Tuscany Walking Tour11 days / Walking Tours
95.4% of reviewers recommend this tourRead Reviews 
About This Experience
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 memorable. 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 Includes
Round-trip airfare & transfers
9 nights in hand-picked hotels
Breakfast daily, 2 lunches, 3 three-course dinners with wine or beer
Multilingual Tour Director
Private deluxe motor coach
7 escorted walks
Select entrance fees
Why You'll Love It
Scenic isn’t a strong enough word for Tuscany’s backdrops
Being so active is a great excuse to eat more pasta
You’ll sip & savor Chianti in Chianti
History is always underfoot in San Gimignano & Volterra
Italian walks are good for the heart (in more than one way)
The Renaissance is still afloat in Florence
Overnight Flight1 night
Montecatini3 nights - hotel info
Let go, enjoy yourself, you’re in Montecatini
Dinner, Breakfast (in flight)
Welcome to Italy! A Go Ahead representative greets you at the airport after you clear customs and then accompanies you to Montecatini, where you’ll be assisted with hotel check-in. Later, meet your fellow travelers at an included dinner.
Take a walk behind (and on) Lucca’s Renaissance-era walls
Optional Excursion - Medieval Lucca & the Flavors of the Countryside
Today is free for you to relax and become acquainted with Montecatini, an inviting spa town in the hills of Tuscany. You might choose to join our optional excursion to Lucca, a walled medieval town, and Colle Verde, a typical Tuscan farm where olive oil is produced.
Medieval Lucca & the Flavors of the Countryside $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.
Italian language, opera, the Renaissance—all born right here
Baptistery of St. John
Take a day trip to the timeless city of Florence, birthplace of the Italian language, the Renaissance and opera. A guided walking tour introduces you to the city’s Renaissance relics. Marvel at Brunelleschi’s masterpiece—Florence’s massive pink, white and green Duomo. Then, discover the Baptistery of St. John. You’ll have the afternoon to explore Florence on your own before returning to Montecatini for the evening.
Siena3 nights - hotel info
When in the Chianti Region: sip, savor, repeat
Breakfast, Lunch, Dinner
Tuscan wine tasting
Making your way to Siena, you’ll spend the morning walking through the world-famous Chianti Region, land of the Chianti League, recently restored in order to preserve the name and trademark of Chianti wine. You’ll then attend a wine tasting to sample the region’s most famous local product, red wine, and enjoy a light lunch. On an afternoon walk, view a panorama of valleys and rolling hills, ending in the town of Vinci, birthplace of Leonardo. Continue on to Siena, a former independent republic the richest city in Italy during the 13th and 14th centuries. Dinner is included tonight.
Walk through the eras, from medieval to Gothic
Siena Cathedral, Piccolomini Library
Today’s walk is near the rounded walls of Monteriggioni, one of Tuscany’s best-preserved medieval towns. On an afternoon guided tour of Siena, enter the Campo, described by Montaigne as the most beautiful square in the world. This is where the annual Palio competition convenes. You’ll then visit the grand Piccolomini Library, a museum inside the Duomo whose well-preserved frescoes depict the life of Pope Pius II.
San Gigmignano is a fortress to be reckoned with
Optional Excursion - Dinner in Siena: Tuscan Culture & Cuisine
Today’s focus is on the fortress town of San Gimignano, with its dramatic skyline of huge, medieval towers. Fourteen of the original 70 towers remain, an ongoing testament to the Guelph-Ghibelline rivalry of the Middle Ages. Following your walk in San Gimignano, visit Volterra, a city with a history dating back 3,000 years to the ancient Etruscan civilization. After returning to Siena for the night, consider joining our optional dinner, featuring traditional Tuscan cuisine.
Dinner in Siena: Tuscan Culture & Cuisine $79* pp
Visit a local restaurant in the heart of Siena, which deliciously blends the traditional and contemporary elements of Tuscan cuisine. Start off your evening with an aperitif, and then get settled in for an evening of Sienese specialties, served up in the tavern’s intimate setting. Typical Tuscan dishes like pici and cantucci parfait showcase why food and wine enthusiasts flock to this region.
Montepulciano Region2 nights - hotel info
Age and beauty meet in Cortona, one of Italy’s oldest towns
Walk through the lovely medieval town of Cortona, which overlooks the fertile plains of Valdichiana. Later, stop in the Umbrian region at Lake Trasimeno, site of the fiercest battle between Hannibal and the Romans in 217 B.C. Continue to the Montepulciano region and walk to the medieval village while enjoying sweeping views of the surrounding countryside. Enjoy some free time in Montepulciano to visit the Duomo and the church of San Biagio. Dinner is included tonight.
Montalcino: once a battleground, now your stomping grounds
Optional Excursion - Montepulciano Wine Tasting & Dinner
Today’s series of walks begins in nearby Montalcino, famous for its fierce battles against Florence and the Medici family’s dominion. Here, you’ll visit Sant’Antimo Abbey, a Romanesque church surrounded by rolling hills. Continue on to Pienza, “Pearl of the Renaissance,” where you’ll have free time to see the Duomo and Gothic churches. This evening, experience Tuscan country ambiance and hospitality as you dine on a traditional meal and sip local Vino Nobile wine on our Montepulciano Evening excursion.
Montepulciano Wine Tasting & Dinner $89* pp
One of things that makes Tuscany so special is the amount of farms and wineries that dot the countryside. For tonight’s dinner, visit a farm and vineyard near the medieval hilltop town of Montepulciano, which is known around Italy for its regional food and wine. Sample a few of their wines, including the world-famous Vino Nobile, and then sit down for a homemade three-course dinner.
Rome1 night - hotel info
Sit back, relax and take the scenic route to Rome
The day begins with a scenic drive to the Monte Amiata region. You’ll have time to explore the charming old town of Abbadia San Salvatore before continuing on to Rome. This evening, enjoy a farewell dinner with your fellow travelers.
Extend Your Stay
Add Rome City Stay $359*
Only in Rome can you sip cappuccino at a cafe 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 exuberant street life, no other city comes close.
Rome2 nights - hotel info
Roam about Rome at your leisure
Optional Excursion - Dinner with Tenors
Embark on an included guided tour of Imperial Rome and discover art and architecture at every turn, from relics of the ancient empire to treasures of the Renaissance. Tonight, you may choose to attend the Dinner with Tenors, an evening of food and live music.
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!
Step into the world’s smallest state: Vatican City
Optional Excursion - Iconic Sights: Vatican City
Spend the day exploring Rome at your leisure. Or, join an optional excursion to Vatican City, including visits to the Vatican Museums, St. Peter’s Basilica and the Sistine Chapel.
Must be booked 70 days before departure
Iconic Sights: Vatican City $89* 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.
Passport & Visa Requirements
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.
Airlines have varying weight restrictions on luggage. Some airlines may impose additional charges if you choose to check any baggage; be advised that you are responsible for any such costs. Contact your airline for detailed information regarding luggage size and weight restrictions for your flight, but please note that Go Ahead travelers are restricted to one checked bag per person due to storage limitations on motor coaches and other internal transfers, which may include train connections or flights. One carry-on bag is also permitted, provided that it does not exceed 45 total inches (length + width + height). Make sure you label your baggage and carry valuables, medication and documents in your carry-on bag.
Clothing & Packing Tips
Hiking boots are recommended for your tour, but if you don’t have them, then sturdy, comfortable athletic shoes and a change of footwear will do. To keep hydrated and better experience the local scenery, you’ll want to keep a plastic water bottle and binoculars handy. Some additional items we recommend carrying with you include: insect repellent, a sun hat, sunscreen, bandages, lip balm and a flashlight. You’ll also want to pack transitional clothing that fits comfortably and can adapt to inclement weather, such as a lightweight sports jacket, rainwear and light, loose-fitting layers. Also, remember that bare legs and shoulders are not allowed in Italy’s churches or other religious sites. Entrance may be denied on this basis.
There are no major health risks associated with traveling to Italy. Travelers should be in reasonable health to take our scheduled walks, although we will make every effort to accommodate those who chose to stay behind. Be sure to check with your healthcare provider for the latest updates and personal travel requirements.
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.
Arrival & Transportation Information
Round-trip flights arrive in Florence and depart from Rome. Upon arrival in Italy, a Go Ahead representative escorts you via private motor coach to Montecatini. 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 may be escorting one of your fellow travelers to the bus at the time of your arrival. All other included transportation on your 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. Rome has one of Europe’s best metro systems, serving all the major attractions from the Roman ruins to Vatican City.
Museums in Florence
If you are interested in visiting any of Florence's many museums during your free time, we recommend that you make reservations in advance. Additional information is available on the Polo Museale website. Please note that the museums are closed on Mondays.
Italy operates on the European standard 220 volts.
Italy is one hour ahead of Greenwich Mean Time (GMT) and six hours ahead of Eastern Standard Time (EST). When it is noon in New York, it’s 6pm in Florence.
The euro is the currency you will be using on your tour. Better rates of exchange are usually available in Italy, although it is 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.
At the conclusion of your tour, it is 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.
95.4% of reviewers recommend this tourRead Reviews 
Memories for a lifetime!
I just returned from the Walking Tuscany Tour and can honestly say that it was one of the best trips I have taken! From our tour guide (Valerio) to our bus driver (Horacio), to the group we spent 12 days with, memories were made that will last a lifetime. First of all, our tour guide was fantastic! He was so knowledgeable and energetic! He helped make the trip so wonderful! Not only did he share information with us, but he gave it a personal touch as well. He enjoyed our group, lively as we were! Our bus driver was also wonderful! He took great pride in getting everyone to our destinations safely and in a timely manner. He was also fun and enjoyed our group as well! Our entire group ended up being so compatible! We had similar interests and enjoyed our time together. I can say that I have made new friends that I will continue to keep in touch with! Although it was a bit overwhelming traveling so far away from my family (yes, I left kids and husband at home to venture out on a girls trip), Go Ahead Tours made sure everything was set and all we had to do was go and enjoy! I would definitely book a tour through Go Ahead again. Did I mention the beautiful Tuscan countryside? Everything I pictured in my head was exactly what I was able to experience. I would highly recommend this tour. There was a nice amount of walking and definitely a great amount of sights to see and enjoy. Thank you all who made this trip so wonderful!
Don't Miss It!
This tour was wonderful. We chose this for our thirtieth anniversary celebration, and are ready to do it again for 31st, 32nd, 33rd, etc! Tuscany is lovely. Good sights to see, great food and wine. Three things made it magical: Italy itself, our tour director, Valerio who was simply the best, and the group of 13 other companions we traveled with. We gelled as a group instantly, had each other's back, and were kindred spirits with a touch of adventure and a dash of mischief. Good hikes, none too challenging if not infirm. I cannot say too many good things here. We loved every minute, and the phrase we said over and over to each other, was "Magical!"
Just came back from this tour, and honestly, it was best vacation we have ever done. Three things made this tour exceptional: 1) The gorgeous Tuscan countryside, history, culture and art (and wine). 2) An enormously informative, friendly, and understanding tour director - Valerio (the Florence/Siena tour guides were also very good, especially Donatella in Siena) 3) Just a really, really fun group of tour-mates, who made the vacation so much more lively, and interesting. Go Ahead has a very well-planned tour, with just the right amount of country-side, and city walks. This is the only way to see Tuscany. I would highly recommend this tour for either first time travelers to Italy, or seasoned travelers. If I had to 'constructively' criticize anything, it would be the hotel selection. The hotel in Siena was very good, and so was the hotel in Pienza, however, the hotel in Montecatini was a little (for lack of a better word) shabby. I think a hotel closer to Florence would a better choice. But overall, a great vacation/tour. Can't wait to start planning for next year. Our tour director said that Puglia is the next Tuscany. We'll have to check that out.
Still Thinking About Tuscany
This was my first trip to Europe and proved to only whet my appetite for more. Flights were well scheduled and smooth arriving in Florence by 9 am. Our tour Director met us as promised and we were on our way to Montecatini where surprisingly we were able to check into the Grand Hotel right away. The hotel is well located in this quiet little city known for its spas although the rooms could stand to be updated. They are dark and the shower situation leaves something to be desired. The public spaces were nice and the food was okay. I think Go Ahead could do a little better than this property. Don't miss visiting Montecatini Alto which is only a cable car ride away. Also don't miss Ricardos's gelato shop and Giovannis pastry shop. The optional tour to Lucca and the olive oil farm was fun and worthwhile. More time is needed for Lucca - a very interesting and picturesque little town. The day in Florence was super with a walking tour and time on our own. Make your reservations for the Uffizi Gallery and the Academe ( David is a big wow) ahead of time by phone (very easy) I think leaving Florence at 5 pm was much too early. The day should be planned so that people can have dinner in Florence instead of returning to Montecatinin where we had already had dinner the previous two nights. Although this tour is rated a 4 (challenging), I didn't really think that is was. I'm not in great shape and was worried about whether I would hold the group up but I did just fine and no walk was more than 2 hours long. Yes, there was some uneven, rocky terrain and a lot of uphills but nothing that most people who enjoy walking can't do plus we were always given the chance to sit out the walk and ride the bus to the destination. Walking really is the best way to experience the countryside and the old villages.By the way our Giotto bus and driver (Arezzio) were excellent as was Raf, the tour director who always did extra and made our travels a lot of fun. Each village that we visited had its own appeal. My favorite was Volterra - the ancient Etruscan walls and the alibaster shops were just great. The Garden Hotel in Siena was very nice although not really walkable to the city. There is a nearby bus stop which we used one night. Siena is a lot of fun and the Cathedral is magnificent. My biggest surprise was the town of Pienza. I had read (Rick Steeves) that there isn't a whole lot there worth visiting but I enjoyed the shops, restaurants and scenery very much. Visiting the cheese shops and sampling was interesting. The Hotel Corsignano was my favorite - so comfortable and my room had a balcony! My favorite church was St. Antimo. Although we didn't get to hear the chanting monks, the church itself has a very special feel. Sunlight streams through those ancient windows enveloping those inside. Plan to do the Rome extension if you haven't been. We were there on the day of the Pope's canonization which was awesome. The Hotel President is a Best Western which seemingly caters to bus tours. It is in a great location across from the Manzoni subway station and a 15 minute walk to the Coliseum. I thought the rooms were just okay and the breakfast buffet was strange (salad on one end, runny eggs on the other and pastries in the middle). Rome is very walkable with a decent map - so much to see and enjoy. I fell in love with Italy and thank Go Ahead for a wonderful first trip across the pond. I'll definitely be back.
Tuscany is gorgeous!
The walking tour of Tuscany was wonderful. We enjoyed a great group of fellow travelers, an excellent tour guide and the breathtaking Tuscan landscape. Throughout the tour, we enjoyed the experience of seeing the gorgeous, opulent Tuscan landscape. We spent the time visiting several ancient towns, experiencing incredibly wonderful churches, and eating at excellent restaurants. Our tour director was enthusiastic, generous with her time and attention, and very knowledgeable. Everyone on the tour appreciated her help, guidance and skill. By of suggestions, I would say that several of the "add-ons" were not good bargains, Two of the eating activities, in fact, were not at all worth the time or money. The Tuscan restaurant meal was not all that good, and the wine tasting didn't include a wine tasting. I wouldn't recommend any of the add-ons except the Vatican Tour.
This Walking Tour of Toscany gets you closed to the land, the farms and the people that make this part of the world so enchanting and gracious The walks are not hard and the places at the end of them are beautiful medieval towns. It includes mega cities like Florence and Rome for the art aficionados and also touristy towns like Montecatini Terme, Siena and Pienza for the shoppers but the best part is the visit to the three vineyards which also produce olive oil. The 3 meals in the farms were superb. The hotels are super fancy and not necessary, I would have prefered smaller not so modern accommodations and a cheaper price. The meals in the two hotels and two restaurants organised by the tour, if they can not be improved, they need to be cancelled because they were poorly prepared. The guess in this tour can find better food in restaurants in the towns at all prices. As a rule the food in Toscany is freshly prepared, healthy and natural. Toscany is the main character in this tour and it shines in its natural beauty and ancient history.
Best tour and director!
This trip was fast-paced and there was a lot of walking, which was expected. Every place we visited was absolutely beautiful. We were in Florence on Easter and in Rome the day of the canonization of two Popes. What a time to be there! I have travelled before, but this was the first organized tour I had been on and I was not disappointed. Our tour guide, Raf, was excellent. He was very knowledgeable in the history of all the places we visited and pointed us in the right direction when it came to the best restaurants, shopping and gelato! A tour guide can make or break a vacation and he worked non-stop to make our trip memorable. Overall, the trip exceeded my expectations. The walks in Tuscany were breathtaking. I am so glad I was able to finally visit this region.
.Tuscany was wonderful. The tour was great. I would not chose a walking tour again as I am a slow consistent walker and many of the other travelers were fast walkers who did not wait for the slower walkers.
WalkinWalking the Beautiful Hills and Towns of Tuscanyf Tuscany
Our time spent in the countryside and hill towns of Tuscany was a magical mix of natural beauty coupled with historic accounts of the Etruscans, Romans and Italians, who had populated in these areas. Our Tour Director was a knowledgeable historian, giving us a better appreciation of the area's people geography and history. The walks were nicely paced, with time to visit each town. The excursions to family vineyards and olive groves was informative, intimate and very tasty. Recalling the entire experience, we were very pleased. It was something we'd gladly do again. A surprise bonus, was the friendly, educated and diverse group of travelers who helped made the trip memorable.
More than I Expected!
Just like the title says. On the second day of our trip I told myself that if this was the end of our trip it would of been well worth it. Everyday I thought that it couldn't get any better or more beautiful, well it did. From the top of the line tour director, dinners, excursions, hikes, towns visited, to the local guides. Everything was well planned. Kudos to whoever planned the tour details. I miss Italy, alot, but Lord willing I will return. Thanks Go Ahead Tours. I'm glad I chose your agency. I was very pleased and have recommended Go Ahead to several of my friends.