Tuscany Small Group Tours
4.6 stars on(9,282 reviews)- Choose from 38 Tuscany tours
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10 best Tuscany small group tours
Compiled by

MelissaTuscany travel expert at TourRadar
- Florence: Amazing Tuscany & Cinque Terre: Independent Tour with shared daily tours 2026 - Small Group
- Gems of Tuscany & Cinque Terre 2026: Semi-Escorted Small Group Tour from Montecatini Terme
- Italian Sojourn with Leaning Tower of Pisa
- Highlights of Northern Italy
- Taste of Tuscany: A 3-Day Escape of Wine, Relax, and Fun
- Pearls of Tuscany
- Authentic Luxury Italy: an Elegant Journey through Rome & the Tuscan Hills
- Tuscany Mon Amour: Love at First Sight 2026! Semi-Escorted Tour
- Flavours of Tuscany 2026 - Semi-Escorted Tour
- Two Hearts in Tuscany: A Romantic Getaway for 2
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
- NZ$2,566
Italian Sojourn with Leaning Tower of Pisa
3 Reviews by TourRadar travelers“The trip was great with a good balance of tours and free time. Accommodations were comfortable and very conveniently located.”
Marie, traveled in October
Small groups make their way to Monteriggioni's medieval walls, savor private Chianti wine tastings, and visit San Gimignano's towers. Local guides accompany visitors at each stop, with comfortable transport through scenic countryside.
Duration 10 days Destinations Rome, Florence, Pisa, Tuscany, Venice Age Range All Ages Welcome Group Size Max Group Size 14 Group Type Group Operator Wanderful Holidays LLC From
- NZ$3,323
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 Ages 15+ Group Size Max Group Size 12 Group Type Group Operator Intrepid Travel From
- NZ$4,395
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
Duration 3 days Destinations San Gimignano, Ulignano, Tuscany Age Range Ages 18+ Group Size Max Group Size 4 Group Type PrivatePersonalized Operator Italy on a Budget Tours From
- NZ$852
Pearls of Tuscany
3 Reviews by TourRadar travelers“Thank you for a great vacation that someone else planned for us and we didn't have to worry about anything.”
Jaromir, traveled in July
Duration 6 days Destinations Pisa, Massaciuccoli, Tuscany, Siena, San Gimignano, Lucca, Florence Age Range All Ages Welcome Group Size Max Group Size 5 Group Type PrivatePersonalized Operator Worldee From
- NZ$460
Authentic Luxury Italy: an Elegant Journey through Rome & the Tuscan Hills
1 Review by TourRadar travelers“Every detail was taken care of. Drivers, tours, skip the line tickets everywhere. All were first class.”
Jena, traveled in March
Duration 7 days Destinations Rome, Vatican City, Montepulciano, Florence, Pisa, San Gimignano, Siena Age Range Ages 6+ Operated in English, German, Italian, Portuguese, French, Spanish, Russian Group Size Max Group Size 10 Group Type PrivatePersonalized Operator Exploro Tours From
- NZ$10,954
Tuscany Mon Amour: Love at First Sight 2026! Semi-Escorted Tour
3 Reviews by TourRadar travelers“An unforgettable mix of culture, beauty, and relaxation! The combination of guided time and free time made it feel relaxing, not rushed.”
Giuseppa, traveled in March
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 8 days Destinations Florence, Montecatini, Montecarlo, Pisa, Vinci, Siena, Monteriggioni, San Gimignano Age Range All Ages Welcome Group Size Max Group Size 8 Group Type Group Operator RANIERI TOUR OPERATOR From
- NZ$2,442
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
- NZ$2,144
Two Hearts in Tuscany: A Romantic Getaway 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 Ages 18+ Operated in English, Italian Group Size Max Group Size 2 Group Type PrivatePersonalized Operator Italy on a Budget Tours From
- NZ$1,988
Reviews of Small Group tours to Tuscany
- Italian Sojourn with Leaning Tower of Pisa
Wanderful was great to work with. Good communication via WhatsApp. Had a booking hiccup for the Vatican Tour where the information held by the local tour company didn't match my group and we weren't able to go. Wanderful staff worked hard to get it fixed but were not able to. We were able to rebook a similar tour ourselves and Wanderful refunded the value of the original booking. We upgraded to 4 star hotels and were happy with the locations and amenities.
- Tuscany Mon Amour: Love at First Sight 2026! Semi-Escorted Tour
Unforgettable Tuscan Escape! This tour through Tuscany was absolutely incredible—an unforgettable mix of culture, beauty, and relaxation! From the moment we landed in Florence, everything was perfectly organized. The hotel in Montecatini Terme was elegant and comfortable, right in the heart of a charming spa town that felt like a hidden gem. Each day brought something special—wine tasting at a beautiful family-run farm, exploring iconic cities like Siena, Pisa, and Florence, and enjoying amazing local food and wine. The guided tours were informative without being overwhelming, and the guides were passionate, friendly, and knowledgeable. One of the biggest highlights was the day trip through the Tuscan countryside—San Gimignano was like stepping into a fairytale, and the views were breathtaking. The combination of guided time and free time made it feel relaxing, not rushed. Montecatini itself was a wonderful home base. We loved the freedom to enjoy a spa treatment or just stroll through the lovely streets. And having a free day to choose extra activities or simply relax was such a thoughtful touch. Every detail was taken care of, and the whole experience felt curated with care and local insight. I’d highly recommend this tour to anyone wanting a true taste of Tuscany—whether you're into history, food, wine, or just soaking in the beauty of Italy. Bravo to the organizers—this was a dream trip come true!
- The Best of Tuscany - 4Days/3Nights
I absolutely loved this trip! It was well worth it and very organized. I cannot wait to plan another trip soon.
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."




















