Top Tuscany Day Trips - page 8

Chianti Vineyards Tours in Private Luxury Van from Florence

(21)

from $834

Get up close and personal with Tuscany’s ineffable scenery, and explore with ease, on a full-day tour by electric bike. Meet your guide in Siena, get familiar with your bike and helmet, and head into the Chianti Hills. With just a small group for company, set off on a tour of the countryside, visit a restored monastery, and head to a local farm/winery, where you can enjoy a traditional meal and generous wine tasting.

Small Group E-Bike Chianti Tour with farm lunch from Siena

Small Group E-Bike Chianti Tour with farm lunch from Siena

6 hoursFree Cancellation

4.8

(37)

from $223

Hiking Tuscany & Chianti Wine - 3 Organic Wineries with lunch

Escape far from the crowds and traffic—and enjoy an immersive way to explore the iconic Chianti countryside that few other visitors get to experience—on this small-group, full-day hiking tour from Florence. Ramble for 4 miles (7 kilometers) on trails through vineyards and olive groves to really soak up the scenery. Along the way, visit three wineries to sample up to 10 wines, and enjoy Tuscan specialties for lunch.

Hiking Tuscany & Chianti Wine - 3 Organic Wineries with lunch

Chianti Classico E-Bike Tour

(30)

from $234

5 to 6 hoursFree Cancellation

(25)

from $305

Pisa, Vinci, Tuscany, Wine tasting all in one day! - Small Group

Strike out beyond Lucca’s medieval city walls and explore the countryside on two wheels with this self-guided bike rental. Get fitted for your bike and download your app-based itinerary in Lucca, then set off on your own to discover historic villas and gardens in the surrounding countryside. Pedal along the Via Francigena that skies the Serchio River past Villa Oliva, Villa Grabau, and Villa Reale.

(10)

from $211

Self guided bike tour in the nature to Villa Reale

Self guided bike tour in the nature to Villa Reale

4 to 7 hoursFree Cancellation

4.5

(8)

from $34

Orvieto, Civita di Bagnoregio, Pitigliano PRIVATE TOUR from FLORENCE

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

(3)

from $728

Private Siena & San Gimignano Day from Florence with Chauffeur

(5)

from $705

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

From Florence: Classic Chianti Villages and Wine Roads by Minivan

6 hours 30 minutesFree Cancellation

4.7

(77)

from $199

Make exploring beyond Florence city limits simple—and visit two other highlights of Tuscany, all in one day—on this seamless, private tour. Following pickup from your hotel, head to Pisa to see its famous Leaning Tower—a UNESCO World Heritage Site—as well as the huge cathedral adjacent. Then, in Lucca, walk its historic city walls, and see some of its most notable Renaissance architecture (admission tickets own expense).

Private Tour: Pisa and Lucca from Florence

Private Tour: Pisa and Lucca from Florence

4.2

(5)

from $858

The historic town of Pietrasanta and massive Carrara marble quarries are two of the top sights near the Tuscan coastline, but both are a challenge to reach with public transportation. With this private day trip, skip the hassle of arranging tricky logistics and explore with a private driver directly from Lucca. Enjoy easy pickup at your Lucca hotel and round-trip transport to both destinations, with free time to explore at your own pace.

Likely to Sell Out

The Carrara Marble Quarries where Michelangelo selected his marble for sculptures David in Florence and La Pietà in Rome

Lucca Private Day Trip to Pietrasanta and the Cararra Marble Quarries

9 hoursFree Cancellation

(4)

from $905

One of the most picturesque corners of Tuscany, Bolgheri is a delightful respite from the crowds. With this tour, skip the hassle of trains and buses and instead relax and enjoy the countryside views during the drive from Livorno. Follow the Cypress Avenue into the medieval center to explore and have lunch on your own. On the return drive, stop for a stroll through the village of Castagneto Carducci.

Wine Tour Bolgheri Half Day Shore Excursion from Livorno Port

9 hoursFree Cancellation

(4)

from $885

Discover the picturesque wine region of Chianti on a half-day excursion from Siena. Enjoy the Tuscan scenery of gently undulating hills and vineyards while tasting Chianti wines. A day journey from Siena to the Chianti region allows you to experience the gorgeous Tuscan landscape. Begin with a visit to Castellina in Chianti, followed by a wine tasting at a nearby vineyard. Immerse yourself in the bright colors of the rolling hills, where the views, smells, and flavors of the region will captivate your senses. Enjoy a stroll in Monteriggioni, a medieval village where time seems to stop. Proceed to another winery in the heart of the Chianti Classico region, where you can have a second wine tasting and sample extra virgin olive oil. A return trip to Siena marks the end of the excursion.

Chianti and Castles Tour from Siena Small Group

Chianti and Castles Tour from Siena Small Group

5 hoursFree Cancellation

3.6

(7)

from $100

Farm To table Experience on an organic hilltop estate in Tuscany

Trade the bustle of Florence for tranquil Tuscany—and enjoy a fully personalized, private experience—on this full-day farm tour and cooking class. With just your guide for company, travel by train (tickets own expense) to an idyllic organic farm. You’ll explore the vineyards and olive groves, pick ingredients, and prepare a farm-fresh lunch with your hosts’ guidance. Then, enjoy it together with accompanying beverages—and have free time to swim or explore later.

Farm To table Experience on an organic hilltop estate in Tuscany

7 hours 30 minutesFree Cancellation

Leave the city’s clatter behind for the serene hum of Tuscany! What sets us apart? First, the "Visual Wine Story": inside a historic family cellar, history literally shimmers on the ancient stone walls through an enchanting interactive projection. You won’t just taste wine; you’ll see its soul come to life. Second, the effortless "zip": our premium e-bikes do the hard work. You’ll glide up to Piazzale Michelangelo for that "wow" skyline shot and through rustling cypress lanes without breaking a sweat. Finally, the "Golden Schedule": we start at 9:30 AM and breezy-glide back by late morning. While others are just starting their bus tours, you’ve already savored 3 boutique wines and a fragrant farm lunch. You return refreshed, inspired, and with the entire afternoon free to roam Florence. It’s the ultimate time-saver with zero compromise on authenticity!

(155)

from $188

Morning Chianti E-Bike: Immersive Wine Experience & Local Lunch

Morning Chianti E-Bike: Immersive Wine Experience & Local Lunch

5 hoursFree Cancellation

4.6

(5)

from $140

Siena - San Gimignano Private Tour

4.9

(14)

from $646

PISA HALF-DAY: from Florence by minivan with Leaning Tower ticket

5 hoursFree Cancellation

4.7

(6)

from $376

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

Super Chianti 2 wineries & meat feast @ Dario Cecchini—max 8 pp

4.8

(6)

from $234

7 hours

Trade Florence’s bustle for a day in the picturesque Chianti wine region: this small-group tour makes it easy to explore the Italian countryside. Meet your group in central Florence and head out of town in the comfort of an air-conditioned minivan. Over the course of the day, you’ll visit two esteemed area wineries, will go behind the scenes and learn how wine is produced and aged, and will enjoy ample opportunities to taste the region’s varietals. This tour also includes a delectable, 2-course lunch.

(298)

from $323

Full-Day Tuscany Castles Tour with Wine Tasting from Florence

6 to 7 hours

(55)

from $329

Visit the Italian cities of Pisa and Lucca on this private tour from Florence. Visit the Leaning Tower of Pisa, part of the World Heritage–listed Piazza dei Miracoli, the Cathedral, Baptistery, and the Monumental Graveyard in Pisa. Then head to Lucca to see Guinigi Tower, an example of Romanesque-Gothic architecture for more insight into Tuscan culture and history. Go beyond the guidebooks with insider knowledge from your guide.

Full-Day Private Pisa and Lucca Tour with optional Leaning Tower

Full-Day Private Pisa and Lucca Tour with optional Leaning Tower

4.6

(20)

from $464

Private Chianti wine tour

5 hours

4.9

(72)

from $505

Swap the busy streets of Florence for the tranquility of rural Tuscany on a private day trip to San Gimignano. A private tour means you can customize your itinerary according to your interests while also receiving the undivided attention of your guide. Plus, letting someone else drive means that you’ll be able to spend less time navigating and more time focusing on the rolling vineyards of Tuscany.

Private Tuscany Day Tour: San Gimignano and Chianti Wine Region from Florence

Immerse yourself in the Chianti region’s spectacular scenery, discover its historic and picturesque villages, and even visit one of its highlight wineries, all in just half a day: this electric-bike tour makes exploring simple. In the morning, set off with just a small group for company: you’ll see the Castello di Montefioralle, will visit the Abbey of Badia di Passignano, and will enjoy wine tastings and lunch at a local winery.

(10)

from $403

Discovering Chianti, e-bike tour - daily experience

Discovering Chianti, e-bike tour - daily experience

6 hoursFree Cancellation

Tuscany Small Group Tour: Siena & San Gimignano with Winery Lunch

(20)

from $329

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Top Attractions in Tuscany

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What are people saying about Tuscany

Tanya_J, Jul 2026

A delightful day in Tuscany.

A fabulous tour, with a fun and friendly team. Our guide, Alyssa was very sweet, and Mike, the driver was great too. Carlos, our guide in Siena was very knowledgeable, and really brought the history and traditions alive, making us want to return someday to experience the horse race! The additional optional tour with Carlos into the Cathedral was definitely worth it. Our free time exploring San Gimignano was just right, and the lunch was good. The timing for everything and the overall length of the tour was perfect.

Florence Vintage Fiat 500 Tour: Tuscan Hills, Food & Chianti Wine

Brandon_S, Jul 2026

A great experience, such a cool memory.

What a cool experience we will remember forever. We travel a lot and this was such a great memory we will never forget. Who else can say they drove through the Italian countryside in a vintage fiat? Im 6'3 I fit no problem although only the wife knew how to drive a stick so I was passenger princess for the day. Our tour guides ella and Chris were second to none. They were patient with everyone and even people who were hesitant about driving a manual ended up doing great after a quick test drive with the instructor (which everyone driving will have to do). They slso had electric fiats if all else failed anf you didnt feel comfortable with the vintage car Very safe, our route had very little traffic. We visited a beautiful monastery in addition to lunch with a few. Book it, you wont regret it. Dont forget to bring your license!

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

Tuongvi_V, Jul 2026

This was an incredible...

This was an incredible experience. Our guides Ignacio and Omi were so knowledgeable and helpful, and the driver Luca was very good too. What I was most impressed with was the organization of the tour. They provided recommended routes and restaurants that allow you to maximize your time in both Florence and Pisa, which is great if you’re coming in totally new. Everything was very clearly communicated and the timing/logistics were very tight, ensuring a stress-free experience. The guides were very helpful as well with practical things such as letting us know how and what tickets to book, where bathrooms were located, as well as providing commentary throughout. Finally, we really appreciated that options for minimizing long walks to the attractions were provided, especially in the summer heat. The excursion even took us directly back to the boat. A very stress free, organized and enjoyable experience. I would highly recommend this excursion!

Cinque Terre and Pisa Full Day Tour from Florence

Patricia_D, Jul 2026

Cinque Terre/Pisa

Cinque Terre/Pisa Tour was amazing! Our tour guide, John was so helpful, friendly and extremely knowledgeable! We toured 2 Villages in Cinque Terre & also visited Pisa. The bus & train rides were air conditioned and comfortable! The day was managed in a very timely fashion. I would highly recommend this tour!

Cinque Terre and Pisa Tower Tour from Florence Semi Private

mathew_r, Jul 2026

stress free experience in the cinque terre

stress free experience, totally beats taking transit or a large coach. you load up in the Mercedes van early in the morning and your guide handles the rest. once you arrive in the region its fairly self guided with the only caveat being a predetermined meet point and time. our guide, Giancarlo was wonderful and I would 100% recommend this to anyone who wants a stress free travel experience.

San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch

Chris_B, Jul 2026

Fun time across Tuscany

This was a great experience if you like great views from medieval like towns. We had a great time exploring these small towns and enjoyed the lunch and wine we were served. If you’re looking for a trip around Tuscany and don’t want to drive around yourself, this is a great option! Our tour guide Aaron was funny and well informed and our bus driver Elis provided a great ride!

From Florence: Tuscany Wine Country Day Trip with Vineyard Lunch

JuanPablo_C, Jul 2026

Amazing Day Tour for family and friends

Federica and the bus driver Chito were amazing. Very welcoming and informative. The tour was very nice, had enough time to explore the cities and have fun at the winery. The winery was also really good! This tour is great to do a lot in one day. We got back around 6:00 PM so still got to enjoy the evening in Florence.

Half-Day Excursion to Pisa and the Leaning Tower from Florence

Judith_S, Jun 2026

Very good experience!!

Everything was great!! The bus was comfortable and even though was a very hot day it felt cool Inside. The guide Federica explained everything in a good manner and with very good pronunciation. We booked everything we could do in Pisa and it is a little bit much because you don’t really have time to sit and eat peacefully. But everything was great.

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

Mauricio_F, Jun 2026

I booked this tour 12...

I booked this tour 12 hours before it started, because an earlier tour had been canceled due to local strikes at the train stations. My family and I couldn’t be any happier with the outcome and the decision that we made. Manolo and Emiliano became family by the end of the tour. Emiliano got us safely from desperate to destination, despite heavy traffic and some sort of local race that was going on. Manolo kept the group entertained, had excellent information, mixed in a lot of humor, and kept everyone from the very young to the very old completely engaged during our times on the bus. I highly recommend this tour to everyone, and hopefully you will also be fortunate enough to have Emiliano and Manolo lead your tour.

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

Miroslava_P, Mar 2026

Tuscan countryside

I loved the trip to Tuscan countryside with winetasting experience. Little villages had a charm. I loved countryside scenery watching from the minibus. So worth it. Our guide Antonio was very attentive and friendly. And I am grateful to our driver for a safe journey. Thank you both. PS. I felt like Picorino icecream in Pienza was one of the best icecreams I tried in Tuscan region. It had a strong yogurty taste and it was a bit salty. Unusual, but delicious. I had to treat myself to 2nd one.

Cinque Terre Full Day Tour with Optional Pisa Stop from Florence

Alison_J, Feb 2026

This was such an amazing...

This was such an amazing tour. We got to see 4 of the 5 villages and explore them at our own pace - our guide Constantino was FABULOUS and gave us a lot of information about the villages before we ventured out into them on our own. REALLY loved the independence you get to see everything you want. This tour was the best part of our trip!