Book Wine Tours & Tastings in Chianti

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Aerial view of Siena's historic rooftops and cathedral in Tuscany, Italy.
Tour bus parked among cypress trees in Tuscany, Italy.
Tourists boarding a bus for the Tuscany in a Day tour, visiting Siena, San Gimignano, and Pisa.
Tourists taking a selfie in front of a historic building in Siena, Italy.
Piazza del Campo in Siena with Torre del Mangia, Tuscany.
Tourists posing near the Leaning Tower of Pisa, Italy.
Leaning Tower of Pisa and Pisa Cathedral in Tuscany, Italy.
Siena Cathedral facade with visitors in Tuscany, Italy.
San Gimignano town square with medieval buildings and tourists exploring.
Siena Cathedral facade with intricate Gothic architecture, Tuscany.
Aerial view of Siena's historic rooftops and cathedral in Tuscany, Italy.
Tour bus parked among cypress trees in Tuscany, Italy.
Tourists boarding a bus for the Tuscany in a Day tour, visiting Siena, San Gimignano, and Pisa.
Tourists taking a selfie in front of a historic building in Siena, Italy.
Piazza del Campo in Siena with Torre del Mangia, Tuscany.
Tourists posing near the Leaning Tower of Pisa, Italy.
Leaning Tower of Pisa and Pisa Cathedral in Tuscany, Italy.
Siena Cathedral facade with visitors in Tuscany, Italy.
San Gimignano town square with medieval buildings and tourists exploring.
Siena Cathedral facade with intricate Gothic architecture, Tuscany.
Aerial view of Siena's historic rooftops and cathedral in Tuscany, Italy.
Tour bus parked among cypress trees in Tuscany, Italy.
Tourists boarding a bus for the Tuscany in a Day tour, visiting Siena, San Gimignano, and Pisa.
Tourists taking a selfie in front of a historic building in Siena, Italy.
Piazza del Campo in Siena with Torre del Mangia, Tuscany.
Tourists posing near the Leaning Tower of Pisa, Italy.
Leaning Tower of Pisa and Pisa Cathedral in Tuscany, Italy.
Siena Cathedral facade with visitors in Tuscany, Italy.
San Gimignano town square with medieval buildings and tourists exploring.
Siena Cathedral facade with intricate Gothic architecture, Tuscany.
Guided Tours
4.5(2,037)

From Florence: Tuscany, Siena, San Gimignano & Pisa Day Trip

from
€84
Free cancellation

You can cancel these tickets up to 24 hours before the experience begins and get a full refund.

Book now, pay later

Book now without paying anything. Cancel for free if your plans change

11 hr 30 min - 13 hr 45 min
Transfers included
Meals included

A complete Tuscan adventure with iconic sights, optional lunch, and wine tasting.

  • Enjoy round-trip transfers by coach or minivan from Florence to the Tuscan countryside and explore its breathtaking landscapes.
  • With the expertise of a multilingual guide, get a taste of the authentic Tuscan experience on a full-day tour.
  • Visit the enthralling city of Siena where you’ll visit the Piazza del Campo, famous for its Palio di Siena horse race.
  • Upgrade to relish a delicious lunch of Tuscan cuisine, and an authentic local wine-tasting tour. Visit the medieval town of San Gimignano and explore to your heart’s desire.
  • Go to Pisa and its stunning Piazza dei Miracoli. Admire the Baptistery and the famous Leaning Tower.

A complete Tuscan adventure with iconic sights, optional lunch, and wine tasting.

  • Enjoy round-trip transfers by coach or minivan from Florence to the Tuscan countryside and explore its breathtaking landscapes.
  • With the expertise of a multilingual guide, get a taste of the authentic Tuscan experience on a full-day tour.
  • Visit the enthralling city of Siena where you’ll visit the Piazza del Campo, famous for its Palio di Siena horse race.
  • Upgrade to relish a delicious lunch of Tuscan cuisine, and an authentic local wine-tasting tour. Visit the medieval town of San Gimignano and explore to your heart’s desire.
  • Go to Pisa and its stunning Piazza dei Miracoli. Admire the Baptistery and the famous Leaning Tower.

Inclusions

  • Full-day tour of Tuscany, Siena, San Gimignano and Pisa
  • Expert English, Spanish, Italian, Portuguese, or French-speaking guide
  • Round-trip transfers from Florence by coach
  • Typical Tuscan lunch with drinks (optional)
  • Wine tasting (optional)

Exclusions

  • Entry to Leaning Tower of Pisa
  • Entry to Siena Cathedral
  • You can cancel these tickets up to 24 hours before the experience begins and get a full refund.
Siena cityscape with historic buildings and lush greenery during Chianti Half Day Wine Tasting Tour.
Women posing playfully with the Leaning Tower of Pisa in Italy.
Pisa Cathedral and Baptistery with tourists exploring the square.
Stone buildings in a sunny Tuscan village square, part of the Highlights of Tuscany tour.
People dining at a long table during Pisa, Siena, and San Gimignano day trip.
Visitors at the steps of a historic church in San Gimignano, Italy.
Bus traveling through Chianti vineyards during Florence wine tour.
Wine bottles and Italian appetizers on a table during a Pisa, Siena, San Gimignano & Chianti day trip.
Tourists enjoying a wine tasting experience in Tuscany during a Pisa, Siena, and San Gimignano day trip.
Siena Cathedral facade with tourists during the day in Siena, Italy.
Siena cityscape with historic buildings and lush greenery during Chianti Half Day Wine Tasting Tour.
Women posing playfully with the Leaning Tower of Pisa in Italy.
Pisa Cathedral and Baptistery with tourists exploring the square.
Stone buildings in a sunny Tuscan village square, part of the Highlights of Tuscany tour.
People dining at a long table during Pisa, Siena, and San Gimignano day trip.
Visitors at the steps of a historic church in San Gimignano, Italy.
Bus traveling through Chianti vineyards during Florence wine tour.
Wine bottles and Italian appetizers on a table during a Pisa, Siena, San Gimignano & Chianti day trip.
Tourists enjoying a wine tasting experience in Tuscany during a Pisa, Siena, and San Gimignano day trip.
Siena Cathedral facade with tourists during the day in Siena, Italy.
Siena cityscape with historic buildings and lush greenery during Chianti Half Day Wine Tasting Tour.
Women posing playfully with the Leaning Tower of Pisa in Italy.
Pisa Cathedral and Baptistery with tourists exploring the square.
Stone buildings in a sunny Tuscan village square, part of the Highlights of Tuscany tour.
People dining at a long table during Pisa, Siena, and San Gimignano day trip.
Visitors at the steps of a historic church in San Gimignano, Italy.
Bus traveling through Chianti vineyards during Florence wine tour.
Wine bottles and Italian appetizers on a table during a Pisa, Siena, San Gimignano & Chianti day trip.
Tourists enjoying a wine tasting experience in Tuscany during a Pisa, Siena, and San Gimignano day trip.
Siena Cathedral facade with tourists during the day in Siena, Italy.
Guided Tours
4.4(3,904)

From Florence: Pisa, San Gimignano, Siena & Chianti Day Trip with Lunch & Tuscan Tastings

from
€78
Free cancellation

You can cancel these tickets up to 48 hours before the experience begins and get a full refund.

Book now, pay later

Book now without paying anything. Cancel for free if your plans change

12 hr - 12 hr 45 min
Transfers included
Meals included
Itinerary
TOTAL DURATION12 hours
MODE OF TRANSFERA/C Bus
Central Florence
Start point

Central Florence

Get direction
77 min by A/C Bus
84.5 km
Pisa

1. Pisa

1 attraction

Highlights

81 min by A/C Bus
78.8 km
San Gimignano

2. San Gimignano

1 attraction

Highlights

Things to do

46 min by A/C Bus
41.9 km
Siena

3. Siena

2 attractions

Highlights

78 min by A/C Bus
77 km
Central Florence
End point

Central Florence

Get direction

Your ending point would be same as your start point

See Pisa, San Gimignano & Siena in a single day with iconic sights, Tuscan charm, and a hearty lunch.

  • Day out to: the Leaning Tower of Pisa, scenic San Gimignano, and historic Siena from Florence.
  • You’ll get round-trip coach transfers, time to explore each destination, and a traditional Tuscan lunch with curated local pours.
  • Pisa & San Gimignano: Snap photos at the Leaning Tower in Pisa and enjoy a countryside lunch paired with regional flavors in San Gimignano.
  • Siena: Wander medieval alleyways, bustling piazzas, and Gothic landmarks in the heart of Siena.
  • Upgrades: Enhance your visit with a guided walking tour of Siena and optional entry to its iconic cathedral.

See Pisa, San Gimignano & Siena in a single day with iconic sights, Tuscan charm, and a hearty lunch.

  • Day out to: the Leaning Tower of Pisa, scenic San Gimignano, and historic Siena from Florence.
  • You’ll get round-trip coach transfers, time to explore each destination, and a traditional Tuscan lunch with curated local pours.
  • Pisa & San Gimignano: Snap photos at the Leaning Tower in Pisa and enjoy a countryside lunch paired with regional flavors in San Gimignano.
  • Siena: Wander medieval alleyways, bustling piazzas, and Gothic landmarks in the heart of Siena.
  • Upgrades: Enhance your visit with a guided walking tour of Siena and optional entry to its iconic cathedral.

Inclusions

  • Full-day trip around Pisa, San Gimignano, and Siena
  • Multilingual assistance on board
  • Pick up from Florence
  • Round-trip AC coach transfer
  • Lunch with local blends in San Gimignano
  • Guided tour of Siena city center (as per option selected)
  • Guided tour of Siena Cathedral and city center (as per option selected)

Exclusions

  • Hotel transfers
  • Personal expenses

What to bring

  • Wear comfortable walking shoes as the tour involves a fair amount of walking.
  • For entry to Siena Cathedral (if selected), wear clothing that covers knees and shoulders.
  • Bring a valid ID if you plan to taste regional pairings.

What's not allowed

  • Alcoholic beverages will not be served to guests under 18 years of age.

Accessibility

  • This experience is not accessible for wheelchair users or pram/strollers.

Additional information

  • Guests under 18 can join the tour only if accompanied by at least one adult.
  • The order of visits may change depending on traffic or local conditions.
  • Hotel transfers are not included.
  • Personal expenses (souvenirs, additional snacks, optional upgrades) are not included.
  • You can cancel these tickets up to 48 hours before the experience begins and get a full refund.
Dirt road leading to a villa surrounded by cypress trees in Chianti, Tuscany.
Tourists enjoying wine tasting in a Chianti vineyard at sunset.
Vineyards and olive groves in Chianti region, Tuscany, Italy.
Visitors walking through a Chianti vineyard with grapevines and a basket of grapes.
Vineyards and cypress trees in the Chianti region landscape, Tuscany, Italy.
Chianti winery tasting room with wooden barrels and set dining tables.
Hand holding a glass of rosé wine in a Chianti vineyard during an e-bike tour.
Dirt road leading to a villa surrounded by cypress trees in Chianti, Tuscany.
Tourists enjoying wine tasting in a Chianti vineyard at sunset.
Vineyards and olive groves in Chianti region, Tuscany, Italy.
Visitors walking through a Chianti vineyard with grapevines and a basket of grapes.
Vineyards and cypress trees in the Chianti region landscape, Tuscany, Italy.
Chianti winery tasting room with wooden barrels and set dining tables.
Hand holding a glass of rosé wine in a Chianti vineyard during an e-bike tour.
Dirt road leading to a villa surrounded by cypress trees in Chianti, Tuscany.
Tourists enjoying wine tasting in a Chianti vineyard at sunset.
Vineyards and olive groves in Chianti region, Tuscany, Italy.
Visitors walking through a Chianti vineyard with grapevines and a basket of grapes.
Vineyards and cypress trees in the Chianti region landscape, Tuscany, Italy.
Chianti winery tasting room with wooden barrels and set dining tables.
Hand holding a glass of rosé wine in a Chianti vineyard during an e-bike tour.
Day Trips
4.5(26)

From Florence: Chianti Wine Tasting Tour

from
€49
Free cancellation

You can cancel these tickets up to 48 hours before the experience begins and get a full refund.

Book now, pay later

Book now without paying anything. Cancel for free if your plans change

5 hr - 5 hr 30 min
Itinerary
TOTAL DURATION5 hours 30 minutes
MODE OF TRANSFERA/C Bus
Florence
Start point

Florence

Get direction
38 min by A/C Bus
30 km
Chianti Classico

1. Chianti Classico

1 activity

Things to do

40 min by A/C Bus
35 km
Florence
End point

Florence

Get direction

Your ending point would be same as your start point

Half-day trip from Florence to two Chianti Classico wineries with guided tastings & transfers.

  • Day out to: Tuscany’s Chianti Classico countryside on a half-day trip from Florence, with round-trip transfers by air-conditioned coach. Journey through the scenic Via Chiantigiana, lined with vineyards, olive groves, and medieval villages.
  • You’ll get: Enjoy a full-day Chianti experience with a licensed English-speaking escort, visits to two family-run wineries, guided vineyard and cellar tours, tastings of signature Chianti Classico wines, regional snacks with olive oil samples, and free time to soak in the countryside charm or browse local shops.

Half-day trip from Florence to two Chianti Classico wineries with guided tastings & transfers.

  • Day out to: Tuscany’s Chianti Classico countryside on a half-day trip from Florence, with round-trip transfers by air-conditioned coach. Journey through the scenic Via Chiantigiana, lined with vineyards, olive groves, and medieval villages.
  • You’ll get: Enjoy a full-day Chianti experience with a licensed English-speaking escort, visits to two family-run wineries, guided vineyard and cellar tours, tastings of signature Chianti Classico wines, regional snacks with olive oil samples, and free time to soak in the countryside charm or browse local shops.

Inclusions

  • Assistance at the meeting point
  • Transport by air conditioned bus with Wi-Fi on board
  • Licensed tour escort
  • Wine tasting
  • This experience is not accessible by wheelchair and pram/strollers.
  • Drinks will not be served to guests under the age of 18 years.
  • Guests under the age of 18 years can join the tour if they are each accompanied by at least one adult.
  • You can cancel these tickets up to 48 hours before the experience begins and get a full refund.
Colorful cliffside village of Manarola in Cinque Terre, Italy, with boats in the harbor.
Colorful hillside village in Cinque Terre with church and terraced houses.
Tour group exploring Cinque Terre village street on a sunny day.
Boats in the harbor of Riomaggiore, Cinque Terre, with colorful hillside buildings.
Couple on a boat during Cinque Terre day trip from Florence, with coastal scenery in the background.
Couple taking a selfie on a boat with ocean and mountains in the background.
Participants enjoying a boat ride on a day trip in Cinque Terre from Florence.
Colorful cliffside village of Vernazza overlooking the sea in Cinque Terre, Italy.
Woman admiring colorful tiles on a wall in Via dell'Arte, Italy.
Colorful buildings and outdoor cafes in a narrow street of Cinque Terre, Italy.
Colorful cliffside village of Manarola in Cinque Terre, Italy, with boats in the harbor.
Colorful hillside village in Cinque Terre with church and terraced houses.
Tour group exploring Cinque Terre village street on a sunny day.
Boats in the harbor of Riomaggiore, Cinque Terre, with colorful hillside buildings.
Couple on a boat during Cinque Terre day trip from Florence, with coastal scenery in the background.
Couple taking a selfie on a boat with ocean and mountains in the background.
Participants enjoying a boat ride on a day trip in Cinque Terre from Florence.
Colorful cliffside village of Vernazza overlooking the sea in Cinque Terre, Italy.
Woman admiring colorful tiles on a wall in Via dell'Arte, Italy.
Colorful buildings and outdoor cafes in a narrow street of Cinque Terre, Italy.
Colorful cliffside village of Manarola in Cinque Terre, Italy, with boats in the harbor.
Colorful hillside village in Cinque Terre with church and terraced houses.
Tour group exploring Cinque Terre village street on a sunny day.
Boats in the harbor of Riomaggiore, Cinque Terre, with colorful hillside buildings.
Couple on a boat during Cinque Terre day trip from Florence, with coastal scenery in the background.
Couple taking a selfie on a boat with ocean and mountains in the background.
Participants enjoying a boat ride on a day trip in Cinque Terre from Florence.
Colorful cliffside village of Vernazza overlooking the sea in Cinque Terre, Italy.
Woman admiring colorful tiles on a wall in Via dell'Arte, Italy.
Colorful buildings and outdoor cafes in a narrow street of Cinque Terre, Italy.
Day Trips
4.4(371)

From Florence: Cinque Terre Day Trip

from
€110
Free cancellation

You can cancel these tickets up to 24 hours before the experience begins and get a full refund.

Book now, pay later

Book now without paying anything. Cancel for free if your plans change

12 hr
Transfers included
Meals included
Itinerary
TOTAL DURATION13 hours
Florence
Start point

Florence

Get direction
2 hr 23 min
182 km
Manarola

1. Manarola

2 attractions

Highlights

5 min
6 km
Riomaggiore

2. Riomaggiore

2 attractions

Highlights

10 min
16 km
Vernazza

3. Vernazza

2 attractions

Highlights

5 min
4 km
Monterosso al Mare

4. Monterosso al Mare

2 attractions

Highlights

Things to do

2 hr 35 min
186 km
Florence
End point

Florence

Get direction

Your ending point would be same as your start point

Traipse through 4 enchanting towns in the UNESCO-listed Cinque Terre, with all transport from Florence sorted!

  • Catch a bus from the city center followed by a train in Cinque Terre to Manarola and Riomaggiore, discovering their quaint squares.
  • Whether you set off to the fishing village of Vernazza by train or boat, it's a panoramic ride hugging the Ligurian coast!
  • At the large hill town of Monterosso, take the perfect dip into Fegina beach's turquoise swells around stacked sandstone.
  • Select the lunch option to arrive at a classic restaurant for a scrumptious spread of local items.

Traipse through 4 enchanting towns in the UNESCO-listed Cinque Terre, with all transport from Florence sorted!

  • Catch a bus from the city center followed by a train in Cinque Terre to Manarola and Riomaggiore, discovering their quaint squares.
  • Whether you set off to the fishing village of Vernazza by train or boat, it's a panoramic ride hugging the Ligurian coast!
  • At the large hill town of Monterosso, take the perfect dip into Fegina beach's turquoise swells around stacked sandstone.
  • Select the lunch option to arrive at a classic restaurant for a scrumptious spread of local items.

Inclusions

  • Full-day trip around Cinque Terre
  • Expert local assistance in English & Spanish
  • Pick up from Florence
  • Round-trip AC bus transfers
  • Train or boat transfers within Cinque Terre
  • Lunch with drinks (optional)

What to bring

  • Keep your official ID or passport readily available for a seamless experience.
  • Bring a swimsuit, sun protection, and water bottles. Comfortable shoes are recommended, as the tour involves a fair amount of walking.

Accessibility

  • This experience is partially accessible for wheelchairs and prams/strollers.

Additional information

  • The tour departs at 7am until 28 February 2026, and at 6:50am from 1 March 2026.
  • Boat rides are not available from November to March.
  • The itinerary may change, and some stops might be skipped due to weather conditions.
  • No refunds are provided in case of delays at the meeting point.
  • Punctuality at each meeting point is strongly recommended during the excursion.
  • You can cancel these tickets up to 24 hours before the experience begins and get a full refund.
Piazza del Campo in Siena with Torre del Mangia and Palazzo Pubblico.
Streets of San Gimignano with historic stone buildings and tourists exploring.
Vineyards and olive groves in Chianti region, Tuscany, Italy.
Hand holding a glass of rosé wine in a Chianti vineyard during an e-bike tour.
Wine barrels in a cellar during Chianti wine tasting tour from Florence.
Tour guide holding a sign in a Chianti village during a wine tour from Florence.
Bus interior with passengers traveling from Tromso to Skjervoy.
Piazza del Campo in Siena with Torre del Mangia and Palazzo Pubblico.
Streets of San Gimignano with historic stone buildings and tourists exploring.
Vineyards and olive groves in Chianti region, Tuscany, Italy.
Hand holding a glass of rosé wine in a Chianti vineyard during an e-bike tour.
Wine barrels in a cellar during Chianti wine tasting tour from Florence.
Tour guide holding a sign in a Chianti village during a wine tour from Florence.
Bus interior with passengers traveling from Tromso to Skjervoy.
Piazza del Campo in Siena with Torre del Mangia and Palazzo Pubblico.
Streets of San Gimignano with historic stone buildings and tourists exploring.
Vineyards and olive groves in Chianti region, Tuscany, Italy.
Hand holding a glass of rosé wine in a Chianti vineyard during an e-bike tour.
Wine barrels in a cellar during Chianti wine tasting tour from Florence.
Tour guide holding a sign in a Chianti village during a wine tour from Florence.
Bus interior with passengers traveling from Tromso to Skjervoy.
Guided Tours
4.6(11)

From Florence: Siena, San Gimignano & Chianti Day Trip with Local Flavors Experience

from
€89
Free cancellation

You can cancel these tickets up to 24 hours before the experience begins and get a full refund.

Book now, pay later

Book now without paying anything. Cancel for free if your plans change

11 hr 30 min
Transfers included
Meals included
Itinerary
TOTAL DURATION10 hours 30 minutes
MODE OF TRANSFERA/C Bus
Central Florence
Start point

Central Florence

Get direction
71 min by A/C Bus
78.3 km
Siena

1. Siena

1 attraction

Highlights

46 min by A/C Bus
41.7 km
San Gimignano

2. San Gimignano

1 attraction

Highlights

57 min by A/C Bus
45.9 km
Chianti Classico

3. Chianti Classico

1 activity

Things to do

50 min by A/C Bus
29.1 km
Central Florence
End point

Central Florence

Get direction

Your ending point would be same as your start point

A classic Tuscan trio—Siena, San Gimignano & Chianti—all in one seamless day trip from Florence.

  • Day out to the medieval gems of Siena and San Gimignano before heading to a charming Chianti countryside estate.
  • You’ll get round-trip coach transfers, a guided tour of Siena, free time in San Gimignano, and a countryside meal with regional pairings.
  • Siena: Join a guided tour of Piazza del Campo and admire the Palazzo Pubblico and Mangia Tower.
  • San Gimignano & Chianti: Stroll San Gimignano’s UNESCO-listed lanes at your pace, then unwind at a Chianti estate with a 3-course Tuscan lunch and curated sips.

A classic Tuscan trio—Siena, San Gimignano & Chianti—all in one seamless day trip from Florence.

  • Day out to the medieval gems of Siena and San Gimignano before heading to a charming Chianti countryside estate.
  • You’ll get round-trip coach transfers, a guided tour of Siena, free time in San Gimignano, and a countryside meal with regional pairings.
  • Siena: Join a guided tour of Piazza del Campo and admire the Palazzo Pubblico and Mangia Tower.
  • San Gimignano & Chianti: Stroll San Gimignano’s UNESCO-listed lanes at your pace, then unwind at a Chianti estate with a 3-course Tuscan lunch and curated sips.

Inclusions

  • Full-day trip around Siena, San Gimignano, and Chianti
  • Multilingual assistance on board
  • Pick up from Florence
  • Round-trip AC coach transfer
  • Expert English-speaking guide in Siena
  • Vineyard visit, lunch, and wine tasting in Chianti
  • Tip: When in San Gimignano, seek out the Rocca di Montestaffoli. This old fortress offers a quieter panoramic vantage with lovely gardens that many tourists miss.
  • This experience is not accessible by wheelchair and pram/strollers.
  • Your safety is our priority. Drinks are not served for guests under the age of 18 years.
  • Minors under the age of 18 years can join the tour if they are each accompanied by at least one adult.
  • You can cancel these tickets up to 24 hours before the experience begins and get a full refund.
Aerial view of San Gimignano with medieval towers and surrounding countryside.
Siena Cathedral with tourists in the square, part of San Gimignano, Siena, Monteriggioni, Chianti day trip.
Group walking through vineyard on Siena, San Gimignano, and Chianti day trip.
Visitors at the steps of a historic church in San Gimignano, Italy.
Wine being poured into a glass during a Chianti tasting on a Florence day trip.
Tourists taking a selfie in front of historic architecture in San Gimignano, Italy.
Aerial view of Monteriggioni's medieval walls and surrounding Tuscan landscape.
Aerial view of Chianti winery with vineyards and Tuscan landscape.
Passengers seated inside a tour bus traveling from Paris to Mont St. Michel's Abbey.
Aerial view of San Gimignano with medieval towers and surrounding countryside.
Siena Cathedral with tourists in the square, part of San Gimignano, Siena, Monteriggioni, Chianti day trip.
Group walking through vineyard on Siena, San Gimignano, and Chianti day trip.
Visitors at the steps of a historic church in San Gimignano, Italy.
Wine being poured into a glass during a Chianti tasting on a Florence day trip.
Tourists taking a selfie in front of historic architecture in San Gimignano, Italy.
Aerial view of Monteriggioni's medieval walls and surrounding Tuscan landscape.
Aerial view of Chianti winery with vineyards and Tuscan landscape.
Passengers seated inside a tour bus traveling from Paris to Mont St. Michel's Abbey.
Aerial view of San Gimignano with medieval towers and surrounding countryside.
Siena Cathedral with tourists in the square, part of San Gimignano, Siena, Monteriggioni, Chianti day trip.
Group walking through vineyard on Siena, San Gimignano, and Chianti day trip.
Visitors at the steps of a historic church in San Gimignano, Italy.
Wine being poured into a glass during a Chianti tasting on a Florence day trip.
Tourists taking a selfie in front of historic architecture in San Gimignano, Italy.
Aerial view of Monteriggioni's medieval walls and surrounding Tuscan landscape.
Aerial view of Chianti winery with vineyards and Tuscan landscape.
Passengers seated inside a tour bus traveling from Paris to Mont St. Michel's Abbey.
Guided Tours
4.1(844)

Siena and San Gimignano Day trip from Florence

from
€79
Free cancellation

You can cancel these tickets up to 24 hours before the experience begins and get a full refund.

Book now, pay later

Book now without paying anything. Cancel for free if your plans change

9 hr - 11 hr
Transfers included
Itinerary
TOTAL DURATION10 hours 30 minutes
MODE OF TRANSFERA/C Bus
Central Florence
Start point

Central Florence

Get direction
71 min by A/C Bus
78.3 km
Siena

1. Siena

2 attractions

Highlights

59 min by A/C Bus
45.5 km
Chianti Classico

2. Chianti Classico

1 activity

Things to do

55 min by A/C Bus
46.4 km
San Gimignano

3. San Gimignano

1 attraction

Highlights

70 min by A/C Bus
61.1 km
Central Florence
End point

Central Florence

Get direction

Your ending point would be same as your start point

Two Tuscan treasures, one unforgettable day: explore Siena and San Gimignano.

  • Day out to Siena and San Gimignano from Florence, all in one day.
  • You’ll get round-trip AC coach travel, a guide on-board, and independent sightseeing in these cities.
  • Siena & San Gimignano: Wander Siena’s historic streets on your own and admire San Gimignano’s medieval skyline, known as the 'Manhattan of the Middle Ages'.
  • Upgrades: Opt for a guided walking tour of Siena and entry to the grand Siena Cathedral for deeper insight.

Two Tuscan treasures, one unforgettable day: explore Siena and San Gimignano.

  • Day out to Siena and San Gimignano from Florence, all in one day.
  • You’ll get round-trip AC coach travel, a guide on-board, and independent sightseeing in these cities.
  • Siena & San Gimignano: Wander Siena’s historic streets on your own and admire San Gimignano’s medieval skyline, known as the 'Manhattan of the Middle Ages'.
  • Upgrades: Opt for a guided walking tour of Siena and entry to the grand Siena Cathedral for deeper insight.

Inclusions

  • Full-day trip around Siena and San Gimignano
  • Multilingual assistance on board
  • Pick up from Florence
  • Free tine to explore Siena, a UNESCO World Heritage Site
  • Free time to explore San Gimignano
  • Round-trip AC coach transfer with Wi-Fi and USB charging on board
  • Guided tour of Siena city center (as per option selected)
  • Entry to Siena Cathedral and Piccolomini Library (as per option selected)
  • Tip: It's possible to walk along the 2176-metre perimeter of the second circle of city walls that mark the historical centre of San Gimignano.
  • This experience is not accessible by wheelchair and pram/strollers.
  • The wine tasting experience is restricted for guests under the age of 18 years.
  • Guests under 18 can join the tour if they are each accompanied by at least one adult.
  • Guests who have opted to visit the Siena Cathedral must wear clothing that covers the knees and shoulders.
  • This tour involves a fair amount of walking, so comfortable shoes are highly recommended.
  • Please note that the order of visits is subject to change.
  • You can cancel these tickets up to 24 hours before the experience begins and get a full refund.
Visitors exploring wine barrels in a Chianti cellar during a guided tour.
Group listening to a guide in a Chianti wine cellar during a wine and olive oil tour.
Group enjoying wine tasting session in Chianti with guide explaining wine details.
Group enjoying wine tasting during Chianti tour.
Cheese, tomatoes, and vegetables on a wooden platter during Chianti wine and olive oil tour.
Olive oil being poured into tasting glasses during a Chianti experience.
Group enjoying wine tasting outdoors in Chianti.
Group enjoying wine tasting outdoors in Chianti countryside.
Private transfer service at Narita Airport with passengers in a luxury vehicle.
Visitors exploring wine barrels in a Chianti cellar during a guided tour.
Group listening to a guide in a Chianti wine cellar during a wine and olive oil tour.
Group enjoying wine tasting session in Chianti with guide explaining wine details.
Group enjoying wine tasting during Chianti tour.
Cheese, tomatoes, and vegetables on a wooden platter during Chianti wine and olive oil tour.
Olive oil being poured into tasting glasses during a Chianti experience.
Group enjoying wine tasting outdoors in Chianti.
Group enjoying wine tasting outdoors in Chianti countryside.
Private transfer service at Narita Airport with passengers in a luxury vehicle.
Visitors exploring wine barrels in a Chianti cellar during a guided tour.
Group listening to a guide in a Chianti wine cellar during a wine and olive oil tour.
Group enjoying wine tasting session in Chianti with guide explaining wine details.
Group enjoying wine tasting during Chianti tour.
Cheese, tomatoes, and vegetables on a wooden platter during Chianti wine and olive oil tour.
Olive oil being poured into tasting glasses during a Chianti experience.
Group enjoying wine tasting outdoors in Chianti.
Group enjoying wine tasting outdoors in Chianti countryside.
Private transfer service at Narita Airport with passengers in a luxury vehicle.
Guided Tours
NEW

From Florence: Chianti Countryside & Olive Grove Semi-Private Tour with Lunch & Gourmet Pairings

from €149
€111.75

25% off

Free cancellation

You can cancel these tickets up to 24 hours before the experience begins and get a full refund.

Book now, pay later

Book now without paying anything. Cancel for free if your plans change

4 hr 30 min - 9 hr
Transfers included
Meals included

Deep dive into Chianti’s rich food and flavor traditions with gourmet pairings and estate visits.

  • Day out to Chianti from Florence with stops at wineries, an olive oil mill, and a traditional countryside lunch.
  • You’ll get Round-trip transfers, expert-led tastings at three estates, a visit to an olive mill, and a Tuscan lunch with regional pairings.
  • Chianti Estates: Visit three unique wineries, explore scenic vineyards and cellars, and enjoy curated pours guided by in-house experts.
  • Olive Mill & Village Views: Stop at a local olive oil mill and take in charming views near a traditional Tuscan village.
  • Upgrades: Enjoy smaller group sizes and enhanced sommelier-led sessions for a more personalized tasting experience.

Deep dive into Chianti’s rich food and flavor traditions with gourmet pairings and estate visits.

  • Day out to Chianti from Florence with stops at wineries, an olive oil mill, and a traditional countryside lunch.
  • You’ll get Round-trip transfers, expert-led tastings at three estates, a visit to an olive mill, and a Tuscan lunch with regional pairings.
  • Chianti Estates: Visit three unique wineries, explore scenic vineyards and cellars, and enjoy curated pours guided by in-house experts.
  • Olive Mill & Village Views: Stop at a local olive oil mill and take in charming views near a traditional Tuscan village.
  • Upgrades: Enjoy smaller group sizes and enhanced sommelier-led sessions for a more personalized tasting experience.

Inclusions

  • Florence pick up
  • Small-group day trip around Chianti
  • Round-trip Mercedes minibus or minivan transfers
  • Guided tour of 1 olive oil mill & 3 wineries with tastings
  • Typical Tuscan lunch
  • Guided tour of a Tuscan village

Exclusions

  • Hotel transfers
  • Personal expenses
  • Tip: If you're a foodie, ask for pairing recommendations! Mill staff can often suggest specific dishes or recipes that highlight the best qualities of their olive oil.
  • This experience is not accessible by wheelchair and pram/strollers.
  • For safety reasons, guests under 18 are not permitted to take part in the tasting experience.
  • Guests under 18 can join the tour if they are each accompanied by at least one adult.
  • Please inform in advance if you have any food allergies or intolerances. Vegetarian needs can also be accommodated with prior notice.
  • You can cancel these tickets up to 24 hours before the experience begins and get a full refund.

Top 5 Reasons to Go on a Chianti Countryside Tour

  • Scenic beauty: Breathe in sweeping views of rolling hills, rustic estates, olive groves, and charming Tuscan villages that look like they’ve leapt out of a postcard.
  • Timeless traditions: Step into a land steeped in centuries of craftsmanship—where age-old methods, passed down through generations, continue to shape local life.
  • Toast to the region: Delight in tastings that showcase the essence of Chianti’s rich legacy—served with stories, hospitality, and a deep-rooted pride in the land.
  • Tuscan Flavors: Feast on hearty, homestyle fare prepared with fresh local ingredients—often accompanied by a curated pour to elevate every bite.
  • Embrace the Adventure: Cycle or drive through sun-drenched landscapes, stopping at historic estates and hilltop towns that radiate pure Italian charm.

Which Chainti wine tour is best for you?

Chianti Wine Guided Tours

Guided Tours

Professional local guides walk you through the Chianti grape region's rich history, culture, and winemaking techniques. The tours include visits to renowned wineries, vineyards, and cellars, along with tastings showcasing the region's finest.

Best for: Curious travelers looking for a deeper dive into Chianti’s rich traditions, guided by local experts who bring the region’s flavors and heritage to life.

Recommended Tours:
Guided Tour of the Chianti Wine Region with 2 Wine Tastings and Vineyards Escape
Tour of Siena, San Gimignano, Monteriggioni & Chianti Wine Tasting from Florence
Guided Immersive Wine & Olive Oil Experience in Chianti
Chianti Wine Tour from Florence with Greve Village Visit

Chianti Wines Private Tours

Private Tours

Tailored to your preferences, private tours offer flexibility in itinerary and timing. This allows you to visit select vineyards and benefit from undivided attention from your guide.

Best for: Those seeking a more personalized and intimate tour, ideal for special occasions or a getaway with loved ones.

Recommended Tours:
Semi-Private Tuscan Grand Tour - Best of Siena, San Gimignano, Chianti and Pisa
Tuscany Wine and Olive Oil Trail: Small-Group Tour From Florence

Chianti Wine and Gastronomy Tours

Wine and Gastronomy Tours

Dive deep into the delectable realm of Tuscan cuisine. These tours not only include regional craft tastings but also gourmet dining experiences, pairing exquisite sips with authentic regional dishes.

Best for: Foodies and vino connoisseurs who appreciate the art of culinary pairing and wish to savor the diverse flavors of Chianti.

Recommended Tours:
Wine Making Experience and Gourmet Dinner in Tuscany: From Florence
Guided Wine Tasting & Dinner Experience in Chianti

VIP and Exclusive Chianti Wine Tours

VIP and Exclusive Tours

Indulge in luxury and exclusivity with VIP and exclusive tours. These high-end experiences often include private transportation, visits to prestigious wineries, special tastings of rare vintages, and unique encounters with winemakers.
Best for: Discerning travelers seeking an opulent adventure with the finest offerings in Chianti.

Recommended Tours:
VIP Semi-Private Super Tuscan Wine Tour with a Masterclass by a Wine Expert
VIP Semi-Private Wineland Safari in Tuscany from Florence

E-Bike Wine Tours in the Chianti countryside

E-Bike Tours

Combine the joy of cycling with the beauty of the Chianti countryside. E-bike tours offer an active and eco-friendly way to explore vineyards and wineries, with stops for tastings and soaking in the breathtaking scenery.

Best for: Adventure enthusiasts and nature lovers who want a fun and eco-conscious experience amidst Tuscany's picturesque landscapes.

Recommended Tours:
3-Hour Guided E-Bike Tour of Chianti with Wine Tasting
Guided E-Bike Rental in Chianti with Dinner

Vino culture in Chianti

Cooking with Chianti wine

From Vine to Table

Witness the seamless connection between vineyards and kitchens. Chianti's pours aren't just reserved for glasses; they become key ingredients in cooking, infusing dishes with a unique and distinctive flair.

Bistecca alla Fiorentina with Chianti Wine

Wine and Tuscan Gastronomy

Savor the rich “Bistecca alla Fiorentina” alongside the bold notes of Chianti Classico, or enjoy the comforting warmth of “Pappa al Pomodoro” with a classic local pour. Chianti’s cuisine and regional pairings come together in a delicious celebration of Tuscan taste.

Chianti Wine Festivals

Celebrate at vino festivals

Join the festivities that showcase Chianti's deep ties with its countryside produce. From time-honored festivals to intimate gatherings at local cellars, immerse yourself in the merriment that radiates the region's passionate spirit.

Chianti region

A historic legacy

Delve into the past as you uncover the rich history of viticulture in Chianti. Passed down through generations, these traditions have stood the test of time, preserving the essence of the region's heritage.

Tuscany Vineyards

Wander through vineyards

Take a leisurely stroll through scenic vineyards in Tuscany. Experience more than just tastings – connect with passionate winemakers and discover the fascinating stories behind each bottle.

The heart of Chianti, uncorked

Chianti Classico wine

Chianti Classico

Chianti Classico is the most well-known and historic label of the region. Made mostly from Sangiovese grapes, it’s known for its bright ruby color, fresh red fruit notes, and balanced acidity. Aged under strict regulations, it reflects the tradition and quality Chianti is famous for.

Chianti Rufina wine

Chianti Rufina

Produced in the eastern part of the Chianti region, Chianti Rùfina stands out for its cooler climate and higher altitude. These conditions give the wines a fresher profile with notes of red and dark fruits, along with subtle herbal tones. It's typically full-bodied and known for its long finish.

Chianti Colli Senesi wine

Chianti Colli Senesi

Produced in the hills around Siena, this type of Chianti is primarily made from Sangiovese grapes. It typically features notes of wild berries and local herbs, with a slightly earthy character. The style is often simpler and more approachable.

Chianti Montalbano wine

Chianti Montalbano

Produced in the Montalbano hills, this lesser-known variety of Chianti is made primarily from Sangiovese grapes. It typically shows straightforward flavors like cherry, plum, and light floral notes. Medium-bodied and easier to palate, it’s a solid option for those exploring different Chianti styles.

Chianti Superiore wine

Chianti Superiore

This classification indicates a step up from standard Chianti, made under stricter production rules and with longer aging requirements. The result is a more structured, fuller-bodied wine that reflects a more refined approach to production. It's a good choice for those looking for a more developed expression of the region.

Chianti Colli Fiorentini wine

Chianti Colli Fiorentini

Produced in the hills around Florence, this type of Chianti is primarily made with Sangiovese grapes. It tends to have clear fruit notes and light floral aromas, with a balanced structure.

Chianti Montespertoli

Chianti Montespertoli

Located in the western section of the Chianti region, this area produces wines that reflect a variety of soil types and microclimates. As a result, the wines range from light and easy-drinking to fuller-bodied options that can develop with age.

Chianti Classico Riserva

Chianti Classico Riserva

A more mature version of Chianti Classico, this wine is made using selected Sangiovese grapes and aged for at least two years, including a few months in the bottle. The result is a fuller-bodied wine with concentrated fruit, firmer structure, and the ability to age well over time.

Before You Go: Exploring Chianti’s Flavors, Views, and Traditions

Timings
What to bring
Visitor tips & hacks
Best time for a Chianti Tour

The timings for your Chianti tour may vary based on the particular experience you seek. Tour durations vary, from a few hours to full-day experiences. Usually the tours begin in the morning or afternoon, unless you are opting for an evening winery tour or a dinner experience.

Best Time to Visit
The best time for a Chianti vino tour is during spring (April to June) and fall (September to October). Enjoy pleasant weather, lush vineyards, and the grape harvest season, making it perfect for exploring vineyards and sampling local pours. However, these tours are available throughout the year, so you can choose a time that aligns with your preferences and travel plans.

Chianti Wine Tours
  • Comfortable clothing: Wear casual, comfortable attire for vineyard exploration.
  • Sunproofing: Bring sunglasses, a wide-brimmed hat, and sunscreen for sunny days.
  • Happy feet: Choose sturdy, comfy shoes for uneven terrain.
  • Capture the moments: Don't forget your camera or smartphone to snap stunning vineyard views.
  • Valid ID: Bring identification for age verification during wine tastings.
  • Payments: Have cash and cards for winery purchases.
  • Easy carry: Use a small backpack or bag to carry essentials.
  • Open mind & appetite: Embrace the culture and savor the diverse flavors of Chianti.
Chianti Tips & Tricks
  • How to taste: Swirl, sniff, and savor – take time to enjoy each sip. Engage with the winemakers to learn more about their creations.
  • Cultural etiquette: Embrace Italian customs – a friendly "Salute!" (cheers) before sipping is a delightful gesture. Respect the winery's rules and traditions.
  • Pacing yourself: Take it easy during tastings. Sip and savor rather than rushing. A little water between your tastings helps too!
  • Cleansing your palate: A sip of water, a plain cracker, or a bite of bread can refresh your palate between different craft blends.
  • Food pairings: Explore delicious food pairings. Pair a bold Chianti Classico with Tuscan pecorino cheese, or a Chianti Rufina with savory prosciutto.
  • Transportation options: Consider a guided tour or transportation service to ensure a safe and carefree journey.

Frequently asked questions about Chianti wine tours

What are the different types of Chianti tours available?

There are various options for Chianti tours, including guided, private, e-bike, and gastronomy-focused experiences.

What can I expect on such a tour?

On a Chianti tour, expect captivating vineyard visits, focused tastings, and insights into Chianti's winemaking heritage.

Do you offer private or group tours in Chianti?

You can choose between private or group tours based on your preferences. We have an array of experiences to suit your taste of ambiance.

What languages are the tours conducted in?

Our wine tours are conducted in multiple languages for your convenience.

Will there be a guide on a Chianti tour?

Absolutely! All our Chianti tours come with knowledgeable guides.

How far in advance should I book a Chianti countryside tour?

To secure your spot, it's best to book in advance, especially during peak seasons.

Do you offer these tours year-round, or are they seasonal?

Our tours are available year-round, each season offering its unique charm.

Can I combine a Chianti tour with other experiences or activities in the area?

Customize your experience by combining wine tours with other activities in the area, like e-bike tours, etc.

Are tastings included in the tour price?

This usually depends on the particular type of ticket you have chosen, but usually, yes, countryside sips and tastings are typically included in the tour price.

Do I need to be a connoisseur to enjoy the tour?

Not at all! Our tours are enjoyable for all participants, regardless of expertise.

Are the tours suitable for solo travelers or couples?

Yes, these tours are ideal to depeen the bond with your significant other, or make new friends if you're a solo traveler. In either case, memories for a lifetime are guaranteed!

Can I cancel or reschedule my booking? What is the cancellation policy?

You can cancel or reschedule your booking; check our flexible policies.

Do you provide refunds in case of bad weather conditions or unforeseen circumstances?

Yes, we provide refunds in case of bad weather or unforeseen circumstances. But it's advisable to check your ticket for clarity on the policies.

Do you provide transportation to and from the tour locations?

Some tours include transportation, while others require personal arrangements.

How long do the Chianti tours typically last?

Tour lengths vary, offering options for shorter or full-day experiences.

Are the wineries and vineyards wheelchair-accessible?

Some wineries and vineyards are wheelchair-accessible; please inquire about specific options.

Can I bring my own food or drinks on the tour?

Kindly refrain from bringing outside food or drinks.

Are there any specific health considerations I should be aware of during the tour?

Inform us of any health concerns to ensure a safe and enjoyable tour.

What makes Chianti estate offerings unique compared to other regions?

The cellar treasures of Chianti boast unique terroir, grape varieties, and a rich winemaking history that sets them apart from other regions.