Tuscany Tours for Solo Travelers
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10 best Tuscany solo travel packages
Compiled by
NadineTuscany travel expert at TourRadar
- A Taste of Tuscany - Hilltop Towns and Vineyards
- Gems of Rome & Florence
- Discovering Florence
- Private Gourmet Wine Tour in Tuscany, Italy
- Tuscany Thrills: A 3-Day Escape of Wine, Relax, and Fun
- Discover Tuscany: Culture, Food & Wine
- Flavours of Tuscany - Semi-Escorted Tour
- Tuscany Highlights, Private Tour
- Tuscany & Cinque Terre Tour Package - 5 Days
- Florence City Break - 5 Days
A Taste of Tuscany - Hilltop Towns and Vineyards
11 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 16 to 85 year olds Group Size Max Group Size 16 Group Type Group Room Type Singles, Shared Operator Explore! From $4,840
6% Off- NZ$4,570You save $270
Gems of Rome & Florence
4 Reviews by TourRadar travelers“Lovely tour, particularly of Siena and San Gimignano. From cathedrals to cobblestones, turrets to towers, this all-day tour was a wonderful experience.”
Yvonne, traveled in June
Florence's historic center and Siena's Piazza del Campo await solo travelers aged 70+. Share moments with fellow guests during wine tasting at local Chianti vineyards and while viewing San Gimignano's medieval towers. Rest at the centrally-located 4-star Hotel Adriatico in Florence.
Duration 6 days Destinations Rome, Florence, San Gimignano, Siena Age Range up to 80 year olds Operated in English, Spanish Group Size Max Group Size 50 Group Type Group Room Type Singles, Shared Operator TUI Italia From $2,594
10% Off- NZ$2,335You save $259
Discovering Florence
2 Reviews by TourRadar travelers“The private tours of the Uffizi and Accademia Galleries were super - the guides were knowledgeable and open to any question.”
kelly, traveled in March
Solo wanderers make up a third of visitors on this Tuscan adventure. Bond with fellow enthusiasts during Uffizi Gallery tours and Chianti wine tasting at Poggio ai Laghi estate. Single rooms available at centrally-located Grand Hotel Adriatico.
Duration 4 days Destinations Florence, Monteriggioni, Siena, San Gimignano Age Range up to 80 year olds Group Size Max Group Size 50 Group Type Group Room Type Singles, Shared Operator TUI Italia From $1,341
10% Off- NZ$1,207You save $134
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
Intimate groups of 2-8 travelers share memorable moments at Chianti estates and medieval towns. Wine tastings and traditional meals create natural connections. Private transportation winds through Tuscany's landscape.
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 Room Type Singles, Shared Operator Soleto Travel From $4,592
15% Off- NZ$3,903You save $688
San Gimignano serves as home base for this Tuscan solo adventure with guided Chianti wine tastings. Fellow travelers gather for group cooking classes (approx. €120) or horseback rides through vineyards (approx. €120).
Duration 3 days Destinations Tuscany, San Gimignano Age Range 18 to 99 year olds Operated in English, Italian Group Size Max Group Size 20 Group Type PrivatePersonalized Room Type Singles, Shared Operator Italy on a Budget Tours From
15% Off- NZ$756
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, Florence, Colle di Val d'Elsa, Siena, Castellina in Chianti, Certaldo, Volterra, Tuscany Age Range up to 80 year olds Group Size Max Group Size 18 Group Type Group Room Type Singles, Shared Operator Exodus Adventure Travels From $4,617
12% Off- NZ$4,070You save $547
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
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, 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 Room Type Singles, Shared Operator RANIERI TOUR OPERATOR From
12% Off- NZ$1,988
Tuscany Highlights, 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 up to 80 year olds Operated in English, German, Italian, French, Spanish Group Size Max Group Size 50 Group Type PrivatePersonalized Room Type Singles, Shared Operator TUI Italia From $6,489
10% Off- NZ$5,840You save $648
Duration 5 days Destinations Florence, Siena, San Gimignano, Monteriggioni, Greve in Chianti, Cinque Terre, Pisa Age Range 4 to 99 year olds Group Size Max Group Size 50 Group Type Group Room Type Singles, Shared Operator Click Tours From $4,042
36% Off- NZ$2,587You save $1,455
Duration 5 days Destinations Florence, Greve in Chianti, Siena, San Gimignano, Monteriggioni Age Range 4 to 99 year olds Group Size Max Group Size 50 Group Type Group Room Type Singles, Shared Operator Click Tours From $3,922
36% Off- NZ$2,511You save $1,412
What people love about touring Tuscany solo
- Icons of Italy: Venice, Florence, Tuscany and Rome Cruise by Rail
Well organized tour with plenty of free time in each destination, it was a good mix of activity and downtime. Elisabetta was a fantastic tour guide and made sure that everyone was taken care of. For the free days, she was very helpful in finding local tours and events to do in the destinations. She set up a group chat on WhatsApp and sent so much great information about the places, activities, foods, things to do, etc. every day so that we would know what to expect or plan what to do.
- Cycle Tuscany
Loved the E-bike particularly on the hills!
- Tuscany Walks & Chianti Wines
This was the best group tour I've taken with a great mix of activities and down time. Also simply fab and idyllic scenery and Liz was a great tour leader
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.