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Tuscany with
Deb Van Pelt

21-26 September 2024

Tuscany with Deb Van Pelt

Tuscany is like a great bottle of wine: rich-hued, complex and full of character. What better way to contemplate this than spending six days (five nights) on a wine-focussed tour with Executive Sommelier Deb Van Pelt.


We shall meet in Florence and then make our way immediately to Cortona, the small jewel of a town in which the movie Under the Tuscan Sun was filmed. This will be our home base for the trip.


"The drive to Cortona is what you would expect from any Tuscan town: beanstalk-like cypress trees, serpentine roads and farm crops that change with the seasons; but what sets this historical hamlet apart from the others is the expanse of sunflower fields that line its foothills (the best time to see them in full bloom is from July to September). A place of outstanding beauty whose soaring position offers 360 degree views across the Valdichiana Aretina, catching a glimpse of Lake Trasimeno on the horizon; it comes as no surprise that Audrey Wells selected this prime location for Under the Tuscan Sun. In Cortona there are many cultural sites that allow you to delve into its Etruscan heritage as well as art-filled spaces, activities in nature and enogastronomic experiences to appreciate the charm of this picturesque hilltop borgo." -- CN Traveler

A personal wine guide will take us on tours through three of Tuscany’s main wine regions: Montalcino (to explore their bold Brunellos); Montepulciano (for their fine Vino Nobile di Montepulciano); and Chianti (for the classic Chianti). We will focus on visiting small, family-run wineries and will have the chance to meet the owners and winemakers themselves. Our guided tours in these locations will give us a true feeling for the winemaking life from grape to bottle.

At the end of the day, we'll have time to explore Cortona on our own or enjoy the comforts of our hotel, which has a great bar and rooftop garden and is an ideal place to have a drink and watch the sun descend over the rooftops of Cortona and set behind the hills of the Val di Chiana. This trip is ideal for anyone who wishes to expand their wine knowledge in a convivial setting and be able to connect tastes with places and people. In order to keep this an intimate experience, spaces are limited on this trip.


  • five nights in a five star boutique hotel in Cortona's historic centre

  • three days exploring three of Tuscany's main wine regions: Montepulciano, Montalcino and Chianti

  • tours and tastings with a local expert and wine guide. We will visit “off the beaten path” wineries, which means you will taste unique wines that are hard or even impossible to buy through stores and other online sources. The winemakers concentrate on quality over quantity, with small production numbers, meaning only the best wine gets bottled.

  • a hands-on cooking class in the countryside outside Siena

  • delicious local food

  • time each day to do as you please. Cortona, where we will be based for the duration of this trip, has a plethora of great restaurants and churches, museums and historic sites that are worth visiting. We will offer a list of suggestions.


Sample day:​

  • 8:30am: breakfast at our hotel

  • 9:30am: depart for our day in Montepulciano, where we will visit two  and sit down for lunch with wine pairing

  • 5pm: return from our day's adventure with plenty of time to relax at our hotel or explore Cortona

  • 8pm: dinner at a local restaurant (optional)


This trip includes:

  • Five nights shared (double) accommodation in a five star boutique hotel in the historic center of Cortona

  • All activities, tours and tastings outlined in the itinerary as well as private transportation to/from these activities

  • Breakfast every day and meals as outlined below:

    • Day 1, September 21st: dinner at our hotel in Cortona 

    • Day 2, September 22nd: visits and lunch in Montalcino 

    • Day 3, September 23rd: visits and lunch in Montepulciano

    • Day 4, September 24th: hands-on cooking class, lunch and visit to Siena

    • Day 5, September 25th: visits and lunch in Chianti 

    • Day 6, September 26th: lunch in Panzano and return to Florence


The trip does not include:

  • Flights

  • Airport transfers 

  • Alcohol outside of included tastings

  • Mandatory medical insurance

  • Optional trip cancellation insurance

  • Incidentals

  • Gratuities

  • Anything not outlined in “included” list

Something to consider: 

We will spend a couple of hours each day in an air-conditioned vehicle, driving through the beautiful Tuscan countryside in order to reach the various wine-growing regions and travel between wineries. Tuscany is 68% hill! Expect to come across some steep climbs and cobblestone paths, but the views are worth it! 

Trip cost:

$5710 Canadian dollars

Join this trip:

This trip is sold out. Please fill out this registration form if you would like to be put on the waiting list and we will let you know if spots become available. Feel free to contact natasha@thevoyagiste for more information.

Tuscany with Deb Van Pelt



Hello, I'm Deb!

I am the Executive Sommelier at Discovery Land Company's Troubadour Golf and Field Club. I am a Court of Master Sommeliers Certified Sommelier and hold a Wine and Spirit Education Trust level 3 award. 

My journey began with a real love of wine. After raising a family, I took a job in a tasting room representing a winery in St. Joseph, MI. There I worked with Dr David Miller, a PHD in viticulture, and became an avid student of wine. My journey took me to Nashville, TN where I began testing in earnest and climbing the Somm ladder, studying, testing and travelling.  I worked in wine programming development for wineries and building wine programs elsewhere. My true passion though is teaching others about the world of wine: what makes it special, the stories behind the bottles, its history and its myriad flavours.

I look forward to exploring these regions that after years of study seem so familiar.

Tuscany with Deb Van Pelt
Tuscany with Deb Van Pelt
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