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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Judith • traveled in October
Overall we are very happy with our experience with TUI Italia. All services were provided as promised and in a timely manner. The itinerary offered us the enjoyment of experiencing Italy in a variety of settings and different experiences. We have some suggestions to help others if interested.
Tuscany Highlights, Semi-Private Tour - 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 - 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
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Italian Sojourn with Leaning Tower of Pisa
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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
Tuscany Highlights, Semi-Private Tour
2 Reviews by TourRadar travelers“All services were provided as promised and in a timely manner. The itinerary offered us the enjoyment of experiencing Italy in a variety of settings and different experiences.”
Judith, traveled in September
Cultural gems shine throughout Tuscany, from Lucca's preserved medieval walls to Siena's curved Piazza del Campo. The elegant Garden Siena and Grand Hotel Adriatico welcome guests exploring Florence's Renaissance masterpieces at the Uffizi Gallery. Family-run Chianti wineries and the fortified village of Monteriggioni complete the experience.
Duration 8 days Destinations Florence, Lucca, Pisa, Siena Age Range All Ages Welcome Operated in English, German, Italian, French, Spanish Operator TUI Italia From $3,961
15% Off- US$3,367You save $594
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
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 $1,721
15% Off- US$1,463You save $258
The Best of Tuscany - 4Days/3Nights
20 Reviews by TourRadar travelers“Loved every minute! Lots of activities with great people.”
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 $596
15% Off- US$506You save $89
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
15% Off- US$2,186
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$1,436
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
15% Off- US$1,848
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 Travelers131 tours- Couples124 tours
- Young Adults (18 - 39)6 tours
- Seniors (50+)52 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.
- popular 36 tours
- 34 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.
- 78 tours
- 134 tours
- popular 140 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 132 tours
- 118 tours
- 124 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 141 tours
- October 2026 135 tours
- 59 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
Joseph
Expert in Tuscany at TourRadar
Joseph 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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