Tuscany Culinary Retreat & Tour


Our Exclusive Tuscany Culinary Retreat is booking up quickly for 2024! 

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Travel to Italy & Live the Mediterranean Lifestyle for a Week

Join your hosts, Internationally Renowned Chef Dario Tomaselli and Best-Selling Author and Rich Life Travel Business Expert Anita Heidema, as they take you on a culinary adventure of a lifetime in Italy.

No more than 20 participants.

Our retreats are conducted in intimate groups of no more than 20 participants. You’ll get to know us and each other on a very deep level and the connections you’ll make during our retreats often last a lifetime.

Unique Experience

When you travel with us, you’ll be as immersed in the local culture as we can get you. We truly believe that the most meaningful travel experience allows you to live as a local for a short time. When you do that, you can allow the culture to change you on a very deep and personal level.

We partner with locals.

Making sure our accommodations and experiences feel like family, intimate and filled with personal connection. It’s a rare type of travel experience that most people never have the privilege of experiencing.




Price, Dates & Details

Your Hosts & Tour Guides

What Our Guests Say


Your Accomodations

Price, Dates & Details

Your Hosts & Tour Guides

What Our Guests Say

Your Itinerary

* Details are approximate and subject to change

Saturday, Sept 21 – Arrive - Welcome to Italy!

  • Transfer from Rome International Airport FCO
  • Downtime to settle into our beautiful Tuscan Villa & unpack
  • Rich Life Rest & Relaxation Session  (sign up ahead)
  • Group Welcome Dinner – Come meet us and your other travel companions and enjoy our first delicious meal together with wine & olive oil pairing and tour of the area

Day 1 – Sept 22

  • Rich Mediterranean Life (RML) morning rejuvenate stretch option
  • Arezzo City Tour – Do you remember the award winning movie “La Bella Vita”? This is where we are going today to take a tour of its history and try some local foods
  • Return to the Villa and take the afternoon to relax by the pool or rest from your travel day yesterday
  • Dinner – Ready to prepare your first Tuscan meal? Join us in the world-class Villa kitchen as we learn and cook our dinner together.

Day 2 – Sept 23

  • Rich Mediterranean Life (RML) Rejuvenate stretch option
  • Siena – Today we’ll travel together to Siena and give you the day to explore one of Italy’s loveliest medieval cities. Guided Tour is in the morning and free time and lunch in afternoon.
  • Dinner at the Villa – We’ll return to the Villa and come together over a delicious dinner prepared for you by incredible local chefs and share the details of our day’s adventures

Day 3 – Sept 24

  • Rich Mediterranean Life (RML) Rejuvenate stretch option
  • Time to Relax by the Pool and take in the sites
  • Dinner Cooking Class – We’ll come together for our second cooking class of the tour and enjoy the fruits of our labor as we dine together
  • Locals Party in the Tuscan Hills – This is truly one of the highlights of this tour. You’ll join us and our local friends for a family-style BBQ, with local people, food, wine, and entertainment. This evening truly embodies the “family” feel of this tour and you’ll be moved and inspired by the connections you’ll make.

    Day 4 – Sept 25

    • Rich Mediterranean Life (RML) Rejuvenate Stretch option
    • Florence – Today we’ll travel to Florence, the “Cradle of the Renaissance” and you’ll have the day to explore the many museums and sights in this incredible city. Tour and free lunch.
    • Dinner – Ready to learn to make pasta? Tonight’s cooking class will teach you everything you need to know and our delicious dinner in the villa will remind you of why Italy is famous for its pasta.

    Day 5 – Sept 26

    Today is full of so many highlights. Make sure to get your rest here or nap on the tour bus.

    • Parma Parmigiano Reggiano Tour – We travel to Parma and go behind the scenes to find out how one of Italy’s most famous cheeses is made
    • Parma Farm pizza making class and lunch with local grains and products. Find out why pizza is of one of the world’s most popular foods (but trust us, you’ve never had pizza this good before)
    • Modena – After the tour, we’ll head to Modena and spend some time learning about balsamic vinegar at famous Guisti, and we’ll cap off the day with Michelin Chef cooking class and out of this world experience for dinner

    Day 6 – Sept 27

    • Sleep in and relax time by the pool and winery to explore or do what you want
    • Rich Mediterranean Life (RML) Workshop (Sign up ahead)
    • Monte San Savino – Today we’ll head to the hills as we visit this quaint village rich in medieval and Renaissance history in the afternoon
    • Dinner – Tonight we’ll dine at the exquisite Aldo Iacomoni. Chianti valley Monte San Savino. Best place to admire enchanting Tuscan sunsets

    Day 7 – Sept 28

    • Tuscan Breakfast – As our time together comes to an end, we’ll come together for a traditional breakfast.
    • Return To Rome transfer morning

    Your Accomodations

    Experience the beauty and charm of Tuscany on our exclusive retreat, located in Arezzo, Italy. Your villa, Podere Di Pomaio,, is designed to delight your senses and enrich your soul. As seen in our video, your luxurious accommodations are set amidst rolling hills and idyllic countryside, offering the perfect blend of comfort and tranquility.

    Your Accomodations

    Experience the beauty and charm of Tuscany on our exclusive retreat, located in Arezzo, Italy. Your villa, Podere Di Pomaio,, is designed to delight your senses and enrich your soul. As seen in our video, your luxurious accommodations are set amidst rolling hills and idyllic countryside, offering the perfect blend of comfort and tranquility.

    Price, Dates & Details

    Couples, Friends and Solos are welcome!


    8 Days/ 7 Nights

    Arrive: Saturday Sept 21st, 2024

    Depart: Sept 28th, 2024

    (Transfers from Rome International Airport)


    Deposit: $750 USD Per Person

    Final Payment: $5,250 USD  Per Person (Double Occupancy)

    Total Price (without discount) $6000 USD

    Early Bird Booking Discount: $250 off the total price if you book and submit your deposit of $750 USD before June 17th, 2023.



    7 breakfasts, 5 lunches, 7 dinners, Wine, Beer & Specialty Drinks, Tours, Gratuities, Private Bus (transfers & tours), Rich Life Relaxation Sessions.Secure Your Spot

    Does Not Include:

    Airfare, 2 lunches off-site & Personal Expenses. You must have Proof of Cancellation & Medical Insurance


    Have questions? Get in touch for more information.

    7 + 15 =

    Your Hosts

    If you’ve explored this website, perused our O’Live Your Life YouTube channel or followed us on social media, then you’re already familiar with our philosophy of healthy eating and embracing a slower, more mindful approach to life – all inspired by the Mediterranean way of living.

    Our team is led by internationally renowned Chef Dario Tomaselli – a multi-lingual, Italian-born entrepreneur, restaurateur, and professor for Chef Post Diploma International Program Italian Cuisine – alongside North American-born and raised Rich Life Strategy Guru Anita Heidema. Anita is an entrepreneur, best-selling author, health advocate, podcast host, and TV personality with extensive travel industry experience. Together, we are thrilled to offer these two one-of-a-kind retreats in Amalfi and Tuscany.

    As your personal tour guides, we bring you an unparalleled level of knowledge and expertise of the region, its food and wine, and its people. We have planned and researched every detail of your 7-day journey, offering a well-curated itinerary of must-see sights as well as spontaneous, authentic experiences that are usually only available to locals.

    Come join us and experience the magic of Italy through the eyes of locals who truly understand and appreciate its beauty and culture!

    Imagine Your Dream Italian Vacation….

    If you’ve always wanted to experience Italy, not as an average tourist but as a local with special privileges, you’ll want to plan to join us for this unique and life-changing experience.

    Past Guests Say…

    We had an incredible time on our Under the Tuscan Retreat with Anita & Dario. We did adventures and tours we would not have seen on any standard tour. We got to experience Italy and all its beauty plus more. Looking forward to when they expand to other areas of the world and will join 100%.

    This culinary retreat and days with Dario & Anita will stay with you forever.
    Patti & Sam

    Food, cooking & adventure oh my!!!! We had so much fun on our culinary retreat to Italy with Chef Dario & Anita. We ate like kings and sang like Boccelli :)….The tours were incredible and nice that we were a smaller group and that Dario knows many of the locals and language. We asked Anita to do a meditation every morning by the pool that started our day right. Perfect balance of activities and relaxation and just what we wanted. Grazie
    Marc & Sally G

    It was an experience of a lifetime travelling with Dario & Anita. We took their culinary retreat to Italy for 7 days on the front of a 2 week vacation. Italy was our dream and it was everything we expected and more. So much fun!!! Thank you.
    Amanda & Jack

    Frequently asked questions

    Q: What makes this travel experience different from other Italian tours?

    A: The tours are with trained and experienced tour guides Dario & Anita, who know the country and people, thus providing a totally unique experience.

    Q: Will I have free time to explore on my own?

    A: Yes you have 2 afternoons in Florence and Siena, plus pool time to relax.

    Q: What if I want a more bespoke experience? Is that possible?

    A: All of our tours are bespoke for each small group, but if you’re looking for something more individual in particular, we’re always happy to add to the beginning or end of the trip

    Q: I have questions that aren’t answered here. How do I get those answered?

    A: Email at [email protected]


    *All prices and itineraries are per person, based on double occupancy, in USD dollars unless otherwise indicated.

    All prices apply to new bookings only, based on availability at the time of booking. This tour requires a minimum of 14 participants to operate.

    Travel Group strongly recommends the purchase of cancellation and emergency travel and medical insurance including COVID-19.

    Please note: Participants must be able to embark and disembark coaches without assistance as well as have a good level of mobility for walking tours in destinations where stairs and traditional cobblestone streets can be challenging.


    Reach out to your hosts Anita & Dario from O’Live Your Life at [email protected] and they will review all of your questions and provide you with what you need.

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