Tuscany Culinary Vacation

Tuscany Culinary Vacation

Experience the food, wine and gorgeous scenery of Florence, Siena and the Tuscany countryside on this 9-day, small-group vacation. Open your appetite to the bold flavors of the region and its wine. Stay 2 nights at a boutique hotel in Florence and 6 nights at a boutique Tuscan countryside hotel in Chianti, surrounded by rolling hills and vineyards. In addition to a Tuscan cooking class and four winery visits, you’ll spend your vacation enjoying the bounty of Tuscany’s food and wine at some of the region’s best restaurants and wine estates.

In addition to all the great food and wine, visit the classic sights of Florence – Michelangelo’s David, the Uffizi Gallery, the Florence Duomo and the Ponte Vecchio. You’ll also visit the Tuscan cities of Siena and San Gimignano.  Take a breathtaking drive through the UNESCO World Heritage Val d’Orcia while stopping in Pienza for a guided visit and cheese tasting and in Montalcino to taste its fabulous Brunello di Montalcino wine. Taste and learn all about the famous wines of Tuscany, like Chianti, Chianti Classico, Super Tuscans, Brunello di Montalcino and Vino Nobile di Montepulciano. This vacation provides it all and it is all-included in your vacation package price.


  • Florence  –  Siena  –  San Gimignano  –  Montalcino  –  Pienza  –  Castellina in Chianti  –  Radda-in-Chianti  –  Greve in Chianti  –  Val d’Orcia



2023 Private-Group Vacation Pricing:

In 2023, this vacation is available only for private-groups. Pricing below is for this vacation with Kathy as your full-time tour leader.

*For discounted pricing information for this vacation without a full-time tour leader, please contact us.

For  a group of 2 people:  $6,275 per person (based upon double occupancy)

For groups of 3 or 4 people:  $5,890 per person (based upon double occupancy)

For groups of 5 or 6 people:  $5,290 per person (based upon double occupancy)

For groups of 8 to 12 people$4,990 per person (based upon double occupancy)



  • To secure your spot on the trip, a non-refundable, transferable deposit of $1,250 per person is required.
  • The remaining balance is due 90 days prior to vacation start date.
  • You can make payments by credit card, bank transfer, or check.



  • 9-days/8-nights accommodations at boutique hotels in Florence (2 nights) and in the Chianti region of Tuscany (6 nights)
  • 17 meals – 8 breakfasts, 6 lunches and 3 dinners (Local wines included with all lunches and dinners)
  • Tuscan cooking class
  • Four winery visits and guided tastings and one Welcome to Tuscany Wine Tasting
  • Guided walking tours of Florence, Siena, San Gimignano, Pienza and Montalcino
  • Visits to Tuscan hill towns of Castellina in Chianti, Greve-in-Chianti, and Radda-in-Chianti
  • Guided visits to see Michelangelo’s David at the Accademia in Florence and to the Uffizi Gallery in Florence
  • Private drive through the UNESCO World Heritage Site Val d’Orcia
  • Guided Pienza cheese tasting
  • Full-Time services, for the entire vacation, of your group leader, Chef Kathy
  • Private round-trip transfer from the Florence Airport at the beginning and end of your vacation, and all transportation for included activities during the week
  • Special pricing 3-night Rome extension vacation package
  • Food Lover’s Odyssey apron and Ebook of our favorite recipes from Tuscany
  • Assistance with making your travel arrangements from the U.S. to Florence, Italy and any pre- and post-tour travel arrangements you’d like to make

**Airfare, transportation to Florence (if flying in from elsewhere in Italy/Europe), travel insurance and expenses of a personal nature (souvenirs and other personal items) are not included in the vacation package price.



“Awesome trip!!! Thank you Kathy for giving us so many amazing experiences, great food and wonderful company to share it with. Best trip ever!” – Michelle (Flower Mound, TX)

“It was absolutely amazing. We had the best guides, the best food, and the best experiences. There is no way I could have planned a trip like this on my own. Can’t wait for my next Food Lovers Odyssey to France in 2018.” – Aimee (Flower Mound, TX)

“What an amazingly fun trip! One of the best adventures I have experienced. Looking forward to traveling with Kathy again next year.” – Judy (Huntsville, AL)

“It was the best trip on so many levels….cooking, food, art, painting and friends. It doesn’t get any better than that!” – Melanie (Dallas, TX)


Day 1: Arrival day – Arrive and Relax at your hotel in the Chianti Countryside – Wine tasting reception and welcome dinner

We’ll have an afternoon pick up scheduled for those flying to Florence’s airport or we will meet you at Florence’s Santa Maria Novella train station at 3:00pm. From there we’ll drive to our countryside villa in Chianti.

Take the afternoon to get settled into your room at and to explore the grounds or relax poolside. In the evening we’ll gather together for an orientation walk through Castellina-in-Chianti.  Afterwards, enjoy a welcome wine-tasting reception and introduction to Tuscan wines. Enjoy a delicious Tuscany welcome dinner together on the terrace with a beautiful view.



Day 2: A Day of Castles, Chianti Wines and Hilltowns – Afternoon in Radda-in-Chianti

Learn all about what makes Chianti wines so special.  Start the day at a historical wine estate. Explore the castle and its grounds and learn the family’s influence on Chianti wines.  Taste wines at the castle’s enoteca and then we’ll have a Tuscan lunch together. In the afternoon you’ll have time to explore the center of Radda-in-Chianti on your own before we return to our hotel in the evening.

(MEALS INCLUDED: Breakfast, Lunch)


Day 3: Tuscan Cooking Class – Afternoon in Greve-in-Chianti

Enjoy a cooking class with one of our favorite Italian mammas.  Create a lavish Tuscan meal and then sit on the terrace to enjoy the fruits of your labor.  After lunch, we will visit Greve-in-Chianti and you’ll have time to explore on your own, and possibly sample more Chianti wines.

Return to Castellina-in-Chianti where you will have the evening free to enjoy as you like.

(MEALS INCLUDED:  Breakfast, Lunch)


Day 4: Gourmet Day in the Val D’Orcia – Winery visit and Wine Tasting Lunch in Montalcino – Afternoon in Pienza and cheese tasting.

We will take a drive along the UNESCO World Heritage Site, the Val d’Orcia. This valley, appears in most of the classic Tuscan photographs that inspire Tuscan vacation dreams. We’ll take a few photo op stops on our way to Montalcino. In Montalcino we will visit its castle and historic center along with a prestigious winery to taste the famous wines of the area, Rosso di Montalcino and Brunello di Montalcino.  Our visit will include a wine-paired lunch.

After lunch, we will visit the  “ideal Renaissance city” of Pienza (designed by Pope Pius II). Pienza is also popular for its pecorino cheese.  We’ll taste some of the area’s delicious cheeses on our guided walk.

(MEALS INCLUDED: Breakfast, Lunch)


Day 5: A Day in Siena 

After breakfast we’ll enjoy a full-day exploring Siena, a beautiful, medieval city. Our local historical guide will join us and provide an expert insider’s view of the city, the Gothic architecture, the famous Piazza del Campo, the history of the contrade and Siena’s Palio, and, its culinary traditions.

We will stop for a light lunch near Piazza del Campo. After lunch we will finish our walking tour with a visit to the Duomo. You’ll have the rest of the afternoon free to explore Siena on your own.

(MEALS INCLUDED: Breakfast, Lunch)


Day 6: San Gimignano – Winery Visit and Picnic Lunch 

We will drive to San Gimignano, also known as the Manhattan of Tuscany. Before arriving at the historic center, we will stop for a photo op from afar and visit a winery.  Enjoy a picnic lunch paired with the winery’s wines.

After lunch take a leisurely walk with a local guide through the San Gimignano with a visit to the Duomo.  After your walk, we’ll stop for a gelato at an award winning gelato shop on the main square and then you’ll have a little free time in San Gimignano.

In the late afternoon we will return to Castellina-in-Chianti for our last evening in Chianti and a fun pizza dinner.

(MEALS INCLUDED: Breakfast, Lunch, Dinner)


Day 7 – Ciao Firenze – Afternoon at the Uffizi Gallery

Today leave your countryside accommodations for the Italian Renaissance city of Florence. On our way into Florence, we’ll stop at the Piazzale Michelangelo for a breathtaking view of the city.

After you check into your hotel, we’ll meet for a group lunch. Spend the afternoon with a local guide at the Uffizi Gallery. You’ll be guided through the history of Florence and its famous families through the art at the Uffizi.

The evening is yours to enjoy on your own.

(MEALS INCLUDED: Breakfast, Lunch)


Day 8 – Full day in Florence – Michelangelo’s David and the Duomo – Farewell Dinner

This morning you’ll meet your local guide for a guided tour of Michelangelo’s David, the exterior of the Duomo and Baptistry, the Piazza Signoria, and the Ponte Vecchio. After your guided walk, you will have the rest of the afternoon to enjoy Florence as you like or you can choose to go on a photo walk with Kathy.

In the evening enjoy a farewell dinner at a favorite trattoria in the Oltrarno.

(MEALS INCLUDED: Breakfast, Dinner)

Day 9 Arriverderci Tuscany
After breakfast, transportation will take you from your hotel to the Florence airport or train station. We will leave at 8:30am.

**Sequence of classes, activities and excursions may vary. The final itinerary will be given to each guest on the first day of the vacation. Whenever there are local festivals or events happening during a tour, we will try to include them with adjustments to the itinerary to enhance your vacation experience.



« | »