From Siena: Chianti and Castles Tour with Wine Tastings
1.From Siena: Chianti and Castles Tour with Wine Tastings
Half-day Chianti castles and wine tastings from Siena with a small-group minivan, two winery stops, and scenic hilltop towns.
Castles & Hill Towns
TUSCANY
10 Best Castles & Hill Towns Tours In Tuscany
Tuscany's standouts.
The 10 castles & hill towns tours travellers book most often across Tuscany. Each one with the price you pay, the operator behind it and the day you actually get when you turn up.
10 Best Castles & Hill Towns Tours In Tuscany
Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle
2.Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle
A 1.5-hour Brunello-focused wine tasting plus a traditional Tuscan 3-course lunch in Castello Tricerchi, Montalcino.
Hidden Castles & Chianti Wine Experience– Small Group
3.Hidden Castles & Chianti Wine Experience– Small Group
A 5-hour small-group Chianti day from Siena with two winery tastings, olive oil, and free time in hilltop villages.
“Our guide Luca was very knowledgeable and gave great information all day throughout the tour. He had good recommendations for restaurants in the cities we visited, and explained the different wines and products very well. The tour itself was nice, with visits to two wineries and some cities with impressive views over the hillside in…”
Wine Tasting & Tuscany Countryside, San Gimignano & Volterra
4.Wine Tasting & Tuscany Countryside, San Gimignano & Volterra
Small-group Tuscany day trip from Livorno with Volterra, a farmhouse wine tasting, and UNESCO-tower San Gimignano, plus port-safe timing.
“Our favorite tour of our trip!!! What a BEAUTIFUL place! Great time at Tunata Winery with Lilo. Fun wine tasting. Just slightly rushed there and would like to have seen a bit more of the vineyard but nonetheless, fantastic. Did feel a little like they were more focused on selling wine than showing us the…”
Private Best of Tuscany Hill Towns Tour with lunch from Florence
5.Private Best of Tuscany Hill Towns Tour with lunch from Florence
Private Florence day trip to Siena and San Gimignano with winery lunch and wine tasting, plus a guided minivan ride through Tuscany.
“Our guide Yaris was the best. He was so knowledgeable and gave us the experience of our lives. My 16 year old daughter thought this was the highlight of our 10 day trip.”
Montalcino: Castle and Vineyards Tour with Tasting
6.Montalcino: Castle and Vineyards Tour with Tasting
Tour Montalcino’s medieval castle and Brunello vineyards in 1 hour, with cellar stops and a 3-wine tasting with local bites.
Full-Day Tuscany Castles Tour with Wine Tasting from Florence
7.Full-Day Tuscany Castles Tour with Wine Tasting from Florence
Florence to Chianti for two winery visits with tastings, a 2-course lunch, and round-trip minivan transport in English.
“The Castles are really manor homes which have been converted to wineries or may have always been wineries. Not really castles in my opinion. They were interesting but one of my friends was really interested in the castle aspect and not so much the wine.”
Siena: Tour and Wine Tasting in a Tuscan Private Castle
8.Siena: Tour and Wine Tasting in a Tuscan Private Castle
Tour Castello Poggiarello in Tuscany: castle gardens and Renaissance chapel walk, then organic wine tasting in a private castle setting, 2h.
Tuscany & Pitigliano Day Tour from Rome with Wine Tasting & Lunch
9.Tuscany & Pitigliano Day Tour from Rome with Wine Tasting & Lunch
Small-group Tuscany day tour from Rome with hotel pickup, Pitigliano and Scansano towns, plus two winery tastings and a 3-course lunch.
“We enjoyed ourselves immensely, but it is a very long day at 12 hours. We loved visiting the towns and vineyards along the way.”
Chianti and Castles Tour From San Gimignano
10.Chianti and Castles Tour From San Gimignano
Half-day Chianti and castles tour from San Gimignano with two winery cellar visits, tastings, village stops, and sweeping hill views in 6 hours.