Tuscany’s landscape says it all: medieval hilltop towns overlooking rolling countryside covered with grapevines and olive trees. The mountains, forests, cypress trees, wildflowers, and winding roads create the perfect backdrop for discovering one of the world’s most revered destinations for culinary tradition, craftsmanship, fine art, historical preservation, and winemaking.

We’ll visit Tuscany in autumn, when the olives and grapes are being picked and pressed to perfection. The locals are foraging for mushrooms, harvesting chestnuts, and swirling Brunello di Montalcino in their glasses. It’s the perfect time of year to savor some of Italy’s – that is to say the world’s – best wines and ingredient driven dishes such as bistecca alla fiorentina (chargrilled T-bone steak) and pici con ragù di cinghiale (hand-rolled pasta with wild-boar sauce).

Join Chef Jenna Arcidiacono and Onward Travel for a week of culinary and cultural discovery in Tuscany. We’ve planned an eight-night tour with a slow food, experience driven, behind-the-scenes theme. Taste olive oil and local seasonal delicacies such as truffles and chestnuts, visit medieval towns and elegant Florence, luxuriate in a villa situated in the heart of Chianti wine country, stroll cobblestone streets with expert local guides, expand your culinary repertoire during cooking classes, dine at some of the region’s best restaurants, and laugh into the night with new friends as part of Amore’s travel and food loving community. 

Saturday, October 6—Welcome to Italy!

  • See Italian craftsmanship in a terracotta workshop
  • Enjoy a gourmet dinner in our stone villa

Benvenuto! Welcome to beautiful Tuscany. This morning we’ll meet at the Florence Airport and then head straight to Chianti. The first stop: Impruneta, a Tuscan town famous for terracotta. The tradition of making terracotta in this area goes back to the 14th century and the clay and craftsmanship combine beautifully! We’ll tour a workshop and kiln and then tuck into our first meal together, a leisurely lunch featuring the local food and wine. After a short transfer, settle in for a week at our villa in the vineyards on the edge of Panzano in Chianti. If the sun is shining, relax at the villa’s swimming pool this afternoon or stroll into town.

We’ll gather tonight on the loggia, or open air porch, to enjoy the million dollar vineyard views and a spritz. A seasonal gourmet dinner will be prepared by a local chef… his orange cake is divine and we’ve got the recipe! Local specialties will pair perfectly with the vino made from the grapes surrounding us. Cheers, indeed!

Sunday, October 7—Drinking in the Landscape

  • Savor a wine tasting lunch at our favorite small scale producer
  • Experience Dario Cecchini’s landmark steak restaurant: Officina della Bistecca

Today, ease into the Chianti lifestyle. We’ll walk into town to enjoy Panzano in Chianti’s weekly outdoor market where the locals shop and gossip. After a leisurely morning we’re off to visit Onward Travel’s favorite local winemakers. Agricola Altiero is a small family operation producing excellent wines. Samuela is a fabulous cook and her signature jams pair perfectly with crostini, pecorino, and salumi. Winemaker Paolo will lead us through a tasting as we enjoy lunch in the sunshine.

Let’s stretch our legs after lunch. We’ll stop in Montefioralle to explore this tiny, hilltop stone village, with 360 degree views of the Tuscan countryside. You’ll feel like you’ve landed in a movie set, but this is real life in Tuscany!

Tonight we’ll head back into Panzano in Chianti for a dinner featuring an icon of Toscana: Bistecca Fiorentina. Dario Cecchini is a famous Italian butcher and at his restaurant the food is served with pride and gusto. Enjoy steak, wine, and a bit of theater as the steaks are grilled right before our eyes on the searing hot grill. Delicioso!

Monday, October 8—Rare & Ancient Treasures

  • Hunt for truffles in the hills of San Miniato
  • Wander an ancient (and we mean ancient!) abbey

This morning we’re off to San Miniato, a hilltop town that serves as the capital of white truffles. The hills around San Miniato are a prime area for truffles. You can’t cultivate the elusive fungus, it grows underground, close to the roots of oak, hazel, poplar and beech trees, and is only found in a handful of places around the world. The family hosting us today has been in the “truffle business” for several generations and they create their own line of truffle products.

We’ll meet our host for a walk through the forest with his well trained truffle-sniffing dog. The flora and fauna are lovely and hopefully we’ll be successful with truffles, too! Once at their house in the countryside, we’ll learn more about truffles and savor a truffle themed lunch complete with Chianti wines.

This afternoon we’ll visit Badia a Passignano, a beautiful ancient abbey still owned by the Vallombrosian monks. While the year of its founding is unclear – some historians claim the year 395, while others push it back to 891 – there is no doubt that the abbey played an important role in Tuscan history.

You’re on your own this evening to enjoy dinner at one of Panzano’s restaurants.

Tuesday, October 9—Medieval Manhattan & Cooking with Chef Jenna

  • Immerse yourself in charming, hilltop town San Gimignano
  • Roll up your sleeves and cook with Chef Jenna

This morning we’ll drive through the Tuscan landscape and feast our eyes on medieval hilltop towns overlooking rolling countryside covered with grapevines and olive trees. Our first stop is Poggibonsi, to visit the morning market. Chef Jenna will design this evening’s hands-on culinary extravaganza with ingredients procured at the market. Next, we’ll visit walled San Gimignano, often called Medieval Manhattan because of the skyline formed by the towers that date back to the 12th-century. Enjoy a guided tour with an excellent local historian who tells the beguiling story of this place. Afterwards, enjoy time for lunch, shopping, and some of Italy’s best gelato.

This evening Chef Jenna will lead us in the kitchen. Enjoy cooking, vino, and conviviality. We’ll gather around the table to enjoy the fruits of our labor.

Wednesday, October 10—Vistas & Vino

  • Choose your own Tuscan adventure this morning
  • Learn about Italian cuisine with our friend, Chef Alessandra

This morning you may choose your own adventure! Head out on a hike in the countryside to slow down, soak up the views, and get some exercise. Or perhaps you’d like to go on an excursion to the charming town Radda in Chianti to sip espresso in the cafe and do some shopping. Or maybe you want to relax and do absolutely nothing! The choice is yours.

Midday we’re off to visit the tasting room of Azienda Agricola Fontodi. Fontodi is a certified organic estate that has been owned by the Manetti family since the 60’s. Our villa is part of the Fontodi estate and we’ll enjoy their wines all week. So let’s go to the source and learn about their winemaking and passion. After an educational tour and tasting, it’s back to the villa because a chef is waiting. Chef Alessandra is based in Cortona (and we enjoyed Amore in Italy cooking classes with her in 2015) and she’s coming to Panzano to teach us about real Italian cuisine. We’ll work together in the kitchen to prepare a fabulous feast (homemade pasta of course) and then enjoy a fun and festive dinner together.

Thursday, October 11—Val d’Orcia Beauty

  • Go back in time in Montalcino
  • Experience gems in the Val d’Orcia: hot springs, olive oil, and gardens

Today we head south to the Val d’Orcia, a region carved out by the Orcia river that inspires everyone from Renaissance painters to you (just wait). The valley’s unique beauty was recently recognized as a UNESCO world heritage site. We will spend the morning in Montalcino, a medieval walled hilltop city with a fortress and a 16th century go-back-in-history vibe. Be sure to enjoy a glass of Brunello di Montalcino; there are many enotecas in town.

After a medieval morning, we’re off to the village of Bagno Vignoni to admire the steaming waters in the central piazza. The therapeutic hot waters have been bubbling since ancient days and it’s a unique site. By now you’ve noticed the ethereal olive trees. This afternoon, at an estate that has been making exceptional olive oils for generations, we’re treated to an olive oil tasting, complete with tastes of traditional recipes. We have one more treat this afternoon: a guided visit of La Foce’s renowned gardens that expertly blend Italian and English traditions and taste.

We’ll drive back to the heart of Chianti as the sun starts to dip and nothing beats driving in Tuscany at the magic hour! After a busy day, we’ll enjoy a relaxing dinner at the villa prepared by an Italian nonna, Vittoria. And of course we’ll bring back a few bottles of Brunello!

Friday, October 12—La Dolce Vita

  • Find an outlet for Tuscan inspiration in a guided watercolor lesson
  • Enjoy an unforgettable pizza party at the villa

Enjoy a slow morning at the villa. We’ll have an al fresco lunch, prepared with fresh ingredients procured from the market. Help cook if you like!

As lunch concludes, a local artist will arrive to lead us in a watercolor painting class. Inspiration abounds and you don’t need to be an artist to enjoy this creative expression with charismatic and talented Roberto at the helm. We’ll sketch and paint, and really see the surroundings.

Stroll the vineyards this afternoon, squeeze in a little more shopping, or relax. Late afternoon we’ll walk into town for a art-inspired storytelling wine tasting experience at Accademia del Buon Gusto… hard to describe but very fun. Our last dinner at the villa will be unforgettable! A talented pizzaiolo is coming to the villa tonight with a portable wood-fired oven to make us a pizza feast. You’re invited to help cook and recipes will be provided. Sip a glass of bubbly while you enjoy a variety of pizzas, focaccia bread, and lemon vodka sorbet. The pizza party of your dreams!

Saturday October 13—The Heartbeat of the Italian Renaissance

  • Walking tour in Florence
  • Ample time to shop and sightsee

We must say goodbye to our beautiful villa this morning but the fun is not over yet.

Today we’ll visit the capital of Tuscany, Firenze, the seat of the Renaissance and a city with a long history in art and craftsmanship. A local guide will take us on a walking tour, concluding at Galleria dell’Accademia where we’ll ogle Michelangelo’s David. Enjoy a long afternoon to sightsee and shop as you please. 

We’ll begin our evening together at Kat’s favorite wine bar on the south side of the river, in the neighborhood known as The Oltrano, or “Across the Arno,” it’s a vibrant, artsy place and it’s where the locals hang out. Then we’ll head out for dinner nearby. Our hotel tonight will be in The Oltrano, too.

Sunday, October 14—Arrivederci!

Return home today with amazing memories of your adventure in Tuscany, or stay on and enjoy more time to explore Florence.

Florence airport is a 15 minute drive from the city center and we will arrange taxis to suit the specific flight times of group members.

  • See Itinerary PDF for all details!
  • $3,775 based on double occupancy
  • Single supplement $650 additional
  • A 3% processing fee applies for credit card payment
  • Air travel is not included but Onward Travel is happy to help you make a flight reservation
  • Contact Molly with questions at 267-825-5880 or molly@onwardtravel.co