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1-Week Tuscany Itinerary: Florence, Siena & Chianti
9 Days
3 Stops
Private transfer
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Trip curated by Roman Karin
ExpertThree nights in Siena rather than extending the Florence stay gives the Tuscany chapter its proper depth, and it's the structural decision I'm most often thanked for. The Piazza del Campo, the back streets through the contrada neighborhoods, and the approach to Montaperti each require time beyond what any day-trip afternoon allows. The Chianti farm visit and cooking class work best on the same day: understanding the terroir in the morning vineyard, then translating that into a kitchen session in the afternoon, grounds the culinary thread in something tangible rather than decorative. For Lucca, cycle the city walls rather than walking them; the 4km circuit above the roofline reveals the Renaissance fortification logic in a way the lanes below, however atmospheric, never quite deliver.
Three nights in Siena rather than extending the Florence stay gives the Tuscany chapter its proper depth, and it's the structural decision I'm most often thanked for. The Piazza del Campo, the back streets through the contrada neighborhoods, and the approach to Montaperti each require time beyond what any day-trip afternoon allows. The Chianti farm visit and cooking class work best on the same day: understanding the terroir in the morning vineyard, then translating that into a kitchen session in the afternoon, grounds the culinary thread in something tangible rather than decorative. For Lucca, cycle the city walls rather than walking them; the 4km circuit above the roofline reveals the Renaissance fortification logic in a way the lanes below, however atmospheric, never quite deliver.
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Florence
Day 1 - 3
Florence, the beautiful capital of the Italian region Tuscany, lies in the center of the country. A small city with a big heart, and an even bigger offering of artistic and historical treasures. For centuries, travelers have journeyed to the birthplace of the Renaissance era to marvel at the many masterpieces of architecture and art: Michelangelo's iconic David, the impressive works of Botticelli, the Uffizi Gallery (packed with works by Caravaggio and Da Vinci), and of course, Brunelleschi's remarkable dome — the religious centerpiece of Florence that dominates the skyline. All are absolute must-sees on any itinerary. Once you've ticked off these renowned attractions, you can take a stroll through the vast Boboli Gardens or climb the hill to the church of San Miniato al Monte for a breathtaking view of this beautiful, enchanting city.
FH55 Grand Hotel Mediterraneo
With a stay at FH55 Grand Hotel Mediterraneo, you'll be centrally located in Florence, within a 5-minute drive of Piazza del Duomo and Ponte Vecchio. This family-friendly hotel is 2.9 mi (4.7 km) from Piazza di Santa Maria Novella and 1 mi (1.5 km) from Piazza della Signoria.
Enjoy recreation amenities such as bicycles to rent or take in the view from a terrace. Additional features at this hotel include complimentary wireless internet access, concierge services, and babysitting (surcharge).
Make yourself at home in one of the 327 guestrooms featuring minibars and LCD televisions. Complimentary wireless internet access keeps you connected, and digital programming is available for your entertainment. Bathrooms feature bathtubs or showers, complimentary toiletries, and bidets. Conveniences include phones, as well as safes and desks.
Your activity
Uffizi Gallery & Accademia
Accademia: Total immersion in the art of Michelangelo to know his most renowned work, the “David”, and other important works of art such as ''I Prigioni'' and ''San Matteo'' and the “Palestrina Pietà”. The young Michelangelo carved the David from a huge block of rough marble in three years, creating an imposing sculpture of absolute beauty, an icon of the renaissance model. He depicted a magnificent nude young man at the height of his physical vigor, whose intense expression of strength and courage, which originated from an absolute faith in God, roses as a symbol of power and invincibility of the Florentine Republic at the time of its maximum splendor.
Uffizi: You can't leave Florence without visiting one of the most famous art galleries in the world. Here you can admire numerous works of art by Botticelli, Michelangelo, Leonardo da Vinci, Raffaello, Giotto, Cimabue, Masaccio and many others.Among the precious exhibition halls of the Gallery, the most renowned one contains the refined works by Botticelli, amongst which the absolute masterpieces: "Primavera" and "Birth of Venus". The latter painting, the icon of the museum, represents the allegory of the birth of the goddess emerging from the sea foam and symbolizes the ideal of beauty as an expression of purity and spiritual quality, typical of the Renaissance Neoplatonic aesthetics. The guided tour ends at the Uffizi Terrace where you can enjoy an amazing and exclusive view of the city’s most important monuments. Once the guided tour is over, it is possible to stay in the museum.
Meeting point - Accademia: at 8:15 am at the corner between Via Ricasoli and Piazza San Marco, in front of the loggiato of Accademia delle Belle Arti.
Uffizi: At 3:00 pm at Travel Store - via dei Tavolini 15r
At both Museums an Assistant waits for you wearing blue clothing with Gray Line logos
Group size - max 18 pax M1C (accademia) - max 9 M2C ( uffizi)
Siena
Day 4 - 5
Spread across three hills in the heart of Tuscany, the compact city of Siena is a historic gem centered around the sloping Piazza del Campo. Overlooked by the magnificent Palazzo Pubblico, the city is known worldwide for the famous Palio, a horse race held around the piazza twice every summer. Siena has remarkably preserved its quaint old-world charm. Its stunning Gothic buildings include the city’s Duomo, which is arguably one of Italy’s most impressive Gothic cathedrals, along with numerous other architectural treasures. The city also boasts a wealth of exceptional early Renaissance art. Meanwhile, Siena buzzes with modern life, and each of its 17 neighborhoods is uniquely captivating.
Quattro Cantoni
Located in Siena (Siena City Centre), Quattro Cantoni is within a 5-minute walk of Piazza del Campo and Pinacoteca Nazionale. This bed & breakfast is 0.1 mi (0.1 km) from Museo dell'Opera del Duomo and 0.1 mi (0.1 km) from National Museum of Archaeology.
Make use of convenient amenities such as complimentary wireless internet access, concierge services, and a vending machine. Getting to nearby attractions is a breeze with the area shuttle (surcharge).
Make yourself at home in one of the 4 individually decorated guestrooms, featuring refrigerators and flat-screen televisions. Complimentary wireless internet access keeps you connected, and digital programming is available for your entertainment. Bathrooms feature showers, complimentary toiletries, and bidets. Conveniences include laptop-compatible safes and desks, and housekeeping is provided daily.
Your activity
Secrets of Siena – Walking Tour
Step into the heart of medieval Tuscany with a private walking tour of Siena—one of the region’s most captivating hilltop cities. Led by a passionate local guide, this immersive experience is perfect for first-time visitors and seasoned travelers alike, offering a deeper understanding of Siena’s rich history, vibrant culture, and timeless beauty.
Your journey begins in the stunning Piazza del Campo, often hailed as one of Europe’s most beautiful squares and home to the legendary Palio horse race. Take in the grandeur of the Palazzo Pubblico and the iconic Torre del Mangia, then wind your way through Siena’s charming cobblestone streets—each one steeped in stories from centuries past.
A highlight of the tour is the magnificent Siena Cathedral (Duomo), a true masterpiece of Italian Gothic design. Admire its striking black-and-white marble façade, intricate interior, and renowned artworks by Michelangelo, Donatello, and Bernini. Interior visits can be arranged upon request for an even more in-depth experience.
As you explore the city’s historic neighborhoods, or contrade, your guide will share the fascinating traditions and rivalries that still define local life today—bringing Siena’s past and present vividly to life.
San Casciano dei Bagni
Day 6 - 9
Situated in the southernmost area of the province of Siena, in Tuscany, Italy, San Casciano dei Bagni is a gorgeous small town famous for its thermal springs. Home to 42 springs with an average temperature of 40 degrees celsius, the wonderful springs have attracted visitors to the town from around 1400, and continue to do so today. Visitors can also explore the surrounding countryside to see ancient Roman tablets which have record of this. The baths were honoured with incredible buildings with sculpted decorations, adding true value to the town. Other historic sites include the fourth-century Pagan Temple of Igea (the goddess of health), numerous beautiful churches, the picturesque 16th-century Palazzo dell’Arcipretura, and the Celle Caste remains. Other highlights include the delicious regional delicacies such as ‘Ciaffagnone’ - a fritter made with caciocavallo cheese - and fresh local produce.
Fonteverde Thermal Spa Resort Tuscany
With a stay at Fonteverde Thermal Spa Resort Tuscany in San Casciano dei Bagni, you'll be 0.1 mi (0.1 km) from Fonteverde Terme and 8.7 mi (14.1 km) from Monte Rufeno Nature Reserve. This family-friendly hotel is 11 mi (17.6 km) from Sarteano Castle and 11.2 mi (18 km) from Fontesecca.
Pamper yourself with a visit to the spa, which offers massages, body treatments, and facials. You're sure to appreciate the recreational amenities, which include 5 indoor and 2 outdoor swimming pools and hot springs. Additional amenities at this hotel include complimentary wireless internet access, concierge services, and babysitting (surcharge). If you'd like to spend the day shopping, you can hop on the shuttle (surcharge).
Make yourself at home in one of the 78 individually furnished guestrooms, featuring minibars and LCD televisions. Complimentary wireless internet access keeps you connected, and satellite programming is available for your entertainment. Private bathrooms with bathtubs or showers feature rainfall showerheads and complimentary toiletries. Conveniences include laptop-compatible safes and desks, and housekeeping is provided daily.
Your activity
ITALIAN PASTA AT A HISTORIC ESTATE
Meet our driver at the lobby of Fonteverde Lifestyle & Thermal Retreat and enjoy a private transfer through the rolling Umbrian countryside toward a renowned winery near Orvieto. Upon arrival, begin a guided tour of the estate. Visit the wine cellars and learn about the winery’s history and production philosophy. Enjoy a pleasant walk through the vineyards, discovering the characteristics of the soil and grape varieties that make this territory so unique. The experience continues with the exploration of fascinating ancient Etruscan caves, where the winery’s prestigious Metodo Classico sparkling wine is aged in ideal natural conditions — a perfect blend of history, tradition, and innovation. Following the estate visit, take part in a pasta experience in small group. Under the guidance of an expert, enjoy a hands-on cooking class where you will prepare three traditional local pasta varieties, learning techniques, tips, and the secrets of authentic Italian cuisine. After the class, sit down and savor the dishes you have prepared, each paired with three selected wines from the estate, carefully chosen to enhance the flavors of your creations. A convivial and immersive culinary experience that perfectly blends food, wine, and tradition. The tour continue to the magnificent hilltop town of Orvieto. Enjoy time to explore its charming historic center, stroll along its medieval streets, admire elegant palaces and artisan boutiques, and visit the impressive Duomo, one of Italy’s finest examples of Gothic architecture. In late afternoon, transfer back to Fonteverde Lifestyle & Thermal Retreat.
Starting time: 9:15 AM
From$2,900
per personAccommodations
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Why plan with an expert?
200+
Plan with professionals who are explorers themselves.
27+ hours of time saved
Our experts plan and book for you.
12+ Bookings managed
Everything is bundled in one place and perfectly planned.
6+ Transfers coordinated
For optimal transport and comfort.
Excellent
Itinerary inspiration
Three nights in Florence and three in Siena, with the Chianti countryside and its farm visits, wine tastings, and cooking class bridging the two halves — a week that covers Tuscany's most significant city, its most characterful medieval rival, and the landscape between them that defines the region as much as either. The Chianti day from Florence is the activity I'd always flag first: the terraced vineyards, the estate tastings, and the hands-on cooking class together give Tuscany a grounded, edible identity that the galleries alone can't provide.
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A detail a lot of travelers miss about Siena: the Piazza del Campo is most rewarding in the late afternoon when the day-trip crowds from Florence have thinned and the setting sun hits the curve of the brick paving from the west. Save the guided walking tour for the morning and the piazza for the evening, and the city will make the most sense in that order.
Day 1–3: Florence
Hotel: B&B Hotel Firenze Pitti Palace al Ponte Vecchio
The hotel sits on the Oltrarno side of the Arno, which puts the Ponte Vecchio and both major galleries within easy walking distance. The Uffizi Gallery and the Accademia are best visited on separate mornings rather than back to back — the Botticelli rooms before 9 a.m., and David with the room still quiet, are each worth the unhurried start. The Chianti day trip fills a full second day well, and the cooking class provides a strong final Florence evening.
Day 4–7: Siena
Hotel: Hotel NH Siena
The guided walking tour through the historic center, the Piazza del Campo and the Palio tradition, the local trattorias, and the optional day trips to Pisa and Lucca across three full days. The Pisa cathedral square — the Duomo, the Baptistery, and the tower in white Carrara marble on the same piece of grass — is considerably more impressive in person than the single-angle photograph suggests, and giving it a proper morning rather than a rushed stop makes the difference. Lucca's walls, best cycled rather than walked, fill a strong afternoon alongside it.
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Tips for your one week in Tuscany itinerary
April–June and September–October are the most pleasant months for Tuscany. These seasons offer comfortable weather for walking tours in Florence, wine tastings in Chianti, and exploring Siena’s Gothic architecture without the midsummer heat.
Hotels range from $55–$90 per night for budget stays, $90–$180 for mid-range, and $180–$270+ for boutique or luxury. Meals cost $15–$30 in trattorias and $50–$100 for fine dining. Activities include vineyard tastings in Chianti from $50, cooking classes, and museum passes in Florence around $90. A week can run from under $1,500 per person on a budget to $2,500 or more with higher-end stays and experiences.
Florence offers the Uffizi Gallery, Michelangelo’s David, and the Boboli Gardens. In Chianti, vineyard visits, wine tastings, and farm tours bring Tuscan traditions to life. Siena’s Piazza del Campo and Duomo showcase medieval heritage. Optional day trips to Pisa’s Leaning Tower and Lucca’s city walls add even more variety.
➔ Things to see Tuscany | Things to see Italy | Activities Italy
Book skip-the-line entry for Florence’s Uffizi Gallery and Accademia in advance. In Chianti, plan tastings with a driver or guided tour for convenience. Staying three nights each in Florence and Siena balances art, city life, and countryside exploration.
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