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Italy Travel Retreats

For Lovers of Cuisine, Tradition, and Culture.

A message from YOur Italian Insider

Cypress Trees, Truly Italy

Experience the true beauty and culture of Italy on a
Truly Italy Travel Retreat! 

How long are the retreats?
7 nights

When are your upcoming retreats?
!!NEW!! Truly Blue Sardinia Sailing Trip - May 24-31, 2025
Truly Tuscany Retreat - Aug 30-Sept 6, 2025

Truly Florence Retreat - Sept 8-15, 2025

What does each retreat cost?
Starts at $7200 per person

Grapes, Truly Italy

Andiamo!! Let's go!!

Experience Tuscany like a local

​Our retreats are held in family-run villas & B&Bs in Florence & Tuscany.


​Our guests are travelers who value being off the beaten path. They trust in their guides who show them experiences they would never seek out on their own. 

Truly Italy is dedicated to providing an immersive and unique experience of Italy. We specialize in small-group tours in Tuscany & Florence, where you can get a real taste of what life is like for a local.

This is for you if you are...

  • looking for more than a vacation but a priceless Italian experience in Italy. ​​​

  • an open-minded, flexible, go with flow kind of person.

  • someone who enjoys having a trip already planned for you, no work on your end.

  • a physically active person who can walk comfortably 3 miles a day on uneven ground. (For example, we walk uphill into town and downhill out of town)

  • a person who wants to immerse themselves in culture, language, and history.

  • someone who likes to take their time when they travel.​

  • someone who is a traveler, not just a tourist.

  • someone who wants to feel like being part of a Tuscan family.​

We pride ourselves on creating unique, authentic, bespoke Italian experiences that you will never forget. 

When you come on a week-long retreat with Truly Italy, you'll experience everything that is special and dear to our hearts. You'll experience slow travel while you travel with ease & peace of mind. We won't be rushing around Tuscany, we'll be present during our daily activity.


We lovingly remind you that Italy has its own culture and things will not be the same as at home. We are very active throughout this trip, be prepared to walk a lot.


Don't be surprised if by the end of the week, you might be speaking and understanding Italian. My husband, Stefano, and my mother in law, Fernanda will be on this journey together. You’ll learn about Italian culture, traditions, language, and our favorite: Tuscan cuisine and wine.

It's not like any other travel experience, you are being welcomed into my Italian family. 

If you are ready to reserve your spot, click on the button below so we can connect.

Vineyard, Truly Italy

How to Sign up for our Retreats


Pay your non-refundable deposit of $500, Sign your Retreat Agreement


Fill out our Intake Form - this helps us know what kind of traveler you are.


Start looking for your ticket to Authentic Tuscany...

Katie Portanova

What to expect on a Truly Italy Retreat

Hi! I'm Katie, your guide who has lived in Florence as a resident for 4.5 years (and still feels like a resident) and I've been traveling to Italy for over 20 years. Our intention at Truly Italy is to show you the hidden gems of the most gorgeous country. My husband, Stefano, (a Florentine) will be our driver throughout the week. My mother-in-law, Fernanda, will be our passionate chef for the week. She makes each meal with her whole heart and it shows. The whole Truly Italy team wants to help you do something extraordinary that you wouldn't normally do on your own. 

  • Each morning you'll enjoy an Italian style breakfast before we set off on our adventure.

  • Each day consists of 1 activity, i.e. a visit to a small town or vineyard and on our Truly Florence retreat, a walking tour or a cooking class. Then the rest of the day is yours to explore the scenery around you. 

  • We'll have lunch together at a quaint trattoria in Florence or a 4 hour wine-tasting at an organic vineyard. 

  • In the afternoon, you can sit poolside and listen to the sounds around you. In Florence, perhaps you want to see the exquisite art in the Uffizi Gallery. You will have the freedom to do what you want and of course receive Katie's guidance.

  • Evenings will be spent at the villa enjoying a delicious meal created by Fernanda. In Florence, we will have a meal at the B&B or venture out and try delicious Tuscan dishes at a local trattoria and osteria


You want a stress-free, already planned, completely taken care of feeling - kind of trip. 

This is the reason why you found us, right?

What you'll take home are stories of pasta-making, walks through Tuscan towns, conversations with locals, and an enormous knowledge of Italian culture and history. 


Best part, you'll leave with new friendships with real Italians.


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

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

Learn how to pay your deposit and save your spot below!

What people are saying...

Casa Lucii Wine Tasting

"The Villa, the home cooked meals, and the vineyards were wonderful. All the restaurants were delightful (and dang tasty). Maria and your beautiful warm Mother in law is a gift. Katie, you and Stefano did a FABULOUS job with attending to all are requests. Bravo!!"
- Mary Jo, Sept 2022

"Our First Experience of Tuscany Felt Wonderful...Intimate Tuscan Life, Meals, Wines, Villages & Countryside. You all Provided Beautiful Opportunities of Siena, Florence and Wineries, Learning their Practices from Planting to Sipping, Culture....our Guides, Interpreters & So Much More....Grazie!"
-Debbie, September 2022

“It was the sauce on top of a great meal, I guess would be one way of describing a great dessert and all it would have been. Having Katie, Stefano and Fernanda made the experience so much richer.”
- Skip, September 2022

Why you chose a Truly Italy retreat?

"Katie was able to explain things to use and explain things for us. Just the ease of it and making us feel at home like we were at home." -Deb 

Truly Italy Retreat Guests

Join us for one of our Upcoming retreats

Pick your Favorite


I know, it's hard!

Truly TuscANY

August 30-September 6, 2025

Starting at $7891 per person

Katie Portanova

Truly Florence Retreat
September 8-15, 2025

starting at $7200 per person


For lovers of Wine, Culture and Relaxation

Our Truly Tuscany Retreat is for lovers of Tuscan wine, culture and travelers looking for a rejuvenating experience. 


Our retreat is held at beautiful and luxurious accommodation owned by close family friends. Villa Antica Sosta is owned by Maria & Vincenzo who have been friends and neighbors of my in-laws for over 15 years. Located on a hill above Castelfiorentino, south of Florence, the villa is a perfect place to relax and enjoy the stunning Tuscan scenery.


The villa offers the perfect setting for your group getaway. Boasting 5 bedrooms, 3 shared bathrooms, a spacious dining and family room with a fireplace and TV, our villa is the ideal place to relax and enjoy quality time with friends and family. The kitchen is fully-equipped and perfect for cooking as a group, including a cooking class. You'll also have full access to the kitchen for coffee, tea, and other beverages, plus merendine (snacks) will be available at any time.


Our secluded pool is surrounded by a lush garden full of vibrant flowers, olive trees, smells of lavender and rosemary, providing ultimate privacy and relaxation. Lounge chairs and umbrellas are available for sunbathing, and an outside dining table allows you to enjoy your meals while admiring the gorgeous views of the Tuscan hills.

During your week long adventure in Tuscany...

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. You'll also be a two-minute walk away from a small café which serves up coffee, cocktails & light snacks. Maria, Vincenzo, and Fernanda prepare and cook your personal pizzas by utilizing the custom pizza oven onsite.


Maria & Fernanda, my mother in law, will teach you how to make Pici pasta from scratch, crostini toscani, and Arista, a simple & delicious pork dish. 

On day trips, we will be visiting small towns like towering San Gimignano, rolling Montefioralle, and a fortress on a hill, Monteriggioni. 

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. 

We'd love for you to join us, learn how to pay your deposit and reserve your spot on this authentic Tuscan experience.

Villa Antica Sosta

For new & old travelers to Florence

Secret Garden Firenze

Truly Florence Retreat is for travelers who want to feel like a local

You'll experience Florence like a local with ease, peace of mind and with expert guidance - you'll leave knowing you had a truly authentic Italian experience

We'd love for you to join us, check out all that is included by clicking the button below. 

Photo gallery from recent trips

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Click on Retreat Sign Up below to start the process

Also check out the FAQ page for more info.

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