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Tuscany Walking Tour

with Rome extension
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Book today and feel good about your decision. If you change your mind, you’ll receive a refund of your deposit through January 1, 2021.See terms
Life seems simpler in Tuscany.

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
Included highlights
  • Florence’s Duomo
  • Basilica of Santa Croce
  • Chianti Region wine tasting
  • Siena
  • Monteriggioni walk
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Day-by-day itinerary
Print itinerary
Overnight Flight1 night
Day 1: Travel day

Board your overnight flight to Florence today.

Montecatini3 nights
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
Excursion (additional cost)
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 Croce, the burial site of Michelangelo, Machiavelli, and Galileo
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
Excursion (additional cost)
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
Excursion (additional cost)
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, enjoy an elegant, four-course farewell dinner. While you dine, you’ll be treated to some of opera's best-loved arias sung by professional tenors.

Please note: The opera performance is seasonal and runs from March through November. Dinner will take place at a local restaurant from December through February.

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
Excursion (additional cost)
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
Excursion (additional cost)
Flight Home
Day 13: Departure
Included meal: Breakfast (excluding early morning departures)

Transfer to the airport for your flight home.

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4.8 average
 Our reviews are authentic and unedited.
Tuscany Walking Tour
by 1st-time traveler 

It was an excellent tour. I would do it again sometime.

Wonderful Walking Tuscany Tour
by 2nd-time traveler 

The beauty of Tuscany was showcased in this wonderful walking tour. The accommodations in Montecatini were great as were the accommodations in Pienze. Both hotels were charming and steps from “downtown” areas. The hotel in Siena was a disappointment. It was too far out and was too generic. Our day i...

Read more +
Outstanding tour, Giorgio was top notch!
by 6th-time traveler 

Our group had a wonderful time. Giorgio was outstanding knitting us together, just the right amount of information and connection to people and places. We loved the playlists that he created for us in off moments on the bus. Fabulous trip, visited an amazing number of places in small cities/towns in...

What's not to love about Italy!
by 2nd-time traveler 

This is my second Go Ahead tour to Italy. I wondered if it could be as amazing as my first trip...it was! This was my first solo tour and I was worried about fitting in, I didn't need to. I loved pulling away from the more well known locations and out into the Tuscany country side. Walks were ve...

Tuscany Walking Tour
by 3rd-time traveler 

Wonderful experience! To start with, this is a walking tour, expect 3 to 4 miles of walking steep hills and rocky roads. Well worth it but be prepared. If you have medical issues maybe select a more leisurely paced tour. Great way to see the countryside and vineyards. The hotels were very nice and a...

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.


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 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...

Ercolini & 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...

Hotel Garden

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...

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...


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
  • Find out more about flights
Print FAQ
Passport & visa requirements
  • 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.
Tour pace
  • 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.
Walks on this tour
  • Depending on local weather conditions, seasons and trail closures, the activities and sequence of your included walks may change.
  • Chianti Region – 3 miles / 1 hour. A paved and gravel path that begins with a steep incline then continues on flat ground through vineyards and farms.
  • Montereggioni – 3–4 miles / 1.5 hours. A downhill hike on a gravel path through woods, wheat fields and farms.
  • San Gimignano – 2–2.5 miles / 1 hour. A gravel path up a small incline for views of surrounding countryside and town.
  • Cortona – 1–2 miles / 1 hour. An easy, downhill walk from St. Margaret’s Church through the town.
  • Montepulciano – 1.5–2 hours / 1 hour. A paved road through the Tuscan countryside with a few inclines and declines.
  • Montalcino – 4 miles / 2–2.5 hours. A walk through the countryside on a mainly flat gravel path with one steep downhill portion.
Transportation & arrival information
  • 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.
Baggage allowance
  • 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.
Clothing & packing tips
  • 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)
  • There are no major health risks associated with traveling to Italy.
  • 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.
  • 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.
Electricity & air conditioning
  • 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.
  • Wi-Fi is available in most hotels, though some charges may apply.
  • There is no Wi-Fi on any of the motor coaches.
  • Please contact your mobile service provider for information on roaming charges.
Time zones
  • 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.
  • You will use the euro on this 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.
  • 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.
  • Tips can only be paid in cash.
Purchasing excursions on tour
  • Most optional excursions will be available for purchase while you are on tour.
  • Your Tour Director will only accept cash (in USD only), Visa or MasterCard as payment for optional excursions.
  • Please be advised that if you pay for an excursion by credit card while on tour, it may take up to three months for your card to be charged.
  • Some optional excursions may only be purchased in advance. See page four of your tour itinerary for more information.
Dates & prices
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May 08
May 18

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