Tuscany Small Group Tours
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10 best Tuscany small group tours
Compiled by
MelissaTuscany travel expert at TourRadar
- Private Gourmet Wine Tour in Tuscany, Italy
- Florence: Amazing Tuscany & Cinque Terre: Semi-Escorted Tour 2025
- Flavours of Tuscany - Semi-Escorted Tour
- Premium Tuscany
- Tuscany Retreat: A 4-days Escape for Two
- The best of Tuscany - 5 days private tour
- Two Hearts in Tuscany: an Escape for 2
- Tuscany Mon Amour: Love at First Sight! Semi-Escorted Tour
- Tuscany and Rome 7 days Private Tour
- Siena & History
Private Gourmet Wine Tour in Tuscany, Italy
4 Reviews by TourRadar travelers“Great accommodations! Fabulous wines and tours. This is a trip well worth it.”
Susan, traveled in October
Groups of 2-8 guests visit prestigious Chianti and Brunello estates. Private transportation enables visits to medieval gems like Volterra and San Gimignano. Family-run vineyards and cellars offer personalized tastings.
Duration 4 days Destinations Florence, Colle di Val d'Elsa, Castellina in Chianti, Val d'Orcia, Montalcino, Siena, Volterra, San Gimignano, Castagneto Carducci, Pisa Age Range 24 to 86 year olds Group Size Max Group Size 10 Group Type PrivatePersonalized Operator Soleto Travel From $4,639
15% Off- NZ$3,944You save $695
Florence: Amazing Tuscany & Cinque Terre: Semi-Escorted Tour 2025
2 Reviews by TourRadar travelers“I was warmly welcomed at the airport, and the transfer to the hotel was easy, even though I was exhausted after all those hours of flying!”
beniamino, traveled in February
Groups of 15-20 people wind through Tuscan hill towns like San Gimignano and Monteriggioni. The intimate size allows for personal attention during Florence walking tours and wine tastings at family-owned Chianti estates.
Duration 8 days Destinations Florence, Siena, San Gimignano, Monteriggioni, Pisa, Lucca, Cinque Terre Age Range up to 100 year olds Operated in English, Portuguese, Spanish Group Size Max Group Size 2 Group Type Group Operator RANIERI TOUR OPERATOR From
15% Off- NZ$2,998
Flavours of Tuscany - Semi-Escorted Tour
2 Reviews by TourRadar travelers“The views, the atmosphere, the place it self and that night we had the pleasure to meet the Company Owner seen she pop out for a quick welcome to our group tour.”
Dilcen, traveled in October
Groups up to 12 guests visit Tuscany's hidden gems, from private tastings at Montecarlo farmhouses to tours of Vinci's Leonardo museum. The select size opens doors to medieval Monteriggioni and family-run Chianti wineries.
Duration 6 days Destinations Florence, Montecatini, Vinci, Montecarlo, Siena, San Gimignano, Monteriggioni, Strada in Chianti Age Range 1 to 100 year olds Operated in English, French Group Size Max Group Size 8 Group Type PrivatePersonalized Operator RANIERI TOUR OPERATOR From
15% Off- NZ$2,009
Premium Tuscany
1 Review by TourRadar travelers“The cities that were explored were both interesting and beautiful.”
Joseph, traveled in August
Groups of 12-15 travelers visit family-run vineyards and medieval towns. The intimate size allows for wine tastings at San Gimignano agriturismos and detailed tours of Siena's Piazza del Campo and Monteriggioni's ancient walls.
Duration 8 days Destinations Rome, Siena, Monteriggioni, San Gimignano, Pisa, Lucca, Florence, Venice Age Range 15 to 99 year olds Group Size Max Group Size 12 Group Type Group Operator Intrepid Premium From $9,545
15% Off- NZ$8,113You save $1,432
Perfect for couples seeking privacy, this tour connects Florence's Renaissance charm with Chianti's rural beauty. With just two travelers, enjoy undivided attention during farmhouse cooking classes and Tuk-Tuk vineyard tours. Personal guides ensure authentic experiences in San Gimignano and Florence's historic center.
Duration 4 days Destinations Florence, Tuscany, San Gimignano Age Range 18 to 99 year olds Operated in English, Italian Group Size Max Group Size 2 Group Type PrivatePersonalized Operator Authentic Italy Adventures From
15% Off- NZ$1,473
Tuscany unfolds through private tours with dedicated guides in each city. Personal air-conditioned transfers connect Florence's Il Duomo, Pisa's Leaning Tower, and Lucca's historic walls. The intimate setting includes 4-star hotels and authentic Italian dinners for deep cultural immersion.
Duration 5 days Destinations Florence, Pisa, Pistoia, Lucca Age Range 8 to 99 year olds Operated in English, Spanish Group Size Max Group Size 7 Group Type PrivatePersonalized Operator Taotravel From
15% Off- NZ$9,545
Two Hearts in Tuscany: an Escape for 2
2 Reviews by TourRadar travelers“We loved every moment. Amazing tuk-tuk ride, easy bag transfers. Exquisite wine tasting with two course meal.”
Marinda, traveled in May
Designed for 2-4 travelers, this Tuscan escape features private tuk-tuk tours through Chianti's vineyards and cooking classes at local farms. Small groups receive individual attention during wine tastings and walks through San Gimignano's medieval streets.
Duration 4 days Destinations Florence, Castellina in Chianti, San Gimignano Age Range 18 to 99 year olds Operated in English, Italian Group Size Max Group Size 2 Group Type PrivatePersonalized Operator Italy on a Budget Tours From
15% Off- NZ$1,854
Two to six guests receive exclusive access to Tuscan treasures. Private transfers from Pisa Airport lead to 4-star Hotel Ercolini in Montecatini Terme, followed by walking tours of Florence's Uffizi and wine tastings at family estates near Montecarlo.
Duration 6 days Destinations Florence, Montecatini, Siena, San Gimignano, Pisa, Montecarlo Age Range 1 to 100 year olds Operated in English, Portuguese, Spanish Group Size Max Group Size 8 Group Type PrivatePersonalized Operator RANIERI TOUR OPERATOR From
15% Off- NZ$1,657
Tuscany reveals its treasures in an intimate private setting, from Florence's Renaissance masterpieces to Pisa's architectural wonders. Personal guides offer focused attention at each stop, including Lucca's churches and Prato's historic Piazza del Comune.
Duration 7 days Destinations Rome, Vatican City, Florence, Pisa, Lucca, Pistoia Age Range 8 to 99 year olds Group Size Max Group Size 6 Group Type PrivatePersonalized Operator Taotravel From
15% Off- NZ$11,460
Groups of 9 delve into Tuscany's cultural heritage. Local farms in Val d'Orcia offer exclusive Pecorino tastings, while Siena's historic center unfolds with dedicated guides. Montepulciano's ancient wine cellars provide intimate experiences.
Duration 4 days Destinations Siena, Pienza, Montepulciano, San Gimignano, Volterra Age Range 12 to 90 year olds Group Size Max Group Size 8 Group Type Group Operator Tuscan Escapes From
15% Off- NZ$1,196
Reviews of Small Group tours to Tuscany
- Private Gourmet Wine Tour in Tuscany, Italy
The best we could ever hope for!! Villa Lecchi was beyond our dreams. The views were spectacular of Tuscany. All of our tour guides were fantastic. And the food and wine was so good. Massimo our driver was incredible. Thank you for planning such a wonderful experience!!
- Florence: Amazing Tuscany & Cinque Terre: Semi-Escorted Tour 2025
I didn't know Montecatini Terme before, but from the moment I arrived, I felt at home. I was warmly welcomed at the airport, and the transfer to the hotel was easy, even though I was exhausted after all those hours of flying! The staff of the local tour operator explained every detail of the itinerary and even provided 24/7 assistance for any needs. Truly wonderful people! It was the perfect balance of exploration and relaxation. We had the chance to unwind and enjoy the peaceful atmosphere of Montecatini with two days off, mixed with planned excursions like wine tasting, where we met a couple from Canada and another from England, all on the same tour with Ranieri Tour Operator, the local provider. We shared an amazing visit to Florence and an unforgettable day at Cinque Terre. I can still almost smell the sea!. Tuscany is absolutely beautiful, even more than I could have imagined, and everything is so easy to get to.
- Two Hearts in Tuscany: an Escape for 2
Perfect getaway for anyone in need of a good rest and quality time with their partner. We loved every moment. Amazing tuk-tuk ride, easy bag transfers. Exquisite wine tasting with two course meal. The hotel in Tuscany with the room walking out onto one of the pools- amazing. Fantastic restaurant on site! Our SPA session was relaxing with a beautiful dinner (spectacular view) afterwards. Walking distance from medieval town.The tour guides were great, high energy, friendly and welcoming. I’m so glad I booked this as our Tuscany experience.
What our customers ask about Tuscany Small Group Tours
What regions of Tuscany are typically covered in small group tours?
Small group tours take you through the heart of Tuscany including Florence Siena San Gimignano and the Chianti wine region. The tours also venture into quieter areas like Val d'Orcia and Garfagnana that larger buses can't reach. A TourRadar traveler shared: "Our intimate group size allowed us to explore hidden gems like Barga and Volterra places larger tours can't easily access." Most tours use strategic accommodation locations such as the Hotel Plaza Lucchesi in Florence and Dimora dell'erbe in Montepulciano as base points for daily excursions.
What are the accommodation options for small group tours in Tuscany?
The accommodations blend boutique hotels with traditional agriturismos (farm stays) across Tuscany. Guests might find themselves at Agriturismo Il Piastrino nestled in Chianti's vineyards or within the stone walls of Palazzo Renieri in Colle Val d'Elsa. Most properties are run by local families creating a more personal connection to the region. As one TourRadar traveler noted: "Staying at smaller family-run hotels like Hotel La Luna in Lucca gave us an authentic feel of Tuscan hospitality and allowed us to connect with local hosts in a way that wouldn't be possible in larger hotels."
What is the best time of year for small group tours in Tuscany?
The optimal seasons for small group tours fall during spring (April-May) and early fall (September-October). These months offer pleasant temperatures and fewer crowds at popular sites like San Gimignano's towers and Siena's Piazza del Campo. Tour data shows May is particularly popular when wildflowers dot the countryside. A TourRadar traveler shared: "Traveling in a small group in May meant we could easily find tables at local restaurants in Siena and had space to really appreciate the art in Florence's galleries."
What dining experiences are available on small group tours in Tuscany?
The small group format opens doors to local dining spots that larger tours can't access. Groups enjoy meals at family trattorias private tastings in Montepulciano wine cellars and dinner in Chianti family homes. As one TourRadar traveler mentioned: "Our group of 12 had fantastic experiences dining at small local restaurants like La Frateria near Cetona where we could interact with the chef and learn about traditional Tuscan cooking techniques."
What level of personal attention can I expect on a small group tour in Tuscany?
Groups typically range from 8-12 travelers per guide ensuring direct access to local expertise. This smaller ratio allows for detailed explanations at sites like Florence's Uffizi Gallery or Siena's Duomo with time for individual questions. One TourRadar traveler commented: "Our guide at Agriturismo La Pietriccia could spend quality time with each person during cooking classes and wine tastings making the experience much more meaningful than in a large group."
What makes small group tours ideal for exploring Tuscany's medieval towns?
The compact size of 8-12 travelers allows easy access through narrow medieval streets artisan workshops and small museums without overwhelming these intimate spaces. Groups can move quickly through towns like San Gimignano and Volterra stopping at local craft shops along the way. A TourRadar traveler noted: "Being in a small group meant we could explore at our own pace and really absorb the medieval atmosphere of these beautiful towns."