I would highly recommend Jayway. You were so accommodating and helpful throughout the entire experience. Thank you.
- Gail, Annette & Jody - Georgia
Custom tour packagesCastellina in Chianti
We have chosen Castellina as one of our key destinations in Tuscany as this small town offers all the facilities most visitors need, while allowing them to enjoy the countryside. Public transport is limited, so you will definitely need a driver or rental car while you're here. On the edge of a village is a Vespa and Cinquecento (vintage Fiat car) rental company, should you want to indulge in a little nostalgic exploration of the surroundings. Close by you'll find San Gimignano, a "medieval Manhattan" well worthy of a day trip, and the walled town of Monteriggioni is even closer.
The quintessential Tuscan hilltop town.
Whether you choose to go wandering in the countryside – there are some nice trails nearby – or visit Tuscany's major towns like Florence and Siena, you'll love coming back "home" to Castellina. This is the heart of wine country and the fruit of the vine is a big part of the culture here. With a choice of eateries from basic pizzeria to fine dining, and one of our favorite gelaterias of all time, Castellina's got a lot to like.
Popular itineraries featuring Castellina in Chianti
Spend some time in Castellina in Chianti on a tour that takes in other cities in Italy and neighboring countries. Our custom tour packages including Castellina in Chianti and other destinations throughout Italy and Europe make multi-city trips hassle-free. We take care of getting you from place to place, accommodation, excursions and activities.
Things to do in Castellina in Chianti
We've got a broad range of city tours, day trips and excursions to keep you busy in Castellina in Chianti. This charming town makes for a calm base from which to explore surrounding Tuscany. Spend a private day trip exploring the Val d'Orcia, visiting Montalcino, Montepulciano and Pienza, or head to Siena (and perhaps also San Gimignano). You can also stay in town for a tasting dinner, or private cooking class with a professional local chef. When we send you your customized itinerary you will be able to choose additional excursions to include in your vacation package or consider adding later.
Off-Road Tuscan Wine Private Tour
Private Cooking Class with Professional Chef in Castellina in Chianti
Siena and San Gimignano Full-day Private Tour from CastellinaWhere to stay in Castellina in Chianti
As one of the larger villages in Chianti, Castellina makes for a great base. With its centuries of history there are some spectacular properties to stay in. Take you pick from farmhouses, palazzos and converted medieval hamlets.
Luxury Boutique Hotel
A Tuscan hilltop hamlet turned into a luxury 17 room boutique hotel.
Design Boutique Hotel
A luxurious hotel in the hills, with great amenities and beautiful surroundings.
Central Historical Palazzo
A luxurious place of real elegance where you can get in touch with the beautiful culture of the Italian countryside.
Where can you go from Castellina in Chianti?
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Glowing Reviews From Our Guests
Jayway makes the travel easy and without worry, especially lodging, making restaurant recommendations and reservations and the ease of transport is wonderful. We loved our short trip to Italy and met the nicest guides, drivers, and lodging staff. I would highly recommend the Jay-Way!
- Pam, Beth, Cynthia & Dona - North Carolina
JayWay travel went above and beyond in every step of our trip. Daniele was the best driver/tour guided we could ask for. So accommodating and gracious. He would say anything is "doable" and that he was just the driver. But, He was so truly so much more than that to the Tarsi family.
- Mary, David, Vincent, Antony & Denise - Pennsylvania
Frequently Asked Questionsabout Travel to Castellina in Chianti
What are Castellina's prices like?
Prices in Castellina are generally quite reasonable, especially compared to larger tourist hubs in Tuscany. Meals at local trattorias and restaurants are affordable, with a typical lunch or dinner costing around €15-€30 per person. Attractions like wineries or historical sites typically have entrance fees of €10-€20, though wine tours and tastings may cost a bit more euros.
How can I get around Castellina?
The best way to explore Castellina is on foot, as the town is small and easy to navigate. Cars are only allowed in a few areas of the town, so walking is ideal for discovering its charming streets. If you'd like to visit neighboring areas, we can arrange private transfers If you are staying outside the town and want to explore, renting a car is the best option, as there are no taxis or public transportation available.
Is Castellina safe?
Castellina is very safe.
Does Castellina have options for those with dietary restrictions?
Although Castellina is small, many pizzerias and restaurants offer gluten-free options, and you'll also find plenty of vegetarian choices at most establishments.
How long should I stay in Castellina?
We recommend staying at least two nights in Castellina to fully enjoy the town and its beautiful surrounding nature and vineyards. Adding a third night will allow you for a day trip to explore more of the area.