Top Florence Day Trips - page 6

Half-day Chianti Classico Wine tour from Florence - Small Group

(16)

5 hoursFree Cancellation

from $180

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

(27)

Experience the best of Chianti from its historic hill towns and rolling landscape to its storied wineries in a single day with this private driving tour. Save hours with a dedicated driver, leaving you time to fit in visits to both San Gimignano and Monteriggioni. Break up your sightseeing with a wine-tasting lunch at a Tuscan farm and cap off your day with a Chianti winery tour and tasting.

from $239

San Gimignano view (Original photo of our tours)

PRIVATE TOUR "Sweet Hills of Chianti and San Gimignano" with Lunch & 2 Tastings

(2)

from $300

Tuscany Highlights Guided Small-Group Tour from Florence

4.5

(36)

11 hours 30 minutesFree Cancellation

from $191

Tuscany Wine Tour: 2 Wineries & Chianti from San Gimignano

Wine Tasting tour from San Gimignano area

4.8

(66)

6 hoursFree Cancellation

from $180

HALF-DAY: Chianti Classic Tour with Wine Experience & visit of San Gimignano

(4)

5 hoursFree Cancellation

from $156

Spend a full day exploring a trio of Tuscany’s best-preserved medieval cities on a private day trip from Florence. Skip the stress of renting a car and let a personal chauffeur take your group directly from your hotel door through the Tuscan countryside and into the historic centers of Siena, San Gimignano, and Pisa. Explore the cities at your own pace, with the help of tips and local guidance from your driver.

Private Tour: Siena, San Gimignano and Pisa Day Trip from Florence

4.5

(2)

from $1,057

Explore the Chianti countryside on this full-day private tour of Siena and San Gimignano. Departing from Florence, head first to Siena for a walking tour of the city’s medieval streets. Admire the palaces and Piazza del Campo, followed by time to explore independently. Then travel via the fortified village of Monteriggioni to the town of San Gimignano and discover the medieval architecture and art on your own before heading back to Florence.

Private Excursion to Siena, San Gimignano and Chianti Landscapes

4.8

(23)

from $677

The Val d’Orcia is one of Tuscany's most picturesque areas, but scarce public transportation and confusing rural roads make exploring on your own tricky. Leave the driving to a professional and focus on views of the UNESCO-listed landscape on this tour of Pienza and Montepulciano from Florence. Marvel at historic architecture and rolling hills, plus enjoy a light lunch and tasting of local Vino Nobile di Montepulciano wines.

Private Tour: Medieval Val d'Orcia by Minivan from Florence

(8)

from $503

Taste some of Tuscany's most renowned varietals on a full-day private Chianti wine tour from Florence. Visit the charming medieval towns of Montalcino, Montepulciano, and Greve, where historic castles and towers appear untouched by time. In each village, stop at wineries and wine bars to sample pours of Nobile, Brunello, and Chianti Classico wines and learn about the cultivation of these prized grapes.

Piazza Grande, Montepulciano- Vino Nobile

The Complete Wine Tour Brunello, Nobile, Chianti wine experience

4.0

(7)

10 hoursFree Cancellation

from $474

Take a break from the crowds of Florence and discover Arezzo and Cortona on a private 9-hour. All-inclusive private transportation from your hotel allows you to comfortably see a long list of attractions in a short amount of time. Visit historical sites, including the 9th-century Etruscan Atrium, as well as filming locations for “Life is Beautiful” and “Under the Tuscan Sun”. Enjoy ample free time to explore both Tuscan towns.

Private tour from Florence to Cortona and Arezzo

4.0

(3)

from $390

Private Full-Day Tour of Assisi and Cortona from Florence

4.7

(23)

10 hoursFree Cancellation

from $654

Explore the Tuscan countryside on this full-day outing to the Italian countryside from Florence to discover the region's wine-making culture. Visit the medieval hill town of Montalcino for a stroll through its streets. Then, continue to Montepulciano—which is famous for the variety of grapes that bear its name—for a wine tasting and a visit to the underground city. On the return journey, drive through the UNESCO-listed Val d’Orcia and make a couple of panoramic stops.

Private tour Brunello di Montalcino and Nobile di Montepulciano wine experience in Tuscany

4.5

(8)

from $498

Private Chianti wine tour

(56)

5 hours

from $516

Experience Tuscany's wine culture on this private wineries tour. Ideal for travelers based in Florence, explore beyond the city without having to hire a car. Travel with a knowledgeable sommelier guide through rolling hills and vineyards, visiting three estates to sample regional wines and olive oil. Enjoy a traditional Tuscan lunch at a family-owned winery paired with wine. Perfect for food lovers looking to immerse themselves in local flavors.

Exclusive Private Tuscany Wine Tour & Food Pairing Session

(70)

from $600

Bike along the rolling hills of Tuscany’s Chianti region as you follow a GPS route and go at your own pace from Florence without getting lost. An e-bike will help with the steeper hills and the map will guide you to beautiful sights, including Machiavelli’s home, a monastery, and beautiful olive oil farms and vineyards. You can stop at one for lunch (not included), or be flexible and explore more.

Special Offer

Enjoy lunch at a farm or anywhere you prefer along the route!

E-bike Tuscany and Chianti Self-Guided Tour with Vineyard Visit

(8)

6 to 7 hoursFree Cancellation

from

$27

$30

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

4.6

(20)

from $474

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 $372

Immerse yourself in Italian automotive history—and come face-to-face with world-famous sports cars and icons of Italian design—on this full-day, private tour. Following pickup from your Tuscany accommodation, travel with your guide in a comfortable, private vehicle. You’ll browse the collections at three top venues—the Museo Ferrari, the Museo Ferruccio Lamborghini, and the Panini Motor Museum—will enjoy a lunch stop in between, and can even upgrade to drive a Ferrari in Maranello.

A Day of Classic Motors - Ferrari, Maserati & Lamborghini museums - private tour

(32)

from $534

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 $877

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 $925

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 $203

From Florence: Cinque Terre & Pisa Day Trip

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Top Attractions in Florence

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

Attractions

What are people saying about Florence

Steven_R, Apr 2026

High Cinque for a perfect day trip

A fabulous day. Cinque Terra is amazing and experiencing the local cuisine, produce and treats was as fabulous as the towns themselves. Such beautiful scenery and lots of time to explore and absorb each location. Pisa was also a great experience, especially climbing the tower. It is much more impressive than I imagined. Elizabeth was the perfect guide and it was probably our favourite day of our holiday so far.

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

John_C, Apr 2026

Our guide Jordano was...

Our guide Jordano was knowledgeable about the area and fun. The 4x4 was great to ride in. The winery where we had our tasting was stunningly beautiful, gave us a great tour of the process, and was generous with their wine. Our second stop for dinner was at a great location. We took awesome pictures of the sunset and had delicious pasta.

The Best Tour in Florence: Renaissance and Medici Tales

beaubrowne, Apr 2026

Alberto-guided tour was perfecto!

Alberto was a really fantastic guide who made this a perfect 2-hour introduction to all things Florence. His incredible knowledge about the city's history, culture, architecture, food, you name it was so evident in not only that which he shared, but always knowing the detailed answers to broad as well as obscure questions from our group. Thanks for making our first day in Florence a perfect start to begin to appreciate what a special place this is. Highly recommend to newbies and seasoned visitors alike.

Cinque Terre Day Trip with Optional Hiking or Pisa

Matthew_H, Apr 2026

Jerry was a fantastic...

Jerry was a fantastic tour guide! He was very knowledgeable during the tour - not just the history and what we were seeing - but also restaurant and gelateria recommendations. It is a long day but the tour is well paced with plenty of time to explore. Strongly recommend. Cinque Terre is beautiful.

Uffizi Gallery Small Group Tour with Guide

Patricia_V, Apr 2026

A great family tour

Excellent guide. I liked that he focused on some key paintings and provided context on how to look at them. Our family group ranged in age from 14 to 83, with different levels of exposure to art. We all enjoyed the tour and learned a lot. In past times, my husband and I had been to the Uffizi several times without a guide and we tried to see as much as possible, but this, more focused visit was more valuable.

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!

Florence Accademia Gallery Tour with Entrance Ticket Included

MarkLouie_L, Apr 2026

David! (In Moira's accent iykwim 😉 )

It was a short tour but definitely one you shouldn't skip while visiting Florence. Unfortunately we couldn't remember the name of our tour guide, but I'm sure most of the time give the same level of knowledge and information of one of Michaelangelo's best creations.

Small group Tuscan Wineries, Olive Oil & Gourmet Lunch or Dinner

Nita_P, Mar 2026

Wine, Dine and have fun

Our bus driver Leo was fantastic and gave us a little history about the Tuscany area and Chianti. The three wineries were all slightly different and the folks there were also very lovely and gave us tons of info and answered all questions. Definitely do a full day tour if you have the time!

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

Abir_A, Mar 2026

Wonderful day spent! Worthy visiting Tuscany!

The Day Trip was very worthy! Such a wonderful view of Tuscany and Sierra! Pisa was Great as expected! I must appreciate our Guide Aaron Dereci for his wonderful facilitation and guidance during the whole trip! Also thanks to our Great Drover Silvio and Michelle

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!