such kind, curious and super-fun people has been an absolute joy. It’s tough to say goodbye! Sooo… we’ll say, until next time. 😊

What an incredible time we’re having with this talented group of floral photographers! From full days of shooting flower...
03/09/2024

What an incredible time we’re having with this talented group of floral photographers! From full days of shooting flowers (from every angle imaginable) to relaxing evening aperitivi, it’s so special to experience Tuscany (and Umbria) through their lenses. 😁

It’s a beautiful morning to kick off our first group of the fall season! I love this time of year, as we phase back into...
01/09/2024

It’s a beautiful morning to kick off our first group of the fall season! I love this time of year, as we phase back into meeting and greeting our amazing guests, in so many diverse tours, workshops and retreats. Here’s to the wonder-filled weeks ahead! 🥂 😊

Are you ready to run around Florence, the Tuscany countryside, and a few other places with me? Honestly, I’m totally in ...
22/08/2024

Are you ready to run around Florence, the Tuscany countryside, and a few other places with me? Honestly, I’m totally in love with this itinerary! Amazing art, stunning architecture, great food and fun people. I mean, what more could we want? YOU! That’s what! Come join me next April, when the wisteria is blooming in Tuscany, for a gorgeous, once-in-a-lifetime experience! 😁 Link is in bio. Use code ARTHISTORY25 for $200 off!

Are you ready to run around Florence, the Tuscany countryside, and a few other places with me? Honestly, I'm totally in ...
22/08/2024

Are you ready to run around Florence, the Tuscany countryside, and a few other places with me? Honestly, I'm totally in love with this tour itinerary! Amazing art, stunning architecture, great food and fun people... I mean, what more could we want? YOU, that's what! Come join me next April, when the wisteria is blooming in Tuscany, for a gorgeous, once-in-a-lifetime trip. 😁 https://stradatoscana.com/art-history-culture/

And it’s open! We’ve just launched a brand new tour and I couldn’t be more excited! Florence to Assisi: Art History and ...
18/08/2024

And it’s open! We’ve just launched a brand new tour and I couldn’t be more excited! Florence to Assisi: Art History and Culture is an immersion into the spectacular beauty of Italy’s art, architecture and culture. You can check out all the details by following the link in our bio, and be sure to use code ARTHISTORY25 upon checkout to get $200 off. I hope you’ll be able to join me, as I’ll personally be leading this tour. 😎

After a day of painting in gardens and vineyards, it’s time to put down the sketch journals and paintbrushes and grab so...
19/06/2024

After a day of painting in gardens and vineyards, it’s time to put down the sketch journals and paintbrushes and grab some pizza and gelato. 🍨 What an amazing group of talented artists! 😊

A big welcome to Simon Roberts and his delightful group of painters. It’s going to be a lovely week of watercolor journa...
16/06/2024

A big welcome to Simon Roberts and his delightful group of painters. It’s going to be a lovely week of watercolor journaling in historic piazzas, medieval alleyways and sweeping vineyards. Let the painting begin!

A beautiful week with a beautiful group of artists. In between painting and learning sessions with there was exploring,...
14/06/2024

A beautiful week with a beautiful group of artists. In between painting and learning sessions with there was exploring, experiencing and sooo much laughter! Feeling so grateful to get to know such lovely people, and to introduce them to so many special people here in our beloved village. 🥰

Grazie to our friends at for a beautiful visit with …and a magical evening dining together under the old olive tree. 😌...
11/06/2024

Grazie to our friends at for a beautiful visit with …and a magical evening dining together under the old olive tree. 😌

We’re thrilled to welcome artist, Jodie King, back to Città della Pieve! It’s going to be a fabulous workshop filled wit...
10/06/2024

We’re thrilled to welcome artist, Jodie King, back to Città della Pieve! It’s going to be a fabulous workshop filled with loads of creativity, inspiration and laughter. Plus plenty of exploring spectacular places and eating exceptional food!

What a lovely experience with this group of talented floral designers! From cutting flowers at an organic flower farm, t...
07/06/2024

What a lovely experience with this group of talented floral designers! From cutting flowers at an organic flower farm, to styling tables in a local restaurant, it’s been such an inspiring week! We’re already looking forward to next year with the amazing Kelly Marie of 🤩

Invasion of floral designers in Città della Pieve! is here this week, with the delightful Kelly Marie Thompson teaching...
03/06/2024

Invasion of floral designers in Città della Pieve! is here this week, with the delightful Kelly Marie Thompson teaching floral design to a wonderful group of students who are curious, creative and downright fun! 💐

One of the most special excursions we take on many of our tours and workshops is to San Casciano dei Bagni, where in 202...
26/05/2024

One of the most special excursions we take on many of our tours and workshops is to San Casciano dei Bagni, where in 2020 archeologists made a remarkable discovery of an Etruscan/Roman sanctuary at the source of the town’s most important thermal spring. In use for about 800 years, and dedicated to various gods linked to healing and hot waters, the site is truly astonishing, and being able to visit this amazing place - especially with our friend, Ludovico, is nothing less than a privilege. ☺️

An incredible week with a truly lovely group of women travelers. When you bring together a group of heart-centered peopl...
24/05/2024

An incredible week with a truly lovely group of women travelers. When you bring together a group of heart-centered people, who lead with a spirit of adventure and curiosity, the results are simply magical. And that’s what these past days have been. Magical.

Oh, Val d’Orcia, you’re so gorgeous! This week we’re exploring from Pienza to Ficulle to San Casciano dei Bagni on our s...
22/05/2024

Oh, Val d’Orcia, you’re so gorgeous! This week we’re exploring from Pienza to Ficulle to San Casciano dei Bagni on our spring Women’s Adventure. And what a fabulous group of ladies! Full of curiosity and kindness. Now that’s a winning combo!


What a magical week it’s been with a truly delightful group of landscape photographers! Daily departures at 4:00am have ...
17/05/2024

What a magical week it’s been with a truly delightful group of landscape photographers! Daily departures at 4:00am have resulted in spectacular photos of some of Tuscany’s most iconic sites, along with some tucked away treasures. As always, it’s been a true pleasure to partner with … an extraordinary photography teacher and dear friend. Here’s to next year! 😍

We love it when Tiffany comes to town! Plus she takes landscape photography to another level, with carefully planned iti...
12/05/2024

We love it when Tiffany comes to town! Plus she takes landscape photography to another level, with carefully planned itineraries that include tucked away sites and best-kept secrets. Here’s to an amazing week ahead!

Such warm, welcoming hospitality of our friends in Sorrento! Pia, Sascha, Luigi, Francesca, Rosella, Rosaria, Nico and F...
11/05/2024

Such warm, welcoming hospitality of our friends in Sorrento! Pia, Sascha, Luigi, Francesca, Rosella, Rosaria, Nico and Ferdinando make our tours here seem like a week spent with family. What a wonderful adventure it’s been! 🥰

Just hanging out on top of a scenic cliff, in a private lemon grove in Sorrento. We walked, we sipped and we cooked. Oh,...
08/05/2024

Just hanging out on top of a scenic cliff, in a private lemon grove in Sorrento. We walked, we sipped and we cooked. Oh, and we laughed… a lot! Thanks to Pia, Francesca and Rosaria for a truly incredible experience!

And we’re off! Our Sorrento Women’s Adventure has begun with a fabulous group of women who’ve come together to enjoy exp...
06/05/2024

And we’re off! Our Sorrento Women’s Adventure has begun with a fabulous group of women who’ve come together to enjoy experiences, scenery and culture (and food!) of this unique part of Italy. Let the fun begin!

So fun!! Thanks, Cristian, for another fabulous experience for our guests. There’s nothing better than an afternoon of l...
02/05/2024

So fun!! Thanks, Cristian, for another fabulous experience for our guests. There’s nothing better than an afternoon of learning, eating and sipping… all in a lovely setting. ☺️ .duca

Nothing like the joy of an excellent dinner, followed by homemade limoncello. Gianluca of Ristorante Da Laura spoils us ...
01/05/2024

Nothing like the joy of an excellent dinner, followed by homemade limoncello. Gianluca of Ristorante Da Laura spoils us with a warm welcome and an exceptional meal…. plus we head back out onto the street smiling and laughing. 😁

And we’re off and running with Sandra Mollon’s delightful group of students for what promises to be a fabulous workshop ...
28/04/2024

And we’re off and running with Sandra Mollon’s delightful group of students for what promises to be a fabulous workshop experience. Stay tuned as these textile artists do amazing things with fabric with Sandra’s expert guidance. 😁

Wowza! Talk about dramatic skies and amazing light! Our day at with Alicia from and her delightful group of students, ...
23/04/2024

Wowza! Talk about dramatic skies and amazing light! Our day at with Alicia from and her delightful group of students, turned from steady rain to blue skies in an instant. The effect was gorgeous… and so were their floral arrangements. 😁

What an amazing workshop by with a truly special group of floral designers! So much laughter, creativity and kindness r...
16/04/2024

What an amazing workshop by with a truly special group of floral designers! So much laughter, creativity and kindness rolled into one. I’m grateful and honored to host such incredible events that spread the love! 💕 Thank you, Paulina and students!

And we’re off! Our spring season has officially kicked off with a fabulous group here for Berri Kramer’s Legacy Workshop...
07/04/2024

And we’re off! Our spring season has officially kicked off with a fabulous group here for Berri Kramer’s Legacy Workshop. We’re enjoying a lovely warm evening in the piazza, and looking forward to the inspiring days ahead! 😁

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What a wonderful day hunting, drawing and eating truffles! Thanks to Andrea and Mario, and especially Livio and Zara 🐕 for an unforgettable experience for @paperpaintingscollage and her students. @truffle.hunting.umbria you’re the best!

Another fabulous lesson with Cristian. This time, cantucci! Served after dinner with vin santo, of course. And they were delicious! 😋 @paperpaintingscollage @bistrot.duca

Grazie mille @rocsanamarina for the beautiful cappuccino art and @anticacaffetteriamatucci for the generous hospitality for @paperpaintingscollage group of artists! 😁

What a magical experience! Grazie infinite to Gigi for an incredible, spectacular ride above Siena and the rolling hills of Tuscany. Joy and awe!!

Winding, medieval avenues are the BEST! Plus you feel like you’re stepping back in time. #medievalvillagesitaly #exploringitaly #offthebeatenpathitaly #stradatoscana

Let's keep our perspective!
Let's keep our perspective!

Cappuccino!
Cappuccino!

Thanks to Mr. Orlandi! [and Italy's Master Artists]
Thanks to Mr. Orlandi! [and Italy's Master Artists]

Sweet Bread? Fancy Cake? What is it, Anyway?
Sweet Bread? Fancy Cake? What is it, Anyway?

Strada TV: Season 2!
Strada TV: Season 2!

Il Pozzo [It's a Deep Subject]
Il Pozzo [It's a Deep Subject]

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What We Do

We create and customize workshops, retreats, weddings and private trips in Italy. A private, Italian-owned villa is reserved exclusively for your group, and we customize your stay with any number of hand-selected excursions and insider experiences. Over the years we’ve explored the countryside, befriending local artisans, experts and residents who are eager to share their passion with you. It’s this network of local connections that is our heartbeat. Because our team is based in both the U.S.A. and Italy, we’re able to seamlessly gather your requests, then make it all come together.