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Tuscany Adventure: Lucca,...

Tuscany Adventure: Lucca, Siena & Maremma

12 days |  14 days with Florence extension
12 days |  14 days with Florence extension
Group size1022 travelers

4.7 star rating

Physical activity
Woman in Lucca Italy walking out of Rocchi P Pizzicheria La Grotta Old Town Lucca Tuscany Italy
Moody view from Tuscany of vineyards
Purple flowers built into a gate in Volterra Italy
Beautiful Tuscany vineyard in Italy at sunset
OverviewItineraryDates & pricesReviewsTraveler photosHotels, flights & FAQ
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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
Read more
Start planning today

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Day-by-day itinerary

Print itinerary
Overnight Flight1 night
Day 1: Travel day

Board your overnight flight to Florence today.

Lucca2 nights
Day 2: Arrival in Florence & transfer to Lucca
Included meal: Welcome dinner

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)

Transfer to the airport for your flight home.

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4.7 star rating

Overall rating 4.7 out of 5

Based on 17 authentic traveler reviews
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    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...

    Read more +

    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...

    Read more +
    EF Go Ahead Tours replied on 11/7/23

    Hi Frank! Thank you so much for taking the time to...

    Read more +

    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...

    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.


    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
    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...

    Read more +
    Hotel Garden Siena
    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 +
    Villa Acquaviva
    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...

    Read more +
    Hotel Corsignano
    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 +
    Starhotels Michelangelo
    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 ...

    Read more +


    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 & entry 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.
    • 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 and searching the code ATT.
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    Tour pacing & mobility
    • 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.
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    Walks & hikes 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.
    • Monteriggioni – 3–4 miles / 1 hour. A gravel path with some rocky areas though the woods into the open countryside with wheat fields and farms.
    • San Gimignano – 2–2.5 miles / 1 hour. A gravel path up a small incline for views of the surrounding countryside and town.
    • Maremma Villages – 5.5 miles / 4.5 hours. A long gravel pathway on flat ground from Sovana to Pitigliano.
    • 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 mostly flat gravel path, with one steep downhill portion.
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    Transportation & arrival information
    • 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.
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    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.
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    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.
    • 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)
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    • 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
    • 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 and searching the code ATT.
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    • 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.
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    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.
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    • 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.
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    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.
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    • 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.
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    • 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.
    • Tips can only be paid in cash.
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    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.
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