Tuscany Tours for Solo Travelers
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10 best Tuscany solo travel packages
Compiled by
NadineTuscany travel expert at TourRadar
- Florence: Amazing Tuscany & Cinque Terre 2026: Independent Tour with shared daily tours - Small Group
- A Taste of Tuscany - Hilltop Towns and Vineyards
- 7 Day Rome, Florence, Tuscany & Venice Tour Package
- Tuscany Walking and Wine
- Two Hearts in Tuscany: A Romantic Getaway for 2
- Gourmet Tuscany
- Tuscany Highlights, Semi-Private Tour
- Flavours of Tuscany 2026 - Semi-Escorted Tour
- Geluxe: Italy: Tuscany and Umbria Vineyard Walks
- Discover Tuscany: Culture, Food & Wine
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
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 Room Type Singles, Shared Operator RANIERI TOUR OPERATOR From
- NZ$3,811
A Taste of Tuscany - Hilltop Towns and Vineyards
12 Reviews by TourRadar travelers“Excellent food and wine visits couldn't have asked for more. Highly recommend this trip.”
Elizabeth, traveled in May
Pasta-making at Fattoria San Donato and wine tasting at Ricasoli Estate bring solo travelers together. Communal experiences at farms and local restaurants create natural bonds. Room sharing available for those interested.
Duration 8 days Destinations Pisa, Livorno, Tuscany, Montalcino, Buonconvento, Pienza, Montepulciano, Siena, Florence, Greve in ChiantiSee all destinations Age Range Ages 16+ Group Size Max Group Size 16 Group Type Group Room Type Singles, Shared Operator Explore! From
- NZ$5,390
San Gimignano's medieval towers, Siena's Gothic Duomo, and Pisa's legendary Leaning Tower unite like-minded travelers. Local wine tastings and guided tours through historic town centers foster new friendships.
Duration 7 days Destinations Rome, Vatican City, Florence, Siena, San Gimignano, Pisa, Venice Age Range All Ages Welcome Group Size Max Group Size 50 Group Type GroupPersonalized Room Type Singles, Shared Operator Tourist Journey From
- NZ$3,545
Tuscany Walking and Wine
24 Reviews by TourRadar travelers“The hotels were very nice, especially the one in Pienza.”
Andrew, traveled in May
Tuscany's heart beckons with shared experiences at family-run wineries like Sovestro. Walks through Val d'Orcia and wine tastings in Montalcino bring travelers together. Group meals in historic Pienza complement visits to medieval San Gimignano.
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 Ages 16+ Group Size Max Group Size 16 Group Type Group Room Type Singles, Shared Operator Explore! From
- NZ$4,880
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
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 Room Type Singles, Shared Operator Italy on a Budget Tours From
- NZ$1,975
Gourmet Tuscany
132 Reviews by TourRadar travelers“I loved the slower pace of the Gourmet Tuscany tour.”
Marianne, traveled in July
Authentic Tuscan experiences await at Vinci's Leonardo Museum, Lucca's Palazzo Mansi, and Chianti's historic wine estates. Montecatini-based travelers (average age 62) join cooking classes at local farmhouses and café-crawls through medieval streets.
Duration 8 days Destinations Montecatini, Vinci Age Range All Ages Welcome Group Size Max Group Size 50 Group Type Group Room Type Singles, Shared Operator Cosmos From $3,750
5% Off- NZ$3,550You save $200
Tuscany Highlights, Semi-Private Tour
2 Reviews by TourRadar travelers“All services were provided as promised and in a timely manner. The itinerary offered us the enjoyment of experiencing Italy in a variety of settings and different experiences.”
Judith, traveled in September
Designed for travelers aged 15+, this tour showcases Lucca's medieval Guinigi Tower and Chianti's family-run vineyards. Boutique 4-star hotels like Alla Corte degli Angeli in Lucca and Garden Siena provide comfort while expert guides reveal Tuscany's hidden gems.
Duration 8 days Destinations Florence, Lucca, Pisa, Siena Age Range All Ages Welcome Operated in English, German, Italian, French, Spanish Group Size Max Group Size 50 Group Type Private Room Type Singles, Shared Operator TUI Italia From $6,907
10% Off- NZ$6,216You save $691
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
Wine tastings at Chianti estates and food tours in Florence bring solo travelers together. Visit Leonardo's birthplace in Vinci and medieval towns from a comfortable base in Montecatini Terme. Suitable for ages 25+.
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 Room Type Singles, Shared Operator RANIERI TOUR OPERATOR From
10% Off- NZ$2,130
Geluxe: Italy: Tuscany and Umbria Vineyard Walks
1 Review by TourRadar travelers“I will be talking about this trip for years to anyone who will listen. Could not be happier!”
Melissa, traveled in May
Tuscany's villages and vineyards set the stage for shared moments. Cooking classes in Città della Pieve, wine tastings at Lamole di Lamole, and walks through medieval San Gimignano bring travelers together.
Duration 8 days Destinations Tuscany, San Gimignano, Colle di Val d'Elsa, Florence, Siena, Monteriggioni, Panzano, Greve in Chianti, Volpaia, MontepulcianoSee all destinations Age Range Ages 18+ Group Size Max Group Size 16 Group Type Group Room Type Singles, Shared Operator G Adventures From
10% Off- NZ$6,919
Discover Tuscany: Culture, Food & Wine
2 Reviews by TourRadar travelers“Kept us informed of daily plans. Ensured our every question and need was met.”
Peter, traveled in October
Hotel Le Renaie welcomes solo travelers for authentic Tuscan experiences. Pasta-making in Castellina and wine tasting at Cesani estate bring people together. Group activities and shared meals foster natural connections.
Duration 8 days Destinations Pancole, San Gimignano, Pisa, Florence, Colle di Val d'Elsa, Tuscany, Siena, Certaldo, Castellina in Chianti, Volterra Age Range Ages 18+ Group Size Max Group Size 18 Group Type Group Room Type Singles, Shared Operator Exodus Adventure Travels From
10% Off- NZ$6,232
What people love about touring Tuscany solo
- Italian Sojourn with Leaning Tower of Pisa
Tours were wonderful and they made the travel from one location to another super easy. Had a wonderful experience with tons of sightseeing, food and wine tasting, and beautiful scenery packed in! Thank you!
- Tuscan Treats
Cooking class Walking tour of Florence with local guide
- The Best of Tuscany - 4Days/3Nights
Overall, I found the trip to be good value and fun! The guides really knew how to take care of the tourists and gave plenty of suggestions and ideas and also information about the history and culture of the city. However, if you’re going to call it a 4day 3 night trip, I would’ve like to have had at least another half day of touring in or around the city. It was really only 2 full days and one evening... The places that we did go to, though, were great.
What our customers ask about Tuscany Tours for Solo Travelers
How social are the Tuscany guided tours for solo travelers?
Tuscany guided tours naturally bring people together through shared experiences. Groups often bond during wine tastings cooking classes and meals together. At Hotel Roma in Florence travelers start their connection during welcome dinners while hands-on activities like pasta making in Bologna create easy conversation starters. The small group sizes mean closer connections. As one TourRadar traveler noted: "Our Tour Leader Emi made the week wonderful. We were a small group of 4 and I felt she went above and beyond to get to know us and ensure we had the best experience possible in each city."
What's the best season for solo travelers to visit Tuscany?
Spring (April-May) and early fall (September-October) offer the best conditions for exploring Tuscany. The weather is mild and key sites like San Gimignano and Siena see fewer tourist crowds. These months also draw the highest numbers of solo travelers making it easier to meet like-minded people. Booking data shows May and September as peak months for single travelers. A TourRadar traveler noted "The walks were certainly moderate and I would not have been keen to do them in the warmer months."
Which areas of Tuscany are best suited for solo travelers?
Florence Siena and San Gimignano stand out as ideal bases for solo travelers. These cities offer easy-to-navigate streets plenty of cafes and natural meeting spots. The historic center of Florence near Hotel De La Pace gives solo travelers a safe vibrant area to explore. As one TourRadar traveler put it: "Florence was a special place and it was nice to have two days there while nipping over to Pisa in the morning on the second day."
How kind of accommodations typically host solo travelers in Tuscany?
Tours place solo travelers in hotels and agriturismos that make meeting others easy. The Hotel Borgo Di Cortefreda in Chianti hosts group wine tastings while the Grand Hotel Adriatico in Florence offers welcoming common areas. One TourRadar traveler noted "The Relais in Pienza was outstanding" pointing to its social atmosphere and shared breakfast space where conversations flow naturally.
Are there dedicated solo traveler departures for Tuscany tours?
Several operators run tours specifically for solo travelers especially from April through June and September through October. Properties like Hotel Le Renaie in Pancole and Grand Hotel Adriatico in Florence cater well to single guests. Data shows solo travelers make up more than half the guests on certain Tuscany tours creating a friendly social setting.
What's the dining experience like for solo travelers on Tuscany tours?
Group meals form the heart of Tuscany's social scene for solo travelers. Tours include shared dining at local restaurants wine estates and cooking classes in family farmhouses. Places like Sovestro winery host tastings that bring the group together. A TourRadar traveler shared their finds: "Best lasagne in Pienza (side street)" and "Best Insalata Caprese in San Gimignano" describing how meals became group highlights.