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Tuscany Adventure: Lucca,...

Undiscovered Tuscany: Lucca, Siena & Maremma

12 days |  14 days with Florence extension
12 days |  14 days with Florence extension
Group size1222 travelers

4.8 out of 5 stars

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
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Start planning today

An expert specializing in tours of this region is here to help.

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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 $175 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 $199 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.

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 $149 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 $159 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 $89 per person

Michelangelo's Florence

From $129 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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4.8 out of 5 stars

Overall rating 4.8 out of 5

Based on 20 authentic traveler reviews
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    5 out of 5 stars

    Positive on Tuscany
    5/16/24 by 2nd-time traveler Paul

    This is an exceptional tour. The sites selected, the hotels ( except the one on Siena), were comfortable and inviting. The Siena hotel had some issues. The tour guide, Barbara, was outstanding. She made the trip more enjoyable by her knowledge, attitude, and support. I fully encourage anyone seek...

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    EF Go Ahead Tours replied on 6/6/24

    It's fantastic to hear that you found the tour of ...

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    5 out of 5 stars

    Best tour ever!! Would do it all over again
    5/4/23 by 1st-time traveler Anonymous

    5 out of 5 stars

    The best tour so far!
    10/5/23 by 4th-time traveler Shapley

    This was our fourth Go Ahead tour, and it was the best we have taken, though all have been great. We met the tour in Lucca, as we had flown in a few days early to spend time in Umbria before beginning the tour. We traveled by train, and made the short walk from the rail station to the hotel, which...

    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 NH Siena
    Hotel NH Siena

    This elegant hotel is located in La Fortezza neighborhood of Siena. Guests enjoy free Wi-Fi, a fitness room and a restaurant. Nearby, you'll find Piaz...

    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 +
    Grand Hotel Adriatico
    Grand Hotel Adriatico

    This charming hotel is located in Florence’s city center. Guests enjoy a restaurant, courtyard, and fitness center. Nearby, you’ll find the Uffizi Gal...

    Read more +


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