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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Larry • traveled in May, 2026
Wonderful tour and exceptional operators throughout the different areas of Italy
Italian Triple Centre with A World Wonder - J
Judy • traveled in April, 2026
Everything was perfect from the moment we arrived. All communication, transfers and drivers were friendly and professional. Villa Casagrande was amazing and Anna led such fun cooking classes and the wine tour of the villa was so informative. Our day trips to the Chianti region, Siena, San Gimignano, Lucca and Pisa were planned such that we experienced the true beauty of the Tuscany region. I would also like to mention Michael from Tour Radar as he was available to answer all questions in a timely manner from the beginning to end of our trip. I highly recommend this tour… my only regret is that we did not stay longer… but we will return.
Timeless Tuscany: A Tuscan Villa Experience - C
Craig • traveled in June, 2025
The tour provided the core requirements for our Italy week. I would only suggest providing suggested hotel transport if not including and adjusting the price.
Italy By High-Speed Train
Traveler Photos & Videos from Tuscany tours
- Italian Sojourn with Leaning Tower of Pisa
- Two Hearts in Tuscany: A Romantic Getaway for 2
- Italy By High-Speed Train
- Italian Triple Centre with A World Wonder
- Classic Tuscany - Cycling from Florence to Pisa - Classic Self Guided
- Tuscany Absolute
- Rome to London Trail (Standard, Summer ( Until Mar '27), Age 18-22)
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
6 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
- US$2,433
Duration 6 days Destinations Florence, Figline Valdarno, Siena, San Gimignano Age Range Ages 10+ Operator Omega Tours From
- US$1,676
Tuscany Mon Amour: love at first sight! | Premium Independent Tour including small-group excursions | 8days/7nights
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$1,414
Italy By High-Speed Train
93 Reviews by TourRadar travelers“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
- US$1,938
Discovering Florence
4 Reviews by TourRadar travelers“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 $939
15% Off- US$798You save $141
Tuscany Walking and Wine
24 Reviews by TourRadar travelers“Walking beautiful countryside. Guide very well informed.”
David, 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, San Gimignano, Castellina in Chianti, Siena, Pienza, San Quirico D'orcia, Montalcino, Florence Age Range Ages 16+ Operator Explore! From $2,870
9% Off- US$2,600You save $270
Best of Rome, Florence & Venice
3 Reviews by TourRadar travelers“The hotels were fine with very good breakfasts. The speed trains were great.”
Diane, traveled in April
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, Greve in Chianti, San Gimignano, Venice Age Range Ages 8+ Operator Omega Tours From
9% Off- US$1,968
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 Travelers145 tours- Couples133 tours
- Young Adults (18 - 39)7 tours
- Seniors (50+)55 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.
- popular 102 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 137 tours
- 122 tours
- 133 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 148 tours
- October 2026 141 tours
- 56 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 41 tours
- 25 tours
- 25 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
Claire
Expert in Tuscany at TourRadar
Claire 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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