Lonely Planet Experiences Private Florence Tour: Hill Towns in Tuscany

  • Best price guaranteed
  • No booking fees
  • COVID-19protected
  • City sightseeing
  • Photography tour
  • Art and architecture
See Itinerary
  • duration 8 hours
  • tour type Group
  • minimum participants 5
  • max group size 5
  • guiding method Live Guide/Instructor
  • Starts Florence, Italy
  • Ends Florence, Italy
  • Get out of the city for the day and soak up the sights and smells of the picturesque Tuscan countryside
  • Visit the stunning historic towns of Siena and San Gimignano and browse artisan shops selling locally made products 
  • Dig into an included lunch of seasonal produce at a beautiful boutique winery, with wine and olive oil tastings
  • Enjoy arguably the most beautiful panorama in Tuscany from the Piazzale Michelangelo
The Lonely Planet Experiences Private Florence Tour: Hill Towns in Tuscany tour starts and ends in Florence. The Lonely Planet Experiences Private Florence Tour: Hill Towns in Tuscany is a city sightseeing tour that takes 8 hours.

Get out of the city and spend some quality time sightseeing around the medieval towns of the dreamy Tuscan countryside, with a local guide by your side. Your full-day tour will take in two of the most charming townships, Siena and San Gimignano, with a lunch stop at a boutique winery and plenty of free time for you to explore. We’ll chat history, see incredible architecture, admire Instagram-worthy views, and drop in on artisan shops to discover locally made products from the region.
This tour is priced for a group size of five travellers. Smaller groups may still book this private experience but will be charged the base rate for five travellers.

Experience the best travel stories for yourself. Join a local expert and uncover hidden gems on this city adventure hand-picked by the world's leading travel publisher. Lonely Planet Experiences powered by Urban Adventures bring stories to life in the best-loved cities around the globe.
5 - Excellent
Based on 802 reviews
  • Mrs. JULIE
  • On Jul 03 2016
5 - Excellent
Mrs. JULIE's review for another Urban Adventures tour
“Our guide, Maria, was awesome. We have been on Urban Adventures excursions before (Venice, Lisbon, Barcelona), and they have never disappointed! Great way to learn local culture, food with knowledgeable local guides to enrich your experience. Maria introduced us to Santiago, and we loved her & every moment of the tour. Will definitely recommend (and have) and look forward to new trips.”
  • Ms. Janie
  • On Jun 05 2016
5 - Excellent
Ms. Janie's review for another Urban Adventures tour
“So much food (perhaps just a little too much) and even though I had already been in Sri Lanka for two weeks I was still able to try a few foods I had not yet tried. A very pleasant way to navigate what can be a hectic and challenging city.”
  • Mrs. Miri
  • On Aug 10 2016
5 - Excellent
Mrs. Miri's review for another Urban Adventures tour
“Yennie was amazing and we all enjoyed our Havana walking tour very much. So much so that we booked a Classic Car tour for the next night. I was impressed with her knowledge and optimism for the future of Cuba. She made some great recommendations for us and also explained some issues, ie the currency, better restaurants etc.”

After meeting your driver and tour leader in your hotel lobby, head off in your own private vehicle for a scenic drive through the rolling hills of the Chianti region, crowded as far as the eye can see with vineyards and olive groves. If you’re looking for heaven on earth, we think you may find it here.

First up, make your way to the town of Siena, stopping at the Basilica of San Domenico. Inside the church are the relics of Saint Catherine, the patron saint of Siena. Take a stroll to the Piazza del Campo to see the political centre of town where the famous horse race ‘Il Palio’ is held twice a year. From there, meander towards the Gothic Cathedral, which boasts an impressive collection of artworks by Michelangelo, Donatello and Bernini. Along the way, pass by a delicatessen that sells wild boar salami – if you fancy it, we can step inside for a tasting. 

Then, it’s onward to lunch at a boutique winery surrounded by the Chianti hills and vineyards. You’ll get to taste the wine, as well as that famous extra virgin olive oil with seasonal produce.  

Your second stop is the beautiful walled town of San Gimignano, a UNESCO World Heritage site that’s known as Italy’s medieval Manhattan because of the 13 towers that dominate its skyline as you drive towards it. The town gained importance during the Middle Ages when it was a stop on the major pilgrim route between Italy and France, known as Via Francigena (the road to France). The townsfolk produced silk and cultivated saffron that still grows around its foothills. Another important industry that still exists here today is that of Vernaccia di San Gimginano, a white wine of the area.

Your tour leader will tell you about the history of the region and fill you in on where to find the best artisanal stores, coffee shops and gelato spots. You’ll also get the chance to check out a selection of artisan stores selling locally made products and stroll the winding streets, admiring spectacular views of the valley beyond.

Afterwards, meet your chauffeur for the transfer back to your accommodation in Florence. On the way, we’ll stop for one last magnificent panorama at Piazzale Michelangelo, where we will gaze upon spectacular views of the city that you won’t forget in a hurry. Before you go, don’t forget to ask your local guide for tips on what else to see, do and eat during your stay in fabulous Florence. 

This tour is priced for a group size of five travellers. Smaller groups may still book this private experience but will be charged the base rate for five traveller

  • Pick up at your hotel.
  •  lunch of seasonal produce at a beautiful boutique winery
  • English-speaking guide and driver
  • Transport in a Mercedes air-conditioned van
  • With wine and olive oil tastings
  • Additional food and drinks
  • souvenirs and personal shopping
  • tips/gratuities for your guide.
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Cancellation for this Lonely Planet Experiences Private Florence Tour: Hill Towns in Tuscany tour is free up to 48 hours before the chosen start date - full refund will be given. If cancellation is made less than 48 hours before the chosen start date, no refund applies.


For any tour departures within 31 July 2021, full payment is required. For tours that depart later than 31 July 2021, a deposit of 100% is required to confirm this tour, and the remaining balance will be charged 0 days before trip departure.

Travel Insurance

Lonely Planet Experiences Private Florence Tour: Hill Towns in Tuscany tour requires that you have adequate and valid travel insurance covering medical and personal accidents, including repatriation costs and emergency evacuation. We recommend using World Nomads' travel insurance.


For this Lonely Planet Experiences Private Florence Tour: Hill Towns in Tuscany tour getting the required visa(s) is the responsibility for each individual traveller, as visa requirements vary depending on your nationality. We recommend to check with your local embassies representing the countries that you are travelling to, as part of this itinerary.

Meeting start point :

Your hotel in Florence city centre.

Meeting end point :

Your hotel in Florence city centre.

Lonely Planet extras
  • Free access to the Lonely Planet mobile app for one year
  • 25% discount on all items in the Lonely Planet Shop
COVID-19 Safety Measures

This trip incorporates the following COVID-19 measures:

  • This tour follows established guidelines that are in line with the World Travel and Tourism Council’s ‘Safe Travels’ framework against COVID-19.
  • This tour follows the local government(s) recommendations for gatherings and group sizes.
  • Wearing a mask, hand washing and sanitizing is highly encouraged on this tour. Frequently touched surfaces are regularly disinfected.
If you have any question about this tour or need help with planning a trip, please do not hesitate to get in touch with us. We're ready to help.
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