This trip is being organized by Carl Landau, (and his wife Diana), host of the popular I Used to be Somebody podcast and newsletter. Just like our show, this adventure is targeting people that are planning to or are recently retiring from their career job. But they don’t want to retire, they want to do something NEW, something more FUN and something more MEANINGFUL. We call this (Un)Retirement!
This is your opportunity to network with creative people just like you, as you begin this new phase of your life. Plus, you get to do this while experiencing the beauty, history, and culture of Italy. Did we mention the amazing food and wine tasting too? (Max size group is 20.)
Three one-hour, lively, educational “I Used to be Somebody” sessions are included in the tour to make your trip complete. (Check with your tax advisor regarding the possibility of a tax deduction for this educational experience.)
Topics include:
#1 Who are you? When you were “someone”, what did you do and where are you in planning or implementing of your new “(Un)Retirement” stage of life?
#2 The 8 secrets to a Successful (Un)Retirement Life.
#3 Plan your (Un)Retirement post-trip, with accountability markers.
(Sipping Italian wine might help to make the discussions even better!)

Unique Experiences

  • Engage in truffle hunting and a cooking class
  • Tour a local pecorino (sheep’s cheese) farm in Pienza followed by a picnic
  • Taste the region’s wines: Brunello di Montalcino, Chianti, Nobile de Montepulciano, Super Tuscans
  • Learn about the art of coffee roasting and chocolate making at a cafe in Arezzo
  • Sample artisanal gelatos and small-batch family made olive oil

About Your Hosts

Carl and Diana are hosts of the popular I Used to be Somebody podcast and newsletter, inspiring 50+ professionals on how to build their (Un)Retirement good life. They are also co-authors of the Amazon best-seller Pickleball for Dummies. Carl and Diana Landau produce the I Used to be Somebody podcast in their tiki bar. Next stop Tuscany!



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Tour Details

Tour Details

  • Tour Date: September 15 – 21, 2024
  • Trip Price Per Person: $4,950
  • Single supplement: $900
  • Tour Size: 20 people
  • Guide: Giovanni Ramaccioni or other Tuscany-based guide
  • Meals: All meals included except two lunches and one dinner
  • General Tour FAQs
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Private Tour Bookings

  • Private Tours are available to book with your own group on any date you choose, given guide and lodging availability
  • Please note –  Our pricing is based on double occupancy lodging. If upon finalizing your private trip, your group has a solo traveler in a room without a roommate, the single supplement becomes mandatory. This amount will differ depending on the itinerary. Please contact our tour operations team for specifics
  • Customizations to the itinerary are possible with additional per person fees
Sonoma Wine Tour Review

Tour Itinerary

Day 1


We meet at our Florence hotel after lunch at 1:00 PM for short introductions. We will then be joined by a local Florence guide for a wonderful historical walk of the city.  (If you wish to visit the David or any of the other impressive historical sites, you should plan on arriving to Florence a day early.)

After our three-hour walk, you have time to change into your evening clothes and enjoy a drink before dinner.

This evening, we’ll then make our way to a quaint family-owned restaurant for a lovely welcome meal. After dinner, we head back to the hotel and rest up for tomorrow’s adventures – our first full food and wine day in Tuscany.

Day 2Tuscany Food & Wine Tour - Day 2 Chianti

After the wonderful hotel breakfast, we will have our first (Un)Retirement Session where we will dive into the following topics: Who are you you? When you were “someone”, what did you do and where are you in planning or implementing of your new “(Un)Retirement” stage of life?

After a reflective morning, we check out of our hotel and are off to one of the most famous wine regions with one of the most famous wine styles in Italy: Chianti. Our first stop is the picturesque city of San Gimignano, a small medieval walled town famous for its dozen or so towers sticking up into the sky. After exploring the town on foot, we’ll head to the local Fattoria Poggio Alloro for a lunch of food products from this farm, such as the Chianina brand of beef and the saffron spice which has been locally grown since the 13th century, paired with the white wine Vernacciadi, also grown on site.

Next on our agenda is the winery Castello di Volpaia, which is located in a fortified village of the same name and where we’ll do a tasting of the famous Chianti Classico wine. After, we check into our charming historic villa out in the countryside and enjoy a delicious dinner of local fare.

Day 3

Tuscany Food & Wine Tour - Cappucino

We drive in the morning to Arezzo to visit Vestri Cioccolato, a chocolate maker that has been producing delicious chocolate for 30 years and which owns its own farm in the Dominican Republic. Not only do they make their own chocolate but they also roast their own coffee. We’ll learn about the chocolate-making and roasting processes and, of course, sample a few of their creations.

We then jump back in our vehicle to transfer to the center of town where you can explore the various cafes and restaurants for lunch on your own. After lunch, we visit the nearby small town of Anghiari, famous as the site of the Battle of Anghiari in 1440 between the armies of Florence and Milan.

We head to the town of Citta di Castello to check into our hotel for our second (Un)Retirement session and an hour’s rest and then visit a combination local wine bar and restaurant that serves outstanding local cuisine in a casual setting.

Day 4


After breakfast, we will head to the medieval town of Sansepolcro to engage in a fun but challenging cooking class with Alessia, owner of the restaurant “Fiorentino” in Sansepolcro. We have been doing cooking classes with Alessia and, before that, with her dad Alessio for over 15 years. The restaurant specializes in “original” Tuscan dishes.

After lunch we will transfer to Pieve Santo Stefano for one of our main events of the day: truffle hunting. We will join a local truffle hunter and his trusted dog in a search for truffles, which can be found in this area at any time of the year.  After truffle hunting – successful or not – we will have a truffle-based dinner in Citta di Castello.”

If you’re not stuffed and tired, but at the end of the day, you can finish it off with a visit to a local gelateria.

Day 5

Tuscany Food & Wine Tour - Assisi

Yes, this is a food and wine tour of Tuscany but nearby Umbria is well worth a visit. We’ll start out with a visit to the very small and local olive oil mill of Emanuele Ragani and his family. Emanuele will not only show us how the mill, with an actual grist stone, operates but will fire up a wood oven, heat up bread, and pour delicious olive oil on top for a tasting.

We then head to Assisi, the city made famous by St. Francis, for a tour of the city and the church where he is buried. Assisi is a great town to walk around on your own, with many shops and restaurants, and we are on our own here for lunch. After lunch, we’ll head to Arnaldo Caprai winery, a leading producer of the wine Sagrantino di Montefalco. If you have never had Umbrian wine before, you will be impressed.

After our wine tasting, our time in Umbria is ended and it is back to Tuscany as we drive to Cortona, made famous by the book Under the Tuscan Sun our home for the evening. We’ll check into our hotel where we will then have the final (Un)Retirement Session and free time to take in the sights and sounds of this beautiful town as well as find a local gem to have dinner on your own.

Day 6

Tuscany Food & Wine Tour - Montepulciano

The Val d’Orcia is one of the most beautiful sections of Tuscany, which is one of the most beautiful provinces of Italy, which is one of the most beautiful countries in the world. We are in a good place!

We’ll start our tour by visiting the city of Pienza, perched high above the valley and designated a UNESCO World Heritage Site. (The entire valley is designated a World Cultural Landscape.) After a quick historical walking tour of the city, we’ll head to a local farm that specializes in making pecorino, the ubiquitous local sheep’s cheese. We’ll learn about the process, have a taste of the fresh cheese, and eat a nice picnic lunch right on the farm.

It is then on to Montepulciano, another famous hilltop town, where you will have an hour to wander the streets on your own. We then gather together again to visit Cantine Gattavecchi for a tour of their barrel room and tasting of the local wine, the outstanding Vino Nobile di Montepulciano. Heading back to Cortona, we’ll share a final meal together at the Locanda al Pozzo Antico, a fine dining establishment run by the owner Paola where we’ll try to outdo our previous successes with Tuscan cuisine.

Day 7

Tuscany Food & Wine Tour

We’ll take a post-breakfast walk of Cortona, as our guide will point out some of the important sites featured in Under the Tuscan Sun. You are then free to take the train or a shuttle onwards to Florence or Rome (Check out Extend Your Stay: What To Do in Italy). Or perhaps you’ll follow the theme of the book and decide to stay in Tuscany?

"What a fantastic trip we had in Tuscany! I can't thank you and Giovanni enough for your kindness, flexibility, and support. It makes for a more relaxing and enjoyable experience." - Dane M.

As is with every Taste Vacation tour, the attention to detail is incredible. Everything from ensuring that participants have enough wine, tasting spectacular wines, visiting exclusive wineries, dining on great food, touring beautiful vineyards, plenty of activities to keep us busy, and enjoying unique restaurants is covered.

Elizabeth & Jake

I was concerned about the limitations of being on a guided tour as well as having to spend the entire time with a group of strangers. What I found was that the tours were extremely well planned and the accommodations, meals, wine tastings, and activities were perfect! And at the end of the trip, the people that began the tour not knowing each other, parted as a group of forever friends planning another adventure together with Taste

Alice T.

Tour Accommodations

Tuscany Food and Wine Tour Hotel San Michele

Night 1: Il Guelfo Bianco, Florence: This boutique hotel is housed in a restored building dating back to the 15th century. It’s perfect central location is near the Cathedral of Santa Maria del Fiore, the Accademia Gallery and the Central Market of San Lorenzo, making it easy to walk around on your own.

Night 2: Villa Lecchi, Chianti: A charming historic villa out in the countryside surrounded by vineyards, olive groves, and cypress trees, overlooking the beautiful Elsa Valley.

Nights 3 & 4: Hotel Tiferno,  Città di Castello: This four-star hotel is actually right over the provincial border in Umbria. The hotel is housed in a former 17th century monastery and sits in a quaint square in the historic centre of Città di Castello.

Nights 5 & 6: Hotel San Michele, Cortona: Enjoy modern comforts in an ancient 15th-century palace, located in the historic center of Cortona. You’ll not only find beautifully and uniquely decorated rooms but incredible ancient artwork in the lobby.

What is Included

  • All Local Transportation
  • Double Occupancy Lodging
  • All Meals Except Two Lunches and One Dinner
  • All Scheduled Activities
  • Wine During Organized Tastings
  • Professional Tour Guide

Not Included: Travel to and from destination, wine with meals, personal expenses, and optional gratuities to local staff and your guide. Travel insurance is also not included, though we highly recommend it.  Check out our Travel Insurance page for more information.

While the general trip itinerary will remain the same, the actual restaurants, hotels, and activities listed are subject to modifications. Changes that are out of our control are common — restaurants close or lose their amazing chef, a winery changes their visiting hours, a hotel gets remodeled, etc. You are entrusting us to create an outstanding vacation for you and so it is possible we may take the liberty of making necessary changes to the itinerary that will improve your overall trip experience. If there is any one experience that is going to make or break your trip, please discuss this with us in advance.

Arrival & Departure

We meet in the early afternoon on the first day of the tour at our downtown Florence hotel, allowing you to arrive either that morning or the day before. The tour finishes in Cortona before lunch on the final day of the tour. Cortona is on the mail rail line connecting Florence to Rome, so you can fly out of either city. One nice option is to fly into Florence and out of Rome, so you can visit both cities.

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