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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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 - 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
DEDiane
Best of Rome, Florence & Venice
SSarahTaylor
Tuscan Treats
MKMarina
Tuscany Absolute
Italy By High-Speed TrainHeather
Tuscany Walks & Chianti WinesPotter
Two Hearts in Tuscany: A Romantic Getaway for 2Belen
Tuscan TreatsDouglas
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
Unique 8 days in Tuscany AdventureMariya
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“Everything was great. I will travel with his company again :)”
Rowena, traveled in August
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$580
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 $2,199
8% Off- US$2,023You save $176
Italian Triple Centre with A World Wonder
5 Reviews by TourRadar travelers“The team do manage to respond to it promptly and not having a disruption on the plans.”
Michelle, traveled in August
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 $2,543
12% Off- US$2,238You save $305
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
12% Off- US$1,397
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
12% Off- US$1,841
Florence City Break - 3 Days/2 Nights
5 Reviews by TourRadar travelers“It was a bit rainy when we went to San Gimignano, but we still had enough time I believe to tour the town.”
Averil, traveled in November
Young travelers (18-39) find the perfect balance between Florence's freedom and guided Chianti wine experiences. Local Brunello and Super Tuscan wines shine at authentic vineyards, while San Gimignano's famous towers beckon. Two nights in central Florence complement this highly-rated tour (4.9/5).
Duration 3 days Destinations Florence, Ulignano, San Gimignano Age Range Ages 18-41 Operator Italy on a Budget Tours From
12% Off- US$347
Tuscany Walking and Wine
24 Reviews by TourRadar travelers“The hotels were very nice, especially the one in Pienza.”
Andrew, traveled in May
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
9% Off- US$2,600You save $270
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 Travelers137 tours- Couples126 tours
- Young Adults (18 - 39)7 tours
- Seniors (50+)51 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.
- 65 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
- 120 tours
- 127 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 144 tours
- October 2026 137 tours
- 57 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
Melissa
Expert in Tuscany at TourRadar
Melissa 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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