Rustic Italy Vacation: Tuscany & Emilia Romagna

Tuscany landscape with a house on a hilltop
A 8 day trip to Italy 
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The true path into the heart of the Italian Peninsula is through the food that is experienced during your customizable culinary tour of rustic Italy in Emilia Romagna and Tuscany. Discover traditional flavors with the esteemed white truffle and indulge in gelato that is crafted by your own hands. Embrace prestigious prosciutto that is made on a family farm and savor herbaceous aromas during a cooking class inside a chef’s private kitchen. Whether searching for luscious olive oil or enjoying fabled wines, your luxurious culinary tour of Italy features the heritage of rustic cuisine that is found in the celebrated regions of Emilia Romagna and Tuscany.

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Most tours are customized for private travel.

General Information

Lush, green rolling hills in Siena, Italy
Devil's Bridge in Lucca, Italy
People enjoying each other's company outside of a coffee shop in Lucca, Italy
Beige and yellow apartment buildings in Bologna, Italy
The Two Towers or Due Torri at sunrise in Bologna, Italy
Woman holding truffles from Tuscany
Volterra church sitting on a hilltop
Italian chunks of parmesan cheese wrapped in saran wrap
Vineyard in Tuscany, Italy
Bird's eye view of a cathedral and town in Florence, Italy
Barrels of Italian balsamic vinegar
Italian pasta salad dish with various vegetables and cheeses
Detailed Itinerary

Places Visited 

Bologna, Lucca, Volterra, Montalcino, San Gimignano, Florence

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Bologna – Arrive in Bologna with a Cultural Tour and Dinner

The splendor of Bologna derives from the preserved, medieval charm that is found in the running arcades, frame boutique shops, exuberant cafes, and restaurants. This city is considered the gastronomic capital of the entire Italian Peninsula. The aromas of simmering meats and indulgent cheeses drift along the cobblestone streets throughout the day and attract locals and visitors to the vendors at outdoor markets or into hidden restaurants that serve the legendary Bolognese pasta or sumptuous tortellini in a fragrant, savory broth.

Your private transfer will greet you at G. Marconi Bologna Airport upon your arrival and escort you to your luxurious hotel, where you can settle into the comforts at the center of the captivating city. Your guide will meet you in the lobby and will be eager to introduce you to the enchanting ambiance of Bologna with a private tour, beginning in the Piazza del Nettuno. The prestigious bronze statue of the sea god adorns the heart of the public square and shines with 16th-century opulence. Your guide will provide insight into the history of the city and its connection to the culinary heart of Italy as you pass the leaning Torre Garisenda, which stands 157 feet tall and leans more than 42 feet from the base to the top.

The towers across the city once acted as signs of wealth for aristocratic families and watchtowers for city defenses. The Gothic allure of the Basilica di San Petronio embodies the former power of the city and dates back to the 14th century. The interior possesses the aroma of frankincense, and the light will filter through the windows, covering the giant sundial that lines the aisle at 222 feet long. In the evening, you will have your first taste of Emilia Romagna’s prestigious cuisine at a Michelin-starred restaurant, where you can indulge in the celebrated flavors of a dish that is similar to a savory soufflé with truffle and asparagus.

What’s Included: airport transfer, accommodation

Day 2: Bologna – Visit Famous Cheese and Balsamic Vinegar Facilities

In the morning, the aromas of fresh fennel and tomatoes overtake the Quadrilatero, which is the grid of streets around Via Clavature that hosts market stalls and vibrant cafes. The scent of cured meats and delicious cheeses from the gourmet delis fade beneath fragrant espresso that is brewed in the neighboring cafes. Your guide will meet you in your hotel lobby after breakfast and escort you close to the city of Parma to tour a stunning cheese factory that produces Parmigiano Reggiano.

Your guide will lead you through the process of producing the famous cheese, which has earned the status of Protected Designation of Origin, safeguarding the process. The scent of boiling milk will fill the room as workers separate the forming curds from the whey. In the warehouse, you will have the chance to knock your knuckle against a wheel of cheese in search of a hollow sound, which is a way of testing the quality of the aging process. When your guide slices off a piece of the aged cheese, you will find a crumbly texture and a lingering nutty and fruity taste.

You will continue to the city of Modena to learn more about the process for making balsamic vinegar, which is known as an acetaia. As you wander through the grounds, your guide will highlight the barrels in which balsamic is traditionally aged and blackened from use over the years. The sweet and sour aroma of the aging grapes will fill the rooms and become more prominent in the cellar, which will become thick with the caramelized scent of balsamic for a delicious and mouthwatering fragrance that will coat the room. Your guide will offer samples of the balsamic vinegar that has been produced on the grounds with a selection that has aged over 20 years, which results in flavors that are reminiscent of dark cherry.

What’s Included: accommodation, tour, breakfast

Day 3: Bologna – Revel in a Truffle Hunting Tour and Bolognese Cooking Class

The shops that are shaded beneath the preserved 13th-century arcades will open their doors in the returning morning line and display the charm of boutique fashion or elegant paperwork. Early in the morning, you will leave Bologna with your private guide and will be bound for the woodlands of Emilia Romagna for a magnificent exploration of the landscape in search of the elusive white truffle. The mist that hangs over the forest floor in the early hours of the day add to the moisture in which the truffles prefer to grow.

You will follow your guide through the undulating scenery and crisp air that is filled with the fresh aroma of pine and listen to sounds of the hunting dogs as they rustle through the underbrush. The dogs will bark when they find the scent of a truffle. You will help dig along the roots of the maple, oak, elm, pine, or chestnut tree, hopefully finding a fabled white truffle that is hidden in the damp soil. During lunch, your guide will turn into a private chef and will showcase the robust flavor of the white truffle with a multi-course meal of simple but deceptively delicious dishes such as scrambled eggs with shaved white truffle.

You will return to Bologna to meet your chef for a private cooking class to celebrate the remarkable flavors of the city that are known as La Grassa because of its indelible connection with flavorful cuisine. The kitchen will fill with the aromas of fresh herbs and vegetables as you begin preparing your multi-course meal that focuses on four traditional dishes, including crafting the famous Bolognese sauce customarily that is served over tagliatelle pasta. You will dig your fingers into soft flour and mix in the eggs to craft fresh noodles before the luscious aromas of simmering meat and tomatoes fill the kitchen.

What’s Included: accommodation, tour, breakfast

Day 4: Tuscany – Sample Artisanal Prosciutto and Famous Florentine Steak

Gourmet delis across Bologna showcase their elegant and delicious prosciutto legs that dangle above the counter or hang in the back to reveal their quality to visitors throughout the day. After breakfast, you will leave the comforts of Bologna to visit a family-owned prosciutto farm before traveling into the legendary Tuscan countryside. Your guide will lead you through the grasses, where pigs forage on chestnuts, and the cool, damp air from the Po River adds to the illustrious flavor of the meats that are produced within the region. When you venture into the cellar, you will find prosciutto legs in various stages of the aging process that have been coated with lard and salt as you wait to sample the fabled cut of meat. The sunlight will wash over the countryside, offering a perfect moment to sample the prosciutto outdoors where the aroma of wet grass enhances the surprising notes of sweetness.

You will continue to the fascinating city of Florence for a private tour of the city that is celebrated as the “Cradle of the Renaissance.” The medieval, cobblestone streets wind beneath an elegant dome that crowns the Cathedral of Santa Maria del Fiore at 376 feet tall. The delicious aroma of roasted pork drifts out of the restaurants and hides among the winding lanes. Your guide will lead you on a private tour of the city that will have you venturing from the Medici chapel that was designed by Michelangelo to the tombs of famous artists that decorate the interior of Santa Croce Basilica.

After crossing the famous Ponte Vecchio over the Arno River, you will find aromatic hints of leather and smelted metal that derive from the artisan shops in the Oltrarno neighborhood. The quieter edge of the former city center retains its reputation as a destination for craftspeople, where you will meet with artists cobbling shoes, shaping gold, binding books, and making ceramics with inlaid stones. After your tour, you will settle into the atmospheric comforts of a Michelin-starred restaurant, which serves dishes that are connected to Tuscan heritage, including a play on the tremendous bistecca Fiorentina.

What’s Included: transfer, accommodation, tour, breakfast

Day 5: Tuscany – Indulge in Lucca Olive Oil and Traditional Volterra Cooking

The aromas of fresh pastries that are stuffed with hazelnut and chocolate cream and accompanied by espresso will fill the dining room of your villa in the morning before you meet your guide. Today, you will be bound for the charming countryside of Lucca and a family-owned olive orchard. The historic farmhouse shines against the backdrop of sprawling trees and views across the radiant Tuscan landscape. After touring the farmhouse and learning about the history and process of making olive oil, your guide will pour a sample of varietals for you to taste. Your guide will relate sampling olive oil to wine tasting. As you inhale the aromas from the cup, you will discover scents of cypress leaves, cut grass, and artichokes. The bitterness that remains on your tongue will reflect the quality of the olive oil and the ripeness of the olives during harvest.

Before traveling to a farmhouse in Volterra for a private and rustic cooking class, you will have time to explore the beauty of Lucca at your preferred pace, enjoying the dramatic Renaissance walls that reach nearly 40 feet tall. When you arrive at the farmhouse in Volterra, your guide will lead you on a tour of the grounds that will reveal the gardens from which you will source the vegetables, fruits, and herbs for dinner. Your meal will be complemented with a welcoming glass of wine to start your friendly, informative introduction to authentic, rustic, and Tuscan cuisine.

What’s Included: accommodation, tour, breakfast

Day 6: Tuscany – Delight in the Ultimate Wine Tour around Siena Province

After breakfast, you will venture into the countryside of Tuscany and the province of Siena to visit stunning wineries that produce fantastic wines in the tradition of favored Brunello. You will first visit Montalcino, which is a picturesque hilltop town that is crowned with an imposing fortress. The narrow, medieval streets wind upwards to the summit and open to sporadic panoramas that sweep across the luscious valley. Small restaurants hide in cellars, and quaint wine shops offer samples of the delectable wines that have been crafted around the province.

The 14th-century ramparts offer fantastic views before you visit the first winery that was owned by a local family. You will tour the grounds with your guide for a private introduction to the history of the vineyard and the barrels that host the wine as it ages. The longer-aged Brunello have more time to develop their flavors, which results in aromas of anise, hazelnut, leather, and dried fig with a lingering, chocolate flavor. Near the end of your wine tour, you will travel to the medieval city of Siena, which once competed with Florence for supremacy over Tuscany. The preserved, cobbled lanes and architecture have turned Siena into an open-air museum that is accentuated by the marble façade of the Gothic cathedral and delicate aromas of sweet, buttery pastries that emanate from the pasticcerie.

What’s Included: accommodation, tour, breakfast

Day 7: Tuscany – Enjoy Saffron, Gelato, and Handmade Pasta Excursions

Your guide will meet you at your villa after breakfast and lead you to the charming town of San Gimignano, where 13 of the original 70 towers that once created the lavish skyline remain standing. The city center brims with colorful facades and brick piazzas that lead to Santa Maria Assunta Church. The 15th-century architecture retains a touch of the original Romanesque design and is enhanced by the fascinating fresco cycles that depict scenes from the New Testament, including the Annunciation. Outside of the city, you will visit one of the saffron fields that brims with the fragrant aromas and colorful petals of blossoming lilacs. You will learn about the history of saffron around the town that dates back to the Middle Ages and the evolution of cultivation techniques before sampling the local cuisine that is shaped around the flavors of fresh ingredients, which results in an exceptional risotto that is complete with mascarpone cheese, artichokes, and saffron.

Before learning how to craft a marvelous variety of fresh, handmade pasta, you will visit a local gelateria for insight into the craft of making memorable gelato flavors. Your instructor will have you sample an assortment of gelato, ranging from rich and chocolatey to subtle and fruity to capture favorite flavors like chocolate and lemon. The seasonal selections of fruit will guide your choice of flavors as you indulge in melon or persimmon, while the aromas of ginger and cinnamon bring decadent spices to the kitchen. 

What’s Included: accommodation, tour, breakfast

Day 8: Tuscany – Depart for Home

In the morning, the sunlight will wash over the grounds of your luxurious villa and will highlight the emerald hills of Tuscany and the quintessential vineyards that ascend the slopes. The aromas of buttery brioche and frothy cappuccino that has been sprinkled with chocolate encapsulate the subtle delicacies of Tuscany and the sweet, relaxed life that Italians are known to enjoy. After breakfast, your private transfer will meet you in the lobby of your villa and will be ready to escort you to Florence-Peretola Airport for your flight home. Instead of completing your rustic culinary tour of Emilia Romagna and Tuscany, you could extend your vacation, which will have you traveling south to indulge in the exceptional gastronomic culture of Campania and the Amalfi Coast. You can also travel north to savor the special cuisine of Piedmont.

What’s Included: airport transfer, breakfast


Starting Price 

This trip is customizable for your private travel.

What's Included 

  • Accommodations
  • In-country transportation
  • Some or all guided tours and activities (dependent on season)
  • Expert trip planning
  • 24x7 support during your trip
The starting price is based on travel during the low season for a minimum of two travelers staying in shared 3-star accommodations. Please inquire for a custom trip quote based on your travel preferences and travel dates.