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Amble through ancient towns in the heart of Tuscany.
It doesn’t get much better than a Tuscan to-do list: Bike along cypress-lined city walls, take leisurely strolls through hilltop towns, and cap each meal off with a glass of Chianti. On this small group Adventure Tour in the heart of Italy, you’ll find yourself eager to say “check, check, and check” as you discover hidden corners of Tuscany (like Maremma!) where time seems to stand still.
Your tour package includes
10 nights in handpicked hotels
10 breakfasts
2 lunches
3 dinners with beer or wine
1 wine tasting
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Included highlights
Bike ride on Lucca’s ramparts
Chianti wine tasting
Siena’s Campo
Piccolomini Library
San Gimignano walk
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Start planning today
An expert specializing in tours of this region is here to help.
Welcome to Italy! Transfer to your hotel in Lucca. Then, meet your Tour Director and fellow travelers at tonight’s welcome dinner.
Day 3: Biking & walking tour of Lucca
Included meal: Breakfast
Lucca features towering, Renaissance-era walls and sits in the heart of Tuscany. Today, get to know the area as you bike and walk through the city with a local guide.
Take a leisurely bike ride along Lucca’s tree-lined ramparts
Take in impressive views of the classic red-tiled rooftops, Guinigi Tower, and the swath of cypress trees below
Descend into the center of town and walk to see San Martino Cathedral and San Michele in Foro, a basilica known for its intricately inlaid facade
Please note: You’ll bike along flat, paved paths without cars during the tour of the Lucca city walls. Travelers can opt to take a self-guided tour of the walls by foot instead of biking.
Enjoy a free afternoon in Lucca or add an excursion.
Farmhouse Wine & Olive Oil Tasting with Lunch
From $129 per person
Siena3 nights
Day 4: Siena via Chianti
Included meals: Breakfast, Lunch, Wine tasting
Pass through the famous Chianti region and the village of Greve in Chianti en route to Siena.
Hike through the vineyards and farmlands of the Chianti region with your Tour Director
Admire sweeping views of the rolling Tuscan hillsides
End your hike at a vineyard and sample the area’s rich red wines during a wine tasting
Enjoy a relaxing lunch overlooking the countryside
Travel to Greve in Chianti and explore the main square and winding side streets at your leisure
Continue on to Siena and settle in to your hotel.
Day 5: Walking tour of Monteriggioni & Siena
Included meals: Breakfast, Tasting
This morning, explore the rolling hills of Monteriggioni with your Tour Director.
Embark on a scenic walk through the woods and countryside of Monteriggioni
View the Romanesque church of Abbadia a Isola
Make your way back to Siena and set off on a guided tour of the charming Tuscan city.
Walk through the Campo, the square that’s the center of civic life, and learn about the Palio horse race that takes place there every summer
Enter Siena Cathedral, home to major works of art by Donatello and Pisano
Discover the town’s black-and-white marble duomo and see brilliantly colored, 16th-century frescoes in the Piccolomini Library
End at a local bakery to try ricciarelli, an almond-flavored cookie
Day 6: Walking tour of San Gimignano & Volterra
Included meal: Breakfast
Spend the day exploring the medieval towns of San Gimignano and Volterra with your Tour Director.
Enjoy a breathtaking view of San Gimignano, a medieval hilltop city known for its towers, as you walk into town
Head to Volterra and visit the cathedral, Roman Theater ruins, or local shops at your leisure
Enjoy a free evening in Siena or add an excursion.
Tuscan Villa Winery & Dinner
From $145 per person
Maremma Countryside2 nights
Day 7: Maremma Countryside via Tuscan farm
Included meals: Breakfast, Lunch
Head south to the Maremma countryside, a unique region of Tuscany where time seems to have stopped and the traditional, centuries-old culture of Tuscan is still alive.
Visit a traditional Tuscan farm and meet the farmers and herders, called butteri
Tour the farm to learn about the daily life and role of a buttero
Taste local specialties during a farm-to-table lunch
Please note: The Maremma Butteri is seasonal and typically open from May-October. From November to April an alternative visit will be offered.
Continue on to your hotel in the Maremma countryside.
Day 8: Hiking tour of Maremma countryside & cooking class
Included meals: Breakfast, Dinner
Today, hike in the Maremma countryside, where time seems to have stopped. Explore some of the region’s most charming villages on a guided hike of Sovana and Pitigliano, and marvel at the quaint, medieval hamlets that dot this countryside.
Visit Sovana, often considered the Matera of Tuscany because of the many stone buildings
Stroll through Piazza del Pretorio and view the classic Tuscan architecture in the main square
Hike along Via Cava, an excavated road dating back to pre-Roman times, from Sovana to the hilltop town of Pitigliano
Discover the history of the ancient road as you admire the towering walls
End your hike in Pitigliano and spend free time exploring
This evening, take part in a hands-on cooking class where you’ll learn how to make Tuscan cuisine. Then, enjoy a dinner featuring the food you’ve crafted paired with local wine.
Montepulciano Region2 nights
Day 9: Walking tour of Cortona & Montepulciano
Included meal: Breakfast
Soak in panoramic views of the Tuscan countryside as you enjoy walks led by your Tour Director in both Cortona and Montepulciano.
Walk downhill from St. Margaret’s Church into Cortona
Spend free time exploring and eating lunch in town
Head to Montepulciano and soak in the views of the countryside on a walk through town before enjoying free time
Day 10: Hiking tour of Montalcino
Included meal: Breakfast
Join your Tour Director on a hike in Montalcino this morning.
Pass through the countryside and end at the Abbey of Sant’Antimo, a Romanesque church surrounded by rolling hills
Enjoy free time to eat lunch and explore
Enjoy a free afternoon in the Montepulciano region or add an excursion.
Pecorino Toscano Cheese Tasting
From $109 per person
Florence1 night
Day 11: Florence via Bagno Vignoni & San Quirico d’Orcia
Included meals: Breakfast, Farewell dinner
Stop in hilltop villages of the Val d’Orcia region, the jewel of the crown of Tuscany, en route to Florence.
Walk through Bagno Vignoni with your Tour Director and learn how the Romans designed the village around thermal pools
Enjoy free time to explore the peaceful town of San Quirico d’Orcia
Tonight, journey to the scenic Etruscan-Roman town of Fiesole. You’ll celebrate your trip with your group on a villa terrace during a farewell dinner.
Flight Home
Day 12: Departure
Included meal: Breakfast (excluding early morning departures)
Transfer to the airport for your flight home or extend your stay in Florence.
Extension to Florence
Not ready to say arrivederci? Continue your trip in the Tuscan capital of Florence, where Renaissance beauty and really (really) good food are practically everywhere. See the highlights alongside a local guide, then lean on your Tour Director’s expert recommendations to seek out even more.
Florence2 nights
Day 12: Walking tour of Florence
Included meal: Breakfast
Join a local guide and set off on a walking tour of Florence, the city at the center of the Renaissance.
View the city’s stunning skyline from Piazzale Michelangelo
Cross over the historic 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
Pass Giotto’s Campanile, a masterpiece of Gothic architecture
View the legendary Florence Cathedral, known as the Duomo
Enjoy free time in Florence or add an excursion.
Tuscan Cooking Class & Dinner
From $115 per person
Day 13: Free day in Florence
Included meal: Breakfast
Spend a free day in Florence or add excursions.
This evening, enjoy a farewell drink as you celebrate your trip with your fellow group members.
Accademia Gallery
From $65 per person
Michelangelo's Florence
From $95 per person
Flight Home
Day 14: Departure
Included meal: Breakfast (excluding early morning departures)
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Reviews
4.7 star rating
Overall rating 4.7 out of 5
Based on 17 authentic traveler reviews
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Featured
5.0 star rating
An Amazing Walk thru Tuscany
10/5/23 by 2nd-time traveler Jonathan
This was a magical trip through the Tuscan region that explored some beautiful locations and gave me great opportunities to experience the food and culture of the region. Our guide, Barbara, was amazing and added such wonderful personality to the sites and locations we visited. I would recommend any...
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4.0 star rating
The good the bad the ugly
10/5/23 by 1st-time traveler Frank
All aspects of the tour were not equal as would be expected
The tour director Barbara, the driver Rafael and the Tuscany preserved villa with dinner were exceptional
The opt tour to prep the food and eat your food prep was also exceptional
Walking the individual villages and observing life was ver...
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EF Go Ahead Tours replied on 11/7/23
Hi Frank! Thank you so much for taking the time to...
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4.0 star rating
Loved this itinerary!
9/7/23 by 1st-time traveler Christine
Great itinerary. I loved the pace of the tour. We had a charming driver named Paolo. He was great! Our tour director, Barbara, was a treasure. She was knowledgeable, enthusiastic, and attended to everyone's needs. I've been to Italy many times, but learned so many fascinating details from ou...
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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.
Albergo Celide Hotel & Spa
Located near Lucca's historic city wall, the Celide Hotel & Spa is only a few steps away from the major historical monuments. Guests enjoy access to a...
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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...
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Villa Acquaviva
This Tuscan style hotel is located on a wine estate in Montemarano of the Maremma region. Guests enjoy the outdoor pool, beautiful grounds, and restau...
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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...
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Starhotels Michelangelo
This modern hotel is located in the Santa Maria Novella neighborhood. Guests enjoy free WiFi, a fitness room, and a wine bar. Nearby, you’ll find the ...
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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.
Beginning in 2025, 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 2025, 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 ATT.
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 and depart from Florence. 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.
Pack a travel water bottle to stay hydrated on hotter, sunnier days.
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 ATT.
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 $8USD 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.
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