Tuscany Small Group Tours
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10 best Tuscany small group tours
Compiled by
MelissaTuscany travel expert at TourRadar
- Tuscany Walking and Wine
- Florence City Break - 3 Days/2 Nights
- Highlights of Italy in Winter
- Private Gourmet Wine Tour in Tuscany, Italy
- Flavours of Tuscany - Semi-Escorted Tour
- Florence: Amazing Tuscany & Cinque Terre: Semi-Escorted Tour 2025
- Two Hearts in Tuscany: an Escape for 2
- The best of Tuscany - 5 days private tour
- Luxury Italy by High-Speed Train
- Treasures of Tuscany
Tuscany Walking and Wine
21 Reviews by TourRadar travelers“The food was great, and the accommodation was all I could have hoped for.”
Grace, traveled in April
Twelve to sixteen travelers visit Tuscany's hidden gems, from organic wineries in Chianti to family cheese makers in Pienza. Private tastings at Castello La Leccia and historic cellars in Montalcino offer authentic local experiences.
Duration 8 days Destinations Pisa, Castellina in Chianti, Castelvecchio National Park, San Gimignano, Monteriggioni, Siena, Pienza, Monticchiello, Montepulciano, San Quirico D'orciaSee all destinations Age Range 16 to 85 year olds Group Size Max Group Size 16 Group Type Group Operator Explore! From
- NZ$4,280
Florence City Break - 3 Days/2 Nights
5 Reviews by TourRadar travelers“Great value for the money. Everything easy enough to find and navigate.”
Carly, traveled in January
Small groups venture through Tuscany, combining independent and guided experiences in Chianti region. Family-run wineries welcome visitors for exclusive tastings of Vernaccia and Brunello wines. Guides like Veronica provide detailed insights into wine production and medieval town history.
Duration 3 days Destinations Florence, Castellina in Chianti, San Gimignano Age Range 18 to 39 year olds Group Size Max Group Size 25 Group Type Group Operator Italy on a Budget Tours From
- NZ$631
Eight to twelve visitors uncover Tuscany's treasures, from Florence's Uffizi Gallery to Pisa's Leaning Tower. Local market visits and authentic Tuscan cooking demonstrations in historic city centers create memorable experiences.
Duration 8 days Destinations Rome, Florence, Pisa, Bologna, Venice Age Range 15 to 99 year olds Group Size Max Group Size 12 Group Type Group Operator Intrepid Travel From $4,320
5% Off- NZ$4,104You save $216
Private Gourmet Wine Tour in Tuscany, Italy
4 Reviews by TourRadar travelers“Drivers were on time, courteous, and the cars/vans were very nice. We added Cinque Terre and Lucca with no problems.”
David, 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 $4,654
15% Off- NZ$3,956You save $698
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 $2,015
10% Off- NZ$1,814You save $202
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 $3,007
10% Off- NZ$2,707You save $301
Two Hearts in Tuscany: an Escape for 2
2 Reviews by TourRadar travelers“The itinerary and people behind 'Italy on a budget' and 'Italy on Wheels' exceeded our expectations. It was magical!”
Belen, traveled in October
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
10% Off- NZ$1,860
The best of Tuscany - 5 days private tour
3 Reviews by TourRadar travelers“Beautiful places, would recommend it 100% to anyone.”
Elen, traveled in October
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
10% Off- NZ$9,574
Intimate groups of 12 maximize Tuscany's charm. Experience personalized wine tastings at family vineyards in Chianti, explore Siena's historic center, and discover San Gimignano's medieval towers. Stay at Florence's luxurious Hotel Antica Torre Tornabuoni with panoramic city views.
Duration 9 days Destinations Rome, Florence, Castellina in Chianti, Siena, San Gimignano, Venice Age Range 10 to 80 year olds Group Size Max Group Size 12 Group Type PrivatePersonalized Operator Flag Travel Holidays From
10% Off- NZ$7,907
Duration 7 days Destinations Florence, Siena, Montepulciano Age Range 8 to 99 year olds Group Size Max Group Size 8 Group Type Private Operator Omega Tours From $4,889
5% Off- NZ$4,645You save $244
Reviews of Small Group tours to Tuscany
- Florence City Break - 3 Days/2 Nights
Great tour guide (Mano) keeps the group entertained and time seemed to fly by really quickly
- Private Gourmet Wine Tour in Tuscany, Italy
The tour operator was very easy to work with. Some changes that we requested were easily handled. Drivers were on time, courteous, and the cars/vans were very nice. The initial tour was 4 days basing out of Mormoraia. We added Cinque Terre and Lucca with no problems. Wine tastings were all very fine and we shipped wine home from two of them. Generally speaking this was a very good way to see a great deal of Tuscany which was our purpose. I can feel good about recommending this tour and operator to anyone wanting to see all of Tuscany.
- Florence: Amazing Tuscany & Cinque Terre: Semi-Escorted Tour 2025
What an incredible experience our trip was last October! Florence captured our hearts with its beauty, and Tuscany was even more amazing than we had imagined. The local staff gave us a warm welcome, and our guides were always friendly and helpful, ready with the best advice. This tour with Ranieri Tour Operator allowed us to see many iconic gems of Tuscany: We explored Florence, Siena, Pisa (where the guide jokingly told us that we had to keep the Leaning Tower high, or it would fall), Lucca and the Cinque Terre (what a beautiful smell in the air). We also enjoyed a fantastic wine tasting in Chianti. It’s a trip we will never forget! We really enjoyed it!
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."