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How to Spend 2 Days in Tuscany

How to Spend 2 Days in Tuscany

Land of jewel-like medieval towns, rolling vineyards, and a wealth of UNESCO-listed architectural sites, Tuscany is one of the most famous regions in the world. With two days, you’ll have time to dip into its charm before moving on its capital city of Florence or the rest of Italy. Here are your best options for spending two days in Tuscany.

Day 1: Chianti

**Morning:**If Tuscany is Italy’s most famous region, Chianti is its scenic crown jewel. Your first day, focus on this paradise of food, wine, and views. Start by joining a driving or Vespa tour along the scenic SS222, which passes some of the most picturesque hilltowns, like Greve in Chianti, Panzano in Chianti, Radda in Chianti, and Castellina in Chianti.

**Afternoon:**No jaunt through Chianti is complete without sampling the area’s food and wine. Visit some of the small family-run cellars hidden in the hills on a wine tour, or explore the wine country by horseback or on bike, stopping for tastings. Foodies can opt for a farmhouse cooking class to learn how to prepare classic Tuscan dishes.

**Night:**End your day in San Gimignano, a spectacularly preserved medieval hilltown that is particularly beautiful in the evening, after the bus-tour crowds depart. Stroll through the old town to take in its 14 soaring towers, Collegiate Church of Santa Maria Assunta, and Piazza Duomo, before relaxing over dinner at a local trattoria.

Day 2: Pisa and Lucca

**Morning:**The Leaning Tower of Pisa is on everyone’s must-see list, but resist the urge to head straight to the Duomo and its famous bell tower in the morning, when these popular attractions are overflowing with bus-tour crowds. Instead, join a guided walking, Segway, or bike tour of Pisa’s handsome historic center, the Piazza dei Cavalieri, and Santa Maria della Spina. 

**Afternoon:**Once the morning crowds have gone, head to Pisa’s famed cathedral complex on a guided tour that includes skip-the-line tickets. This glorious UNESCO World Heritage Site includes the gothic Duomo and baptistry, the iconic Leaning Tower, the Opera del Duomo Museum, and the Camposanto cemetery.

**Night:**From Pisa, continue on to Lucca, a lovely walled town that has a refreshing un-touristed feel. Take a walking or biking tour through the old town to visit the Duomo, Guinigi Tower, the Church of San Michele in Foro, and other highlights. End your two-day Tuscan adventure by joining the locals in the evening passeggiata (stroll) along Via Fillungo. 

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14 Tours and Activities

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Wine Tasting at a Private Medieval Winery in Chianti - Tuscany

Wine Tasting at a Private Medieval Winery in Chianti - Tuscany

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66
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
From
$124.07
From
$124.07

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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20
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
From
$86.64
From
$86.64

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
$201.90
Price varies by group size
From
$201.90
Price varies by group size

Walking Tour and Exploration of Lucca

Walking Tour and Exploration of Lucca

star-4.5
160
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
From
$10.90
From
$10.90

CSTRents - Pisa Segway PT Authorized Tour

CSTRents - Pisa Segway PT Authorized Tour

star-4.5
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
From
$167.48
Price varies by group size
From
$167.48
Price varies by group size

Pisa Guided Walking Tour in Miracoli Square

Pisa Guided Walking Tour in Miracoli Square

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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
From
$17.00
From
$17.00

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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70
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
From
$26.57
From
$26.57

Small-Group Chianti Wine-Tasting and Castles Trip from Siena
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Small-Group Chianti Wine-Tasting and Castles Trip from Siena

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41
Discover the fine wines and rich historical heritage of Chianti on a full-day trip from Siena. With a knowledgeable guide, travel through the sublime Tuscan countryside and visit castles cradled by rolling green hills and sprawling vineyards. Visit Castello di Brolio, the esteemed birthplace of Chianti wine, and delve into the opulent chambers of Castello di Ama. Pleasure your palate with fine samples of Chianti Classico wine during tasting sessions and feast on a traditional Italian lunch during your tour. Enjoy an intimate atmosphere on this small-group tour, limited to only eight people.
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  • 8 hours
  • Free Cancellation
From
$170.02
From
$170.02

Off-Road Tuscan Wine Tour from Castellina
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Off-Road Tuscan Wine Tour from Castellina

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12
Travel off-road through the Chianti valley on this day-long Tuscan wine tour. As your guide drives a vintage SUV, you'll gaze out at the gentle green hills and grapevine groves that typify the landscape. Stop at three wineries to sample several varietals of wine along with local products such as honey and olive oil, then relax over a traditional Tuscan picnic for lunch at your final stop. The tour starts and ends in the village of Castellina in Chianti.
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  • 4 hours
  • Free Cancellation
From
$270.97
Price varies by group size
From
$270.97
Price varies by group size

Horseback Riding tour with lunch and Wine Tasting
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Horseback Riding tour with lunch and Wine Tasting

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2
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
From
$297.53
Price varies by group size
From
$297.53
Price varies by group size

VESPA Tour in Tuscany
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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
From
$286.91
Price varies by group size
From
$286.91
Price varies by group size

The best of Chianti Classico Wine Private Tour with Dinner in a boutique Estate
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The best of Chianti Classico Wine Private Tour with Dinner in a boutique Estate

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2
Sample some of Tuscany's best-known wines during this private tour of the Chianti region from Florence. Stop for two wine tastings and visit two charming medieval villages before sitting down to a traditional Tuscan dinner in the vineyards. Upgrade for a stop in San Donato, set within a fortified castle.
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  • 6 hours
  • Free Cancellation
From
$425.05
Price varies by group size
From
$425.05
Price varies by group size

San Gimignano Private Walking Tour
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San Gimignano Private Walking Tour

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4
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
From
$148.77
per group
From
$148.77
per group

Private Vintage 500 Fiat tour in Tuscany
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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
From
$286.91
Price varies by group size
From
$286.91
Price varies by group size