Where to Stay in Tuscany: The Ultimate Guide to Choosing the Perfect Base
Timeless Wanderers: Posted December 22, 2025
Choosing where to stay in Tuscany can feel overwhelming — and for good reason.
Tuscany isn’t a place you visit once and move on; it’s a region of hill towns, vineyards, art cities, coastlines, and slow country roads.
Where you base yourself will shape your entire experience.
Some travellers want museums and food tours on their doorstep.
Others dream of waking up among vineyards or medieval streets where evenings are quiet and local.
There’s no single “best” place to stay in Tuscany — only the best base for how you want to travel.
This guide breaks it all down.
We’ll start with what to consider before booking, then explore our eight favourite bases in Tuscany, with five recommended places to stay in each, followed by FAQs and final thoughts.
Table of Contents
Essential Things to Consider Before Choosing Where to Stay in Tuscany
Firstly: What Do You Want to Do in Tuscany?
Tuscany rewards different travel styles. Before choosing accommodation, think about what excites you most:
Art, museums, and food tours → cities like Florence or Siena
Wine tasting and countryside drives → Chianti, Val d’Orcia, Montepulciano
Medieval towns and quiet evenings → Volterra or Cortona
Coastal escapes mixed with culture → Lucca
Your “perfect” base depends on whether you want culture-heavy days, scenic drives, or slow evenings.
Secondly: How Many Days Will You Be Here?
Short stays (3–5 days) work best with one base.
Longer trips (7–14 days) benefit from two or three bases, reducing driving time and allowing deeper exploration.
Thirdly: How Many Bases Do You Want?
Changing hotels every night kills the Tuscan magic. We recommend:
1 base for short trips
2 bases for balanced itineraries
3 bases for slow, immersive travel
Fourthly: How Will You Get Around?
This matters more than most travellers realise.
No car → Florence, Lucca, Siena
With a car → Chianti, Val d’Orcia, Montepulciano, Cortona, Volterra.
Car rental – If you plan to visit countryside towns and vineyards, a rental car is invaluable.
Florence – Tuscany’s Cultural Heart and Best First Base
Tuscany’s capital city and main transport hub, Florence is where most trips to the region naturally begin.
Whether you’re arriving by plane, train, or car, Florence works as both a cultural anchor and a practical base for exploring the rest of Tuscany.
A true Renaissance masterpiece, Florence is packed with world-class art, architecture, and history.
The city is home to iconic museums like the Accademia and the Uffizi, extraordinary churches and palaces shaped by the Medici family, and masterpieces by Michelangelo, Botticelli, Donatello, Giotto, and Caravaggio.
Even with multiple visits, there’s always more to discover.
To do Florence justice, plan on at least two full days in the city.
Beyond its cultural riches, Florence also makes an excellent base for day trips.
Lucca, Pisa, and Siena are all easily reached by public transport in under 90 minutes.
With a car—or organised tours—you can explore Chianti, San Gimignano, and Volterra without changing accommodation.
It’s one of the easiest places in Tuscany to combine city life with countryside experiences.
Car rental – If you plan to visit countryside towns and vineyards, a rental car is invaluable.
Recommended Places to Stay in Florence
Hotel Palazzo Guadagni
Housed in a historic Renaissance building, this atmospheric hotel blends original architectural details with beautifully furnished rooms. Elegant, character-filled, and quietly luxurious, it’s one of the most memorable stays in Florence.
Approx. €280–€370 per night
Hotel Calimala
Exceptionally central and surrounded by historic landmarks, this stylish boutique hotel pairs modern design with artistic flair. Ideal if you want to walk everywhere and stay right in the heart of Florence.
Approx. €260–€320 per night
La Maison du Sage
A gorgeous mid-range boutique hotel in Santa Croce, with some rooms overlooking the basilica itself. Warm, elegant, and perfectly located for dining and evening strolls.
Approx. €230–€330 per night
Room Mate Luca
A colourful, modern hotel with spacious rooms and a playful design. Comfortable, well-run, and slightly boutique in feel, it offers great value for its quality and location.
Approx. €140–€280 per night
Hotel Silla
Excellent value near Piazzale Michelangelo, with attractive rooms and a more local neighbourhood feel. Close enough to walk everywhere, but quieter than the historic core.
Approx. €140–€190 per night
Locanda de’ Ciompi
A small, cosy inn located on one of Florence’s liveliest streets. Rooms book out quickly, but if you can secure one, it’s fantastic value in a vibrant part of the city.
Approx. €140–€190 per night
Residenza San Gallo 79
A beautifully renovated B&B just north of the Duomo area. Bright, spacious rooms with high ceilings make this a comfortable and affordable option close to the action.
Approx. €100–€180 per night
P.S. You can read my full guide on Where to Stay in Florence for more hotel recommendations and insights!
Other accommodation in Tuscany.
Best Day Trips from Florence
Pisa (½ day)
Lucca (full day)
Siena (full day)
San Gimignano & Volterra (full-day duo)
Chianti wineries
Val d’Orcia road trip (ideal with a Car Rental:)
Lucca – Relaxed, Walkable, and Effortlessly Tuscan
Lucca is one of Tuscany’s most liveable and quietly charming cities. ( Our Favorite Tuscan Town)
Fully enclosed by Renaissance walls, it feels compact, calm, and wonderfully self-contained — the kind of place where days drift by easily and evenings are meant for slow dinners and sunset walks.
Unlike Florence or Siena, Lucca doesn’t feel overwhelming.
The historic centre is flat, making it ideal for walking or cycling, and the wide tree-lined walls double as a circular park that locals use daily.
Inside, you’ll find Roman ruins, elegant piazzas, beautiful churches, and a relaxed café culture that feels refreshingly local.
Lucca also works well as a strategic base.
Pisa is just 30 minutes away by train, Florence is reachable in about 90 minutes, and the Tuscan coast — including Viareggio and Forte dei Marmi — is close enough for a day trip.
If you’re travelling without a car and want a slower-paced alternative to Florence, Lucca is an excellent choice.
Recommended Places to Stay in Lucca
Hotel Ilaria
A consistently popular choice just inside the city walls. Comfortable rooms, friendly service, and thoughtful extras make this a reliable and well-priced base in the historic centre.
Approx. €180–€250 per night
Hotel Palazzo Alexander
An elegant boutique hotel set in a restored historic palace. Warm interiors, attentive staff, and a quiet location inside the walls make it ideal for couples.
Approx. €220–€300 per night
Hotel Alla Corte degli Angeli
Romantic and atmospheric, with rooms inspired by Renaissance and Baroque styles. A lovely option if you want character and charm without sacrificing comfort.
Approx. €200–€280 per night
Hotel San Martino
A smaller, understated hotel with a calm feel and excellent location near the cathedral. Great value for travellers who want simplicity and comfort inside the walls.
Approx. €160–€230 per night
Villa Romantica
Located just outside the historic walls, this peaceful villa-style hotel offers a more residential feel while remaining walkable to the centre. Ideal if you prefer quieter evenings.
Approx. €150–€220 per night
* If you’ve got specific dates in mind, don’t wait too long to secure your spot. You’ll often get better rates by booking early to! Other accommodation in Lucca.*
Chianti – Classic Wine Country and Rolling Hill Landscapes
Chianti is what most people picture when they imagine Tuscany: vineyard-covered hills, stone farmhouses, olive groves, winding roads, and long lunches with a view.
Staying here is less about ticking off sights and more about slowing down and settling into the rhythm of the countryside.
Unlike Florence or Lucca, Chianti isn’t centred around one town.
Instead, you’ll find small villages like Greve, Castellina, Radda, and Gaiole, all connected by scenic roads.
Having a car is essential, but the reward is complete freedom — to stop at wineries, explore back roads, and enjoy quiet evenings far from crowds.
Chianti works best as a second base after Florence or Lucca.
Spend a few days sightseeing in the city, then move into the countryside to relax, taste wine, and enjoy the landscape.
It’s ideal for couples, wine lovers, and travellers who want a more rural Tuscan experience.
Car rental – If you plan to visit countryside towns and vineyards, a rental car is invaluable.
Greve in Chianti
Often considered the gateway to Chianti, Greve is lively, welcoming, and easy to reach from Florence. Its main square, Piazza Matteotti, is lined with wine shops, cafés, and delis, making it a great introduction to Chianti wines and Tuscan food culture without feeling overly touristy.
Castellina in Chianti
Castellina sits dramatically on a ridge between Florence and Siena and blends history with beautiful views. Walk the medieval Via delle Volte, explore small museums, and enjoy panoramic countryside scenery. It’s a fantastic base if you want charm, history, and easy access to surrounding vineyards.
Radda in Chianti
Radda is one of Chianti’s most atmospheric medieval towns, enclosed by stone walls and surrounded by vineyards. Quieter and more refined, it’s ideal for slow travel, wine tastings, and evening strolls. If you want Chianti at its most authentic and peaceful, Radda is a standout choice.
Gaiole in Chianti
Gaiole feels more rural and less polished than other Chianti towns, which is part of its appeal. Surrounded by castles and historic estates, it’s perfect for wine lovers, cyclists, and road trippers. It’s also a great base for exploring remote vineyards and scenic backroads.
Recommended Places to Stay in Chianti
Castello di Spaltenna (Gaiole in Chianti)
A beautifully restored medieval castle surrounded by vineyards and forest. Elegant rooms, a spa, and excellent dining make this one of Chianti’s standout luxury stays.
Approx. €350–€500 per night
Borgo Scopeto Relais (Castelnuovo Berardenga)
Set on a historic estate just outside Siena, this refined countryside hotel offers panoramic views, polished service, and a classic Tuscan atmosphere.
Approx. €300–€450 per night
Hotel Le Fontanelle (Pianella)
A sophisticated wine resort with a spa, Michelin-starred dining, and immaculate grounds. Ideal if you want countryside luxury with resort-level comfort.
Approx. €400–€600 per night
Villa Bordoni (Greve in Chianti)
A smaller boutique hotel with vineyard views, cooking classes, and a warm, personal feel. A great choice if you want charm without formality.
Approx. €250–€350 per night
Agriturismo Il Segreto di Pietrafitta (Castellina in Chianti)
An authentic farm stay offering apartments, countryside views, and excellent value. Perfect for longer stays or travellers wanting space and independence.
Approx. €150–€230 per night
* If you’ve got specific dates in mind, don’t wait too long to secure your spot. You’ll often get better rates by booking early to! Other accommodation in Chianti.*
Siena – Medieval Elegance and Timeless Tuscan Traditions
Siena feels wonderfully self-contained, a city where medieval life never really disappeared.
Encircled by ancient walls and largely untouched by modern development, it’s one of Tuscany’s most atmospheric bases — compact, historic, and deeply proud of its traditions.
The heart of the city is Piazza del Campo, a shell-shaped square that hosts the famous Palio horse race twice each summer.
Even outside Palio season, Siena buzzes with local life, from evening passeggiatas to long dinners tucked into stone-walled trattorias.
Its Gothic cathedral, narrow lanes, and contrade neighbourhoods make wandering the city a pleasure in itself.
Siena works beautifully as a base if you want medieval character with excellent access to the countryside.
From here, you can easily explore Chianti, San Gimignano, Monteriggioni, and the Val d’Orcia by car.
Public transport also connects Siena well to Florence, making it a good option for travellers without a vehicle.
Plan for 2–3 nights to fully enjoy the city without rushing — more if you want to use it as a central base for southern Tuscany.
Recommended Places to Stay in Siena
Grand Hotel Continental Siena
The city’s only true five-star hotel, housed in a 17th-century palazzo steps from the Duomo. Grand interiors, frescoed ceilings, and an unbeatable location.
Approx. €350–€500 per night
Hotel Athena
Set just inside the city walls, this elegant hotel offers spacious rooms, a terrace restaurant, and rare on-site parking — a big plus if you’re driving.
Approx. €220–€350 per night
Hotel Palazzo di Valli
A refined boutique hotel in a quiet residential area, about a 10–15 minute walk from the centre. Lovely views and a relaxed, local feel.
Approx. €180–€280 per night
Relais degli Angeli
A beautifully restored B&B near Piazza del Campo with modern comforts and thoughtful design. Ideal for travellers who want charm without formality.
Approx. €150–€230 per night
Hotel Minerva
Excellent value just outside the historic walls, with clean, comfortable rooms and easy access by car. A practical choice without sacrificing location.
Approx. €120–€180 per night
* If you’ve got specific dates in mind, don’t wait too long to secure your spot. You’ll often get better rates by booking early to! Other accommodation in Siena.*
Val d’Orcia – Iconic Landscapes and Slow Tuscan Living
If Tuscany exists in your imagination as rolling hills, cypress-lined roads, stone farmhouses, and golden light, chances are you’re picturing the Val d’Orcia.
This UNESCO-listed valley south of Siena is the visual heart of Tuscany — cinematic, peaceful, and made for slow travel.
Unlike Florence or Siena, Val d’Orcia isn’t about museums or must-see monuments.
It’s about slowing down.
Long lunches, morning fog lifting over vineyards, thermal baths in medieval villages, and drives where every bend in the road feels postcard-worthy.
It’s an ideal base if you want to unwind, reconnect with the countryside, and truly slow down.
The valley is dotted with small, character-filled towns like Pienza, San Quirico d’Orcia, Bagno Vignoni, and Castiglione d’Orcia.
Having a car here is essential, and staying in the countryside — rather than a single town — allows you to experience the region at its best.
Plan for 3–4 nights minimum. Anything less feels rushed, especially if you want to enjoy thermal baths, winery visits, and unhurried evenings under the Tuscan sky.
Car rental – If you plan to visit countryside towns and vineyards, a rental car is invaluable.
Pienza
Pienza is the picture-perfect heart of Val d’Orcia, known for its Renaissance design, sweeping countryside views, and excellent pecorino cheese.
It’s compact, elegant, and easy to explore in a few hours, making it an ideal base or stop on a scenic Val d’Orcia drive.
San Quirico d’Orcia
San Quirico d’Orcia feels quietly authentic, with medieval streets, a lovely main square, and fewer crowds than nearby towns.
It’s a great overnight base, especially if you want a slower pace, local restaurants, and easy access to surrounding countryside and hot springs.
Bagno Vignoni
Bagno Vignoni is unlike anywhere else in Tuscany, famous for its central stone piazza filled with steaming thermal water.
Tiny and atmospheric, it’s best visited as a short stop to soak up the scenery, enjoy a spa visit, or combine with nearby San Quirico or Pienza.
Castiglione d’Orcia
Castiglione d’Orcia is a traditional hill town with panoramic views, medieval ruins, and a more local feel.
Less polished than Pienza, it’s ideal for travellers who enjoy quiet streets, countryside walks, and an authentic slice of Val d’Orcia away from tour buses.
Recommended Places to Stay in Val d’Orcia
Castello di Velona Resort & Spa
A luxurious castle-turned-spa overlooking the Orcia valley, with thermal pools, sweeping views, and refined dining. A destination in its own right.
Approx. €450–€700 per night
Hotel Corsignano (Pienza)
A comfortable, well-located hotel just outside Pienza’s historic centre. Easy parking, valley views, and a relaxed atmosphere make it a great base.
Approx. €180–€280 per night
Agriturismo Podere Brizio
A classic Tuscan farmhouse stay surrounded by fields and vineyards. Warm hospitality, peaceful setting, and an authentic countryside experience.
Approx. €150–€230 per night
Locanda in Tuscany
An intimate countryside retreat between Pienza and San Quirico, with stylish rooms and a highly regarded restaurant. Perfect for food-focused travellers.
Approx. €220–€350 per night
Hotel Palazzuolo (San Quirico d’Orcia)
Charming, family-run hotel inside the village walls. Traditional, welcoming, and perfectly placed for exploring the valley.
Approx. €120–€180 per night
* If you’ve got specific dates in mind, don’t wait too long to secure your spot. You’ll often get better rates by booking early to! Other accommodation in Val d’Orcia.*
Montepulciano – Wine, Views, and Hilltop Grandeur
Montepulciano is one of Tuscany’s most rewarding hill towns — dramatic, elegant, and deeply connected to wine.
Rising above the Val di Chiana on a long limestone ridge, the town blends Renaissance architecture with a relaxed, lived-in feel that makes it easy to stay longer than planned.
This is the home of Vino Nobile di Montepulciano, one of Tuscany’s great red wines, and tastings are woven directly into the historic centre.
Ancient cellars sit beneath noble palazzi, meaning you can sample exceptional wines without ever leaving town.
Add sweeping countryside views, beautiful piazzas, and atmospheric evening strolls, and Montepulciano becomes an ideal base for travellers who want culture and countryside.
You’ll want 2–3 nights here to enjoy the town properly, visit nearby villages like Pienza and Monticchiello, and explore wineries in the surrounding hills.
While Montepulciano itself can be explored on foot, a car is strongly recommended for countryside stays and winery visits.
Car rental – If you plan to visit countryside towns and vineyards, a rental car is invaluable.
Recommended Places to Stay in Montepulciano
Hotel Palazzo Carletti
A refined boutique hotel set in a historic palazzo near Piazza Grande. Spacious rooms, elegant décor, and attentive service.
Approx. €220–€350 per night
Agriturismo Sanguineto
offers finely fitted accommodation in the lush greenery of the Tuscan countryside, a fascinating setting rich in picturesque hills, world renowned vineyards and ancient olive groves.
Approx. €160–€260 per night
Meublè Il Riccio
A charming, well-priced guesthouse inside the old town. Simple, friendly, and perfectly located for exploring on foot.
Approx. €120–€180 per night
Agriturismo Il Serraglio
A peaceful countryside stay surrounded by vineyards, offering rustic elegance, warm hospitality, and memorable sunsets.
Approx. €180–€280 per night
Relais Villa Grazianella | UNA Esperienze
Classic Tuscan farmhouse luxury with a pool, vineyard views, and excellent dining. A wonderful base for wine lovers.
Approx. €250–€400 per night
* If you’ve got specific dates in mind, don’t wait too long to secure your spot. You’ll often get better rates by booking early to! Other accommodation in Montepulciano.*
Cortona – Sunlit Streets and Timeless Tuscan Views
Cortona is one of Tuscany’s most atmospheric hill towns — warm, golden, and effortlessly romantic.
Perched high above the Val di Chiana, it delivers some of the most breathtaking views in the region, especially at sunset when the countryside below glows in soft shades of green and gold.
The town has a strong Etruscan past, medieval lanes that curve and climb, and a lively yet authentic local rhythm.
Cortona feels artistic and soulful rather than polished, with flower-filled balconies, family-run trattorias, and quiet corners perfect for lingering.
It’s also famously associated with Under the Tuscan Sun, but thankfully the town retains its depth and charm well beyond that connection.
Plan for 2–3 nights here to soak up Cortona itself, enjoy slow mornings and golden evenings, and explore nearby Lake Trasimeno or surrounding vineyards.
Cortona’s historic centre is walkable but steep, so good shoes are essential.
A car is highly recommended if you’re staying outside the walls or planning day trips.
Recommended Places to Stay in Cortona
Hotel Villa Marsili
An elegant historic villa just outside the old town walls, offering refined rooms, excellent service, and panoramic valley views.
Approx. €250–€400 per night
Monastero di Cortona Hotel & Spa
A beautifully restored 15th-century monastery with a spa, stylish rooms, and a peaceful atmosphere just steps from the centre.
Approx. €220–€350 per night
Hotel Italia Cortona
A classic, well-located hotel inside the historic centre with comfortable rooms and some of the best views in town.
Approx. €160–€250 per night
Relais La Corte dei Papi
A romantic countryside retreat surrounded by vineyards, known for its exceptional service, fine dining, and tranquil setting.
Approx. €300–€500 per night
Agriturismo Il Torrino
A charming farmhouse stay with sweeping views, warm hospitality, and an authentic Tuscan feel just outside Cortona.
Approx. €150–€240 per night
* If you’ve got specific dates in mind, don’t wait too long to secure your spot. You’ll often get better rates by booking early to! Other accommodation in Cortona.*
Volterra – Ancient Stone, Etruscan Roots & Timeless Tranquillity
Volterra feels older than time itself.
Sitting high on a windswept plateau between Pisa and Siena, this stone-built town is one of Tuscany’s most atmospheric destinations, with deep Etruscan roots, Roman ruins, and medieval streets that seem untouched by modern life.
Unlike some of Tuscany’s busier hill towns, Volterra remains calm and quietly captivating.
Alabaster workshops line narrow lanes, views stretch endlessly over rolling countryside, and evenings are wonderfully peaceful once day-trippers leave.
It’s a place for slow wandering, history lovers, and travellers who appreciate authenticity over polish.
Plan to spend 1–2 nights in Volterra. It pairs beautifully with San Gimignano, the Cecina Valley, or a scenic drive through the Tuscan countryside.
Having a car is strongly recommended, as public transport connections are limited and the surrounding landscape is part of the experience.
Car rental – If you plan to visit countryside towns and vineyards, a rental car is invaluable.
Recommended Places to Stay in Volterra
Hotel La Locanda
A refined boutique hotel inside the historic centre with stylish rooms and a cosy, intimate feel.
Approx. €180–€280 per night
Hotel San Lino
Set in a former convent with a garden and pool, just outside the city walls. Peaceful, charming, and very well located.
Approx. €150–€230 per night
Agriturismo Casale Giulia
offering a unique and charming atmosphere.A beautifully restored countryside villa offering space, tranquillity, and sweeping views just minutes from Volterra.
Approx. €100–€180 per night
Agriturismo Podere Campaini in Volterra
offers a country house with a swimming pool boasting stunning views, a lush garden, and free WiFi.
Approx. €120–€200 per night
* If you’ve got specific dates in mind, don’t wait too long to secure your spot. You’ll often get better rates by booking early to! Other accommodation in Volterra.*
Suggested Itineraries
3-Day City Break
Day 1: Florence – Uffizi, Ponte Vecchio, evening Christmas market stroll.
Day 2: Day trip to Siena for the market and Gothic architecture.
Day 3: Lucca’s city walls by bicycle and hot chocolate in Piazza dell’Anfiteatro.
5-Day Countryside Escape
Days 1–2: Florence highlights.
Day 3: Chianti for winery tastings and olive oil sampling.
Day 4: Val d’Orcia—Pienza and Montepulciano under a winter mist.
Day 5: Hot springs soak in Bagno Vignoni.
How to Spend 7 Magical Days in Tuscany by Car
Car rental – If you plan to visit countryside towns and vineyards, a rental car is invaluable.
8 FAQs About Visiting Tuscany
1. How many days should I spend in Tuscany?
For a complete experience, 7–10 days is ideal. This allows 2–3 days in Florence and 1–2 days in each surrounding base.
2. When is the best time to visit Tuscany?
Spring (March–May) and autumn (September–October) offer mild weather, fewer crowds, and stunning landscapes. Summer is busy but great for festivals and long days.
3. Is a car necessary for Tuscany?
A car is essential if you want to explore hill towns, vineyards, and countryside at your own pace. For Florence or Siena alone, public transport works well.
4. What should I pack for Tuscany?
Layers for variable weather, comfortable walking shoes, a light raincoat, sunglasses, and a hat. Summer requires sun protection; winter needs warmer layers.
5. Are Tuscan towns walkable?
Yes, most towns are compact with pedestrian-friendly streets. Hilltop towns like Cortona and Volterra require some uphill walking.
6. Can I visit multiple bases in one trip?
Absolutely! Using Florence, Siena, or Chianti as central bases makes day trips easy. 2–3 bases is manageable for a 7–10 day itinerary.
7. Are wineries open year-round?
Yes, but availability varies. Spring and autumn are ideal for tastings and tours, while summer and winter may have limited schedules.
8. What’s the cuisine like in each region?
Florence offers classic Tuscan dishes, Chianti and Montepulciano focus on wines and hearty fare, while hill towns like Cortona and Volterra emphasize seasonal produce and local specialties.
Car rental – If you plan to visit countryside towns and vineyards, a rental car is invaluable.
Do You Need Travel Insurance for Tuscany?
(Short Answer: Yes — It’s Still a Smart Idea)
Travel insurance isn’t legally required to visit Tuscany, but it’s one of the smartest things you can have when travelling in Italy.
Even in a relaxed destination like Tuscany, things can go wrong — from delayed flights and lost luggage to medical issues, rental car damage, or unexpected trip cancellations.
And while Italy has excellent healthcare, medical treatment for visitors can still be costly without proper coverage.
As long-term travellers living in Italy, we’ve found SafetyWing to be a practical option for trips around Europe, offering coverage for medical care, travel delays, and lost belongings without complicated fine print.
SafetyWing
(Best for Long-Term Travel & Affordability)
We personally use SafetyWing, and have since 2019.
It’s perfect for travelling, spending multiple weeks or a whole year abroad.
You can get a Quote here.
It’s the kind of insurance you hope you never need—but you’ll be very glad you have if something unexpected happens.
Final Thoughts: Tuscany Travel Guide
Tuscany is a region that balances iconic cities with timeless hill towns, rolling vineyards, and charming villages.
By planning your trip around Florence, Lucca, Siena, Chianti, Val d’Orcia, Montepulciano, Cortona, and Volterra, you can experience art, history, food, wine, and scenery in a single journey.
Choosing the right bases, accommodation, and pace makes all the difference—whether you prefer boutique hotels, luxury estates, or budget-friendly guesthouses.
With fewer crowds in spring or autumn, a rental car for flexibility, and thoughtful planning of each base, Tuscany transforms from a travel destination into an unforgettable experience.
From Renaissance masterpieces in Florence to the serene hills of Val d’Orcia and the Etruscan charm of Cortona, every corner tells a story.
This guide gives you everything you need to explore Tuscany with ease, comfort, and lasting memories.
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.