Feel good about booking your tour today. Enroll in AutoPay or pay in full when you book and if you change your mind, you have 60 days to receive a full refund of your payment.
In the land of cypress trees and Chianti, a leisurely stroll may not be the fastest way to get around, but it’s certainly the most preferred. On this walking tour of Tuscany, you’ll step into historic cities like Florence and Siena, and amble through charming hamlets like Montalcino and Cortona for an authentic glimpse into the heart of Italy.
Your tour package includes
9 nights in handpicked hotels
9 breakfasts
1 lunch
4 dinners with beer or wine
6 guided walks
Read more
Included highlights
Florence’s Duomo
Basilica of Santa Maria Novella
Chianti Region wine tasting
Siena
Monteriggioni walk
Read more
Start planning today
An expert specializing in tours of this region is here to help.
Day 2: Arrival in Florence & transfer to Montecatini
Included meal: Welcome dinner
Welcome to Italy! Arrive in Florence and transfer to your hotel in Montecatini. Then, meet your Tour Director and fellow travelers at tonight’s welcome dinner.
Day 3: Free day in Montecatini
Included meal: Breakfast
Enjoy a free day in Montecatini or add an excursion.
Medieval Lucca & Farmhouse Lunch
From $155 per person
Day 4: Sightseeing tour of Florence
Included meal: Breakfast
Set off on a day trip to Florence, the city at the center of the Renaissance, for a tour led by your local guide.
Visit the legendary Florence Cathedral, known as the Duomo
Pass Giotto’s Campanile, a masterpiece of Gothic architecture
Walk past Piazza della Repubblica to the medieval Ponte Vecchio
Stroll along the Arno River and through the courtyard of the Uffizi Gallery to Piazza della Signoria, center of Florentine life
Step inside the Basilica of Santa Maria Novella, of Tuscany’s most important Gothic churches with artwork by Masaccio, Ghirlandaio, and Giotto
Siena3 nights
Day 5: Siena via Chianti
Included meals: Breakfast, Lunch, Dinner
Pass through the famous Chianti region and the village of Greve en route to Siena.
Traverse the vineyards and farmlands of the Chianti region on a local walk
Sample the area’s rich red wine over an included lunch and wine tasting
Explore the main square and winding side streets in the village of Greve
Continue on to Siena and sit down for an included dinner this evening.
Day 6: Monteriggioni & Siena
Included meal: Breakfast
Today, explore the rolling hills of Monteriggioni and culturally rich streets of Siena.
Embark on a scenic walk through the woods and countryside of Monteriggioni
View the Romanesque church of Abbadia a Isola
Enjoy a guided tour of the UNESCO-listed historic center of Siena
Pass Piazza del Campo
Enter the Piccolomini Library and Siena Cathedral
Day 7: San Gimignano & Volterra
Included meal: Breakfast
Take a day trip to the medieval towns of San Gimignano and Volterra, where you’ll do some exploring.
Enjoy a breathtaking view of the town as you walk into San Gimignano, a medieval hilltop city known for its towers
Embark on an afternoon trip to Volterra, where you can visit the cathedral, Roman Theater ruins or local shops
Enjoy a free evening in Siena or add an excursion.
Tuscan Villa Winery & Dinner
From $165 per person
Montepulciano Region2 nights
Day 8: Cortona & Montepulciano
Included meals: Breakfast, Dinner
Enjoy sweeping views of the Tuscan countryside as you enjoy guided walks in both Cortona and Montepulciano.
Walk downhill from St. Margaret’s Church to explore the town of Cortona
Transfer to the town of Montepulciano, where you’ll pass the cathedral and enjoy breathtaking views of the Tuscan hills
Sit down for an included dinner this evening.
Day 9: Montalcino & Pienza
Included meal: Breakfast
Explore the scenic Montalcino area and the beautiful town of Pienza, nicknamed “the Pearl of the Renaissance.”
Walk through the countryside of Montalcino, ending at the Abbey of Sant’Antimo, a Romanesque church surrounded by rolling hills
Continue to Pienza, where you’ll have free time to see the cathedral and the town’s Gothic churches
Enjoy a free evening in the Montepulciano region or add an excursion.
Montepulciano Wine Tasting & Dinner
From $115 per person
Rome1 night
Day 10: Rome via Monte Amiata
Included meals: Breakfast, Farewell dinner
Leave the Montepulciano region for Rome, stopping in the Monte Amiata region on the way to visit the charming town of Abbadia San Salvatore.
This evening, join your group for a farewell dinner. As you dine, you'll be treated to a multi-course traditional Italian meal with a live musical entertainment.
Flight Home
Day 11: Departure
Included meal: Breakfast (excluding early morning departures)
Transfer to the airport for your flight home or extend your stay to further explore the history of Rome on foot.
Extension to Rome
Have your sights on more art, history, and street life? Rome is sure to deliver. Only in the Italian capital can you sip cappuccino in front of the Pantheon and have an audience with the pope all in one morning. See the city’s highlights during guided sightseeing, and then look to your Tour Director’s expert suggestions to uncover even more.
Rome2 nights
Day 11: Walking tour of Rome
Included meal: Breakfast
Follow in the footsteps of the ancient Romans during a guided walking tour of the Eternal City.
Soak up over 2,000 years of history in Imperial Rome, viewing the Arch of Constantine and the Arch of Titus
Enter the Colosseum, the largest amphitheater of the Roman Empire
Walk through the ruins of the Forum, once the setting of parades, elections, and trials
Pass the Imperial Forums, Trajan’s Market, and Trajan’s Column as you stroll along Via dei Fori Imperiali
Head to Piazza Venezia to see the Vittorio Emanuele II Monument and Mussolini's balcony
End your tour in the Jewish ghetto neighborhood
Enjoy free time in Rome or add an excursion.
Rome Home-Hosted Dinner
From $89 per person
Day 12: Free day in Rome
Included meal: Breakfast
Spend a free day in Rome or add an excursion.
This evening, enjoy a farewell drink as you celebrate your trip with your fellow group members.
Iconic Sights: Vatican City
From $145 per person
Flight Home
Day 13: Departure
Included meal: Breakfast (excluding early morning departures)
I cannot express enough how amazingly beautiful & special this tour was with our guide, Laura. The weather was perfect. Every excursion & local guide were excellent. I have fallen in love with Italy!
EF Go Ahead Tours replied on 12/22/21
Dear Emily,
Thank you for your review! We are so ...
Read more +
Still thinking of Tuscany!
08/04/19 by 1st-time traveler Kevin
I'm writing this 18 months after it happened. However, I still remember how amazing the entire experience was. Highly recommend this tour of Italy. Bring good footwear as you will be hiking!!
Beyond Wonderful
09/23/18 by 1st-time traveler Kathryn
Walking in the countryside of Italy was such an amazing experience. We walked through woods, olive orchards, vineyards with spectacular views. It was glorious. We walked up a country road past lovely farm houses and emerged at the top in vineyards where we were amongst the workers harvesting grapes....
Read more +
Show more reviews
Traveler photos
Hotels, flights & FAQ
Here's the nitty-gritty—where you’ll stay, how you’ll get there, and what to know about your destination before you go.
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.
Hotel Ercolini e Savi
This relaxing hotel is located in the heart of the city, near the train station. Guests enjoy a restaurant, bar, and free Wi-Fi. Nearby, you’ll find g...
Read more +
Hotel Garden Siena
This charming hotel is located near the city center of Siena. Guests enjoy a pool, restaurant, and bar and lounge. Nearby, you’ll find 18th-century ga...
Read more +
Hotel Corsignano
This comfortable hotel is located in the heart of Pienza. Guests enjoy a bar, relaxation room, and free Wi-Fi. Nearby, you’ll find the Pienza Duomo, P...
Read more +
Best Western Hotel President
This modern hotel is located near Termini Station. Guests enjoy free WiFi, a minibar, and laundry center. Nearby, you'll find Arcibasilica di San Giov...
Read more +
Flights
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 package 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
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.
There is no visa required for U.S. or Canadian citizens.
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 WAT.
You will walk for at least 2.5 hours daily across uneven terrain, including unpaved paths and cobblestone streets, with some steep hills.
Travelers should be healthy enough to participate in all included walks without assistance. Adding optional excursions may increase the total amount of walking on your tour.
You should feel comfortable managing your own baggage at times.
Go Ahead Tours and the Tour Director who accompanies your group are unable to provide special, individual mobility assistance to travelers on tour. The responsibility of the Tour Director is to ensure the group as a whole enjoys a relaxing and informative journey, and he or she cannot be relied upon to provide ongoing, individualized assistance to any one traveler.
If you have any mobility concerns or physical restrictions, please contact our Customer Experience Team.
Round-trip flights booked through Go Ahead Tours arrive in Florence and depart from Rome. When you first arrive, a representative from Go Ahead Tours will meet you at the airport. Please remain in the arrivals lounge, as the representative may be escorting fellow travelers to the bus at the time of your arrival.
Transfers to and from the airport at your destination are included for travelers who have purchased their flights through Go Ahead Tours. Travelers who purchase their own flights may request airport transfers with Go Ahead Tours for an additional cost.
All other included transportation on this tour is by private motor coach.
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 and other transfers, which may include train connections or flights.
Contact your airline(s) for baggage size and weight restrictions for your flights, which may include on-tour flights in addition to your round-trip flights to and from tour. Please note that your included on-tour flights may have more restrictive baggage limits.
Some airlines may impose additional charges if you choose to check any baggage or exceed baggage size and weight restrictions. Be advised that you are responsible for any baggage fees incurred on all flights.
Make sure you label your baggage and keep valuables, medication, and documents in your carry-on bag.
We recommend packing lightweight, loose-fitting clothing that can be easily layered to accommodate varying temperatures, as well as a light jacket or rainwear.
Light hiking boots or sturdy sneakers are recommended for the cobbled stones and uneven terrain.
You may want to consider packing a collapsible walking stick for more challenging walks.
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)
At least 60 days prior to departure, check with your doctor or healthcare provider for the latest updates and entry requirements, or visit the Center for Disease Control and Prevention website at cdc.gov.
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.
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 call our Customer Experience Team.
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 WAT.
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.
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.
Italy operates on the European standard 220-240 volts and uses Types C, F, or L plugs with two or three small, round pins.
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.
The strength of the air conditioning in European hotels is often not as strong or as cool as what you might be used to in the U.S. or Canada. When air conditioning is available, it is usually regulated seasonally and controlled centrally by the hotel.
Your hotel may provide hairdryers, irons and other small appliances. However, these amenities cannot be guaranteed.
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.
Inform your bank and credit card company of your travel plans so that they won’t confuse your international purchases for fraudulent charges.
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.
At the conclusion of your tour, it’s 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 $7USD to $10USD per person per day for your Tour Director and the equivalent of $3USD per person per day for your driver.
If applicable, we also recommend the equivalent of $2USD per local guide.