
Food & Wine of Italy: Tuscany & Umbria
11 days | 13 days with Rome extension |
From February 15 to April 6, 2026, the city of Assisi will commemorate the 800th anniversary of the death of St. Francis, who was born and died there. For the first time, the Basilica of St. Francis will publicly display his relics: Hundreds of thousands from around the world will make the pilgrimage, and the church will close most of its grounds to accommodate the event. If you’d like to pay homage, be sure to connect with your Tour Director in the Go Ahead app before your trip—they’ll help you determine if it’s possible.
On this tour, coccoli—and baci, and crostini, and more—steal the show.
From endless plains to elegant hilltop towns, Tuscany and Umbria have plenty in common—including a culinary tradition that would make your nonna proud. As you drive with your group across these regions, you’ll find fine wines and humble, time-honored bites at each stop. And don’t overlook those classic sights: Feast your eyes on Florence and Siena (and Rome on the extension) to truly savor this country’s big, bold culture.
Your tour package includes
- 9 nights in handpicked hotels
- 9 breakfasts
- 4 lunches
- 3 dinners with beer or wine
- 4 wine tastings
- 1 cooking lesson
- 4 tastings
- 4 sightseeing tours
- Expert Tour Director & local guides
- Private deluxe motor coach
Included highlights
- Mercato Centrale
- Tuscan cooking lesson
- San Gimignano
- Chianti wine tasting
- Montalcino wine tasting
- Siena Cathedral
- Cortona
- Collegio del Cambio
- Perugia’s Rocca Paolina
- Montefalco wine region
Itinerary

Overnight Flight1 night
Day 1: Travel day
Board your overnight flight to Florence today.
Florence3 nights
Day 2: Arrival in Florence
Included meal: Welcome dinner
Ciao! Touch down in Italy and transfer to your hotel. Tonight, you’ll get to know your Tour Director and fellow travelers—and set the tone for the coming days—over a three-course dinner at a local restaurant, served with beer or wine.
Day 3: Sightseeing tour of Florence
Included meals: Breakfast, Tasting, Dinner
Once the beating heart of the Renaissance, Florence still echoes the aesthetic of the time. Today, you’ll sync up with the rhythm of the city on a food-themed walking tour, seeing (and sampling) its richest highlights.
- Begin with a typical Italian breakfast—a steaming cappuccino paired with buttery brioche. Then, head into Florence’s UNESCO-listed historic center to view its exquisite 15th-century cathedral—the Basilica di Santa Maria del Fiore, or Duomo.
- Pass Giotto’s Campanile. A masterpiece of Gothic architecture, this bell tower rises nearly 280 feet above the city and features the same red, white, and green marble found on the Duomo’s facade.
- Pause in the courtyard of the Palazzo Pazzi, a lavish brick-and-stucco residence built for one of Renaissance Florence’s leading families.
- End in the lively Mercato di Sant’Ambrogio. Smaller than its more famous counterpart, the Mercato Centrale, it has served locals for more than 100 years. Walk among its market stalls, tasting beloved finger foods like coccoli (fried dollops of dough stuffed with prosciutto and stracchino cheese).
If all that snacking piqued your appetite, you’re in luck: This evening, you’ll join a local chef for a Tuscan cooking class. Make pasta by hand, put together two types of bruschetta, and prepare a tiramisu—then enjoy it all for dinner, paired with Italian wines.
Day 4: Free day in Florence
Included meal: Breakfast
An optional excursion awaits you on your first free day on tour: a journey to medieval Lucca for a rustic lunch at an agriturismo, or farm stay, on the city's outskirts. If you choose to stay in Florence for some self-guided exploration, check out the Boboli Gardens. Located behind the grand Palazzo Pitti, this peaceful oasis's pathways weave through a vast green space, leading past a collection of stunning sculptures.
Siena2 nights
Day 5: Siena via San Gimignano & Chianti
Included meals: Breakfast, Tasting, Wine tasting
Bid farewell to Florence and roll farther into the golden hills of Tuscany. You’ll end the day in the enchanting city of Siena—but before then, you’ll make a pair of stops. Up first: San Gimignano, the Town of Fine Towers.
- Admire its UNESCO-recognized historic center, replete with medieval architecture, during your free time. Keep your eyes trained upward: Once home to some 72 towers, 14 remain, punctuating San Gimignano’s skyline as an enduring reminder of local rivalries.
- Indulge in a tasting at a gelateria before hitting the road. Made with less milk fat and churned more slowly than ice cream, silky-smooth gelato is a world-famous dessert. (One spoonful might leave you scrambling to buy a pint!)
Leave San Gimignano, then detour northeast to Chianti—a prized winegrowing region—for a vineyard tour. After learning about the grapes and techniques behind the area’s famous vintages, pop into an agriturismo to see that theory put into practice. You’ll get to taste three types of wine, paired with cold cuts and crostini; enjoy, then continue to Siena.
Day 6: Montalcino & Siena
Included meals: Breakfast, Wine tasting, Tasting
This morning, strike out from Siena to tour Montalcino, a hill town settled since Etruscan times. Its lower slopes are blanketed with vineyards and olive orchards; after wandering Montalcino’s centuries-old streets, stop at a winery for a tasting and light lunch. (The town specializes in Brunello di Montalcino, a protected appellation elaborated using Sangiovese grapes. You’ll get to try three of these revered reds at lunch!)
Bellies full, ride the bus back to Siena. History’s imbued in the fabric of this city, from its UNESCO-listed medieval center and Renaissance cathedral to the centuries-old landmarks that dot its streets. Follow along on a guided sightseeing tour—with a culinary twist—and see what Siena has to offer.
- Walk through the Piazza del Campo, the longtime heart of the town. Twice each summer, locals and travelers alike flock here for the Palio di Siena, a frantic three-lap horse race around the square.
- Enter Siena Cathedral. Hewn from black and white marble, this architectural masterpiece houses even more treasures within—major works of art by Donatello, Pisano, and other talents.
- Visit the adjacent Piccolomini Library, adorned with 16th-century frescoes by the Renaissance painter Pinturicchio, before ending at a bakery to snack on ricciarelli. Delightfully chewy, these almond cookies are synonymous with Siena, and no stay’s complete without trying some.
Umbria3 nights
Day 7: Umbria via Cortona & Lake Trasimeno
Included meals: Breakfast, Lunch, Tasting
Forge your way even deeper into Italy today, driving inland to the central regional of Umbria. En route, you’ll make a pit stop in Cortona, a hillside town overlooking the fertile plains of the Val di Chiana.
Explore and shop at your leisure, then head to nearby Lake Trasimeno. Now the heart of a regional park, this shallow lake was once a theater of the Second Punic War—the Carthaginian general Hannibal crushed a Roman army on its shores.
After a traditional Umbrian lunch (think: antipasto, lake-caught fish, and the like), continue to your final stop of the day, Perugia. A major city in Etruscan times, it now serves as Umbria’s capital, and has the landmarks to match. Check them out on a guided tour.
- Walk to the Palazzo dei Priori, a palace built over the course of 150 years, and enter the Collegio del Cambio Hall. Look around: Exemplary works of art by Perugino and Raffaello grace its walls and ceiling.
- Pass the imposing Gothic facade of Perugia Cathedral before descending into the passageways of the Rocca Paolina. All that remains of this 16th-century fortress is its basement, with underground tunnels that link four parts of the city center.
- Wrap up at a local cafe and learn about one of the city’s greatest exports: Baci Perugina. As you sample some, you’ll understand how these melt-in-your-mouth bites of hazelnuts, cocoa, and dark chocolate got so popular.
End your day by transferring to your hotel and unwinding for the evening.
Day 8: Free day in Umbria
Included meals: Breakfast, Dinner
Want to spend your free day with us? Add our optional outing to Assisi—the birthplace of St. Francis himself—and cap it with lunch and a tour at an Umbrian farm. Or, sit back and let the tempo of countryside life revitalize you.
Whatever you choose, you’ll rejoin your groupmates in the evening for a three-course dinner at an agriturismo, served with beer or wine.
Day 9: Montefalco wine region
Included meals: Breakfast, Lunch, Wine tasting
Named after the lovely town perched atop its hills, the Montefalco wine region encompasses roughly 1,100 acres of vineyards spread between the village of Bevagna and its eponymous settlement. It produces some uniquely Italian vintages, and today, you’ll get to sample some.
Begin in Bevagna, a town with pre-Roman roots, and take some time to explore its medieval center. After, you’ll head out to one of the region’s vineyards, where you’ll taste four different wines—one for each course of your included lunch. Pay extra attention to the reds: These Montefalcos are partially made with Sagrantino grapes, a hyperlocal variety grown almost exclusively in Umbria.
Rome1 night
Day 10: Rome via Orvieto
Included meals: Breakfast, Farewell lunch, Wine tasting
You’ll end the day in Rome—but you’ll make one stop en route. Dominated by a monumental cathedral, the town of Orvieto stands on the summit of a flat, rocky hill, towering over its surroundings in stunning fashion. Enter its Gothic cathedral, the Duomo di Orvieto; marvel at the intricate frescoes of the Chapel of San Brizio; and enjoy some free time to explore before reconvening for a farewell lunch.
After dining on a three-course meal, paired with a sampling of Umbrian vintages and served with beer or wine, continue to Rome, where you’ll check into your hotel and prepare for tomorrow’s flight home.
Flight Home
Day 11: Departure
Included meal: Breakfast (excluding early morning departures)
Transfer to the airport for your flight home—or “mangia, mangia” and feast on the best bites (and sights) that the Eternal City has to offer. You’re already in town, so why not stay a while longer?
Rome extension
Rome wasn’t built in a day—and, if you ask us, it wasn’t meant to be enjoyed in a day, either. Whether you play time traveler while hopping between historic sites or live out your best take on “Roman Holiday,” the choice is in your hands, and we’re here to help. Ask your Tour Director for their favorite ways to savor the city—like their secret spot for pasta carbonara—and get going.
Rome2 nights
Day 11: Sightseeing tour of Rome
Included meals: Breakfast, Tasting
From the Forum to the Pantheon to the holy confines of Vatican City, Rome bursts with UNESCO-listed landmarks. Today, you’ll follow in the footsteps of the ancients as you explore the capital of modern-day Italy on a guided sightseeing tour.
- Soak up more than 2,000 years of history in Imperial Rome, viewing the fourth-century Arch of Constantine—the largest surviving Roman triumphal arch.
- Stop outside the iconic Colosseum, a nearly 2,000-year-old amphitheater that’s both a UNESCO World Heritage Site and one of the Seven New Wonders of the World.
- Pass the Imperial Fora, the ruins of a series of monumental public squares; the Piazza Venezia, one of Rome’s principal plazas; and the museum-lined Piazza del Campidoglio as you walk to the city’s Jewish Quarter.
- Step inside a bakery to sample kosher Roman Jewish delicacies, then end your walk at the Porticus Octaviae. Also known as the Portico di Ottavia, this ancient ruin marks the center of the medieval Roman ghetto and was used as a fish market until the 19th century.
The neighborhood of Trastevere is something of a hidden gem—an eccentric, mostly car-free district filled with narrow streets and delectable trattorias. If you choose to add our snack-filled walking tour this afternoon, you’ll explore this art-filled haven while eating your way through pasta, pastries, and gelato. Otherwise, enjoy some free time to yourself (and maybe scope out some landmarks you absolutely want to see).
Day 12: Free day in Rome
Included meal: Breakfast
Master the art of Italian cuisine with an optional pizza-making class today, where you'll learn to stretch dough, select toppings, and bake your creation to perfection before enjoying the fruits of your labor. Or stay in Rome and explore on your own. To try one last marvelous morsel, return to the Jewish Quarter and track down carciofi alla Giudia—simply seasoned, double-fried artichokes
This evening, raise a farewell drink with your groupmates and celebrate a successful trip.
Flight Home
Day 13: Departure
Included meal: Breakfast (excluding early morning departures)
Transfer to the airport for your flight home.
Reviews
Hotels
We handpick every hotel to strike the balance of comfort, location, and local charm. Specific accommodations will vary based on your departure date, but these are frequently used hotels for this tour and we're confident you'll be satisfied.
Umbria - Valle di Assisi
See detailsFlorence - Grand Hotel Adriatico
See details
Siena - Hotel NH Siena
See detailsRome - Genova Hotel
See detailsFlights
Round-trip flights are one more thing we handle to make your journey as smooth as possible. Our team of travel experts will find the best flight itinerary for you at a competitive rate, thanks to our partnerships with top airlines.
Add our airfare and you’ll get:
- Round-trip flight for your tour
- Airport transfers at your destination
- A great price locked in today
- 24/7 support from our dedicated service team
- Options for arriving early, staying longer, or requesting an upgrade
- Flexible rebooking options if your tour itinerary changes
FAQ
- In order to enter Italy, U.S. and Canadian citizens need a valid passport with an expiration date extending at least six months beyond the date of reentry.
- We recommend having at least one blank passport page for entry stamps.
- Beginning in 2026, U.S. and Canadian passport holders must register for an ETIAS travel authorization in order to enter many European countries.
- Passport holders from over 60 visa-exempt countries (including the U.S. and Canada) will need to apply for an ETIAS travel authorization in order to visit 30 European countries. That means that even if you’ve previously traveled to any of these European countries without a visa, starting in 2026, you’ll need to get ETIAS authorization to visit them again. If you’re traveling to multiple countries with this requirement, you only need to complete the form once. All Go Ahead travelers are responsible for obtaining their own ETIAS travel authorization before departure. For more details, please visit our Help Center.
- If you are not a U.S. or Canadian citizen, you must contact your destination country’s consulate for your specific entry requirements.
- You can see the most up-to-date entry requirements for the destination(s) you’ll visit on tour by going to goaheadtours.com/entry-requirements and searching the code TOT.
- Round-trip flights booked through Go Ahead Tours arrive in Florence and depart from Rome.
- Transfers to and from the airport at the beginning and end of the tour are included for travelers who purchased their flights through Go Ahead Tours. Travelers who booked their own flights are responsible for securing their own airport transfers.
- When you arrive in Florence, a Go Ahead representative will be waiting for you in the arrivals hall with a Go Ahead sign or a sign with your name(s). If you don’t see a representative immediately, please be patient and stay in the arrivals area. They may be assisting another traveler who has also just arrived and will be back shortly.
Physical Activity Level
This is a high physical activity-level tour. You can expect to be on the move on a regular basis throughout the course of the tour.
Tour Pacing
This is a brisk-paced tour. The pace of a tour itinerary considers how often you’ll switch hotels, the amount of planned daily activities, and how you’ll get from place to place. You can expect:
- One 1-night stay
- Most days full of included activities (more if you add excursions)
- All transportation by motor coach
- Daily bus time varies and can be lengthy
Walking, Terrain & Physical Requirements
- Travelers should be prepared to walk 2-3 miles per day - this includes city streets, cobblestones, stairs, and hills.
- Stone pathways and cobblestone streets can become slick when wet.
- Travelers should be healthy enough to participate in all included walks without assistance.
- Please Note: Adding optional excursions may increase the total amount of walking on tour.
Climate Considerations
- In the summer months (June-September), travelers can expect heatwaves with temperatures consistently above 90F.
Physical Activity & Tour Pace Questions
- Go Ahead Tours and the Tour Director who accompanies your group are unable to provide special mobility or luggage handling assistance to travelers on tour. The responsibility of the Tour Director is to ensure the group enjoys a smooth and informative journey, and they can’t be relied on to provide individualized assistance to any one traveler.
- This tour moves at a reasonable pace to avoid missing scheduled stops. The rest of the group cannot miss any scheduled activities because of the needs of an individual.
- Due to the pace and physical activity level of this tour, mobility aids such as wheelchairs or walkers will be difficult to use and are not recommended. Please notify Go Ahead Tours before your departure if you plan to bring these on tour with you.
- If you have mobility concerns or tour pace questions, please visit our Help Center or send a message to our Customer Experience Team. We’re here to help!
- Most transportation on this tour is by private motor coach. Private motor coaches have steps required to board and often do not provide access to ramps or lifts.
- Please note that our travelers are limited to one checked bag and one carry-on bag per person due to storage limitations on motor coaches.
- Some airlines may impose additional charges if you exceed baggage size and weight restrictions. Be advised that you are responsible for any baggage fees incurred on all flights.
- Contact your airline(s) for baggage size and weight restrictions for your flights.
- Make sure you label your baggage and keep valuables, medication, and documents in your carry-on bag.
- Travelers must manage their own luggage throughout tour as porters are not guaranteed. This includes at hotels and airports.
- We recommend packing lightweight, loose-fitting clothing that can be easily layered to accommodate varying temperatures, as well as a light jacket or rainwear.
- A sturdy pair of walking shoes or sneakers is recommended for sightseeing.
- You may want to pack dressier attire if you plan to visit a high-end restaurant or attend a special performance.
- It is preferable not to visit churches or other religious sites with bare legs and shoulders (and entrance may be denied on this basis).
- We recommend packing a reusable water bottle to cut down on single use plastic waste.
- We recommend packing a universal adapter, as well as a voltage converter if you plan on using your own hairdryer or other device without a built-in converter.
- In case of emergencies, we also recommend packing your medical insurance card in your carry-on.
- Go Ahead handpicks every hotel you’ll stay at, striking a balance between comfort, location, and local charm.
- Specific properties will vary based on your departure date, but are typically three-to-four-star hotels; always include private bathrooms; and usually have in-room safes for valuables. Additionally, your hotels will have Wi-Fi, but access may be limited to common areas. There may also not be elevators.
- Unfortunately, we can’t guarantee that your accommodations will have laundry services or facilities. We recommend checking directly with your hotels once they’ve been confirmed, about 30 days prior to departure.
- Some hotels on this tour are situated on narrow streets; as such, our buses can’t drop you off right out front. In these instances, you’ll have to walk your luggage to the property, no more than a few blocks.
- Please be advised that the strength of the air conditioning in European hotels/buildings is often not as strong or as cool as what you might be used to in the U.S. or Canada.
- Italy operates on the European standard 220-240 volts and uses Types C, F, or L plugs with two or three small, round pins.
- Specific accommodations will vary based on your departure date.
- Excursions are available for purchase prior to departure, and most excursions will be available for purchase while you are on tour directly through your mobile app for an additional $10 USD.
- We recommend purchasing excursions at least 3 days prior to your tour departure. Please note some excursions have advance booking deadlines. Check your tour itinerary for more information to ensure you don’t miss the deadline to add them.
- Optional excursions may be canceled on tour due to reasons like low enrollment, weather or unexpected closures. If an excursion you signed up for is canceled by Go Ahead Tours, you will be refunded the full cost of the excursion. Please note it may take up to 60 days for your refund to be processed.
- Your Tour Director may offer their own optional excursions which can only be purchased on tour via cash (in local currency).
- At least 60 days prior to departure, check with your doctor or healthcare provider for the latest updates and entry requirements, or visit the Centers for Disease Control and Prevention's website at cdc.gov.
- If you have dietary restrictions and/or food allergies, please notify Go Ahead Tours at least 30 days prior to your departure by logging in to your account and updating your traveler info. To update this information closer to your departure date, please contact our Customer Experience Team.
- If you have medication that you take daily, be sure you have enough for each day of the tour as well as any possible delays encountered.
- Most of our itineraries include headsets used during certain sightseeing tours so travelers can hear their guides or Tour Director. If you use an assisted listening device, such as a hearing aid or cochlear implant, please visit our Help Center for more information or contact our customer experience team. Please note that at this time not all our destinations offer headsets due to supplier limitations.
- The water is safe to drink throughout your tour unless posted otherwise.
- You can see the most up-to-date entry requirements for the destination(s) you’ll visit on tour by going to goaheadtours.com/entry-requirements and searching the code TOT.
- This tour includes four lunches and three dinners. Included meals may be plated set menus, buffet or family style depending on the location. The menus for each meal are curated to give travelers a taste of each region’s specialties, while delving into the historical and cultural significance of ingredients. For beverages, travelers will typically have the option of one glass of beer, wine, or soft drink and water.
- Breakfast each morning is also included at the hotel and is typically buffet style with hot and cold options.
- Tuscany is world-famous for its wine, oil, sauces, and pasta. Menus favor subtle, lighter pastas and desserts made with nuts, fruit, and honey. Try a dish featuring the region’s Chianina beef, perhaps the most prized breed of cattle in all of Italy. For wine, popular Tuscan reds include Chianti, Brunello di Montalcino, and Vino Nobile di Montepulciano, which are primarily made from the Sangiovese grape. Well-known white wines are also made around the San Gimignano region.
- In Umbria, don’t miss sampling both the reds and whites produced around Orvieto and Perugia.
- For more authentic meals, try local trattorias, small restaurants set away from the main piazzas. A typical Italian meal includes wines and the occasional beer, followed by a few sips of after-dinner drinks like grappa or limoncello.
- At the conclusion of your tour, it is customary to offer your Tour Director and driver a gratuity in local currency. Please keep current exchange rates in mind.
- We recommend tipping the equivalent of $10USD to $12USD per person per day for your Tour Director and the equivalent of $4USD per person per day for your driver.
- If applicable, we also recommend the equivalent of $2USD per local guide.
- Tips can only be paid in cash.
- If you are traveling to multiple countries with different currencies and the same Tour Director, ask them what currency they prefer for their tip.
- The cost of porterage is included in your tour price, and it is not necessary to tip baggage handlers.
- You will use the euro on tour.
- Better rates of exchange are usually available overseas, 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 withdraw 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.
- International banks and businesses primarily accept debit and credit cards that work with the EMV chip system. If you do not already have at least one debit or credit card with a chip in it, we strongly recommend requesting one from your bank prior to your tour.
- Plan ahead and bring cash to tip your tour director, local guides, and bus drivers. We also recommend keeping coins in the local currency on hand, as some public bathrooms may charge a fee for use.
- To ensure you feel prepared before traveling on tour, we strongly recommend you download the EF Go Ahead Tours mobile app. The app is free and provides important deadlines, entry requirements, your detailed itinerary, packing tips and more. You can also connect with fellow travelers through the chat feature in the app.
- Wifi is available in most hotels, though some charges may apply.
- There is no Wifi on any of the motor coaches.
- Please contact your mobile service provider for information on roaming charges.
- Your Tour Director will be leading your group throughout your journey. You will have the same Tour Director throughout your tour.
- The role of the Tour Director is not only to provide information and context on the destinations you visit, but also to confirm services, coordinate inclusions, prepare each days’ activities and support travelers while on tour. As such, they must focus on the success of the group, and cannot provide individualized assistance to any one traveler.
- One of the benefits of traveling with EF Go Ahead Tours is our on tour emergency support team.
- Our extensive network of offices around the world, and our integration of ISO 31000: Risk Management Guidelines, help our dedicated 24/7 Emergency Service teams anticipate and address on-tour challenges in a flexible and iterative way.
- This team supports travelers and Tour Directors using a combination of extensive training, simulations, incident response planning, and decades of experience to help manage emergencies if they arise, ranging from personal health concerns or injuries to major world events.
- As needed, On Tour Support can facilitate additional support for travelers on tour, arrange assistance from outside specialists, and liaise with local and international authorities to help solve on-the-ground issues. In addition, the team is dedicated to supporting and facilitating communication between travelers and families in the event of an emergency while on the road or at home.
- Italy is one hour ahead of Greenwich Mean Time (GMT) and six hours ahead of Eastern Time (ET).
- When it’s noon in New York, it’s 6pm on tour.
- When you travel with Go Ahead Tours, you’ll make a positive impact on the places you visit and the people and animals you meet along the way. That’s because our three core Responsible Travel commitments—protecting the environment, supporting local communities, and promoting animal welfare—are at the heart of every tour we offer.
- Travel, when done responsibly, can have an enormous socioeconomic impact on communities. To maximize your impact, eat at locally owned restaurants and shop at small businesses. Ask your Tour Director to point out restaurants they recommend.
- Prepare for your trip: Be aware of monetary norms such as tipping and negotiating in a market; learn about the destination’s forms of etiquette; and take some time to learn a few words in the local language.
- When interacting with locals, make sure to ask people for permission before you take their picture, and approach cultural differences with empathy and an open mind.
- Go Ahead Tours encourages travelers to limit their waste while on the road, especially single-use plastics. You can cut back on generating plastic waste by packing your own toiletries, using electronic documents, and bringing a reusable water bottle and shopping bag. If you need to use plastics or paper, please recycle.
- If you are interested in visiting any of Florence's many museums during your free time, we recommend that you make reservations in advance. See uffizi.org for the Uffizi Gallery or accademia.org for the Accademia Gallery. Please note that the museums are closed on Mondays.















































































