Tuscany Tours for Solo Travelers
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10 best Tuscany solo travel packages
Compiled by
NadineTuscany travel expert at TourRadar
- Tuscany Walking and Wine
- A Taste of Tuscany - Hilltop Towns and Vineyards
- Discover Tuscany: Culture, Food & Wine
- Gems of Rome & Florence
- Highlights of Italy in Winter
- Discovering Florence
- Private Gourmet Wine Tour in Tuscany, Italy
- 4 Day Florence City Break with Cooking Classes - Small Group
- Tuscany Highlights, Private Tour
- Tuscany Thrills: A 3-Day Escape of Wine, Relax, and Fun
Tuscany Walking and Wine
21 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 16 to 85 year olds Group Size Max Group Size 16 Group Type Group Room Type Singles, Shared Operator Explore! From
- NZ$4,280
A Taste of Tuscany - Hilltop Towns and Vineyards
11 Reviews by TourRadar travelers“The winetasting was a great time. Walk from Buonconvento was great as was farm visit.”
CJ, 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 $5,390
5% Off- NZ$5,120You save $270
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
5% Off- NZ$4,400You save $217
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 $2,629
15% Off- NZ$2,235You save $394
Cultural immersion in Tuscany includes Florence's Galleria dell'Accademia and Uffizi Gallery. A hands-on pasta-making class in Bologna and wine tastings unite travelers (75% solo, average age 38). Comfortable hotel stays throughout.
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 Room Type Singles, Shared Operator Intrepid Travel From $4,320
5% Off- NZ$4,104You save $216
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 $1,359
15% Off- NZ$1,155You save $204
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
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 $4,654
15% Off- NZ$3,956You save $698
Duration 4 days Destinations Florence Age Range 4 to 99 year olds Group Size Max Group Size 22 Group Type Group Room Type Singles, Shared Operator Click Tours From $2,650
31% Off- NZ$1,829You save $822
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 $6,576
15% Off- NZ$5,590You save $986
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$766
What people love about touring Tuscany solo
- Private Gourmet Wine Tour in Tuscany, Italy
The best we could ever hope for!! Villa Lecchi was beyond our dreams. The views were spectacular of Tuscany. All of our tour guides were fantastic. And the food and wine was so good. Massimo our driver was incredible. Thank you for planning such a wonderful experience!!
- Icons of Italy: Venice, Florence, Tuscany and Rome Cruise by Rail
Elisabetta was the absolute best guide we could’ve had. She took us shopping on the free days, and accompanied me to the hospital during an emergency. I wish she was staying with us the entire trip. She is the very best at what she does. She loves her job, and it shows through to everyone on the tour.
- Cycle Tuscany
Great time traveling with others, tour was organized but felt organic. Great restaurants and I loved my e-bike, particularly on the hills!
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.