8 STUNNING TOWNS TO VISIT IN TUSCANY (2025 GUIDE)
Tuscany Beyond the Postcards
While many travelers rush through its cities, it’s the smaller towns that truly are the soul of the region. Golden hills, medieval towers, Renaissance charm, and trattoria dinners are found in abundance once you leave the highways behind.
When we first explored Tuscany, we realized that the magic wasn’t only in the iconic cities, but in the quiet backstreets of tiny towns, the early mornings on hilltop piazzas, and the simple joy of a shared bottle of wine overlooking a valley. That’s why we created this guide—to help you experience Tuscany the way we fell in love with it: slowly, personally, and with open eyes.
Whether you’re a seasoned traveler or discovering Tuscany for the first time, this 2025 guide to 8 stunning towns will help you explore it like a local. And there’s no better place to start than the region’s capital, Florence.
Table of Contents
1. Florence – The Gateway to Tuscany
Florence is not only Tuscany’s capital, but one of Italy’s most magnificent cities—a perfect introduction to the region’s culture, art, and energy. While technically a city, Florence is the ideal springboard to explore Tuscany’s quieter towns, especially with its excellent train and bus connections.
What to Do: Visit the Uffizi Gallery and Accademia to see world-renowned Renaissance art. Climb the Duomo for sweeping views of the city. Wander the artisan shops in the Oltrarno district and catch golden hour from Piazzale Michelangelo.
Where to Stay: Stay central at Hotel Brunelleschi or choose a boutique option like AdAstra in the Oltrarno. For a peaceful retreat, look to villas just outside the city in Fiesole.
Local Tip: Grab an early-morning coffee in Sant’Ambrogio Market and enjoy Florence before the crowds.
2. Pienza – The Ideal Renaissance Town
Pienza is often described as the “ideal Renaissance town,” designed by Pope Pius II in the 15th century to reflect humanist principles of order and beauty. Today, its harmonious architecture and breathtaking views make it one of Tuscany’s most romantic spots.
What to Do: Wander Corso Rossellino and explore the Duomo and Palazzo Piccolomini. Take in sweeping views of the Val d’Orcia from the town walls and enjoy the quiet, contemplative atmosphere.
Where to Stay: Stay at La Bandita Townhouse for boutique charm or Agriturismo Il Macchione for countryside views and homemade breakfasts.
Local Tip: Try Pienza’s famous pecorino cheese, especially during the September cheese-rolling festival.
3. San Gimignano – The Town of Towers
San Gimignano’s 13 medieval towers pierce the skyline, earning it the nickname “Medieval Manhattan.” Despite its popularity, the town retains its magic, especially in the early mornings or evenings.
What to Do: Climb Torre Grossa for views of the countryside. Visit the Duomo to see frescoes by Ghirlandaio. Wander Piazza della Cisterna and sample award-winning gelato from Gelateria Dondoli.
Where to Stay: Hotel La Cisterna offers rooms with tower views. For a vineyard stay, try Fattoria Poggio Alloro just outside town.
Local Tip: Sip Vernaccia di San Gimignano, a crisp white wine native to this region.
4. Cortona – Under the Tuscan Sun
Cortona found fame through Frances Mayes’ memoir Under the Tuscan Sun, but its beauty speaks for itself. With sweeping views over the Val di Chiana and Lake Trasimeno, this hillside town is charming, walkable, and rich in history.
What to Do: Explore Etruscan artifacts at the MAEC museum, climb up to the Medici Fortress, and relax in Piazza della Repubblica with a glass of wine.
Where to Stay: Villa di Piazzano offers luxury in the countryside; for something more central, try Hotel San Michele.
Local Tip: Don’t miss La Bucaccia for authentic local cuisine in a rustic setting.
5. Montepulciano – A Wine Lover’s Dream
Known for its elegant architecture and world-class wine, Montepulciano is a hilltop town surrounded by vineyards and history. It offers a great blend of culture, wine, and Tuscan countryside.
What to Do: Visit Piazza Grande, explore underground wine cellars like De’ Ricci, and enjoy panoramic views from the clock tower. Take a walk to the stunning San Biagio church.
Where to Stay: Palazzo Carletti offers upscale rooms in the town center. For a vineyard escape, stay at Agriturismo Nobile.
Local Tip: Taste the rich Vino Nobile di Montepulciano with pici pasta and wild boar.
6. Volterra – Timeless and Tranquil
Volterra feels like a step back in time. With fewer crowds than other hilltop towns, it boasts an authentic feel, rich history, and incredible views.
What to Do: Visit the Roman Theatre, stroll through the Piazza dei Priori, and explore the Etruscan Museum. Stop into a local alabaster shop to learn about this ancient craft.
Where to Stay: Hotel La Locanda offers comfort right in the historic center, while Apartment Villa Mascagni has countryside views.
Local Tip: Visit in the late afternoon when the crowds thin and golden light bathes the rooftops.
7. Lucca – The Walled Jewel
Lucca is unique in that its entire Renaissance-era city wall is still intact—and it’s walkable (or bikeable) along the top. With leafy boulevards, charming piazzas, and quiet cobbled lanes, Lucca is a Tuscan gem and our favorite tuscan town.
What to Do: Cycle the 4km loop on the walls, visit the Piazza dell’Anfiteatro, climb Guinigi Tower, and check out a Puccini concert.
Where to Stay: Stay at Palazzo Dipinto for boutique luxury or Albergo San Martino for a traditional feel.
Local Tip: Lucca’s food scene is underrated—try farro soup or tordelli lucchese at a local trattoria.
8. Siena – Medieval Majesty and Palio Passion
Siena is a Tuscan icon, known for its dramatic Gothic architecture, fan-shaped main square, and the thrilling Palio horse race. It’s a larger town, but still walkable and full of personality.
What to Do: Admire the black-and-white Siena Cathedral, climb the Torre del Mangia for city views, and visit the Civic Museum in Palazzo Pubblico.
Where to Stay: Grand Hotel Continental Siena is a five-star option near the heart of town. For boutique charm, try Palazzetto Rosso.
Local Tip:
Even if you’re not in town for the Palio (July 2 and August 16), visit a contrada museum to understand Siena’s deep neighborhood pride. Siena is a Tuscan icon, known for its dramatic Gothic architecture, fan-shaped main square, and the thrilling Palio horse race. It’s a larger town, but still walkable and full of personalaity.
Best Tuscany tours
Looking for the easiest way to explore Tuscany? Guided tours from Florence take the hassle out of planning and transport. You’ll enjoy skip-the-line access to the Leaning Tower, expert commentary at historical landmarks, and free time to explore charming towns . Many tours include comfortable transportation, a knowledgeable local guide, and even lunch or wine tastings. Whether you prefer a small group or private tour, it’s the perfect way to see two Tuscany without the stress of navigating on your own.
Getting Around Tuscany: Car vs Train
Tuscany’s beauty lies in its rural landscapes and hilltop towns—many of which are best accessed by car. If you plan to visit places like Volterra, Montepulciano, or Pienza, renting a car is the most convenient option, offering freedom to explore at your own pace and detour into the countryside.
However, Tuscany’s train network is excellent between major hubs. Florence, Lucca, Pisa, and Siena are well connected, making an ideal and easy visit: train between big cities, then rent a car for 4–5 days to explore the smaller towns.
Public buses exist for more remote areas, but they can be infrequent and time-consuming, especially on weekends.
Tips:
Book rental cars in advance, especially during summer.
Driving in ZTL (limited traffic zones) is restricted in most towns—park outside the walls and walk in.
Consider an automatic car if you’re not used to driving manual.
SUGGESTED Itinerary
Day 1: Arrive in Florence. Explore the Duomo, Uffizi, and Ponte Vecchio.
Day 2: Morning train to Lucca. Cycle the walls, overnight in Lucca.
Day 3: Travel to San Gimignano, with an optional quick stop in Pisa on the way.
Day 4: Visit Siena. Stay overnight and soak in the atmosphere.
Day 5: Head to Volterra for a more relaxed and historic hill town.
Day 6: Travel to Montepulciano. Enjoy wine tasting and views.
Day 7: Explore nearby Pienza and the Val d’Orcia.
Day 8: Spend a relaxed day in Cortona.
Day 9: Return to Florence or continue your Tuscan journey.
Best Times to Visit
Spring (April–June): Ideal weather- Wildflowers, mild weather, and open countryside.
Autumn (September–October): Grape harvests, golden hills, fewer crowds.
Summer (July–August): Lively festivals, but hot and busy—explore early or late in the day.
Winter (November–March): Our favorite time to be in Tuscany- Peaceful and atmospheric, perfect for food and wine lovers.
Final Thoughts: Slow Days, Lasting Moments
We didn’t try to see everything in Tuscany—we just tried to see what mattered to us. A quiet walk. A glass of wine. Homemade pasta, cobblestone streets, charming Piazzas, that’s where the magic was for us.
Each town in this guide gave us something different: a view we’ll never forget, a meal we still talk about, or a moment that made us feel at home. And the more we slowed down, the more we saw—not just the places, but the way of life here.
Our advice? Go slow. Leave room for detours and unplanned stops. Stop when something catches your eye. Sit down when a spot feels just right. That’s how Tuscany reveals itself—not all at once, but bit by bit.
We hope this guide helps you find your own way into its heart. Take your time. That’s how the best stories begin.
PLAN YOUR TUSCANY ADVENTURE
These are our favorite companies we use when planning a trip, they consistently have the best prices, great customer service, and overall, are better than their competitors.
BOOK YOUR FLIGHT – Going is a great search engine if you are flexible about your travel destination and dates. Sign up for their newsletter and get the latest deals on destinations around the world. GOING is our new go to.
CAR RENTAL – We recommend using Discover Cars or Rental Cars when booking a car rental, they work with hundreds of companies worldwide to help you find the best car for your needs.
TRAINS – TRAINLINE – is our favorite, this site is very reliable and easy to use.
BUS – OMIO – this website allows you to book train or bus tickets to travel from city to city the best and cheapest way. FLIXBUS is another terrific website with routes between 20 European countries.
ACCOMMODATIONS
BOOKING.com – is our go to for hotel searches around the world, we find they always have the cheapest rates and offer different payment options. In addition, VRBO is another terrific website for all types of accommodations.
HOSTELWORLD – is great if you’re traveling on a budget, and if you need a cheap place to stay.
SIGHTSEEING TOURS
GET YOUR GUIDE – is our favorite; they have stacks of tours and excursions available in cities all over the world. VIATOR is another great website for all types of tours.
TAKE WALKS – This walking tour company provides inside access to attractions and places you can’t get elsewhere.
TRAVEL INSURANCE
SAFETY WING – is our go to travel medical insurance company, especially for longer trips. You can either purchase a monthly plan or a plan for specific trip dates (i.e. 1-2 week trips). They cover people from all over the world, while outside their home country.
ARC’TERYX – is a go to reliable brand for outdoor adventure and travel, their wide range includes light weight durable, easy to clean travel gear.
Check out our RESOURCE PAGE for more additional planning.