Tuscany Small Group Tours
Tuscany - the word alone makes you shiver in anticipation! Tuscany's rolling hills between vineyards and olive groves create iconic landscapes, begging to be explored. Head to Florence, the birthplace of the Renaissance, and check out the famous Leaning Tower of Pisa! Lucca and Arezzo are also must-visits, all with the laid-back Tuscan charm.
10 best Tuscany small group tours
Compiled by
MelissaTuscany travel expert at TourRadar
- Florence: Amazing Tuscany & Cinque Terre 2026: Independent Tour with shared daily tours - Small Group
- Florence Cultural Experience – 4 Days (Small Group)
- Gems of Tuscany & Cinque Terre 2026: Semi-Escorted Small Group Tour from Montecatini Terme
- Two Hearts in Tuscany: A Romantic Getaway for 2
- Tuscany Absolute
- Best of Rome, Florence & Venice
- My First Italian Adventure - 7Day
- Taste of Tuscany: A 3-Day Escape of Wine, Relax, and Fun
- Flavours of Tuscany 2026 - Semi-Escorted Tour
- Private Gourmet Wine Tour in Tuscany, Italy
Florence: Amazing Tuscany & Cinque Terre 2026: Independent Tour with shared daily tours - Small Group
2 Reviews by TourRadar travelers“Florence captured our hearts with its beauty, and Tuscany was even more amazing than we had imagined.”
Alberto, traveled in October
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, Pisa, Cinque Terre Age Range All Ages Welcome Group Size Max Group Size 2 Group Type Group Operator RANIERI TOUR OPERATOR From
- US$2,218
Duration 4 days Destinations Florence, Tuscany Age Range All Ages Welcome Group Size Max Group Size 14 Group Type Group Operator Click Tours From $1,320
36% Off- US$845You save $475
Hidden gems of Tuscany open to small groups, featuring private tastings at family-run Montecarlo vineyards and guided tours of Vinci's medieval streets. Exclusive access to Leonardo's birthplace and UNESCO-listed Montecatini Terme creates memorable experiences.
Duration 8 days Destinations Florence, Montecatini, Montecarlo, Cinque Terre, Vinci, Siena, San Gimignano, Monteriggioni Age Range All Ages Welcome Operated in English, Italian, French Group Size Max Group Size 10 Group Type Group Operator RANIERI TOUR OPERATOR From
36% Off- US$1,484
Two Hearts in Tuscany: A Romantic Getaway 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 Ages 18+ Group Size Max Group Size 2 Group Type PrivatePersonalized Operator Italy on a Budget Tours From $1,114
15% Off- US$947You save $167
Tuscany Absolute
12 Reviews by TourRadar travelers“From enchanting vineyard visits to tastings of exquisite wines, every moment celebrated Tuscan flavors.”
Stephen, traveled in May
Twelve travelers maximum join this Tuscan adventure. Personal attention highlights Vino Nobile tastings in Montepulciano and pici pasta making. Expert guides illuminate Florence's Accademia Gallery and Siena's historic contrade neighborhoods.
Duration 7 days Destinations Florence, Siena, San Gimignano, Castellina in Chianti, Montepulciano Age Range All Ages Welcome Group Size Max Group Size 3 Group Type PrivatePersonalized Operator Flag Travel Holidays From $3,059
20% Off- US$2,447You save $612
Best of Rome, Florence & Venice
3 Reviews by TourRadar travelers“The hotels were fine with very good breakfasts. The speed trains were great.”
Diane, traveled in April
Family-owned Chianti vineyards and medieval San Gimignano's towers welcome small groups for intimate exploration. Personal attention enhances traditional lunch experiences and guided walks through Siena's historic center.
Duration 7 days Destinations Rome, Vatican City, Florence, Siena, San Gimignano, Tuscany, Venice Age Range Ages 8+ Group Size Max Group Size 8 Group Type PrivatePersonalized Operator Omega Tours From
20% Off- US$1,819
Experience Tuscany's charm in small groups, visiting family-owned Chianti wineries and exploring Florence's Renaissance treasures. Personal attention from local guides enriches visits to the Leaning Tower of Pisa and Boboli Gardens. Enjoy authentic experiences with fellow travelers aged 18-99.
Duration 7 days Destinations Rome, Florence, Pisa, Tuscany, Venice Age Range Ages 18+ Operated in English, Italian Group Size Max Group Size 15 Group Type GroupPersonalized Operator Authentic Italy Adventures From $1,876
15% Off- US$1,595You save $281
Taste of Tuscany: A 3-Day Escape of Wine, Relax, and Fun
1 Review by TourRadar travelers“The accommodations were full of charm, right in the heart of a historic hilltop town with views that didn't feel real.”
Jane, traveled in June
Three family-run Chianti wineries open their doors to groups of just 2-4 travelers. Winemakers share insights about Super Tuscan and Vernaccia production techniques during these intimate visits. Small group numbers create space for personalized attention while tasting truffle-infused olive oil and aged balsamic vinegar. San Gimignano's 14 medieval towers stand within the UNESCO-listed historic center, and you'll walk through them without the usual crowds. Private group format allows you to set your own pace through rolling Tuscan hills. Optional activities like horseback riding or Vespa tours can be added - these options aren't available to larger tour groups.
Duration 3 days Destinations San Gimignano, Ulignano, Tuscany Age Range Ages 18+ Group Size Max Group Size 8 Group Type GroupPersonalized Operator Italy on a Budget Tours From $528
15% Off- US$449You save $79
Flavours of Tuscany 2026 - 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, Montecarlo, Siena, San Gimignano, Monteriggioni Age Range All Ages Welcome Operated in English, French Group Size Max Group Size 8 Group Type Group Operator RANIERI TOUR OPERATOR From
15% Off- US$1,240
Private Gourmet Wine Tour in Tuscany, Italy
4 Reviews by TourRadar travelers“Villa Lecchi was beyond our dreams. The views were spectacular of Tuscany.”
Colleen, traveled in September
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 Ages 24+ Group Size Max Group Size 10 Group Type PrivatePersonalized Operator Soleto Travel From $3,471
20% Off- US$2,777You save $694
Reviews of Small Group tours to Tuscany
- Florence: Amazing Tuscany & Cinque Terre 2026: Independent Tour with shared daily tours - Small Group
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!
- Flavours of Tuscany 2026 - Semi-Escorted Tour
I had the pleasure to explore Tuscany gem places/towns and some wineries with this tour operator Ranieri... and what a TRIP!!! Where. Let me beginning with saying the communication is on point and prompt, their Team clearly had the experience and had beeing doing this for a while as they said. Then since the moment we arrived, my husband and I they took care of every single detail of our trip, it was My Birthday week so it was a big relief for my husband not having to worry about anything but just enjoying AMAZING TUSCANY and enjoying the TASTE of it, we are two foodie people and toor was very focused on the Culinary and wine aspects of the region, Just being at FLORENCE was a dream and 5 starts treatment we were receiving from the guides and tour lead. Luke walking inside a art paint while trying all the good food along the way Then going to a country side farm and trying there the local produce, jellies, food, and of course the great Tuscany wine was just the start of it. 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. What a lovely lady she is, that was a treat for sure. CHIANTI wineries were an enchanted place to be, we also had a tasting there and some olives and little bites food tasting... I Love the medieval architecture so just coming on the private buss we were being transported and seeing San Gimignano up on top of the hills with those impressive walls and Italian cypress trees got my heart raising...even better the great walking experience inside of it. However I have to say for me SIENA stole my heart ❤️ the whole trip was so worthy but Siena is out of this world, they have everything ready to explore the city, that is where I have my bday dinner, it was surreal to be seated at the piazza surrounded but the beautiful buildings and walls, my head was going 360 trying to catch up with all that beauty. Oh btw in every place we stopped they gave us recomendaciones of were to sho go shopping, or takes breaks. I Love that part that they were conscious about giving us FREE time for us to enjoy in our onw but always guided, we felt so safe and cared at every moment. Thank you Letizia for all your great work and for taking care of our amazing experience. I DEFINITELY recommend and would use this tour operator again in the future. I had been wanting to make a review since then, better now than never. Until next time Italy ?? ? ❤️ ??
- The Best of Tuscany - 4Days/3Nights
Amazing time, amazing people, amazing places. I would highly recommend this tour. The tour guide was exceptional and everything was so gorgeous. It's a great way to see such a grand area in a short time without missing anything.
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."