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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Many thanks to Zufi, Amy and Ronnie who guided us thru our recent trip to Rome, Florence and Venice. Everything went smoothly because of the constant support and message's coming thru WhatsApp, for which we were very grateful.
Italian Triple Centre with A World WonderThe three-day tour was very comprehensive and took me to the major sites without the need for a car. Our tour guides were informative and helpful and gave us a lot of insights into the culture of Siena and Tuscany. My hotel was attractive and convenient, but I probably would have chosen a different one next time as the bathroom needed some updating. In summary, I was very pleased with the tour and recommend it highly to anyone interested in Tuscany.
Siena & HistoryGreat way to travel. Liked the tours, guides were excellent, knowledgeable & easy to understand. Also liked the openness of making our own plans for other tour sites. Accommodations were good. Locations were great for getting around the cities.
Italy By High-Speed Train
Traveler Photos & Videos from Tuscany tours
- Italian Sojourn with Leaning Tower of Pisa
- Timeless Tuscany: A Tuscan Villa Experience
- Tuscany Walks & Chianti Wines
- Gems of Rome & Florence, Semi-Private Tour
- Two Hearts in Tuscany: Florence & Chianti Romantic Escape | 4 Days
- Bike Across Tuscany - Guided
- Italian Triple Centre with A World Wonder
- Tuscan Treats
- A Taste of Tuscany - Hilltop Towns and Vineyards
- Italy By High-Speed Train
- Local Living Italy - Tuscany San Gimignano (9 destinations)
- Best of Rome, Florence & Venice
- Classic Tuscany - Cycling from Florence to Pisa - Classic Self Guided
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
Italian Triple Centre with A World Wonder
“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, Tuscany, Venice Age Range All Ages Welcome Operator Wonderful Holidays UK From $2,377
9% off- US$2,163
Siena & History
“The three-day tour was very comprehensive and took me to the major sites without the need for a car.”
Shrila, traveled in September
The elegant Hotel Athena in Siena serves as your base to take in UNESCO Val d'Orcia landscapes, San Gimignano's medieval towers, and authentic farm lunches near Pienza. Traditional alabaster workshops in Volterra and historic cellars in Montepulciano round out this Tuscan adventure.
Duration 4 days Destinations Siena, Pienza, Montepulciano, San Gimignano, Volterra Age Range Ages 12+ Operator Tuscan Escapes From
9% off- US$811
Discovering Florence
“The hotel was convenient and comfortable and included a substantial buffet breakfast.”
Roslyn, traveled in September
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, San Gimignano, Monteriggioni, Siena Age Range All Ages Welcome Operator TUI Italia From $901
10% off- US$811
Tuscany Absolute
“We loved the cooking classes, wine tours, city tours - all of it. Hotels were outstanding also.”
Ray, traveled in October
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, Arezzo, Cortona, Montepulciano, Pienza, San Quirico D'orcia, Montalcino, Tuscany Age Range All Ages Welcome Operator Flag Travel Holidays From $3,154
20% off- US$2,523
Italy By High-Speed Train
“TourRadar made our vacation so seemless and worry-free! The hotels and tours they arranged for us were fantastic!”
Teresa, traveled in April
Hotel Executive Florence serves as the perfect base for Tuscan adventures. UNESCO sites like San Gimignano's towers and Siena's historic center await exploration, complemented by Chianti wine tasting. High-speed train travel, daily breakfast, and expert-led walking tours enhance the experience.
Duration 7 days Destinations Rome, Florence, Siena, Castellina in Chianti, San Gimignano, Venice Age Range Ages 10+ Operator Flag Travel Holidays From $2,300
20% off- US$1,840
Tuscany Mon Amour: love at first sight! | Premium Independent Tour including small-group excursions | 8days/7nights
“Everything went smoothly and could not have been more helpful.”
Julie, traveled in September
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 Montecatini, Pisa, Montecarlo, Cinque Terre, Vinci, Siena, Monteriggioni, San Gimignano Age Range All Ages Welcome Operator RANIERI TOUR OPERATOR From
20% off- US$1,499
Gems of Rome & Florence, Semi-Private Tour
“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, Vatican City, Florence, San Gimignano, Siena, Monteriggioni Age Range All Ages Welcome Operated in English, Spanish Operator TUI Italia From $1,627
10% off- US$1,464
Travel Tuscany your way
More travel styles:
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
Who are you traveling with?
Top Tuscany travel itineraries to fit your plans
Demographics
Solo Travelers129 tours- Couples133 tours
- Young Adults (18 - 39)6 tours
- Seniors (50+)51 tours
Best time to visit Tuscany
- 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.
- October 2026 popular 113 tours
- 63 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 51 tours
- 46 tours
- 47 tours
- Spring 2027
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.
- 68 tours
- 92 tours
- popular 99 tours
- Summer 2027
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 93 tours
- 79 tours
- 89 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
Kaitlyn
Expert in Tuscany at TourRadar
Kaitlyn 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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