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How to Spend 3 Days in Tuscany

How to Spend 3 Days in Tuscany

With three days to explore Tuscany, you’ll be able to savor picture-perfect hill towns, scenic vineyards, and world-class art and architecture while also visiting the iconic Leaning Tower of Pisa. Here’s how to make the most of three days in Tuscany. 

Day 1: Siena, the Crete Senesi, and the Val d’Orcia

Begin by visiting one of the most beautifully intact historic towns in Tuscany: Siena. With a historic center rich in architectural masterpieces and views across the rolling landscape of Crete Senesi and the woodlands of Val d’Orcia, Siena offers both culture and scenery. Start the day with a skip-the-line tour of the city’s exquisite Gothic cathedral to admire works by Donatello, Michelangelo, and Bernini before moving on to the crypt, baptistry, museum, and Piccolomini Library. Then take a deep dive into the city’s medieval center with a tour of the Piazza del Campo, home to the Palazzo Pubblico and Torre del Mangia, and the Basilica di San Domenico. 

In the afternoon, strike out through the surrounding countryside by vintage Fiat 500, bike, or horseback to savor some of the most unforgettable vistas in Tuscany and stop at picturesque towns like Pienza, Montepulciano, and Montalcino.

Day 2: Chianti and San Gimignano

Head to Tuscany’s Chianti countryside and take a driving or Vespa tour through the sleepy hilltowns of Greve in Chianti, Panzano, Radda in Chianti, and Castellina in Chianti. In the afternoon, focus on the region’s beloved cuisine: Wine tours by car, bike, or horseback are all great options for exploring the vineyard-covered hills dotted with tiny cellars where you can sample some of the area’s best wines. This is also an ideal area to join a hands-on cooking class in the countryside and learn to prepare classic Tuscan dishes.

 

From Chianti, continue on to San Gimignano to take in its delightful medieval old town in the quieter hours of the evening. Tour highlights like the city’s 14 historic towers, the Collegiate Church of Santa Maria Assunta, and Piazza Duomo on foot before tucking into a Tuscan dinner.

Day 3: Pisa and Lucca

On your final day, make your way to one of Tuscany’s headliners: the Leaning Tower of Pisa. Topping Italy’s list of highlights, this bell tower can be uncomfortably crowded in the morning, so begin your day with a guided tour of Pisa’s historic center on foot or via Segway or bike. In the afternoon, join a tour that includes skip-the-line tickets to take in the spectacular UNESCO-listed Piazza dei Miracoli. Follow your guide through the gothic Duomo and adjacent baptistry, the Leaning Tower, the Opera del Duomo Museum, and the Camposanto cemetery to fully appreciate these architectural masterpieces. 

End your three days in the exquisite (and much less crowded) town of Lucca. Take a walking or biking tour of the highlights in the historic center before capping off the day with an evening “passeggiata” (stroll) along Via Fillungo. 

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16 Tours and Activities

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Skip the Line: Siena Duomo and City Walking Tour

Skip the Line: Siena Duomo and City Walking Tour

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232
Indulge in one of Italy's most beautiful cities, Siena, during this sightseeing tour. An expert guide gives you an insider's view of this UNESCO World Heritage-listed town. Linger for a while in Piazza del Campo, the superlative square that is home to the Palio, a wild horse race that takes place every July and August. Stroll the streets with your guide learning about the history of the place. Visit the Duomo, Siena's stunning cathedral, and stroll right in thanks to your skip-the-line ticket. 
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$35.41
From
$35.41
Taking safety measures

Vintage Fiat 500 Tour from Siena: Tuscan Hills and Winery Lunch
Likely to Sell OutLikely to Sell Out

Vintage Fiat 500 Tour from Siena: Tuscan Hills and Winery Lunch

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27
See Tuscany in classic Italian style by exploring the rustic region via a vintage Fiat 500, the classic, beloved and diminutive Italian automobile. Get picked up at your hotel in Siena and then ride to the stunning hilltop town of Monteriggioni, cruising through the rolling hills of Chianti along the way. Stop at a local vineyard and sample some delicious Italian wines with a hearty lunch of local fare. Follow the guide in a caravan. The number of participants on this small-group tour is limited to just ten, so you’re sure to get plenty of personalized attention from the guide.
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  • 8 hours
  • Free Cancellation
  • Taking safety measures
From
$177.06
From
$177.06
Taking safety measures

Skip-the-line Leaning Tower of Pisa Guided Small-Group Tour

Skip-the-line Leaning Tower of Pisa Guided Small-Group Tour

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18
The Leaning Tower of Pisa is a UNESCO World Heritage site and one of Italy’s most famous landmarks, so it’s no surprise that queues can be long. This 1-hour skip-the-line tour ensures you don’t waste any time, with a guided walking tour of the magnificent Piazza dei Miracoli, followed by priority access to climb the Leaning Tower.
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  • 1 hour
  • Free Cancellation
  • Taking safety measures
From
$96.24
From
$96.24
Taking safety measures

Tuscany Hiking Tour from Siena Including Wine Tasting

Tuscany Hiking Tour from Siena Including Wine Tasting

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24
Become a pilgrim of sorts and take a scenic hike on the historic Via Francigena, an old pilgrimage route that stretched from Canterbury in England to Rome. The rural route takes you through villages, vineyards, and some of the most scenic countryside in Tuscany. Best of all, once you get to the medieval village of Monteriggioni you're rewarded with a wine tasting. At the end, head back to Siena via train.
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  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
$53.12
From
$53.12
Taking safety measures

Walking Tour and Exploration of Lucca

Walking Tour and Exploration of Lucca

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126
Explore the traditional Tuscan town of Lucca on a walking tour of the historic center. Stroll the cobblestone streets, bustling piazzas and old Renaissance walls; trace the city’s Roman past along Via San Paolino and Piazza San Michele; and see the birthplace of local composer Giacomo Puccini. Keep your camera poised as you admire the medieval buildings along Via Fillungo, peek inside San Frediano church and visit landmarks like the Cathedral of San Martino, Piazza Anfiteatro and Torre delle Ore.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$12.11
From
$12.11
Taking safety measures

Wine Tasting at a Private Medieval Winery in Chianti - Tuscany

Wine Tasting at a Private Medieval Winery in Chianti - Tuscany

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56
Discover the long winemaking conditions of Tuscany on this half-day tasting tour from Florence. Travel to a privately owned 12th-century winery in Chianti for a tour of the estate, vineyards, and family cellars. Learn about the region's distinctive and famous varietals from expert guides, and then savor the excellence for yourself with a guided tasting of estate wines, paired with a delicious Tuscan lunch.
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  • 5 hours
  • Free Cancellation
  • Taking safety measures
From
$137.82
From
$137.82
Taking safety measures

2-Hour Small-Group Walking Tour of Pisa Off The Beaten Path

2-Hour Small-Group Walking Tour of Pisa Off The Beaten Path

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47
Discover Pisa’s star attractions and get under the skin of the city on a 2-hour walking tour. Explore hidden lanes and secret gems, seek out the highlights of the city’s four main districts, and learn about Pisan history and culture. Stop to view the Piazza dei Cavalieri, River Arno, and other famous spots, and finish by admiring Pisa Cathedral and the Leaning Tower. This leisurely paced tour is limited to a maximum of 15 people.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$25.97
From
$25.97
Taking safety measures

Small Group E-Bike Tour from Siena with Wine Tasting and Lunch
Likely to Sell OutLikely to Sell Out

Small Group E-Bike Tour from Siena with Wine Tasting and Lunch

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6
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 and travel by van into the Chianti hills, where you’ll receive your bike and helmet and will get familiar with the gear. With just a small group for company, set off on a tour of the countryside, visit a restored monastery, and head to a local winery, where you can enjoy a traditional meal and generous wine tasting.
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  • 6 hours
  • Free Cancellation
  • Taking safety measures
From
$177.06
From
$177.06
Taking safety measures

CSTRents - Pisa Segway PT Authorized Tour

CSTRents - Pisa Segway PT Authorized Tour

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6
Explore Pisa on this comprehensive 3-hour Segway tour. Led by a local guide, glide through the Piazza dei Miracoli to see the Duomo, Baptistery and the iconic Leaning Tower of Pisa. Check out where Galileo once studied at the Sapienza Palace and hear the history behind the Scuola Normale as you pass through Knights’ Square. Numbers are limited to eight people to ensure an intimate experience.
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$186.04
Price varies by group size
From
$186.04
Price varies by group size
Taking safety measures

Horseback Riding tour with lunch and Wine Tasting

Horseback Riding tour with lunch and Wine Tasting

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1
Saddle up to explore the stunning countryside of the Chianti wine region on this private half-day horseback riding tour from Castellina. Suitable for all abilities, you’ll ride through scenic vineyards, olive groves, and medieval villages, and stop along the way for a typical Tuscan lunch and wine and olive oil tastings.
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  • 5 hours
  • Free Cancellation
  • Taking safety measures
From
$306.90
Price varies by group size
From
$306.90
Price varies by group size
Taking safety measures

VESPA Tour in Tuscany

VESPA Tour in Tuscany

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5
Experience the Tuscan countryside from a perspective rare to visitors on a private Vespa tour with round–trip transport from your Siena hotel. In addition to navigating for you, your guide ensures the best views and stops for photo opportunities along the way. The day includes a Tuscan–style lunch and complimentary wine tasting with vineyard views.
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  • 5 hours
  • Free Cancellation
  • Taking safety measures
From
$271.49
Price varies by group size
From
$271.49
Price varies by group size
Taking safety measures

Brunello E-Bike Tour

Brunello E-Bike Tour

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6
Pedal through the Tuscan countryside during this half-day e-bike tour through Brunello. Bike along unpaved roads with ease on your electric bike towards local Tuscan vineyards. Enjoy a wine tasting at the Abbey of Sant’Antimo and learn about the ancient winemaking process. Sample three glasses of wines, including the Brunello di Montalcino, before heading to the medieval town of Montalcino to explore.
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  • 5 to 6 hours
  • Free Cancellation
From
$224.28
Price varies by group size
From
$224.28
Price varies by group size

Pisa Guided Walking Tour in Miracoli Square

Pisa Guided Walking Tour in Miracoli Square

star-3
19
Discover the sights of Pisa on an hour-long walking tour, and stop at the key sights to learn about their history. Check out the UNESCO World Heritage–listed Leaning Tower of Pisa as well as grandiose landmarks like the cathedral at Pisa and Campo Santo — the city’s monumental cemetery. Your informative guide will take you on a thorough guided walking tour of Piazza dei Miracoli and its monuments which are called “miracles” because of their incredible beauty and uniqueness.
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  • 1 hour
  • Free Cancellation
  • Taking safety measures
From
$18.89
From
$18.89
Taking safety measures

San Gimignano Private Walking Tour

San Gimignano Private Walking Tour

star-5
1
Explore the historic hill town of San Gimignano with this 2-hour walking tour. Learn about the many Medieval towers that give the town such a distinctive skyline.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$165.26
per group
From
$165.26
per group
Taking safety measures

Private Vintage 500 Fiat tour in Tuscany

Private Vintage 500 Fiat tour in Tuscany

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1
Discover the Tuscan countryside behind the wheel of a classic Fiat 500 on a private six-hour tour. Starting from Florence, hit the open road with your guide.  Along the drive, you’ll visit three historic villages, stopping whenever you like.  Later, enjoy a traditional Tuscan lunch with wine tasting  at a 19th century villa.
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  • 6 hours
  • Free Cancellation
  • Taking safety measures
From
$318.71
Price varies by group size
From
$318.71
Price varies by group size
Taking safety measures

Tuscan Hills Horseback Riding Tour from Siena

Tuscan Hills Horseback Riding Tour from Siena

star-4
30
Giddy up! Traverse the hills of Tuscany via a unique mode of transportation with this guided horseback tour from Siena. Roam the rolling hills, some clad in grapevines, others blanketed with olive groves, as you and your horse calmly explore the region. Pass through rustic villages, all while learning about the history of the place from your guide. See stunning scenery that you would not have had the chance to encounter.
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  • 2 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$82.63
From
$82.63
Taking safety measures