Top Florence Day Trips - page 8

Montepulciano, Montalcino, Pienza from Florence

(17)

from $478

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

4.7

(74)

6 hours 30 minutesFree Cancellation

from $202

Treat your senses to a memorable day in the world-famous Chianti wine region on this private tour from Florence. Travel in a luxury minivan through a landscape of historic vineyards, rolling hills and medieval villages, with a private driver at your disposal throughout the day. Taste renowned Chianti wines and authentic Tuscan cuisine at estates of your choosing, or let your local driver make suggestions for the best places to wine, dine and explore.

Chianti Vineyards Tours in Private Luxury Van from Florence

(20)

from $826

Get a taster of Tuscany on this private tour that features a selection of the region's highlights. Visit Siena, the Chianti countryside, and San Gimignano all in the same day, without having to hire your own car. Enjoy an itinerary that includes historic sightseeing and regional wineries, with the option to try local varietals (extra cost). Ideal for travellers who are only in the area for a short time.

Likely to Sell Out

Private Tour of Chianti Siena and San Gimignano by Minivan

(74)

8 to 9 hoursFree Cancellation

from $777

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

(107)

7 hours 30 minutesFree Cancellation

from $191

Savor the sights and tastes of Tuscany on this private wine-tasting tour of the famed Chianti region. From Florence, journey across the Chianti hills, covered with vineyards and olive groves, toward Greve where you will make a first stop before heading for a respected Chianti winery to visit the cellars and learn about the production methods of the Chianti Classico. After a Tuscan-style lunch paired with wine, you'll head towards a second Chianti winery for another wine tasting.

Chianti Wine Tour - Private Wine experience in Tuscany Countryside

(19)

from $754

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.

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

(3)

from $406

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

(20)

5 hours 30 minutesFree Cancellation

from $371

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

(5)

Skip the stress of following a map along Tuscany's winding country roads on this guided bicycle tour through the picturesque Chianti hills. Travel by van to the heart of the famous wine region, where you’ll climb on a bike to follow your guide for a day of adventure. Take in picture-perfect vistas and stop at a family-run winery for a tour of the cellar and traditional Tuscan lunch with wine tasting before the return van ride back to Florence.

from $238

Full-Day Tuscan Countryside Bike Tour

4.5

(26)

5 hoursFree Cancellation

from $178

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

4.2

(5)

from $873

Getting around Tuscany by public transport can be daunting. Skip the hassle of coordinating train and bus schedules and cover two top Tuscan towns in a single day with this San Gimignano and Siena tour. Explore the medieval old town of San Gimignano and enjoy a wine tasting before continuing on to Siena. Skip the line to enter the magnificent cathedral and explore the sights, shops, and eateries at your own pace.

Florence: San Gimignano & Siena Tasting Experience

4.5

(14)

Discover a piece of ancient Tuscany with this hassle-free private round-trip transfer from Florence to San Gimignano. Set off from your Florence hotel for the idyllic small town that transports you back to the Middle Ages with its perfectly preserved center. Enjoy a few hours of free time to explore the city walls and five impressive entrance gates plus well-preserved old town. Then simply sit back, relax, and enjoy the return ride to your Florence hotel.

from $120

Private car trip to San Gimignano from Florence (4 h)

(1)

4 to 5 hoursFree Cancellation

from $717

Avoid the hassle of trying to navigate your way around the Tuscan countryside and visit two top wineries in a single day with this small-group Chianti wine tour. Leave the driving to a professional and sip worry-free as you stop to sample local reds and whites at traditional cellars in the hills of Tuscany. Learn more about the area's wine-producing history and culture plus enjoy a tasting lunch while taking in views over the Chianti countryside.

Small group Chianti-side wine tour with Mercedes V class Van

(44)

5 hoursFree Cancellation

from $335

Spend a day in Tuscany visiting the city of Siena, the castle of Monteriggioni and the medieval village of San Gimignano. With a private English speaking driver, you will enjoy greater flexibility in your itinerary with plenty of free time. Enjoy a walk through the historic center of Siena then have fun tasting the famous Chianti wine with a lunch in a family-run winery (tasting and lunch not included in the price) and then admire the view of the Tuscan countryside from San Gimignano where you can taste the best ice cream in Italy. Finish the tour with a visit to Piazzale Michelangelo before returning to Florence.

Private tour Siena, San Gimignano and Monteriggioni, lunch in the cellar

(9)

8 to 9 hoursFree Cancellation

from $920

Taste your way through Tuscan wine country on a private, full-day tour from Florence. Travel through the scenic Orcia Valley and visit the birthplaces of several prized Italian wines. Explore the medieval villages, tour historic wine cellars and vineyards, or savor a farm-fresh lunch (own expense): your private driver and guide customizes the itinerary for you. Price is per group, based on a maximum of 7 passengers per vehicle.

Private Tour: Orcia Valley to Montalcino and Montepulciano with Brunello Wine Tasting

(16)

from $1,180

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

(3)

6 to 7 hoursFree Cancellation

from $380

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.

Tuscany Tour from Florence: Small Group Wine & Lunch

4.4

(770)

11 hours 30 minutesFree Cancellation

from $166

Embark on an unforgettable Chianti adventure with a private tour from our office, where you will be greeted by your experienced local guide and driver in an exclusive vehicle. Your journey begins at Tenuta Le Lame, a historic family-run winery nestled in the lush Chianti hills. Then, enjoy a traditional Tuscan lunch at "La Cantinetta di Rignana", a pretty restaurant nestled in the Tuscan hills of Greve in Chianti. Here, you can sample local specialties such as cold cuts, cheeses, Tuscan croutons, extra virgin olive oil and homemade pasta or meat dishes, all paired with fantastic regional wines. The last stop on the tour is the Castello di Brolio, where you will take a private tour of the castle and its vineyards, steeped in history as the Baron Ricasoli family has been producing exceptional wines since the 12th century. At the end of the visit you can taste fantastic wines in the exclusive wine shop located at the foot of the castle

Chianti Winery + Brolio Castle Private Tour

(6)

from $687

Visit the historic town of San Gimignano and discover a hidden gem— local wineries where the views are almost as good as the wine. Enjoy wandering through two wineries, take in views of the vineyards and the surrounding rolling countryside, and learn about how wine is made. Then taste some of the local wine with your hosts, and visit the cellars where wine is kept in wooden barrels to age.

Bella Toscana - San Gimignano plus 2 Chianti Wineries and lunch

(13)

from $447

Experience the treasures of Tuscany on a private day trip from Florence. Travel by luxury minivan through countryside full of historic vineyards, medieval villages, and olive groves. Visit the charming medieval city of Siena and the town of Montalcino. Your professional, English-speaking driver shares local history and can recommend the best places to visit, shop, and dine for a customized experience.

Private Tour to Siena and Montalcino from Florence

(5)

from $1,016

Spend a day experiencing Tuscany on your own terms, without the hassle of renting a car. This tour will take you to the region, where you’ll enjoy free time to explore the towns of Pisa and Lucca. Wander in Tuscan villages, explore history, and see medieval architecture. You'll also have the option to head to a family-run winery for a traditional Tuscan meal and guided wine tasting (for an additional fee).

Pisa and Lucca Tour from Florence

(9)

from $1,097

Savor Italy’s finest flavors on a private gastronomic tour from Florence. Travel to Parma, where a local dairy reveals the secrets of authentic Parmigiano Reggiano cheese, and enjoy a guided tasting. Head to a producer of prosciutto for a second sampling experience and enjoy a light lunch of regional specialties such as salami and local wine. Finish your day in Modena to explore the world of traditional balsamic vinegar.

From Florence: Balsamic Vinegar, Parmigiano Reggiano & Prosciutto

(2)

10 hoursFree Cancellation

from $663

Discover the essence of Tuscany on this immersive wine tour through the beautiful Chianti region. Visit three distinct wineries, where you'll explore traditional vineyards and enjoy multiple tastings of exquisite Chianti wines. Savor a sumptuous Tuscan lunch featuring homemade pasta and local delicacies, paired perfectly with the wines. With a knowledgeable guide leading the way, you’ll learn about the art of winemaking while soaking in the stunning countryside views. Perfect for adults seeking a delightful day of wine and camaraderie.

Likely to Sell Out

Small-Group Tuscany Wine Tour: 3 Wineries and Traditional Lunch

(1)

6 to 7 hoursFree Cancellation

from $215

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Top Attractions in Florence

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Michelangelo’s David statue at the Accademia Gallery in Florence, Italy.

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What are people saying about Florence

The Best Tour in Florence: Renaissance and Medici Tales

Erin_W, Apr 2026

Alberto is a great guide!

Alberto was a fantastic guide. He made sure we all understood clearly what he was teaching us, he showed us the city highlights, told about the history of the Medici family, and gave us great advice on other places to visit in Florence and made great recommendations. He was funny and entertaining and most importantly did not bore my teenagers.

From Florence: Cinque Terre & Pisa Day Trip

Don_R, Apr 2026

It was a great day,...

It was a great day, despite dampening weather that is due to how Nathan guided us from the start to the end. Nathan was very clear with instructionss, timing and best way to maximise the experience. He even provided recommendations for great restaurants.

Cinque Terre Day Trip with Optional Hiking or Pisa

Autumn_P, Apr 2026

Very well organized

We loved this tour! They were so well organized and we got to see all 5 towns. There was free time at each location so we also got to choose what our day was like. The meeting points throughout the day were clear and communication was great. Jo was an amazing tour guide!

Uffizi Gallery Small Group Tour with Guide

Ashley_C, Apr 2026

Excellent tour with Guido!

This was a great way to get an in-depth experience for the Ufizzi Gallery and to learn a lot about Florence, the Medicis and the art in the museum. Our guide Guido was so knowledgeable and engaging, and managed the crowds with ease! Even at 9 am the museum was very crowded, but this helped us to skip most of the line. He even took time after the tour for other Florence suggestions for our trip. Highly recommend this tour!

SMALL-GROUP Wine Safari: Tuscany Wine Tasting Tour from Florence

Jonathan_C, Apr 2026

Christoff and Alessandro...

Christoff and Alessandro were great. They took us on a bus through the Tuscan hills to a winery in the Chianti classico region. Alessandro explained the history of the region and the grapes very well. After the winery they took us to a restaurant in the area with a great view of all the wineries. Would highly recommend for anyone looking to a do wine tour while in Florence.

Tuscany: Day Trip to Pisa, Siena, San Gimignano, and Chianti

Tenia_K, Apr 2026

Taste of Tuscany

The experience was amazing! The guide who escorted us on the bus was fantastic,.his name is Aaron with caf tours in Florence as well the driver, Enrico. We got lost atvsome point and Aaron was so polite and supportive. The guided tour in Siena was also really good, full of information and fhe ancient spirit of the town. We would definitely recommend this tour if you don't have a lot of time to see Tuscany

Half day Chianti Vineyard Escape from Florence with Wine Tastings

Lori_Q, Apr 2026

Wine tour

It was very nice. The tour guide told stories about the area while driving. It was an hour and a half ride out but she only talked at the beginning giving people time to enjoy a quiet ride. The wine locations were very nice. The host at Grace winery did a fantastic job telling about the vineyards and wine business. And I loved the set up in both locations where they did the tastings.

Cinque Terre and Pisa Full Day Tour from Florence

Tracy_L, Apr 2026

Cinque Terre and Pisa are worth the time to visit!

In the spring, be prepared for cool to warm weather. Get a cappuccino and cornetto from the food station before your departure, so yummy! Wear sunblock is you don't want a little sun kiss. Bring a collapsible shopping bag over a backpack. Have a few 1€ coins for public toilet. Don't forget to get the train ticket package. Be willing to put your toes in the ocean. Buy the scarf or linen outfit. The train experience was such fun! If you get Jon Marco, you won't be disappointed! When you return, the taxi stand is just in front of the train station, so convenient!

Siena, San Gimignano and Chianti Wines Day Tour from Florence

Amy_K, Mar 2026

Great trip!

Excellent experience.... loved this day trip! San Gimignano was my favorite and would have loved more time there. Also...take the umbrella or poncho... you never know when they'll be a downpour on a 0% chance rain day. 😂 You ARE allowed to leave things on the bus, so you won't have to carry them around every stop.

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

Joel_D, Mar 2026

Easy half day tour of Cathedral and tower of Pisa

After meeting our guide it was a seamless experience traveling by bus and then walking to the town square of Pisa. The cathedral was breathtaking! Our guide even had storage lockers preserved for our bags while we climbed the leaning bell tower. We had adequate free time to continue exploring on our own and to take more pictures. We arrived on schedule back to Florence. Highly recommend for a half day trip from Florence!