Top Tuscany Day Trips - page 10

Full-Day Tuscan Countryside Bike Tour

5 hoursFree Cancellation

4.5

(26)

from $179

Montepulciano Pienza Montalcino Tour from Florence

9 hoursFree Cancellation

(12)

from $1,180

Discover the countryside of Lucca riding a Vespa 125 Primavera. The iconic scooter, in its most modern version, offers the perfect means to explore the natural surroundings of the city. We offer two different itineraries, one heading north towards Montecarlo, and one heading south towards the Lake of Massaciuccoli. After a little briefing, we'll provide an itinerary to follow on Google Maps and offer some suggestions of spots where to stop for lunch and things to see along the way. You can also choose to stop for a picnic at our partner winery or have an olive oil tasting in a local mill. In this self-tour type of experience, we encourage the visitors to take their time, enjoying this beautiful region at their own pace. On a Vespa, the trip is just as important as the destination. Please note that experience in driving scooters/motorcycles is mandatory. If the customer shouldn't have this, we reserve the right to deny rental for safety reasons, and there won't be a refund.

Vespa Self Guided Tour Around Luccas Countryside

4 to 8 hoursFree Cancellation

(7)

from $108

We will hike through one of the wildest natural parks in Tuscany, with a unique wealth of biodiversity, and we will reach a high altitude lake. Walking in the silence of centuries-old woods and mountain streams we will slowly approach the high altitude grasslands, the must-see Apennine ridges. There you can enjoy a breathtaking view and relax on the shore of the lake. Lunch at mountain lodge or packed lunch can be bought locally.

Trekking on the roof of Tuscany

5 to 6 hoursFree Cancellation

Get a personal introduction to Siena and Chianti with a full-day, private tour from Florence in a luxurious van. Stroll Siena’s gothic streets with a local guide, and discover the art and black-and-white architecture of its UNESCO-listed historic center. Explore rolling vineyards and olive groves then taste your way through famous wineries, family cellars, local olive oils and aged balsamic vinegar.

(8)

from $61

Siena and Chianti Wineries Excursion by Private Luxury Van from Florence

from $839

Once your cruise ship docks in the Livorno port, know that your day is planned in advance by booking this private tour to Florence and Pisa. Escape the crowds of the cruise ship and enjoy personalized attention and the ability to travel at your own pace. Stops in Florence include Piazzale Michelangelo, Basilica di San Miniato al Monte, the Duomo Complex, and the Palazzo Vecchio. In Pisa, make a photo stop at the famous tower, and visit the Cathedral and the Baptistery.

Private Shore excursion from Livorno to Florence and Pisa

4.4

(17)

from $957

Tuscany Wine Tastings with Panoramic View - Florence to Chianti

5 hoursFree Cancellation

4.7

(14)

from $84

Visit two of the most captivating villages in the Tuscan countryside on this private day tour from Florence. Travel in a Mercedes minivan to the Etruscan town of Volterra, known for its 3,500 years of history, ancient city walls and museums. Stop at a local farm or restaurant for an optional lunch before visiting the UNESCO-listed medieval village of San Gimignano. Enjoy the personalized attention of a private guide and a customized itinerary to match your interests. Price is per group, based on a maximum of eight passengers per vehicle.

Florence Day Trip to Volterra and San Gimignano

9 hoursFree Cancellation

from $1,126

Explore the highlights of two of Tuscany's most famous cities, Florence and Pisa, on this small-group full-day trip from Rome. Walk through the historic center of Florence to see Brunelleschi's beautiful dome over the cathedral and learn more about the Italian Renaissance. Admire the Leaning Tower of Pisa, one of Italy's best-known monuments, and tuck into a delicious lunch at a local restaurant (if option is selected)

Private Tour: Day Trip to Florence and Pisa from Rome with Lunch

12 hoursFree Cancellation

3.8

(65)

from $479

Spend a day uncovering the charm of Siena, San Gimignano, and Chianti with a private tour from Florence. Enjoy an intimate experience exploring Siena's vibrant main square, the picturesque hilltop town of San Gimignano, and the market town of Greve. Complete your adventure with a visit to a local winery for a taste of the famous Chianti blend and insight into how sangiovese grapes are cultivated.

Private guided tour: Siena San Gimignano and Chianti

10 hoursFree Cancellation

3.5

(6)

from $467

Embark on an unforgettable day trip from Florence to the enchanting city of Venice, a city built on water and steeped in history. Depart from Florence aboard a comfortable highspeed train and be whisked away to the Venetian lagoon. Once in Venice, your journey through the city’s winding alleys and along the iconic Grand Canal, where history and stunning architecture come to life. Venice was once an independent maritime republic with a fascinating blend of European and Arab influences, which you’ll discover throughout the tour. Enjoy free time to shop for unforgettable Venetian treasures, intricate Murano glass, traditional Venetian masks or other unique souvenirs, and experience the artistry of local glassblowers. To truly immerse yourself in Venice’s charm, add a gondola ride to your experience. Drift along the serene canals, taking in the breathtaking views as your gondolier guides you through the heart of the city. Book your spot now!

Florence: Day Trip to Venice with Bell Tower Tickets

10 hours

3.6

(7)

from $191

Visit Orvieto and Civita di Bagnoregio with the convenience of a private driver and vehicle on this full-day tour from Florence. Skip the hassle of driving with private transfer service that takes you through the picturesque Italian countryside to Orvieto and Civita di Bagnoregio. Have several hours to explore the medieval towns on your own, and, if time allows, add a stop at Pitigliano Centro Storico.

Orvieto, Civita di Bagnoregio, Pitigliano PRIVATE TOUR from FLORENCE

10 hours

from $743

Spend a day in the Tuscan countryside without having to puzzle through tricky transportation on this Chianti and San Gimignano day trip that includes a driver from Florence. Stop in Montefioralle for photos, then visit a Tuscan winery in Greve in Chianti, where you’ll tour the vineyards, learn about the wine-making process, and enjoy tastings of Chianti Classico and other regional specialties. Next, explore the medieval town of San Gimignano before heading to a nearby farm for a light lunch with Tuscan appetizers, wines, and oils.

From Florence: Classic Chianti Villages and Wine Roads by Minivan

6 hours 30 minutesFree Cancellation

4.7

(74)

from $202

Pisa & Florence highlights shore excursion from Livorno port

8 to 9 hoursFree Cancellation

(8)

from $863

Explore Tuscany's countryside without hiring a car with this private driving tour of the region. Perfect for travelers staying in Florence, enjoy hotel pickup and relax as you are taken to a range of destinations based on your interests. Visit the Florence American Cemetery, the medieval hamlet of Castello di Montefioralle, and take in the view at Piazzale Michelangelo. For wine lovers, opt to visit a Chianti winery (at an additional cost) and enjoy tastings of local varities.

Likely to Sell Out

Private Tuscany Excursion. Florence American Cemetery, Greve in Chianti, Winery

from $407

Our self-tour itineraries are an intimate way of exploring the Tuscan countryside of Lucca aboard our vintage cars at your very own pace, with no hurries or tight schedules. Planned to take you away from traffic through pretty back roads and lovely sceneries, these programs will allow you to live your day aboard our Fiat 500s to the fullest! Explore the diverse countryside of Lucca, on charming roads surrounded by olive groves, rolling hills and historical architecture. Our itineraries have been studied on purpose to offer you a unique perspective on the territory, and drive on relaxing roads away from traffic so that you can truly enjoy the driving experience. Our aim is to offer you a laid back day, experiencing Tuscany like a real local and making unique memories to last you a lifetime.

Fiat 500 Self-Tour: Visit the Tuscan Countryside in a Vintage Car

from $341

Taste the famous flavors of Tuscany's wines and olive oils on this private tour from Florence. Travel through the Chianti region in a luxury tour vehicle, taking in the sights of the rolling hillsides covered with groves of olives and grapes. Take tours of several vineyards and learn about their production through guided commentary. Enjoy tastings of Chianti varietals and tuck into a tasty 3-course lunch with more wine.

Chianti from Florence:PRIVATE Wine, Olive Oil Tasting in the Tuscan countryside

6 to 7 hoursFree Cancellation

from $381

Discover the Tuscan hills in a unique way: on horseback. This private horse riding tour from Florence is tailored to your experience level and takes you through a stunning landscape dotted with olive groves and vineyards. After your ride, you'll head for a medieval castle or historic farm specializing in olive oil production where you'll enjoy an olive oil tasting paired with local cheeses, Tuscan ham and bruschetta, and Chianti wine.

Horse ride, Olive Oil and local foods tasting in a Tuscan farm

5 hours 30 minutesFree Cancellation

(20)

from $371

When visiting Florence (or Siena), spend a delicious day winery hopping in the renowned Chianti wine region. Visit two of the best estates for tastings of Chianti Classico and other top varietals, and enjoy a gourmet lunch of Tuscan specialties. There's also time to soak up countryside culture and history with a stop in San Gimignano or Monteriggioni, two of the best-preserved medieval towns in Tuscany.

Chianti and San Gimignano - 2 Wineries with Pairing Lunch

6 to 8 hoursFree Cancellation

Take a break from the crowds in Florence and experience a Tuscan culinary tradition on this exclusive truffle hunt adventure from Florence. Travel by coach to the hilly landscape surrounding San Miniato, a Tuscan town famous for its delectable truffles. With the help of an experienced hunter and his trusty dog, make your way through the woodland, scanning the earth for this regional specialty. Afterward, reward your search with a 2-course lunch in Chianti, including a wine tasting and truffle pasta.

(72)

from $274

Full-Day Small-Group Truffle Hunting in Tuscany with Lunch

7 hours

(138)

from $401

Explore the charming towns of Siena and San Gimignano on this full-day minivan tour from Florence, with a photo stop at Monteriggioni. Discover the medieval and Gothic architecture of the towns and learn their histories from your informative guide. Visit the main attractions of each city and sample their delicious cuisine—at your own expense—while walking around and absorbing the atmosphere of the cities.

Likely to Sell Out

From Florence: Tour to Siena and San Gimignano by Minivan

Chianti & Montalcino Wine Tour from San Gimignano

4.8

(5)

from $238

Likely to Sell Out

Break from the hustle and bustle of Florence for a tour into the heart of the Tuscan countryside. On this small-group excursion, visit the villages of Certaldo and Monteriggioni, learn to make authentic Tuscan dishes during a cooking class, and sample several Chianti wines during a guided tasting and lunch. This tour includes a balanced mix of guided exploration with free time at each destination.

(4)

from $168

Tuscany Tour from Florence: Small Group Wine & Lunch

11 hours 30 minutesFree Cancellation

4.4

(770)

from $167

Montecatini Terme cycle and wine tasting visit

5 hoursFree Cancellation

From Florence: Tuscany Wine & Oil Tour with typical Tuscan Meal

(21)

from $204

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Top Attractions in Tuscany

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What are people saying about Tuscany

Louise_M, May 2026

An absolute must when visiting Florence.

An absolute must when visiting Florence. Our guide was very knowledgeable, personable and funny. We stopped at three wineries where we tasted delicious wines, olive oil and learned about the process to make both. Communication with tour company was easy and finding the meeting point was no trouble at all. Would do this tour again

Florence: Cinque Terre Park Day Trip with Optional Pisa

Nina_T, May 2026

Absolutely worth it!

The tour was absolutely amazing and super fun!!! The weather was perfect for pictures! We got to taste amazing food, but my favorite part was getting to walk by the ocean. Our tour guide John, was also amazing. I would totally recommend getting him as your tour guide! We only missed out on one city, because it was raining the day we went so we couldn’t go on the boat ride. But, we got extra time at the other places to make up.

Full day Shore Excursion to Florence from Livorno with tasting

Sarah_D, May 2026

Great tour guide, tight...

Great tour guide, tight time limits. Our tour guide Ignacio was THE BEST we have ever had. He had physical maps marked with colored in pathways based on sights/experiences handed to us and a what’s app group to join for announcements from him along with pinned map locations for Google Maps. So organized. The bummer was we only booked Florence to have more time there and not enough people chose that so they cancelled but offered the Florence/pisa combo to us at no extra charge. We didn’t have much other options so we said yes. Pisa took needed time from Florence. Florence was very rushed and we wish we had the wiggle room that 1.5 hours of time in Pisa and boarding buses took from us. But what can you do with 1 day on a cruise? Ignacio is fantastic and he did a GREAT job.

From Florence: Tuscany Wine Country Day Trip with Vineyard Lunch

Wendy_F, Apr 2026

A must do!!!

Absolutely wonderful adventure. Sienna and San Giamno were absolutely gorgeous. Our tour guide Fredericka and driver Chio shared wonderful information and provided a very relaxed and beautiful tour. The winery was EXCELLENT!!!! Very well done. Our sommelier, David, at the winery was extremely knowledgeable and the food and wines were delicious. Just a beautiful day! Highly recommend.

Siena and San Gimignano: Small-Group Tour with Lunch from Florence

Lauren_C, Apr 2026

Excellent day trip

The side trips to Siena and San Gimignano from Florence was a highlight of our trip. I thought the winery would be my favorite part of the day but Siena stole the show. At first, I didn’t love the early departure time but am so glad we were to Siena early. When we walked around, it was almost as if we had it to ourselves and the history and culture there are amazing. By the time we left, it was much busier. The winery meal was excellent and they were knowledgeable about ingredients so that I could eat despite allergies. The wine was great and the views were breathtaking. We sat family style and had fun with others on the tour. They spent time explaining both the wines and the olive oils. We walked to the top of San Gimignano and enjoyed a glass of wine which I recommend, although others really enjoyed their gelato. Lorenzo, our tour guide, was excellent. Very knowledgeable and attentive from start to finish. Had plenty of recommendations for how to spend free time and made everyone feel comfortable being able to navigate to the meeting points. Other info that may be helpful if booking: - we were in a small air conditioned coach. Each seat had the ability to charge a device via the ceiling, which helped with all the pictures we took. -really pay attention to the directions to arrive at the meeting point in Florence. The route Google Maps originally suggested would not have worked (goes through train station) and I only knew that because I read their instructions to not use that route.

Cinque Terre and Pisa Tower Tour from Florence Semi Private

Janelle_B, Apr 2026

Perfect for a couple or a small group

Booked a semi private tour so we didn't have to trail behind a huge crowd all day, and could venture around freely. Our driver/chauffer Lapo was very kind, friendly, and kept us on track for the day. He also had great recommendations for restaurants and shared a wealth of knowledge and history of each place we visited. Thanks again for the amazing tour.

Florence Day Trip to Siena & San Gimignano with Scenic Views

Jill_M, Apr 2026

Fantastic day! We were...

Fantastic day! We were two couples and thoroughly enjoyed the tour! The bus was comfortable, the driver and tour guide were both excellent. Everything was easy to follow and clearly communicated! We enjoyed our time in both places and even when there was an issue in the town with a totally separate tour company’s bus breaking down and cause a traffic jam, our guide kept us informed and she arranged an alternate route and we only lost 10 minutes! We had a great time! Highly recommend!

Full day shore excursion to Florence and Pisa from Livorno with tasting

Gail_T, Apr 2026

Pisa and Florence with Igna

It’s a great experience. If you want to go into the Bapistry or Durmo get priority tickets as the lines were huge. Drink plenty of water. Igna was a great guide. Very knowledgeable and very funny. Loved his little personal stories. He made us feel as if we’d known him forever.

Florence Day Trip: Pisa, San Gimignano and Siena with Lunch

Lisa_S, Apr 2026

Worthwhile tour of the Tuscany region

This was an excellent trip. There was a lot of walking up and down hills, so be prepared for that. We took beautiful photos on a perfect weather day. Marco and Julia and one other guide, whom I have forgotten her name, sorry, we're excellent and extremely helpful and friendly. Even when tour was completed, they helped us use the tram. Our favorite part of the trip was the wine tasting and lunch at Poggio ai laghi vineyard. By the time we reached Pisa, we took our photos with the tower and then sat near the leaning tower with a Gelato. Perfect day. Perhaps the only unforseen problem was traffic, perhaps an accident, on our return trip to Florence which took approximately 1 additional hour. We would highly recommend this tour.

Full Day Tour to Val d'Orcia and Gladiator's Fields with Wines

Nikolaos_S, Oct 2025

Get ready for an...

Get ready for an unexpected beauty!! Fantastic landscape and meeting with wine producers with centuries long experience. On top of that we would like to stress the excellent, gentle and sensitive guidance of Gianmarco and also the professional and skillful driving of Cosimo! Highly recommended tour!!