Private Florence Tour: Hill Towns in Tuscany
Florence, Italy
From USD 221.96
Office phone number: +39 320 250 3173
Private Florence Tour: Hill Towns in Tuscany
Florence, Italy





Culture shock rating
Worried we’re going to shock your senses? Relax! We believe part of the fun of travel is immersing yourself in the destination and its culture, meeting the people, and learning what makes the place tick. We’ve got a wide range of tours with something for everybody. The cultural shock rating ranks how different the experience is from most Western cultures. But no matter the level, don’t worry, you’ll have a local, in-the-know guide with you every step of the way.
Low
Consider these tours your 101 intro to a place. Transportation might be private or a very comfortable public option, and the activities are usually visits to iconic sites and locations that are familiar to most Western cultures – but that will still give you fantastic insight into a destination.
Medium
Expect to rough it for parts of this tour, whether that’s on a packed public bus or in a local market off the tourist trail. There might be a few language barriers or unfamiliar cultural customs, and you’ll get an experience different from what you're used to at home.
High
You're out there in the global community! We’re going to take you down streets you’d rarely explore on your own, introduce you to local customs and languages, and take you for a ride in whatever transport is available. Get ready to take it as it comes, whatever comes. There might be a shock, but oh man, it’s worth it.

Physical rating
Worried our tours are too tough? Relax! From leisurely strolls to muscle-burning treks, we’ve got a wide range of tours with something for everybody. The physical grading gives you an idea of how much huffing and puffing you can expect on the tour.
Low
Slow and steady is all you need here. These tours have very limited physical activity, such as walking relatively flat streets, sites, or markets, and climbing in and out of the transport provided.
Medium
Not too hard, not too soft, these tours are just right! You can expect a bit of physical activity, but nothing overly challenging – perhaps walking up and down hills, riding a bike for up to 30 kilometers along mostly flat terrain, or jumping in a kayak for a gentle paddle on flat water.
High
Get ready for a workout! These tours are our most challenging and involve intense walking, hiking, kayaking, swimming, or bike riding. You could be making steep climbs by foot or pedal, or working your core in the water. We recommend you have a good level of fitness to join this tour.
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Tour snapshot
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.
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Highlights
- 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
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Schedule details
- Duration: 8 hours
- Pickup location:
Your hotel in Florence city centre.
- Pickup time: 9.00 AM
- Drop off location:
Your hotel in Florence city centre.
Language: English
Inclusions: Local, English-speaking guide and driver, transport in a Mercedes air-conditioned van, lunch of seasonal produce at a beautiful boutique winery, with wine and olive oil tastings, pick up at your hotel.
Exclusions: Additional food and drinks, souvenirs and personal shopping, tips/gratuities for your guide.
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
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Additional information
Inclusions: Local, English-speaking guide and driver, transport in a Mercedes air-conditioned van, lunch of seasonal produce at a beautiful boutique winery, with wine and olive oil tastings, pick up at your hotel.
Exclusions: Additional food and drinks, souvenirs and personal shopping, tips/gratuities for your guide.
Confirmation of booking: If you have your voucher, your booking is confirmed. We'll see you at your hotel for pick up. Please check your hotel details are correct on the voucher. If your details are not correct, it is very important to please email us to confirm your correct pick up hotel using the contact details on the voucher. If you prefer you may also phone the change through to us during business hours.
Additional Information: Please note that starting February 1, 2022, the additional activities, including day tours, previously allowed with a basic green pass now require a super green pass. A Super Green Pass is valid up to six months from the time of the most recent vaccination (fully vaccinated). Please check your vaccine certificate and make sure you are within the 6-month time limit from your second dose or booster shot, before joining the tour.
Child Policy: No age limit: This is a child-friendly tour. Children between the ages of 6 and 11 inclusively are permitted on this tour at the rate listed above. Please select ‘child’ above when booking. Children under the age of 6 are permitted to join this tour free of charge. Please inform us at the time of booking if you’ll be bringing a child under the age of 6. You can do so in the special request box on the checkout page.
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Dietary Notes
We can accommodate vegetarians and other dietary restrictions. Please notify us in advance if you have any dietary requests. You can do so in the ‘Additional information’ box at checkout, or by emailing us at italycustomized@gmail.com
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Local contact
Office phone number: +39 320 250 3173
Email address: italycustomized@gmail.com
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