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 - D
Dianne • traveled in November, 2025
Tours were wonderful and they made the travel from one location to another super easy. Had a wonderful experience with tons of sightseeing, food and wine tasting, and beautiful scenery packed in! Thank you!
Italian Sojourn with Leaning Tower of Pisa - K
Ken • traveled in October, 2024
I can't say enough about Caspin Journeys. The hosts were wonderful and made us feel like family right away. So well organized and planned out. The views were incredible along the way and even though there was a lot of walking, the pace was comfortable. Every detail was planned perfectly. The food was outstanding, and the small group size made it easy to get to know everyone. Would definitely recommend this tour company to anyone thinking of going to Europe.
Tuscany Walking & Hiking Tour
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
DEDiane
Best of Rome, Florence & Venice
Italy By High-Speed TrainHeather
Tuscan TreatsDouglas
Two Hearts in Tuscany: A Romantic Getaway for 2Belen
Tuscany Walks & Chianti WinesPotter
MWMaria
A Taste of Tuscany - Hilltop Towns and Vineyards
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
The best Tuscany tour packages
Compiled by
MelissaTuscany travel expert at TourRadar
The Best of Tuscany - 4Days/3Nights
20 Reviews by TourRadar travelers“This was the perfect blend of independent and guided. We had the opportunity to do what we wanted.”
Erin, traveled in June
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
- US$591
Italian Sojourn with Leaning Tower of Pisa
4 Reviews by TourRadar travelers“The trip was great with a good balance of tours and free time. Accommodations were comfortable and very conveniently located.”
Marie, traveled in October
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
- US$2,099
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
- US$4,314
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
- US$1,424
Italian Triple Centre with A World Wonder
5 Reviews by TourRadar travelers“This was an excellent tour. We very much enjoyed the Coliseum/Forum tour. This was a highlight as was the Crypt and Catacomb tour.”
James, traveled in June
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 $2,426
12% Off- US$2,135You save $291
Tuscany Absolute
12 Reviews by TourRadar travelers“From enchanting vineyard visits to tastings of exquisite wines, every moment celebrated Tuscan flavors.”
Stephen, traveled in May
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
12% Off- US$3,082
Best of Rome, Florence & Venice
3 Reviews by TourRadar travelers“This trip provided a wonderful opportunity to become introduced to these three different regions, each different and unique in its own way.”
Christopher, traveled in May
Florence's Hotel Executive serves as your gateway to UNESCO-listed San Gimignano and historic Siena. Family-owned Chianti vineyards offer wine tastings, while traditional Tuscan lunches and Florence's best panoramic viewpoints create lasting memories.
Duration 7 days Destinations Rome, Vatican City, Florence, Siena, San Gimignano, Tuscany, Venice Age Range Ages 8+ Operator Omega Tours From
12% Off- US$1,831
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
Demographics
Solo Travelers139 tours- Couples128 tours
- Young Adults (18 - 39)7 tours
- Seniors (50+)52 tours
Best time to visit Tuscany
- 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.
- 70 tours
- 134 tours
- popular 142 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 136 tours
- 119 tours
- 128 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 145 tours
- October 2026 138 tours
- 58 tours
- Winter 2026 / 2027
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.
- popular 36 tours
- 24 tours
- 23 tours
Tuscany travel guides - curated by our experts
What is the best time to visit Tuscany (Italy) in 2026/2027?
Discover the best time to visit Tuscany in Italy to enjoy its stunning landscapes, vibrant culture and unique experiences with TourRadar.
Weather in Tuscany 2026/2027
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
Andrei
Expert in Tuscany at TourRadar
Andrei 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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