Tuscany Tours & Trips
Ever thought about sipping Chianti wines in rolling Tuscan hills where cypress trees line medieval roads? Tuscany charms with Florence's David, Siena's Piazza del Campo, Lucca's old walls, and San Gimignano's medieval towers. Cycle through vineyards, taste local gelato, and find Pisa's famous Leaning Tower. La dolce vita begins here.
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Omead • traveled in November, 2025
Well planned and enjoyable
The Best of Tuscany - 4Days/3Nights - Y
Yvonne • traveled in June
Lovely tour, particularly of Siena and San Gimignano. From cathedrals to cobblestones, turrets to towers, Pinocchio dolls to pasta, and reds to whites, this all-day tour was a wonderful experience to cherish and remember years from now. Special praise to Yvonne from Tui Italia for her outstanding responsiveness, communications, and agility.
Gems of Rome & Florence, Semi-Private Tour - C
Cynthia • traveled in November, 2025
Well done Wanderful tours. The tour organizer at Wanderful Holidays UK was quick to respond to my questions and concerns . The included Hotels are within walking distance to train the stations. I’d recommend the hotel upgrade to stay right on the island of Venice. It was delightful to do the grand canal vapperetto after dark with an audio tour I had downloaded. My only concern would be earlier details of included tour starting time and ending time. This knowledge would have been helpful to help plan dinner reservation or other gallery visits.
Italian Triple Centre with A World Wonder
Traveler Photos & Videos from Tuscany tours
Italian Sojourn with Leaning Tower of Pisa
Brendan
Italian Triple Centre with A World WonderCynthia
MKMarina
Tuscany Absolute
SSarahTaylor
Tuscan Treats
Italy By High-Speed TrainHeather
Two Hearts in Tuscany: A Romantic Getaway for 2Belen
DEDiane
Best of Rome, Florence & Venice
MWMaria
A Taste of Tuscany - Hilltop Towns and Vineyards
Tuscany Walks & Chianti WinesPotter
Tuscan TreatsDouglas
Private Gourmet Wine Tour in Tuscany, ItalySusan
Bike Across Tuscany - GuidedFrank
AAnthonyLawler
Classic Tuscany - Cycling from Florence to Pisa - Classic Self Guided
MIMelanie
Contrasts of Italy
Table of contents
- The best Tuscany tour packages
- Travel Tuscany your way
- Best tour companies for Tuscany tours
- Popular Tuscany Cruise Ships
- Best places to start your Tuscany tour
- Discover Tuscany tours for every budget
- Tuscany tours for every type of group
- Top Tuscany travel itineraries to fit your plans
- Demographics
- Best time to visit Tuscany
- Tuscany travel guides - curated by our experts
- Contact our Tuscany travel experts
- What our customers ask about Tuscany Tours & Trips
The best Tuscany tour packages
Compiled by
MelissaTuscany travel expert at TourRadar
The Best of Tuscany - 4Days/3Nights
20 Reviews by TourRadar travelers“You won't find better options without paying significantly more. A professional company provides enjoyable travel experiences.”
Adam, traveled in March
The iconic Duomo complex and San Lorenzo market await in Florence, followed by Tuscany's finest sites. Two Chianti wineries offer authentic tastings, while San Gimignano's famous towers and Vernazza's beaches provide cultural contrast. YellowSquare Hostel serves as home base with stunning rooftop views.
Duration 4 days Destinations Florence, Pisa, Cinque Terre, San Gimignano, Tuscany Age Range Ages 18+ Operator Italy on a Budget Tours From $579
15% Off- US$492You save $87
Gems of Rome & Florence, Semi-Private Tour
4 Reviews by TourRadar travelers“Lovely tour, particularly of Siena and San Gimignano. From cathedrals to cobblestones, turrets to towers, this all-day tour was a wonderful experience.”
Yvonne, traveled in June
Artistic heritage flourishes at Florence's 4-star Hotel Adriatico, launching point for Tuscan countryside adventures. San Gimignano's iconic towers, traditional Chianti estates, and Siena's magnificent Piazza del Campo await. Expert guides lead private transfers, with daily breakfast and winery lunch included.
Duration 6 days Destinations Rome, Florence, San Gimignano, Siena Age Range All Ages Welcome Operated in English, Spanish Operator TUI Italia From $1,673
15% Off- US$1,422You save $251
Italian Triple Centre with A World Wonder
5 Reviews by TourRadar travelers“Thank you for essentially planning all of our excursions and planned activities.”
Michael, traveled in September
Medieval Monteriggioni and UNESCO-listed San Gimignano showcase Tuscany's historic charm. A Chianti estate welcomes visitors for premium wine tasting, while Siena's Piazza del Campo displays magnificent Gothic architecture. A comfortable 3-star Florence hotel, rated 80+ reviews, includes daily breakfast.
Duration 10 days Destinations Rome, Florence, Pisa, Tuscany, Venice Age Range All Ages Welcome Operator Wonderful Holidays UK From $2,135
15% Off- US$1,815You save $320
Tuscany Mon Amour: Love at First Sight 2026! Semi-Escorted Tour
3 Reviews by TourRadar travelers“An unforgettable mix of culture, beauty, and relaxation! The combination of guided time and free time made it feel relaxing, not rushed.”
Giuseppa, traveled in March
A 4-star hotel in UNESCO-listed Montecatini Terme puts you at the heart of Tuscany's wonders. The tour includes Florence's Uffizi Square and Ponte Vecchio, wine tastings at San Gimignano's rustic estates, and Siena's Piazza del Campo. Guided tours, farm-to-table experiences, and traditional cantuccini tasting in Montecarlo complete the experience.
Duration 8 days Destinations Florence, Montecatini, Montecarlo, Pisa, Vinci, Siena, Monteriggioni, San Gimignano Age Range All Ages Welcome Operator RANIERI TOUR OPERATOR From
15% Off- US$1,399
Italian Sojourn with Leaning Tower of Pisa
4 Reviews by TourRadar travelers“Had a wonderful experience with tons of sightseeing, food and wine tasting, and beautiful scenery packed in!”
Dianne, traveled in November
Tuscany's medieval treasures await with visits to Monteriggioni, UNESCO-listed San Gimignano, and Siena's Gothic Cathedral. Sample wines at a Chianti estate, plus spend a full day at the iconic Leaning Tower of Pisa with expert guides. The 4-day Tuscan adventure includes 3-star lodging in Florence, earning perfect 5.0 scores for accommodation and dining.
Duration 10 days Destinations Rome, Florence, Pisa, Tuscany, Venice Age Range All Ages Welcome Operator Wanderful Holidays LLC From $1,899
21% Off- US$1,500You save $399
Tuscany Walking and Wine
24 Reviews by TourRadar travelers“Extremely helpful and passionate about his home country.”
John, traveled in April
Rolling vineyards of Castellina lead to Val d'Orcia's iconic hills. Organic wineries like Castello La Leccia, UNESCO-listed Pienza, and Chianti wine tastings paint a perfect Tuscan picture. Historic hotels and guided walks complete this regional immersion.
Duration 8 days Destinations Pisa, Castellina in Chianti, Castelvecchio National Park, San Gimignano, Monteriggioni, Siena, Pienza, Monticchiello, Montepulciano, San Quirico D'orciaSee all destinations Age Range Ages 16+ Operator Explore! From $2,870
20% Off- US$2,300You save $570
Discovering Florence
3 Reviews by TourRadar travelers“The private tours of the Uffizi and Accademia Galleries were super - the guides were knowledgeable and open to any question.”
kelly, traveled in March
Florence's Grand Hotel Adriatico provides access to Michelangelo's David and Botticelli's masterpieces. UNESCO-listed San Gimignano's medieval towers, Siena's Gothic cathedral, and Chianti wines at Poggio ai Laghi estate create unforgettable memories. Suitable for ages 15+, daily breakfast included.
Duration 4 days Destinations Florence, Monteriggioni, Siena, San Gimignano Age Range All Ages Welcome Operator TUI Italia From $926
15% Off- US$787You save $139
Tuscany Walking & Hiking Tour
1 Review by TourRadar travelers“The views were incredible along the way and even though there was a lot of walking, the pace was comfortable.”
Ken, traveled in September
Tuscan paths lead from Cortona's Etruscan tombs to Pienza's Renaissance architecture. The cypress-lined roads of Val d'Orcia wind through medieval villages and thermal springs. A luxury farmhouse serves as base while savoring regional wines and authentic Tuscan cuisine over 8 memorable days.
Duration 8 days Destinations Cortona, Monticchiello, Montepulciano, Siena, Pienza, San Quirico D'orcia, Bagno Vignoni, Buonconvento, Asciano, SI Age Range Ages 25+ Operator Caspin Journeys From
15% Off- US$4,236
Tuscany Absolute
12 Reviews by TourRadar travelers“Florence is a daydream, Siena and San Gimignano are unique in the world. It is hard not to fall in love with Italy and its incredible beauty.”
Amy, traveled in November
Florence's Accademia Gallery and Ponte Vecchio join Siena's medieval Piazza del Campo and Montepulciano's prestigious wineries in this cultural feast. Hotel Executive and Villa Cicolina host guests for 8 days, featuring pasta making classes and wine tastings at approx. $320 per day.
Duration 7 days Destinations Florence, Siena, San Gimignano, Castellina in Chianti, Montepulciano Age Range All Ages Welcome Operator Flag Travel Holidays From $3,020
20% Off- US$2,416You save $604
Florence: Amazing Tuscany & Cinque Terre 2026: Independent Tour with shared daily tours - Small Group
2 Reviews by TourRadar travelers“Florence captured our hearts with its beauty, and Tuscany was even more amazing than we had imagined.”
Alberto, traveled in October
Florence serves as your base for visiting medieval gems like Monteriggioni and San Gimignano. Sample Chianti wines, admire Siena's Piazza del Campo, and walk Lucca's Renaissance walls. Tour includes visits to Pisa's famous Leaning Tower.
Duration 8 days Destinations Florence, Siena, San Gimignano, Pisa, Cinque Terre Age Range All Ages Welcome Operator RANIERI TOUR OPERATOR From
20% Off- US$2,195
Travel Tuscany your way
More travel styles:
Best tour companies for Tuscany tours
If you're weighing up Tuscany tour options, Italy on a Budget consistently delivers solid experiences - their guides Lorenzo, Veronica and also Gabriela really know their stuff. Our travelers particularly love their Chianti wine tours where you can taste local wines right at the vineyards. Those looking to splash out a bit more should consider Premium Tuscany. TourRadar customers often mention how much they enjoy the private guided walks through Florence and Rome, plus you get to have lunch in an actual Roman aristocrat's home which adds something quite special to the experience. For something more active, Cycle Tuscany lets you really get to know the region. You'll stay in local accommodations and bike through medieval towns at a nice relaxed pace. Just one thing to note - we've had mixed feedback about some of the guides, so it's worth asking who'll be leading your specific tour date. The quality of the guide can make quite a difference to your overall experience.
Popular Tuscany Cruise Ships
Best places to start your Tuscany tour
Most of our travelers kick off their Tuscany tours from Florence - about 33% start here in the Renaissance city. Rome comes in as the next popular choice, while Pisa and Montecatini share third place and Venice fills the fifth spot. You'll want to plan ahead - our booking patterns show most people lock in their Tuscany trips around 100 days before travel, just over 3 months out. This early planning really matters in summer when the good tours fill up fast. Our guests often mix in special activities like cooking in old farmhouses, visits to Montecatini's thermal spas and guided walks through less-visited hill towns. The agriturismo stays are a real highlight - you get to live the day-to-day pace of rural Tuscan life while enjoying meals and wine made right there on the estate. We've found May and late September hit that sweet spot for weather and crowds, with nice temperatures and lots of local festivals and harvest events happening.
Discover Tuscany tours for every budget
Tuscany tours for every type of group
Who are you traveling with?
Top Tuscany travel itineraries to fit your plans
7 Day Itineraries
10 Day Itineraries
Demographics
Solo Travelers125 tours- Couples117 tours
- Young Adults (18 - 39)5 tours
- Seniors (50+)51 tours
Best time to visit Tuscany
- Winter 2025 / 2026
Winter in Tuscany offers a quieter side of Italy when tourist numbers drop. Our multi-center trips from Rome northward let you take your time in the Vatican Museums and Sistine Chapel without the usual crowds. You'll warm up with cooking classes in grand Roman homes and taste rich Chiantis in centuries-old wine cellars. The Italian Triple Centre tour is a customer favorite - people tell us they love having extra time to explore Florence's art collections at their own pace. These winter routes mix guided walks through peaceful medieval streets with plenty of stops for hot chocolate and local dishes in family-run cafes.
- 27 tours
- popular 39 tours
- 33 tours
- Spring 2026
Spring makes Tuscany really come alive. Our cycling routes take you through rolling hills dotted with fresh wildflowers and past Leonardo da Vinci's birthplace into charming spots like medieval Barga. Many guests combine Florence's art scene with wine experiences in Chianti, where you'll see the first vine buds and learn about wine production. The Budget Florence packages work well as a springtime base - you can explore the city and take guided trips out to San Gimignano and nearby vineyards. Cyclists particularly appreciate having e-bikes available for the steeper sections and enjoying authentic lunches at small local trattorias.
- 72 tours
- 125 tours
- popular 131 tours
- Summer 2026
Our triple-center tours let you experience Rome's timeless sites, Florence's art treasures and then Venice's waterways with a natural flow between cities. The free days built into routes give travelers space to venture out solo when temperatures climb - something our guests consistently praise. E-bikes make those sun-warmed Tuscan hills manageable, while premium tours include carefully chosen hotels with pools overlooking cypress-studded landscapes and authentic lunches in noble Roman residences, where owners share stories across grand dining tables. Many travelers opt for tours blending guided walks through Florence's historic heart with wine tastings in Chianti vineyards, timed perfectly to finish before midday heat sets in. The social atmosphere peaks in summer as younger guests connect at local bars while discovering Florence's evening culture, with convenient hostel locations just 5 minutes from tour meeting points.
- popular 124 tours
- 109 tours
- 117 tours
- Fall / Autumn 2026
Fall shows off Tuscany's harvest season with golden landscapes and bustling wineries. The cycling tours really shine now, following paths through Lucca's countryside and along the Serchio River in perfect temperatures. Our October travelers tell us they love combining bike rides with visits to marble quarries in the Apuan Alps and afternoons exploring medieval Castelnuovo di Garfagnana. Wine tours get special treatment in autumn - you might join the grape harvest at family vineyards, learn traditional wine-making and taste young wines paired with seasonal truffles and fresh olive oil. These fall tours balance active mornings with relaxed afternoons in historic towns, which our guests say creates just the right mix.
- popular 132 tours
- October 2026 127 tours
- 54 tours
Tuscany travel guides - curated by our experts
What is the best time to visit Tuscany (Italy) in 2026?
Discover the best time to visit Tuscany in Italy to enjoy its stunning landscapes, vibrant culture and unique experiences with TourRadar.
Weather in Tuscany 2026
Experience the magic of Tuscany, from rolling hills to wine tastings to timeless cities. Plan your Italian adventure with TourRadar.
Contact our Tuscany travel experts
Alex
Expert in Tuscany at TourRadar
Alex is one of our seasoned Tuscany Travel Experts. Reach out to us to get all your questions about Tuscany tours answered!
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+1 844 311 8331What our customers ask about Tuscany Tours & Trips
How can I best explore Tuscany's diverse landscapes from hills to coast?
You'll find driving gives you the most freedom especially when you want to discover those charming hilltop towns like Montalcino or venture down the strade bianche those lovely white gravel roads that wind through the countryside. If you'd rather not drive the "A Taste of Tuscany - Hilltop Towns and Vineyards" tour takes care of everything with comfortable transport and carefully planned experiences. The trains are great too connecting Florence Pisa and Lucca making it easy to do day trips even out to places like Cinque Terre.
Where can I find authentic Tuscan experiences away from the tourist crowds?
Head to Volterra where you can watch artisans carve beautiful pieces from alabaster it's been an Etruscan tradition here for centuries. There's this wonderful medieval town called Buonconvento right on the historic Via Francigena pilgrimage route you can walk or cycle along its ancient paths. Up in the Garfagnana valley you'll love Castelnuovo di Garfagnana with its amazing views of the Apuan Alps and don't miss the gelato at Fronte della Rocca they've been making sweets since 1885.
What local foods should I absolutely try to get a real taste of Tuscany?
You've got to try bistecca alla Fiorentina it's this incredible grilled T-bone steak that Florence is famous for. The rustic soups are amazing too like ribollita packed with bread and vegetables and pappa al pomodoro this comforting tomato bread dish you'll find at lovely farmhouse restaurants like Pieve a Salti. Make sure to taste Pienza's pecorino cheese made from Sardinian sheep's milk it pairs perfectly with local wines especially Brunello di Montalcino. The pasta dishes are incredible fresh-made pici con le criciole with crispy breadcrumbs and pappardelle sulla lepre with hare sauce are particularly good in Siena.
What are some unique ways to experience local culture beyond wine tasting?
Get your hands dirty at a cooking class in a place like Fattoria San Donato where you'll learn to make pasta the traditional way using local ingredients and ancient grains. The artisan workshops in Volterra and San Gimignano are fascinating you can watch craftspeople working with alabaster pottery and leather. The local festivals are really special too like the chestnut festival in Castiglione di Garfagnana where you can really dive into Tuscan traditions and seasonal harvests.
Which natural areas should I explore to see Tuscany's countryside?
The Val d'Orcia is absolutely stunning a UNESCO site with those classic Tuscan views rolling hills vineyards and cypress trees lining the roads you might recognize it from movies like Gladiator. Up in Garfagnana the Orecchiella National Park around Pania di Corfino peak is amazing for wildlife you might spot wolves deer and even golden eagles. The Serchio River path between Barga and Lucca offers beautiful walks or bike rides through typical Tuscan landscapes you'll want to take lots of photos.