A Taste of Tuscany & Umbria: Eurochocolate Festival 10 days / Food & Wine Tours, Special Event Tours
About This Experience
Here’s a chance to sate your sweet tooth and indulge in a savory round up of Italy’s culinary capitals. Sip regional Brunello di Montalcino in the Tuscan hills. Walk among the life-sized chocolate sculptures lining Perugia’s EuroChocolate Festival. Learn the craft of Italian cooking in the birthplace of the Renaissance. Gastronomy takes new meaning in a country where eating and art have always been revered as one and the same (and trust us, there are many, many masterpieces to be discovered).
Your Tour Includes
Round-trip airfare & airport transfers
Breakfast daily, 3 lunches, 4 three-course dinners, 3 wine tastings
Multilingual Tour Director
8 nights in hand-picked hotels
Private deluxe motor coach
Why You'll Love It
You’ll taste regional vintages on rolling vineyards
A Tuscan chef reveals the secrets of Italian cooking
Chocolate becomes art at the Eurochocolate Festival
Rural, tucked-away hill towns are a breath of fresh air
Italians insist on leisure—so bring on the riposo
The Renaissance still thrives in Florence

Overnight Flight1 night
Florence3 nights - hotel info
Day2
Find your fill of great food and new friends in Firenze
Breakfast (in flight), Dinner
Welcome to Italy! A Go Ahead representative welcomes you at the airport and escorts you to your hotel. The rest of the day is free for strolling along the cobbled streets and stone bridges of Florence or just relaxing in your hotel. This evening, become acquainted with your fellow travelers as well as the region’s famed cuisine at this evening’s Welcome Dinner.
Day3
Get behind the kitchen and try your hand at Tuscan cooking
Breakfast, Dinner
Tuscan cooking class, Church of Santa Croce
Discover the timeless city of Florence, birthplace of opera and the Italian language. Today’s guided tour introduces you to the city’s Renaissance splendor. Marvel at Brunelleschi’s masterpiece— Florence’s massive pink, white and green Duomo. This evening, learn to make cuisine the Italian way at a private Tuscan cooking class. Then enjoy the freshly prepared meal with your fellow chefs.
Day4
A foodie’s dream: sampling fresh-pressed olive oil in rural Tuscany
Breakfast
Bask in a free day to explore the Renaissance City on your own. Browse the shops of the Ponte Vecchio or simply people-watch as you sample some tasty gelato. Or opt to join a pastoral excursion to the walled city of Lucca and Colle Verde, a rural farm where olive oil is pressed. Tonight, join an optional dinner at a historic trattoria-style restaurant in the heart of Florence’s old town.
Optional Excursions
Florentine Dinner $89* pp
Enjoy a traditional meal at a bustling trattoria in the heart of Florence, the capital of Tuscany. Sit back as you sip a glass of wine, charmed by the rustic restaurant's atmosphere and warm Italian hospitality. Enjoy a delectable and satisfying meal beginning with antipasto or soup. Then, enjoy a main course featuring pork, beef, veal or lamb, as well as seasonal vegetables. Finish with a dish of creamy gelato or biscuits and a glass of sweet dessert wine. This evening promises to be not only an exceptional dinner, but an authentic Tuscan experience.
Optional Excursions
Lucca & Colle Verde $119* pp
Visit the gorgeous Tuscan town of Lucca, famous for its Renaissance-era city walls, medieval churches and awe-inspiring towers. Then travel to Colle Verde, a farm where some of Italy’s highest-quality olive oil is pressed. During your excursion, learn about the process by which olive oil is extracted and refined. Then, enjoy a light lunch and an olive oil tasting session.
Siena2 nights - hotel info
Day5
Take a riposo in San Gimignano, glass of wine in hand
Breakfast, Dinner
Tuscan wine tasting
En route to the enchanting city of Siena, stop in San Gimignano, “the city of beautiful towers.” Take in views of glorious scenery before continuing to a local wine tasting, where you’ll have the opportunity to sample some of the region’s fine wines. Arrive in Siena for this evening’s included dinner.
Day6
Sip the famous Brunello di Montalcino wine in its hillside home
Breakfast, Light lunch
Brunello wine tasting, Siena Cathedral, Piccolomini Library
This morning, travel through vineyards and olive groves to the hilltop town of Montalcino, famous for its Brunello di Montalcino wine. Enjoy the opportunity to taste this local treasure, as well as an included light lunch. Follow a local expert guide on this afternoon’s tour of Siena, longtime rival of nearby Florence. Visit Siena’s Romanesque Duomo, which houses major works of art by Donatello and Nicola Pisano, along with the famous Piccolomini Library. Walk along medieval streets to the Piazza del Campo. Each summer, daredevils race horses bareback around this main piazza during the famed Palio.
Perugia2 nights - hotel info
Day7
Simple, down-to-earth and in a word, delicious: Umbrian cooking awaits
Breakfast, Dinner
Museum of the Etruscan Academy of Cortona
Continue your travels across the Italian landscape to reach Perugia. Stop for lunch near Lake Trasimeno to indulge in regional specialties. Continue on to Cortona, perched on a Tuscan hillside for panoramic views of the plains below. Meander through the steep, narrow streets and look for the remains of the original city wall before a visit to the Museum of the Etruscan Academy of Cortona, home to an impressive collection of Etruscan artifacts. Cross over the Tuscan border into the Umbrian region, and arrive in Perugia.
Day8
Chocolate, chocolate, chocolate and still more chocolate
Breakfast
Eurochocolate Festival
On today’s tour of Perugia, a notable artistic center, you will stop at the Cathedral of S. Lorenzo, the Palazzo dei Priori, the Basilica of San Domenico, the Etruscan Arch and the Church of San Severo to see Raphael’s fresco. This afternoon, take part in Perugia’s famed Eurochocolate festival. Savor chocolate delicacies like never before while persuing the many chocolate “exhibits” on display at the festival. It’ll be an experience your sweet tooth will never forget!
Rome1 night - hotel info
Day9
Both sacred: Saint Francis’ birthplace and Orvieto’s vineyards
Breakfast, Light lunch, Dinner
Funicular ride, Orvieto wine tasting
Journey across the Umbrian valleys today en route to Rome. Stop for a guided tour of Assisi, a hilltop medieval town that was the birthplace of Saint Francis. Marvel at the restoration of the Basilica of San Francesco, a UNESCO World Heritage Site, after twin earthquakes shook the city in 1997. Next, take the funicular up to Orvieto, to indulge in a wine tasting followed by a light lunch. Arrive in Rome, the Eternal City, in time for this evening’s Farewell Dinner.
Extend Your Stay
Add Rome $299*
Only in Rome can you sip cappuccino at a café in front of the Pantheon, buy grapes at a centuries-old market, and have an audience with the pope—all in one morning. For a mix of spectacular art, grand history and vibrant street life, no other city comes close.
Rome2 nights - hotel info
Day1
Explore modern, bustling Rome or take a step back in time
Breakfast
Stay in Rome for another two days to examine the myriad treasures of the Italian capital. With a free day to explore on your own, you might linger over a sumptuous meal at a sidewalk café in Piazza Navona. Or experience the grandeur of the Roman empire on our optional Imperial Rome tour.
Optional Excursions
Imperial Rome $85* pp
Follow in the footsteps of Rome's emperors through the city's Imperial landmarks. Highlights include a visit to the Colosseum, where 50,000 spectators cheered their favorite gladiators to victory, and a panoramic bus tour of the city's Roman ruins. You might also stop to snap a photo of the ruins of the Roman Forum, from which the caesars ruled their vast empire.
Day2
Frescoes to arias, this city’s masterpieces are endless
Breakfast
Spend another day at your leisure in Rome or take an optional tour of Vatican City, with visits to the Vatican Museum, St. Peter’s Basilica and the Sistine Chapel. Tonight, enjoy a festive evening at our optional Dinner with Tenors.
Optional Excursions
Vatican City $85* pp
This guided tour takes you inside the world’s smallest state, Vatican City. Upon arrival, you'll first visit the Vatican Museums, which recently celebrated a 500-year anniversary and hold many of the world's most important Classical and Renaissance-era sculptures. Next, you'll visit the Sistine Chapel, where you'll gaze on what is perhaps Michelangelo's greatest masterpiece. Finally, you'll visit the enormous St. Peter’s Basilica, the epicenter of the Roman Catholic faith. The artists whose efforts have contributed to its glory are some of the best Italy has ever known, including Bramante, Peruzzi, Raphael and Michelangelo. Masterpieces await at every turn, from Bernini’s magnificent bronze canopy to Michelangelo’s Pietà. Please note: This excursion is not available on Sunday. Advanced reservation and booking is required prior to your final payment deadline.
Optional Excursions
Dinner with Tenors $79* pp
End your day with an elegant four-course dinner at one of our favorite Roman restaurants. While you dine, you’ll be treated to some of opera's best-loved arias…and you might even join the singers on stage. Don’t miss this lighthearted evening of food and fun!
About This Experience
Here’s a chance to sate your sweet tooth and indulge in a savory round up of Italy’s culinary capitals. Sip regional Brunello di Montalcino in the Tuscan hills. Walk among the life-sized chocolate sculptures lining Perugia’s EuroChocolate Festival. Learn the craft of Italian cooking in the birthplace of the Renaissance. Gastronomy takes new meaning in a country where eating and art have always been revered as one and the same (and trust us, there are many, many masterpieces to be discovered).
Your Tour Includes
Round-trip airfare & transfers
8 nights in handpicked hotels
Breakfast daily, 3 lunches, 4 three-course dinners with beer or wine, 3 wine tastings
Private deluxe motor coach
Multilingual Tour Director
Why You'll Love It
You’ll taste regional vintages on rolling vineyards
A Tuscan chef reveals the secrets of Italian cooking
Chocolate becomes art at the Eurochocolate Festival
Rural, tucked-away hill towns are a breath of fresh air
Italians insist on leisure—so bring on the riposo
The Renaissance still thrives in Florence

Overnight Flight1 night
Florence3 nights - hotel info
Day2
Find your fill of great food and new friends in Firenze
Breakfast (in flight), Dinner
Welcome to Italy! A Go Ahead representative welcomes you at the airport and escorts you to your hotel. The rest of the day is free for strolling along the cobbled streets and stone bridges of Florence or just relaxing in your hotel. This evening, become acquainted with your fellow travelers as well as the region’s famed cuisine at this evening’s welcome dinner.
Day3
Get behind the kitchen and try your hand at Tuscan cooking
Breakfast, Dinner
Tuscan cooking class
Discover the timeless city of Florence, birthplace of opera and the Italian language. Today’s guided tour introduces you to the city’s Renaissance splendor. Marvel at Brunelleschi’s masterpiece—Florence’s massive pink, white and green Duomo. This evening, learn to make cuisine the Italian way at a private Tuscan cooking class. Then enjoy the freshly prepared meal with your fellow chefs.
Day4
A foodie’s dream: sampling fresh-pressed olive oil in rural Tuscany
Breakfast
Bask in a free day to explore the Renaissance City on your own. Browse the shops of the Ponte Vecchio or simply people-watch as you sample some tasty gelato. Or opt to join an excursion to the walled city of Lucca and Colle Verde, a rural farm where olive oil is pressed. Tonight, join an optional dinner at a historic trattoria-style restaurant in the heart of Florence’s old town.
Optional Excursions
Florentine Dinner $89* pp
Enjoy a traditional meal at a bustling trattoria in the heart of Florence, the capital of Tuscany. Sit back as you sip a glass of wine, charmed by the rustic restaurant's atmosphere and warm Italian hospitality. Enjoy a delectable and satisfying meal beginning with antipasto or soup. Then, enjoy a main course featuring pork, beef, veal or lamb, as well as seasonal vegetables. Finish with a dish of creamy gelato or biscuits and a glass of sweet dessert wine. This evening promises to be not only an exceptional dinner, but an authentic Tuscan experience.
Optional Excursions
Lucca & Colle Verde $119* pp
Visit the gorgeous Tuscan town of Lucca, famous for its Renaissance-era city walls, medieval churches and awe-inspiring towers. Then travel to Colle Verde, a farm where some of Italy’s highest-quality olive oil is pressed. During your excursion, learn about the process by which olive oil is extracted and refined. Then, enjoy a light lunch and an olive oil tasting session.
Siena2 nights - hotel info
Day5
Take a riposo in San Gimignano, glass of wine in hand
Breakfast, Dinner
Tuscan wine tasting
En route to the enchanting city of Siena, stop in San Gimignano, “the city of beautiful towers.” Take in views of glorious scenery before continuing to a local wine tasting, where you’ll have the opportunity to sample some of the region’s fine wines. Arrive in Siena for this evening’s included dinner.
Day6
Sip the famous Brunello di Montalcino wine in its hillside home
Breakfast, Light lunch
Brunello wine tasting, Siena Cathedral, Piccolomini Library
This morning, travel through vineyards and olive groves to the hilltop town of Montalcino, famous for its Brunello di Montalcino wine. Take the opportunity to taste this local treasure, as well as an included light lunch. Follow a local expert guide on this afternoon’s tour of Siena, longtime rival of nearby Florence. Visit Siena’s Romanesque Duomo, which houses major works of art by Donatello and Nicola Pisano, along with the famous Piccolomini Library.
Perugia2 nights - hotel info
Day7
Simple, down-to-earth and in a word, delicious: Umbrian cooking awaits
Breakfast, Lunch
Museum of the Etruscan Academy
Continue your travels across the Tuscan landscape to reach Lake Trasimeno, the historic location of the battle between Hannibal and the Romans. After a lunch of Umbrian specialties, transfer to the hillside town of Cortona, where there will be time to meander through the steep, narrow streets and look for the remains of the original city wall, before a visit to the Museum of the Etruscan Academy of Cortona, home to an impressive collection of Etruscan artifacts. Cross from Tuscany into Umbrian and arrive in Perugia by nightfall.
Day8
Chocolate, chocolate, chocolate and still more chocolate
Breakfast
Eurochocolate Festival
On today’s tour of Perugia, a notable artistic center, you will stop at the Cathedral of S. Lorenzo, the Palazzo dei Priori, the Basilica of San Domenico, the Etruscan Arch and the Church of San Severo to see Raphael’s fresco. This afternoon, take part in Perugia’s famed Eurochocolate festival. Savor chocolate delicacies like never before while persuing the many chocolate “exhibits” on display at the festival.
Rome1 night - hotel info
Day9
Both sacred: Saint Francis’ birthplace and Orvieto’s vineyards
Breakfast, Light lunch, Dinner
Funicular ride, Orvieto wine tasting
Journey across the Umbrian valleys today en route to Rome. Stop for a guided tour of Assisi, a hilltop medieval town that was the birthplace of Saint Francis. Marvel at the restoration of the Basilica of San Francesco, a UNESCO World Heritage Site. Next, take the funicular up to Orvieto, to indulge in a wine tasting followed by a light lunch. Arrive in Rome, the Eternal City, in time for this evening’s farewell dinner.
Extend Your Stay
Add Rome $359*
Only in Rome can you sip cappuccino at a café in front of the Pantheon, buy grapes at a centuries-old market, and have an audience with the pope—all in one morning. For a mix of spectacular art, grand history and vibrant street life, no other city comes close.
Rome2 nights - hotel info
Day1
Discover Rome, from ancient and evocative to vibrant and modern
Breakfast
Colosseum
Start the day with a guided tour of Imperial Rome, where a local guide will show you around Piazza Venezia, the Forum and the Colosseum. With the rest of the day to explore on your own, you might linger over a sumptuous meal at a sidewalk café in Piazza Navona.
Day2
Frescoes to arias, this city’s masterpieces are endless
Breakfast
Spend another day at your leisure in Rome or take an optional tour of Vatican City, with visits to the Vatican Museum, St. Peter’s Basilica and the Sistine Chapel. Tonight, enjoy a festive evening at our optional Dinner with Tenors.
Optional Excursions
Vatican City $85* pp
This guided tour takes you inside the world’s smallest state, Vatican City. Upon arrival, you'll first visit the Vatican Museums, which recently celebrated a 500-year anniversary and hold many of the world's most important Classical and Renaissance-era sculptures. Next, you'll visit the Sistine Chapel, where you'll gaze on what is perhaps Michelangelo's greatest masterpiece. Finally, you'll visit the enormous St. Peter’s Basilica, the epicenter of the Roman Catholic faith. The artists whose efforts have contributed to its glory are some of the best Italy has ever known, including Bramante, Peruzzi, Raphael and Michelangelo. Masterpieces await at every turn, from Bernini’s magnificent bronze canopy to Michelangelo’s Pietà. Please note: This excursion is not available on Sunday. Advanced reservation and booking is required prior to your final payment deadline.
Optional Excursions
Dinner with Tenors $79* pp
End your day with an elegant four-course dinner at one of our favorite Roman restaurants. While you dine, you’ll be treated to some of opera's best-loved arias…and you might even join the singers on stage. Don’t miss this lighthearted evening of food and fun!
Passport & Visa
In order to enter Italy, U.S. and Canadian citizens need a valid passport. The expiration date must extend at least six months beyond the date of your return home. No visa is required for U.S. or Canadian citizens. If you are not a U.S. or Canadian citizen, you must contact the Italian consulate for your specific entry requirements.
Health
There are no major health risks associated with traveling to Italy. Travelers should be in reasonable health to take our scheduled walks, although we’ll make every effort to accommodate those who chose to stay behind. Be sure to check with your doctor or local health care provider for the latest updates and personal travel requirements.
Cuisine
This tour is specifically designed to highlight the celebrated cuisine of the Italian countryside. Nevertheless, the itinerary also allows for plenty of free time for you to explore the Italian fare on your own. Be sure to try those less familiar pasta sauces and the vast range of cured hams, cheeses, rustic breads and desserts. Tuscany is known for its wine, oil, sauces and pasta, favoring subtle, lighter pastas and desserts (mostly cookies and breads) made with nuts, fruit and honey. For authentic meals, try local trattorias, small restaurants often with only a couple of open tables and hand-printed menus. Italians tend to indulge in long, often boisterous meals featuring wines and the occasional beer, followed by the requisite after-dinner drinks, grappa or limoncello.
Transportation / Walking on tour
Round-trip flights arrive in Florence and depart from Rome. When you first arrive at the airport in Italy, a Go Ahead representative will meet you after clearing customs. Please remain in the arrival lounge, as the representative might be escorting one of your fellow travelers to the bus at the time of your arrival. All other included transportation on this tour is by private motor coach. In your free time, you may wish to explore the major cities of Florence and Rome by public transportation. Florence is split up into two separate sections by the Arno River, with most of the attractions spread out around the Duomo. The city is walkable, although frequent local buses are also available.
Baggage Allowance
Airlines have varying weight restrictions on luggage. Some airlines may impose additional charges if you choose to check any baggage. Please contact your airline or refer to its website for detailed information regarding your airline’s checked baggage policies. Bear in mind that your luggage will probably weigh more on your return trip due to souvenir shopping. We allow only one suitcase per person. One carry-on bag is also permitted, provided that it does not exceed 45 inches (length + width + height). There may be times when you will have to handle your own bags, and you’ll find that lightweight luggage provides a distinct advantage. Make sure you label your baggage and carry valuables, medication and documents in your carry-on luggage.
Clothing & Packing Tips
To ensure you’re comfortable while out exploring, we recommend packing lightweight, loose-fitting clothing that can be easily layered. For sightseeing, we suggest bringing a sturdy pair of walking shoes or sneakers, as well as a lightweight sports jacket or rainwear. If you’re planning a visit to a high-end restaurant or performance, you may also want to bring dressier attire. Also, please remember that it’s preferable to avoid showing bare legs or shoulders during visits to churches or other religious sites (entrance may be denied on this basis).
Currency
The euro is the currency you’ll be using on your tour. Better rates of exchange are usually available in Italy, although it’s worth ordering some currency from your local bank to use when you first arrive. We strongly advise that you take debit/bank cards and credit cards, which can be used to access cash at local banks, as needed. You can use most debit/credit cards at ATMs on the international networks Cirrus and Plus, but make sure to check with your home bank about withdrawal fees. We suggest informing your bank and credit card company of your travel plans, so they don’t confuse your international purchases for fraudulent charges.
Tipping
At the conclusion of your tour, it’s customary to offer your Tour Director and driver a gratuity. We recommend tipping in your tour country’s currency, the equivalent of $3USD/CAD per person per day for your driver and $6USD/CAD to $9USD/CAD per person per day for your Tour Director. If applicable, we also recommend the equivalent of $2USD/CAD per local guide. Tips can only be paid in cash. Please keep current local currency exchange rates in mind when tipping.
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Tuscany, Umbria, Eurochocolate
This trip was amazing! Worth every penny and more. Linda, our tour guide, was outstanding and made this the trip of a lifetime for me. I never felt that she was doing a job while touring with us and she seemed to enjoy the trip as much as we all did even though she lives in Rome and has probably seen the Italian countryside hundreds of times. Her knowledge and enthusiasm was evident all day, every day! The winery tours, churches, museums, restaurants and cooking school were fabulous. The tour group was fantastic and I hope to stay in touch with many of the people I met on this trip. Thanks Goahead for such an wonderful experience!
Trip of a Lifetime
This tour is a wonderful balance of history through guided tours, free time for shopping, and really, really fun planned activities like private cooking lessons from Florentine chefs. The wine tastings are so much fun, as well. I recommend this tour for anyone who wants to get a genuine "taste" of true Italian/Tuscan culture.
Great Trip
This was a wonderful tour. We got to see much of authentic Italy. The small villages were breathtaking and so steeped in history dating back many centuries. The Go Ahead Tour Guide was extremely knowledgeable and made all of the landmarks and destinations come to life before we ever arrived. Thank you for being organized and thorough. Enjoyed it immensely and would highly recommend it.
Food, Wine and History
This tour was a great combination of exploring history, art and culture along with wonderful food and wine. Visiting Lucca, San Gianamo, Cortuna, Assisi, Montalacina and Orveita as a bonus in between such great cities as Florence, Siena, Perugia and Rome was such a treat. One note of concern was the Pace rating though - it is more of a three since the cities are mostly inaccessible by bus and those with limitations in mobility had a difficult time reaching some of the cities and keeping up on tours. They need to be prepared to get a taxi since uphill, cobblestone streets and canes are not a good fit. The Tour Director was fantastic and extremely educated and helpful. My group had a fantastic time and would really love to see even more of Italy and drink more wine!
Had a great time.
Really enjoyed getting to go see so many places. The food and wine was excellent, so were the accommodations. Looking forward to planning another trip soemtime.
YUM YUM
The wine tastings with nibbles were memorable. The cooking lesson was great fun. Special dinners were indeed special. All with the sights of Tuscany and Umbria! Lovely!


