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Private Italian Retreats

"You may have the universe if I may have Italy."

Giuseppe Verdi

Tuscany Private Retreats

Our Private Retreats are for private GROUPS who are interested in customizing an authentic Italian experience with Italian Insiders. From girls trips, sister trips, family reunions, business trips, we can accommodate groups that start around 6-8 people up to 20 people. Please note that prices will be higher for less participants.


To start planning your group trip to Tuscany, we first have you fill out a questionnaire and then we'll have a face to face consultation via video call and talk about your wants/needs and then we'll create a customized package.

We require a deposit to finalize the holding the retreat dates, and can facilitate all program sign-ups, payments, guest management and communication.

Full details will be provided on a customized basis.

Pizza Party
Italian coffee
Retreat Guests

What's included?

Depending on what accommodation you choose, there might be other excursions, activities, and day trips that can be added.

  • Accommodation for 6 days/7 nights in a private villa with exclusive pool & garden

  • All meals at the villa

  • Pizza Party made with a wood burning oven onsite

  • 3 Wine-tastings & tour of a small, family run vineyard

  • A visit to one of the oldest churches in the Florentine diocese

  • An excursion to learn about beekeeping

  • Access to a fully stocked kitchen throughout the week

  • All excursions including wineries

  • A dinner out to an authentic Family Run Restaurant

  • Tuscan Hike and a tour of a Terra Cotta workshop

  • Italian Cooking class and dinner

  • Transportation to/from each excursion

  • Pick up/drop off at the Chiusi train station

  • Visits to cities like Florence, Greve in Chianti, San Gimignano, Siena, Montefioralle, San Casciano Val di Pesa

What's NOT included?

  • Airfare

  • Travel Insurance

  • Meals outside of villa/B&B/agriturisimo

  • Transport from/to airport

OUr Tuscan Villas

Villa Antica Sosta - Castelfiorentino, Tuscany

Camporsevoli - Cetona, Tuscany

Our Authentic Touch

Montefioralle Winery

We speak Italian

Katie has been traveling/living to Italy for over 20 years. She speaks fluent Italian. Stefano, her Florentine husband, will be on this adventure with us as our driver. Fernanda, Stefano's mom, will be our chef for the week. She speaks little English. She has a heart of gold and a great talent of making the most delicious and simple recipes.

Small Group Travel 

Truly Italy prides itself on being focused on small group travel. Our goal is creating unique, authentic, bespoke Italian experiences that you will never forget. We seek out experiences you would not choose on your own. Welcome to authentic Tuscany!

Italian Family

You'll be among family while you are with us. No big coach buses. No tour guides holding a huge flower to follow. 

Italian insiders, Katie & Stefano as your guides and Fernanda filling our bellies with delicious Italian dishes. 

We'll enjoy intimate dinners where we'll reminisce on our day exploring the hidden treasures of Tuscany. 

Authentic Italian Travel Retreats that are...

Intimate ~ Personal ~ Educational

About the Hosts

Katie Portanova

Italy Travel Consultant & Retreat Host

Ciao! I'm Katie born in the US but my heart has remained in Florence.


From a young age, I always followed my heart’s desire. I’ve been living on and off in Florence since 2002 when I studied abroad through Saint Mary's University in Winona, MN.


I’ve got almost 20 years under my belt of taking trains, buses, and visiting the most beautiful, secluded places in Italy. In order to live in Florence legally, I went as far as getting UK citizenship to obtain residency in my most favorite city in the world. It was well worth the wait. My heart leapt with joy once I made Florence my permanent home from 2009-2013.


During those years, I was lucky to find the love of my life. Stefano and I have a strong love for Florence & Tuscany. Being a Florentine, his heart, like mine never left. On our retreats, you'll meet Stefano who will be our driver and part-time chef. 

Since moving back home, my goal has been to keep Italy in my life any way possible, and thus, Truly Italy was born!

Throughout your week in Tuscany, you'll be present amongst delectable wines, splendid views, simple recipes and great company-


- You'll leave refreshed and that you had an authentic Italian Experience. 

Let's get you to Italy! :)

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Katie Portanova

traveling is about finding those things you never knew you were looking for

Stefano Portanova

About the Hosts

Stefano Portanova

Florentine, Our Driver, Katie's Husband

Stefano is first and foremost a Florentine who fell in love with a 'chicagese' in 2011. After 10 years of being a couple, we certainly have learned that travel is the most important thing in life. It's where you connect with others, learn about culture and indulge in delcious food.


Stefano will help out cooking the steaks on the grill as well as telling stories about his childhood living in the city of Florence. 

He can't wait to show you his favorite places in Tuscany!


About the Hosts

Fernanda Portanova 

Born a Trentina, now a Tuscan, Our Chef, Katie's MIL

Fernanda is Katie's mother in law and such a great addition to our Truly Italy Team. She's a warm and loving person who loves meeting new people. She speaks a little English but as we all know, you can easily communicate with someone when you try and also if you have google translate. :) 

Fernanda can't wait to meet you and share her delicious, simple recipes during our Tuscany Travel Retreats.

"Not all who Wander are lost"
J.R.R. Tolkien

How to Sign up

Retreat Guests
Step 2: An automated email will arrive in your inbox with a Calendly link to set up a video call with Katie.

This call is to help answer any questions about our retreat. We will also discuss which payment plan you choose.

**Add to your contacts so the email doesn't go to spam.**
Step 3: If you choose to come with us (YAY!), We'll send you an email with your payment plan quote, Retreat Terms & Conditions to read and sign, & finally the link to pay your non-refundable deposit of $500.

**Payment plans are available**
Step 4: Start searching for flights to Bella Toscana!

The Trick to getting through life is always having a holiday to look forward to.


One activity a day

Small Group Travel

Family Atmosphere

Authentic Italy

Each day consists of 1 activity, i.e. a visit to a small town, family run vineyard, a hike or a bike tour.


With plenty of free time, you can take a stroll through the Renai neighborhood, taking photos of the stunning scenery, and experience the serenity of the Tuscan hills.

After a Truly Italy retreat, you’ll feel connected, grounded, and recharged.

Ready for your fully planned Tuscany adventure with an Italian insider?

Let's see if this authentic Italian experience is for you.

Fill out this questionnaire

"Nothing except time is wasted in Italy"
-Thomas Bailey Aldrich


Join us in Italy for your next Trip!

Click the button below to get started!

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