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Tuscany in the Fall: Traditional Food and Italian Wine

 November 1-6, 2019  **SOLD OUT**

This Fall, join Grace Cular Yee, Pineapple7, on an exclusive tour to discover the timeless splendors of Tuscany.  

Imagine yourself strolling through the old cobblestone-paved streets where Da Vinci, Michelangelo, and Dante wandered. Explore the roads less traveled and learn fascinating tales from the city’s rich history. Feast through Florence sampling Italy’s traditional treats, and journey along the picture-perfect rolling hills of Tuscany tasting Italian wines along the way. Stay on a stunning Tuscan estate surrounded by the landscapes and vineyards of Siena and Cortona. And naturally, we'll enjoy the tradition of the aperitivo!

Treat yourself to this journey and join me on an intimate small--group experience (8-12 adult travelers total) to visit Tuscany's treasures and explore its hidden gems. Together with my local contacts in Italy, we have curated a one-of-a-kind adventure packed with the culinary, historical, and local traditions of the region.

I have visited and designed several vacations to Italy and I'll be on-hand to take care of the details. All you have to do is enjoy Tuscany with me and a select group of like-minded travelers. Our small group tour is the ideal getaway for friends, solo travelers, and couples, but this exclusive tour has very limited availability and is sure to sell out quickly, so reserve your spot today. 

For more details, please call Grace at 571.338.0408 or email.

Tuscany in the Fall: Tour Itinerary


November 1

Welcome to Italy!

Arrive at Florence Airport. After clearing customs, board our private transfer to Florence. We'll check into a deluxe boutique hotel on the Arno. The rest of the day is at leisure to explore the city. Florence is a unique and beautiful monument to the Renaissance, the artistic and cultural reawakening of the 15th century that heralded notables including: Dante, Michelangelo, Galileo, Da Vinci. Aperitivo and orientation in the evening followed by a welcome dinner at one of the best trattorias in town.


November 2

Taste of Florence and Highlights of the Renaissance

Breakfast at the hotel.  Mid to late morning, we'll begin our adventure with an Italian Chef who will take us to the best wine bars, pastry shops, and delicatessens. We'll be discovering Florence at its most delicious! Our private group will have the chance to see and savor the best of Florence and get an insider’s guide to the city’s hot spots for gourmets and wine connoisseurs. It will be a treat for your taste buds and your brain, covering everything from old favorites to trending newcomers, swank sit-downs to casual counters, and food emporiums to purveyors of kitchenware. It'll be our own VIP tasting tour around the City of Lillies.​

This afternoon, we'll take in all the highlights of Florence on another private tour: the art and architecture of the Birthplace of the Renaissance and experience its enviable way of life. We'll explore Piazza della Signoria, visit the masterpieces in Uffizi Gallery. At the Accademia, we'll have the opportunity to gaze in awe at Michelangelo’s majestic David.

We'll head back to our hotel to relax for a little while before meeting this evening for an aperitivo on the rooftop bar and then heading to our dinner at L’Ortone.


November 3

Heart of Tuscany

After our breakfast, we'll check-out of the hotel and enjoy a leisurely private transfer from Florence to an Italian estate where we will stay for 3 nights. This a stunning property set within the gorgeous Tuscan countryside – lovingly restored by one of Italian fashion’s most famous families: the Ferragamos. Our lodging is nestled in the Tuscan hills between Florence and Arezzo, an area rich in history and tradition. The surroundings are not only breath-taking, but also extremely fertile, providing “kilometre-zero” produce including wine, olive oil and honey.


We'll have leisure time to relax or wander the property before we meet with our private guides, Sandra and Ulisse, in the afternoon.

Sandra and Ulisse have been farming the land for decades. They'll share what life is like on an organic farm and we'll get to sample some of its farm-to-fork goodness. Our journey will take us through the rolling hills of Tuscany’s Val d’Orcia and along a winding road flanked by stately cypress trees. The estate’s hilltop setting offers commanding views of the patchwork fields, tidy rows of grapevines and distant mountains, and the storybook farm bustles with the sound of bleating goats, grunting cinta sinese pigs (a breed that dates back to the Etruscans!) and buzzing bees. We’ll explore the estate and learn about their cultivation techniques before moving to the wheat mill.

Back at the farmhouse kitchen, we'll grab an apron and start our Italian cooking class using the same flour to learn how to make pasta using Sandra’s tried and true techniques. Dinner is a veritable farm-to-fork feast with ‘zero-kilometer ingredients’ like vegetables and herbs from the orto; Ulisse’s award-winning pecorino toscano cheese; spreads, honeys, wines and olive oil made right on the premises and your own homemade pasta, all served in the dining room at the former stables.

Sample Menu:

  • Homemade bread from the wood oven

  • Varied salads according to the season

  • Selection of cold meats from the Siena province

  • Range of cheeses (sheep & goat) of local production

  • Cooked vegetables (for example swiss chard, spinach)

  • Wheat / spelt / chestnut pasta with ricotta or tomatoes and basil

  • Homemade dessert

  • 1⁄4 of wine per person 

  • 1⁄4 of water per person 

  • Coffee


November 4

Siena and San Gimignano

After breakfast, we'll cruise the region’s picture-perfect rolling hills to Siena and San Gimignano. Our private guide is a proud Toscano and we'll explore the many charms of Tuscany and learn about the local people, their exciting past, and their beloved food and wine. Once in Siena, you’ll have ample time to explore and see the Piazza del Campo, site of the Palio races, Torre del Mangia offering panoramic views, and the striped Duomo perched on a hill. Make sure and ask your driver for recommendations on traditional trattorias to sample local favorites like rich Pici pasta and ruby-red Chianti Classico.  

Next, we'll wind our way through the vineyards and farms to San Gimignano. You’ll love wandering through the ancient cobblestone lanes, visiting antique stores and art galleries, peeking into bottegas filled with local olive oils, wines and delicacies, and marveling at the amazing medieval art and architecture. Don’t miss the stroll along the old city walls for those picture-postcard views!

After San Gimignano, we will reach the Tenuta Torciano estate for a special wine tasting and lunch. Whether you are a wine novice or expert, you will enjoy this intimate wine-tasting in an authentic Tuscan winery. Sample a range of Tuscan wine alongside local food. As you sip, you’ll learn about the different areas of the wine-making region, the secrets of Italian cuisine, learn about the combinations between wine & food, discover Tuscan wine making techniques and more.


November 5

Tuscany by Fiat and Wine Tastings

The Fiat 500 represents the epitome of Italian style. Fiat 500’s shape, dimensions and its aesthetics make this car one special and authentic symbol beyond its simple use for transportation, simply ideal both on asphalt and those famous tiny countryside roads. After breakfast, we'll drive through Tuscany’s iconic landscapes. Be part of a magical experience that will throw you back in history and immerse yourself in some breath-taking landscapes. Local drivers and experienced tour guides will be at our complete disposal. Let your mind focus on all the beauty surrounding you: old trees, ancient hills, country roads. Immerse yourself in the amazing Tuscan atmosphere and discover the secrets of these awarded wine and oil makers visiting our precious selection of cellars, while sampling some of the best wines in the world. The experience ends in a local winery where a delicious lunch of local and genuine products is served. 

This afternoon, we'll go on a private tour of the Art Gallery at Il Borro and then we'll visit the wine cellar to taste four Il Borro wines and their Olive Oil. Appetizers will be served depending on seasonality.

This evening, we will enjoy one last aperitivo before heading to our Farewell Dinner at Osteria Il Borro. Chef Andrea Campani and his staff use a large tailor-made traditional oven to prepare generous grilled dishes cooked over a wood fire. Getting back to its roots, in direct contact with the flame, our final group dinner will be homespun, rustic, and truly Tuscan.

Plane on Runway

November 6


We'll enjoy one more breakfast before our private transfer back to Florence airport.

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Tuscany in the Fall

Tour Inclusions:

  • 2 nights deluxe accommodations in Florence. Well-appointed Arno view rooms.

  • 3 nights accommodations at an exclusive Tuscan estate turned 5-star boutique hotel. Spacious rooms are rustic and uniquely designed.

  • 5 Breakfasts reflective of the region and season.

  • 2 Dinners at some of Florence's best restaurants.

  • Farewell Tuscan Dinner.

  • Exclusive foodie walking tour of Florence led by an Italian Chef.

  • Private walking tour of Florence Highlights - includes admission to the Accademia and the Uffizi Gallery.

  • Leisure time to experience the breathtaking natural beauty of the area.

  • Join in an intimate, private cooking lesson you will never forget. Using the freshest ingredients from the Tuscan organic farm, you will learn to prepare a classic Tuscan meal. Eat what you make!

  • Private Wine Tasting & Lunch in an authentic Tuscan winery in San Gimignano.

  • Wine Tastings around Tuscany by Fiat plus Lunch at a winery.

  • Private Art and Wine Tour at Il Borro.

  • Shopping & exploring the local villages of the area in Florence, Siena, and San Gimignano.

  • Round-trip transfers to Tuscany/Florence Airport on November 1 and November 6.

  • **Please note that wine is included during wine tastings, but not at all meals. Wine will be charged based upon consumption outside of the above noted events.


3820 € shared room

5600 € private room

1200 € deposit required to reserve space.  Contact Grace for more details or to reserve your spot.

See you in Italy!

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