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

From Siena: Chianti and Castles Tour with Wine Tastings

From Siena: Chianti and Castles Tour with Wine Tastings - Castellina in Chianti and Monteriggioni: towers, walls, and that Tuscan walk

1.From Siena: Chianti and Castles Tour with Wine Tastings

Most Popular 4.6

Half-day Chianti castles and wine tastings from Siena with a small-group minivan, two winery stops, and scenic hilltop towns.

“Fabio was an excellent tour guide with great insight into the region and a good sense of humour. Fabio took us around the Chianti area countryside safely and expertly and made our visit to the region an enjoyable one. Thank you Fabio, you were excellent !!”

Check Availability →Read the review →

Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle

Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle - The 1.5-hour format: vineyard walk, then tasting, then lunch

2.Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle

4.6

A 1.5-hour Brunello-focused wine tasting plus a traditional Tuscan 3-course lunch in Castello Tricerchi, Montalcino.

“The place, the tour and the lunch were all excellent. However, when we bought a bottle of Montalcino from the estate, it actually costs more than if we were to buy outside, which was disappointing for us.”

Check Availability →Read the review →

Hidden Castles & Chianti Wine Experience– Small Group

Hidden Castles & Chianti Wine Experience– Small Group - Entering Chianti Country: Minivan Ride, Meeting Point, and Motion-Sickness Reality

3.Hidden Castles & Chianti Wine Experience– Small Group

4.5

A 5-hour small-group Chianti day from Siena with two winery tastings, olive oil, and free time in hilltop villages.

“Valeska was a wonderful tour guide and both tastings were great! We had thought about going to a couple of vineyards on our own but it was well worth the little bit extra for the tour. I definitely recommend it.”

Check Availability →Read the review →

Wine Tasting & Tuscany Countryside, San Gimignano & Volterra

Wine Tasting & Tuscany Countryside, San Gimignano & Volterra - Getting started at Livorno: the meeting point and the time pressure

4.Wine Tasting & Tuscany Countryside, San Gimignano & Volterra

5.0

Small-group Tuscany day trip from Livorno with Volterra, a farmhouse wine tasting, and UNESCO-tower San Gimignano, plus port-safe timing.

“Wonderful We met our Driver at the parking lot Carlo our driver was very nice very helpful and made sure we were back to our cruise on time. We met four new friends from our same cruise. Beautiful drive to the country side Stopped at a winery, wine tasting then to the most beautiful old…”

Check Availability →Read the review →

Private Best of Tuscany Hill Towns Tour with lunch from Florence

Private Best of Tuscany Hill Towns Tour with lunch from Florence - Siena’s Palio spirit: more than a postcard square

5.Private Best of Tuscany Hill Towns Tour with lunch from Florence

4.5

Private Florence day trip to Siena and San Gimignano with winery lunch and wine tasting, plus a guided minivan ride through Tuscany.

“Fantastic tour. The scenery was amazing and the wineries and towns we visited were just perfect. The van was very comfortable for the drive and the length of the tour was just right. Our guide Fabrizio (forgive me if I've spelled his name wrong) was the best. He went out of his way to pick…”

Check Availability →Read the review →

Full-Day Tuscany Castles Tour with Wine Tasting from Florence

Full-Day Tuscany Castles Tour with Wine Tasting from Florence - Castello del Trebbio: old cellars and a tasting of five wines

Montalcino: Castle and Vineyards Tour with Tasting

Montalcino: Castle and Vineyards Tour with Tasting - Entering the medieval castle walls: bridge and chapel stops

7.Montalcino: Castle and Vineyards Tour with Tasting

4.2

Tour Montalcino’s medieval castle and Brunello vineyards in 1 hour, with cellar stops and a 3-wine tasting with local bites.

“Esperienza carina, visita guidata di 10 minuti all’esterno del castello e poi alle cantine. Con la degustazione dei vini sarebbe gradito un accompagnamento con prodotti locali al posto dei grissini.”

Check Availability →Read the review →

Siena: Tour and Wine Tasting in a Tuscan Private Castle

Siena: Tour and Wine Tasting in a Tuscan Private Castle - Two entrance options: private entrance or visitor entrance

Tuscany & Pitigliano Day Tour from Rome with Wine Tasting & Lunch

Tuscany & Pitigliano Day Tour from Rome with Wine Tasting & Lunch - Scansano: The Lunch Stop That Feels Like Tuscany, Not Just a Meal

Chianti and Castles Tour From San Gimignano

Chianti and Castles Tour From San Gimignano - Castellina in Chianti: a guided history stop with room to roam

10.Chianti and Castles Tour From San Gimignano

3.8

Half-day Chianti and castles tour from San Gimignano with two winery cellar visits, tastings, village stops, and sweeping hill views in 6 hours.

“Contraté un tour en español y ambas visitas a bodegas eran en inglés. El conductor (guía de la excursión) era buen conductor, conversador y pudimos entendernos en español. Las dos bodegas son buenas, la primera es mucho mejor porque te ofrecen alguna y algo para ir comiendo entre los vinos, la segunda parecía que querían…”

Check Availability →Read the review →

Most recent

Explore Tuscany