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 - GM
Giuseppa • traveled in May, 2025
Unforgettable Tuscan Escape! This tour through Tuscany was absolutely incredible—an unforgettable mix of culture, beauty, and relaxation! From the moment we landed in Florence, everything was perfectly organized. The hotel in Montecatini Terme was elegant and comfortable, right in the heart of a charming spa town that felt like a hidden gem. Each day brought something special—wine tasting at a beautiful family-run farm, exploring iconic cities like Siena, Pisa, and Florence, and enjoying amazing local food and wine. The guided tours were informative without being overwhelming, and the guides were passionate, friendly, and knowledgeable. One of the biggest highlights was the day trip through the Tuscan countryside—San Gimignano was like stepping into a fairytale, and the views were breathtaking. The combination of guided time and free time made it feel relaxing, not rushed. Montecatini itself was a wonderful home base. We loved the freedom to enjoy a spa treatment or just stroll through the lovely streets. And having a free day to choose extra activities or simply relax was such a thoughtful touch. Every detail was taken care of, and the whole experience felt curated with care and local insight. I’d highly recommend this tour to anyone wanting a true taste of Tuscany—whether you're into history, food, wine, or just soaking in the beauty of Italy. Bravo to the organizers—this was a dream trip come true!
Tuscany Mon Amour: Love at First Sight 2026! Semi-Escorted Tour
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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
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
- US$573
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 $2,299
8% Off- US$2,115You save $184
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
8% Off- US$1,381
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 $2,646
12% Off- US$2,329You save $318
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, Greve in Chianti, San Gimignano, Venice Age Range Ages 8+ Operator Omega Tours From
12% Off- US$1,809
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
12% Off- US$4,184
Tuscany Absolute
12 Reviews by TourRadar travelers“From the charming vineyards to the picturesque landscapes, every moment was a postcard come to life.”
Gilbert, 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, Castellina in Chianti, Montepulciano Age Range All Ages Welcome Operator Flag Travel Holidays From
12% Off- US$2,990
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 Travelers142 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.
- 59 tours
- 136 tours
- popular 141 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
- 129 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 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 37 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
George
Expert in Tuscany at TourRadar
George 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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