Where to Stay in Tuscany, Italy: 6 Best Areas & Hotels

Planning a trip to Tuscany and wondering where to stay? You’ve found the experts. 

This famous region is one of the most beautiful parts of Italy, known for its vine-draped hills, medieval towns, and sun-soaked countryside. But Tuscany is also quite large and diverse, which can make choosing the right base a little tricky.

Don’t worry—we’ve done the research for you. After exploring this central region and comparing the top destinations, we’ve put together this guide to the six best areas to stay in Tuscany, along with our favorite hotel recommendations for every budget. This way, you can focus on planning your dream Tuscan adventure instead of stressing over logistics. Let’s get started!

Where to Stay in Tuscany map

Overview of the Best Areas to Stay in Tuscany

Tuscany is a surprisingly varied region, and the best place to stay often depends on how you plan to explore it. A few areas, like Florence, Lucca, and central Siena, are compact, walkable, and easy to explore by train. But much of the countryside people picture, including Chianti, Val d’Orcia, and rural Cortona, is spread along winding roads where short distances can take longer than expected.

Most travelers explore Tuscany in one of two ways. Some stick to the main cities and take day trips by train or tour, while others rent a car and follow the classic Tuscany road-trip route. Having your own vehicle makes it much easier to reach hilltop villages, wineries, scenic viewpoints, and countryside stays, especially in regions like Chianti or Val d’Orcia.

That said, driving in historic Italian cities can come with a few challenges. Many old towns have ZTL restricted traffic zones, parking can be limited or expensive, and steep medieval streets can make hauling luggage uphill an adventure. Taxis are also less common outside major cities, so it’s worth choosing your base carefully.

One final tip: Tuscany is extremely popular in peak season, especially from June through September (with July and August being the busiest months). Many countryside and vineyard stays sell out well in advance, so it’s a good idea to book early if you’re visiting during the summer.

Here’s a quick look at some of the best areas to stay in Tuscany:

• Florence – Best for first-time visitors – Florence is the region’s most famous city, packed with Renaissance art, historic landmarks, and lively piazzas, making it a fantastic introduction to Tuscany. For spacious apartments with incredible views of Florence’s iconic cathedral, Palazzo Gamba Apartments al Duomo offers a comfortable and stylish stay right beside the Duomo.

• Siena – Best for a classic medieval stay – A beautifully preserved hill city centered around the iconic Piazza del Campo, Siena feels like stepping straight into the Middle Ages. Albergo Chiusarelli is a welcoming mid-range hotel just a short walk from the historic center and many of the city’s top sights.

• Chianti – Best for wine lovers – This scenic countryside between Florence and Siena is filled with vineyards, wineries, and charming hill towns perched among rolling hills. For a tranquil stay in Chianti, Ultimo Mulino Country Hotel offers a relaxing retreat surrounded by classic Tuscan scenery.

• Val d’Orcia – Best for couples & iconic scenery – Known for its sweeping landscapes and romantic villages like Pienza and San Quirico d’Orcia, Val d’Orcia captures the Tuscany many travelers dream of. Relais Il Chiostro Di Pienza is a historic convent hotel offering incredible valley views right in the heart of Pienza.

• Lucca – Best for a slower city stay – A charming walled city where you can bike along tree-lined ramparts and relax in lively yet laid-back piazzas, Lucca is a wonderful place to slow down and enjoy Tuscany. Just outside the historic walls, Hotel San Marco offers a comfortable mid-range stay with easy access to the old town.

• Cortona – Best for a quiet hill town base – Cortona is a peaceful hill town known for its sweeping valley views, stone streets, and timeless Tuscan atmosphere. For a stay within the historic walls, Hotel Villa Marsili offers boutique charm and beautiful panoramic views of the countryside.

Where to Stay in Tuscany

Florence

BEST FOR FIRST-TIME VISITORS

Pros

• Historic center packed with iconic Renaissance sights
• Easy to explore on foot with great restaurants, shops, and museums 

Cons

• Can be crowded, especially in peak season
• Hotels and dining in the center tend to be more expensive

Florence is the kind of place that instantly feels like the Tuscany you’ve been dreaming about. With its Renaissance architecture, lively piazzas, and world-class museums, it’s easily the best base for first-time visitors who want to see Tuscany’s most famous sights without needing a car. We love staying here because everything is within walking distance, and every corner seems to reveal another postcard-worthy view.

The historic center is compact and incredibly easy to navigate. Within just a few minutes’ walk, you can stand beneath the massive dome of the Duomo (Cathedral of Santa Maria del Fiore), cross the famous Ponte Vecchio with its rows of jewelry shops, or wander through Piazza della Signoria to see Palazzo Vecchio rising above the square. At the same time, art lovers could easily spend half a day inside the Uffizi Gallery, home to masterpieces by Michelangelo and Leonardo da Vinci.

Florence is also a great jumping-off point for exploring the rest of Tuscany. Trains connect easily to places like Pisa and Lucca, while guided tours or rental cars open up wine regions like Chianti. And if you want one of the best views in the city, head up to Piazzale Michelangelo at sunset. Watching the rooftops glow orange from up there is something we never get tired of.

FH55 Hotel Calzaiuoli – $$$ 

If you want to be right in the center of Florence’s historic action, FH55 Hotel Calzaiuoli is a fantastic place to stay. Located on the lively Via Calzaiuoli, the hotel sits just a two-minute walk from the Duomo and within easy reach of major sights like the Uffizi Gallery and Accademia. It’s an ideal base for first-time visitors who want to explore the city entirely on foot.

Rooms are comfortable and well-appointed, featuring minibars, air conditioning, soundproofing, and free Wi-Fi, with some offering lovely rooftop views over Florence. Guests can start the day with a generous buffet breakfast featuring Florentine pastries and Tuscan specialties, and the cozy reading lounge with complimentary drinks is a relaxing place to unwind after sightseeing.

Rates range from €200 to €650 per night, depending on the room and season, so it’s a great choice for travelers who want a central stay without sacrificing comfort. 

If FH55 Hotel Calzaiuoli is fully booked, Hotel Berchielli is a nice alternative along the Arno. Just a short stroll from Ponte Vecchio and the Uffizi Gallery, this long-standing Florentine hotel offers elegant rooms, classic decor, and a generous breakfast with views over the river.

Hotel degli Orafi is another standout nearby. Set inside a former 13th-century convent beside the Uffizi and overlooking Ponte Vecchio, it combines historic charm, frescoed interiors, and a rooftop terrace with cathedral views right in the heart of Florence.

Palazzo Gamba Apartments al Duomo – $$

Palazzo Gamba Apartments al Duomo is where to stay for unforgettable views and plenty of space to breathe. These stylish apartments sit directly opposite Florence’s famed Cathedral, giving you an unbeatable front-row seat to the Duomo. No zoom lens required!

With options ranging from cozy one-bedrooms to spacious suites, each apartment features a full kitchen, soundproof windows, and thoughtful touches like a dishwasher and coffee machine. But what really sets this stay apart is the space. You get the comforts of home (hello, washing machine!) combined with the feel of a boutique hotel. 

It’s perfect for longer stays, families, or travelers who want flexibility without compromising location. Prices typically range from €150 to €300 per night, depending on the room type and the time of year.

Set right on Piazza della Signoria, Relais Piazza Signoria is another exceptional stay in the Historic Center. With fully equipped kitchenettes, apartment-style layouts, and even a private terrace overlooking Palazzo Vecchio in select units, it offers independence and unbeatable views just steps from the Uffizi and a five-minute walk to the Duomo.

For a more traditional Florentine atmosphere, Hotel Davanzati is also an excellent backup nearby. Set inside a historic building just steps from Ponte Vecchio, it pairs classic charm with genuinely warm service in one of the most walkable pockets of the city.

Residence La Repubblica – $

Residence La Repubblica proves that you don’t have to sacrifice location for affordability. Set directly on Piazza della Repubblica, one of Florence’s liveliest squares, these self-catering apartments offer unbeatable access to everything: the Duomo, Ponte Vecchio, and Uffizi are all within a five-minute stroll.

Each unit includes a compact kitchenette, air conditioning, and hardwood floors, with some featuring views over the bustling square below. It’s not a full-service hotel, but for travelers who value space, centrality, and the option to cook a simple meal or two, it hits the mark. 

Bonus—you’ll find a washing machine in some units, which is a game-changer for longer stays. Prices can start as low as around €100 per night, depending on room size and season.

Another one of our favorite stays in the Historic Center is Hotel Dali. Just a short walk from the Duomo, Piazza della Signoria, and the Uffizi, it offers air-conditioned rooms and practical amenities like kitchenettes and washing machines, which work great for travelers who want flexibility in a truly central location.

If keeping costs low is the priority, Hotel Giappone is another practical choice nearby. Housed in a historic building close to both the Duomo and the train station, it delivers simple rooms and helpful staff who can assist with museum bookings, making it ideal for travelers who plan to spend most of their time out exploring.

Siena

BEST FOR A CLASSIC MEDIEVAL STAY

Pros

• One of the most beautifully preserved medieval cities in Italy
• Compact historic center that’s easy to explore on foot

Cons

• Steep hills and lots of stairs throughout the old town
• Fewer train connections compared to Florence

If your idea of Tuscany includes winding brick streets, historic towers, and lively piazzas that haven’t changed much in centuries, Siena delivers in the best way. The entire historic center is a UNESCO World Heritage Site, and wandering through it reveals centuries of Gothic architecture and narrow alleyways climbing up the surrounding hills.

The city’s focal point is Piazza del Campo, a stunning shell-shaped square that’s widely considered one of the most beautiful in Italy. It’s the social heart of Siena and the site of the famous Palio di Siena, a centuries-old horse race that takes place twice each summer. Sitting on the warm bricks with a gelato in hand while watching locals and visitors wander through the square is easily one of our favorite things to do here. 

A short walk away is the striking Siena Cathedral (Duomo di Siena), famous for its black-and-white marble exterior and richly decorated interior. Climbing the Torre del Mangia rewards you with sweeping views across the terracotta rooftops and the surrounding countryside.

Keep wandering, and you’ll stumble across places like Santa Maria della Scala, a massive former hospital turned museum, or the hilltop Basilica of San Domenico overlooking the city. Discoveries like these are what make Siena such a rewarding base for travelers looking for a smaller city full of history and personality.

Grand Hotel Continental Siena – $$$

For travelers who want a truly elegant stay in Siena, Grand Hotel Continental Siena delivers classic Italian luxury right in the heart of the historic center. Set inside a beautifully restored 17th-century palace, this five-star hotel feels like stepping into Siena’s aristocratic past, with frescoed ceilings, antique furnishings, terracotta floors, and marble details throughout the rooms and suites.

The location couldn’t be better, either. Piazza del Campo is just a short stroll away, meaning Siena’s famous square and winding medieval streets are right on your doorstep. After a day of exploring, guests can enjoy gourmet Tuscan cuisine at Sapordivino, sip a drink at the elegant lounge bar, or unwind in the refined historic surroundings.

Prices vary by season but usually range from €400 to €600 per night, which feels fitting for a stay inside one of Siena’s most beautiful historic palaces.

Those wanting a quieter base just outside the city center should also consider Hotel Certosa Di Maggiano. Set in a beautifully restored 14th-century monastery surrounded by gardens and olive trees, it offers a peaceful countryside retreat just a short drive from Siena, complete with elegant rooms and sweeping Tuscan views.

Albergo Chiusarelli – $$

If you’re looking for a comfortable stay in Siena that won’t break the bank, Albergo Chiusarelli is a fantastic mid-range choice. Housed in a charming 19th-century building, this welcoming hotel blends historic character with modern comforts, making it a great base for exploring the city. 

Its location is a big plus, too. Piazza del Campo and Siena’s historic center are just a short walk away, so you can easily wander the medieval streets, visit the cathedral, and return to the hotel without needing transportation. Rooms feature classic Tuscan décor with modern touches, offering a cozy and relaxing place to unwind after a day of sightseeing. 

In the morning, guests can enjoy a complimentary buffet breakfast, and the on-site restaurant serves up traditional Tuscan dishes for dinner. Prices typically range from €120 to €180 per night, depending on the season.

Hotel Athena is another excellent option nearby, especially for visitors who want great views along with easy access to Siena’s historic center. Located just inside the city walls, the hotel features comfortable rooms and a panoramic terrace restaurant overlooking the Tuscan countryside.

For a similar mid-range stay with fantastic scenery, Hotel Minerva is also worth considering. Many rooms and the breakfast terrace offer sweeping views across Siena’s rooftops and the surrounding valley, and it’s only about a 10-minute walk from Piazza del Campo.

Albergo Bernini – $

Travelers on a budget will appreciate the simple charm and unbeatable location of Albergo Bernini. This small, family-run hotel sits inside a historic building in Siena’s old town and is just a short walk from Piazza del Campo, the cathedral, and many of the city’s best cafés and bars.

Rooms are modest but comfortable, offering free Wi-Fi and work desks, with the option of either private or shared bathrooms. What really makes this stay special, though, is the panoramic terrace. You’ll want to linger with a glass of wine while taking in the city’s historic skyline.

With everything within walking distance and prices typically ranging from €70 to €120 per night, Albergo Bernini is a great pick for travelers seeking an affordable base right in the heart of Siena.

If Albergo Bernini is sold out for your travel dates, Hotel Duomo is a great backup for staying as close as possible to Siena’s most famous landmark. Sitting right beside the cathedral, this welcoming hotel provides simple rooms, many with lovely views of the Duomo, plus a terrace where you can enjoy breakfast while overlooking the historic center.

Set just outside Siena’s historic walls, Villa Elda Boutique Hotel offers a peaceful retreat within easy walking distance of the city center. The elegant villa features cozy rooms and a panoramic terrace with sweeping views across the Tuscan countryside.

Chianti

BEST FOR WINE LOVERS

Pros

• Rolling vineyard landscapes and classic Tuscan countryside views
• Fantastic wineries, farm-to-table restaurants, and charming hill towns

Cons

• A car is almost essential to get around
• Towns and accommodations can be spread out across the countryside

Chianti is where Tuscany’s countryside really comes to life. This famous wine region stretches between Florence and Siena and is filled with vineyard-covered hills and olive groves, quiet country roads, and medieval hill towns perched on ridges. Staying here is less about ticking off big landmarks and more about slowing down and soaking up the atmosphere.

Unlike Florence or Siena, Chianti isn’t a single town but a broad region made up of small villages and rural estates. That means accommodations vary widely, from boutique hotels in historic town centers to countryside agriturismos surrounded by vineyards. Having a rental car is key here, since many of the most beautiful spots are tucked along winding country roads.

Several towns make great bases for exploring the region. Greve in Chianti is one of the most well-known, with its charming triangular Piazza Matteotti lined with wine bars and shops. Nearby Panzano in Chianti is famous for its excellent restaurants and scenic viewpoints, while Castellina in Chianti and Radda in Chianti offer classic hill-town charm with stone streets and sweeping countryside views.

Another highlight is Badia a Passignano, a historic abbey surrounded by vineyards that perfectly captures the region’s peaceful character. For travelers who want vineyard stays, wine tastings, and some of Tuscany’s most beautiful scenery, Chianti is an unforgettable base.

Borgo Scopeto Wine & Country Relais – $$$

Dreaming of a classic Tuscan countryside stay surrounded by vineyards? Borgo Scopeto Wine & Country Relais is hard to beat. Set within a beautifully restored 13th-century hamlet in the Chianti hills, this elegant retreat feels worlds away from busy cities yet is only about a 20-minute drive from Siena.

Rooms and suites are spacious and designed in calming colors with touches of rustic Tuscan style, along with modern comforts like flat-screen TVs, minibars, and free Wi-Fi. Outside, two panoramic swimming pools overlook the surrounding vineyards and olive groves, creating the kind of view you picture when imagining Tuscany. 

Guests can linger over tastings of the estate’s wines and olive oils, enjoy Tuscan cuisine at the restaurant, or relax in the spa with its indoor pool, Turkish bath, and hot tub. Prices typically range from about €340 to €1,000+ per night, depending on the room and season.

Another countryside stay that we love is Villa Campomaggio Resort & SPA, located among vineyards just outside Radda in Chianti. This restored stone estate offers spacious rooms and apartments, a relaxing spa, and a panoramic pool overlooking the rolling Tuscan hills.

Travelers who prefer staying right in a historic hill town may enjoy Hotel Palazzo San Niccolò & Spa in the heart of Radda in Chianti. Set inside a historic building along the town’s quiet stone streets, the hotel combines medieval character with modern comforts like a wellness center and indoor pool.

Ultimo Mulino Country Hotel – $$

If you’re hoping to stay somewhere that truly captures the rustic charm of Chianti, Ultimo Mulino Country Hotel is a wonderful choice for you. Set inside a restored old mill in the hills near Gaiole in Chianti, this peaceful countryside retreat is surrounded by sweeping views across the Tuscan landscape.

The property blends traditional character with modern comforts, with guest rooms featuring exposed wooden beams, rustic stone details, air conditioning, flat-screen TVs, and spacious bathrooms. Outside, the panoramic pool overlooking the hills is the kind of spot where it’s easy to lose track of time.

We especially enjoy the relaxed atmosphere here. Afternoons are perfect for a swim, followed by a glass of Chianti on the terrace. In the evening, the restaurant serves classic Tuscan dishes based on traditional recipes, paired with excellent local wines. Prices usually range from about €120 to €300 per night, depending on the room and season.

A similarly charming stay in this area is Palazzo Leopoldo Dimora Storica & Spa in the hill town of Radda in Chianti. Set inside a historic palace overlooking the countryside, this elegant stay pairs old-world character with modern perks like a wellness center, spa treatments, and beautiful valley views.

If you love the idea of staying on a working Tuscan estate, La Pensione di Vignamaggio is a wonderful pick just outside Greve in Chianti. Surrounded by vineyards and gardens on a historic wine estate, it offers a peaceful countryside setting that’s perfect for slow mornings, wine tastings, and long dinners under a starlit sky.

Hotel Colle Etrusco Salivolpi – $

Guests who want the charm of a Tuscan farmhouse without straying too far from town will find that Hotel Colle Etrusco Salivolpi is a wonderful place to stay in Chianti. This beautifully converted country house sits just outside the hill town of Castellina in Chianti, surrounded by relaxing countryside views.

The hotel blends rustic style with comfortable modern touches. Guest rooms feature details like exposed wooden beams, wrought-iron beds, air conditioning, and free Wi-Fi, creating a cozy place to unwind after a day exploring Chianti’s winding wine roads. 

Outside, the private garden and swimming pool provide a quiet place to relax, while mornings start with a homemade breakfast that feels distinctly Tuscan. Plus, you can easily walk into Castellina’s historic center for dinner or a glass of wine. Prices typically range from about €100 to €280 per night, depending on the room and season.

Albergo Villa San Michele is another popular countryside option near Castellina in Chianti. Set in a restored farmhouse surrounded by vineyards and olive trees, it offers a peaceful setting with a pool and beautiful valley views while still being just a short drive from the region’s hill towns.

Those who prefer staying right in a historic village might enjoy Albergo Casa Al Sole in nearby Greve in Chianti. Located in the town’s charming main square, this welcoming hotel offers simple, comfortable rooms and an unbeatable location just steps from restaurants and local shops.

Val d’Orcia

BEST FOR COUPLES & ICONIC SCENERY 

Pros

• Some of Tuscany’s most famous rolling hill landscapes
• Romantic villages, quiet countryside stays, and scenic drives

Cons

• A rental car is essential to explore the area
• Small villages mean fewer restaurants and nightlife options

Just south of Siena, Val d’Orcia is the Tuscany that many people picture before they even arrive in Italy. This UNESCO-listed region is known for its sweeping hills, winding cypress-lined roads, and stone farmhouses sitting alone on ridgelines. 

Staying here is all about the scenery and the relaxed pace of life that comes with it. You may spend your days exploring quiet hill towns, stopping at scenic overlooks, or lingering over a long lunch at a countryside trattoria. 

Several charming towns make great bases for exploring the region. Pienza is one of the most popular and famous for its beautifully preserved historic center and incredible views across the valley. Nearby San Quirico d’Orcia is another charming village with medieval streets and peaceful gardens. At the same time, the tiny hamlet of Bagno Vignoni is known for its unusual thermal baths, set right in the middle of the main square.

Some of the most photographed spots in the region are also found here, including the Cappella della Madonna di Vitaleta, a small chapel surrounded by golden fields. And gardens like La Foce offer even more epic views of the countryside, making Val d’Orcia a dream destination for travelers looking for romance, scenery, and a truly peaceful Tuscan escape.

Il Miraggio in Val d’Orcia Relais & Spa – $$$

For a romantic countryside retreat surrounded by some of Tuscany’s most iconic scenery, Il Miraggio in Val d’Orcia Relais & Spa is a beautiful place to stay. Located near the charming village of San Quirico d’Orcia, this elegant property sits in the heart of the Val d’Orcia landscape, with views of sun-drenched hills and endless country roads.

The hotel blends modern luxury with the calm atmosphere the region is famous for. Guest rooms are spacious and thoughtfully designed, with private balconies or terraces that let you take full advantage of the views. You can relax in the garden outside, sip a drink on the terrace, or unwind in the spa with wellness treatments and relaxation areas. 

It’s the kind of place where slow mornings and sunset views over the valley feel completely effortless. Prices typically range from about €170 to €450 per night, depending on the room and season.

Albergo Le Terme is a wonderful backup option in the tiny village of Bagno Vignoni, famous for its historic thermal baths set right in the middle of the main square. Guests can soak in the spa’s mineral-rich waters after a day of exploring Val d’Orcia’s scenic drives and hill towns.

Travelers looking for something small and stylish may enjoy VILLA LIBERTY Boutique Hotel in nearby San Quirico d’Orcia. This elegant boutique stay offers beautifully designed rooms, a peaceful garden setting, and easy access to many of the region’s most famous viewpoints and villages.

Relais Il Chiostro Di Pienza – $$

Staying at Relais Il Chiostro Di Pienza means spending the night inside a beautifully restored 15th-century convent in the heart of one of Tuscany’s most charming villages. Located just steps from Pienza’s cathedral and historic square, this unique hotel combines centuries of history with stunning views over the Val d’Orcia.

The property still retains much of its original character, with peaceful cloisters, gardens, and stone architecture that reflect its monastic past. Guest rooms are comfortable and thoughtfully designed, some even featuring original ceiling frescoes or views across the valley. 

The panoramic terrace and pool are perfect for relaxing after a day wandering Pienza’s cobbled streets. And the restaurant terrace is the perfect spot to enjoy classic Tuscan dishes while taking in views of the countryside. Prices typically range from about €100 to €320 per night, depending on the room and season.

Just outside Pienza’s historic center, Il Rondò Boutique Hotel offers a quieter place to stay while still being close to all the action. This small boutique hotel is known for its welcoming atmosphere, elegant rooms, and a peaceful garden terrace overlooking the Val d’Orcia countryside.

History lovers may appreciate PALAZZO DEL CAPITANO Wellness & Relais in nearby San Quirico d’Orcia. Housed in a beautifully restored medieval palace, the hotel blends centuries-old character with modern comforts like a wellness area and a well-regarded Tuscan restaurant.

Hotel Panoramic Montepulciano – $

Set high on a hillside overlooking the Tuscan countryside, Hotel Panoramic Montepulciano lives up to its name with wide-open views across the surrounding Montepulciano. Located just a 5-minute drive from the historic town, this relaxed hotel offers a peaceful base for exploring the Val d’Orcia while still being close to thermal baths and charming villages.

The atmosphere here is laid-back and comfortable, with spacious rooms featuring parquet floors, air conditioning, flat-screen TVs, and free Wi-Fi. Many rooms include balconies where you can enjoy views of the surrounding countryside. Plus, there’s a large garden and outdoor pool with hydromassage that are perfect for relaxing after a day of sightseeing.

We also really like that this hotel runs entirely on renewable energy and is carbon neutral. Prices typically range from about €60 to €140 per night, depending on the room and season.

A great alternative in the historic center is La Terrazza Di Montepulciano, a small guesthouse known for its incredible terrace views over the Val d’Orcia. Staying here puts you within easy walking distance of Montepulciano’s wine bars, restaurants, and historic piazzas while still offering that classic Tuscan scenery.

Those looking for a stay with a bit more wellness focus may enjoy Hotel Villa Ricci & Benessere, located just outside Montepulciano’s old town. This comfortable hotel offers spacious rooms and a wellness center where you can unwind after a day exploring the region’s vineyards and hill towns.

Lucca

BEST FOR A SLOWER CITY STAY

Pros

• Charming historic center that’s easy to explore on foot or by bike
• Lively but relaxed atmosphere with great restaurants and cafes

Cons

• Fewer major landmarks compared to Florence or Siena
• Evenings can feel quiet outside the main squares

Lucca is one of Tuscany’s most charming small cities, known for its beautifully preserved historic center and laid-back atmosphere. Surrounded by impressive Renaissance-era walls, the city feels wonderfully contained, making it an easy and enjoyable place to explore at a relaxed pace. 

One of the most unique features of the city is the Lucca City Walls (Mura di Lucca). Unlike most historic walls in Italy, these are wide enough to walk or bike along, creating a peaceful green loop that circles the entire old town. We love renting bikes here and riding beneath the shady trees while looking out over the rooftops and piazzas below.

Inside the walls, Lucca’s streets are filled with historic churches, elegant squares, and plenty of inviting cafés. Via Fillungo is the city’s main shopping street and a great place to wander, while nearby Piazza dell’Anfiteatro stands out for its unusual oval shape, built on the site of an ancient Roman amphitheater. Another highlight is the Guinigi Tower, famous for the oak trees growing from its rooftop garden.

Be sure to step inside the beautiful Lucca Cathedral (Duomo di San Martino), too. Together with its scenic streets and easygoing pace, it’s all part of what makes Lucca such a wonderful base for travelers looking for a more local feel while exploring Tuscany.

Hotel Ilaria – $$$

Hotel Ilaria is a fantastic luxury option located just inside Lucca’s historic walls, making it an ideal base for exploring the city’s charming streets and piazzas on foot. Tucked beside the peaceful gardens of Villa Buonvisi, this elegant hotel blends historic character with modern comforts while offering a slightly quieter setting within the old town.

Accommodations are spacious and thoughtfully designed, with air conditioning, flat-screen TVs, and Wi-Fi. You’ll love the little extras here, like complimentary snacks and drinks served on the terrace each afternoon. You can also borrow the hotel’s free bicycles to ride along Lucca’s famous city walls, which is one of our favorite ways to experience the city.

Plus, after a day of sightseeing, the terrace hot tub and garden views offer a relaxing place to unwind. Prices typically range from about €120 to €500 per night, depending on the room and season.

Palazzo Dipinto is another excellent stay located inside Lucca’s historic center, especially for travelers who appreciate contemporary design. Set within a beautifully restored palace, this boutique hotel blends sleek modern interiors with historic architecture while placing you within easy walking distance of Lucca’s main squares and restaurants.

For something equally stylish, The Tuscanian Hotel delivers a refined boutique experience right in the heart of the old town. The rooms are beautifully designed with modern touches, and the location makes it incredibly easy to step outside and immediately start exploring Lucca’s charming streets, cafés, and shops.

Hotel San Marco – $$

For a solid mid-range choice just outside Lucca’s historic walls, Hotel San Marco gives you great value, comfortable rooms, and an easy walk into the old town. Located about a 10-minute stroll from the city gates near Porta San Jacopo, it’s a convenient base for exploring Lucca while avoiding the higher prices often found inside the historic center.

Rooms are simple, yet modern and comfortable, with air conditioning, flat-screen TVs, and free Wi-Fi. One of the standout features here is the outdoor swimming pool and garden terrace, which is especially welcome during the warm summer months. 

Breakfast is served buffet-style, often overlooking the garden, and the hotel offers bicycle rentals, making it easy to ride along Lucca’s famous tree-lined city walls. Nightly rates usually range from about €100 to €370, depending on the season and room type.

If you prefer staying inside Lucca’s historic walls rather than just outside them, Hotel Alla Corte degli Angeli is a wonderful boutique option. This romantic hotel is known for its beautifully decorated rooms with themed interiors and elegant details, creating a unique and memorable base in the heart of the old town.

San Luca Palace offers another top choice within the city walls, occupying an elegant, restored historic building close to Porta San Donato. The spacious rooms and quiet location are a relaxing place to stay, just a short walk from Lucca’s main squares and attractions.

Hotel Rex – $

Hotel Rex is a reliable budget-friendly option near the train station, making it especially convenient for travelers arriving by rail or planning day trips around Tuscany. Located just outside Lucca’s walls, the hotel is only about a 5-minute walk from the historic center, so you can easily explore the old town without needing a car.

You’ll love the simple and welcoming atmosphere here. Accommodations are practical, with air conditioning, satellite TVs, free Wi-Fi, and private bathrooms—everything you need for a convenient and relaxed stay while exploring the city.

Each morning starts with a generous sweet-and-savory breakfast buffet, and the friendly staff is always happy to offer tips on visiting the city and the surrounding countryside. Prices generally range from about €80 to €150 per night, depending on the season.

Albergo San Martino & Depandance is also a great option for travelers who want to stay inside the historic center while keeping things affordable. Located just steps from the beautiful Lucca Cathedral, this welcoming hotel offers cozy rooms and a fantastic location to easily explore the city’s main sights on foot.

Right in the middle of Lucca’s old town, Hotel La Luna offers a comfortable stay within easy walking distance of the city’s most famous squares and churches. Its rooftop terrace is a highlight, providing peaceful views over the rooftops after a day exploring the city.

Related Read: Wondering what to pack for your trip? Our Italy Packing List has 19 items you don’t want to forget!

Cortona

BEST FOR A QUIET HILL TOWN BASE

Pros

• Peaceful hilltop town with beautiful countryside views
• Authentic atmosphere with fewer crowds than larger cities

Cons

• Steep streets and stairs throughout the historic center
• Limited public transport, so a car is helpful

Perched high above the Valdichiana valley, Cortona is the kind of Tuscan hill town that feels instantly timeless. With its stone buildings, flower-filled balconies, and widespread views across the countryside, it’s easy to see why so many people love it here. 

Cortona is smaller and quieter than places like Florence or Siena, making it a wonderful place for travelers looking to slow down and enjoy the charm of a traditional Tuscan village. Wandering through the historic center is part of the experience here. Narrow cobblestone streets lead to small piazzas, local shops, and family-run restaurants where we’ve had some of our favorite slow Tuscan dinners.

The main gathering place is Piazza della Repubblica, where you’ll find the town hall and several cafés perfect for sitting with a coffee while watching daily life go by. And history enthusiasts can visit the Museo dell’Accademia Etrusca (MAEC), which highlights the region’s ancient Etruscan roots.

If you keep wandering uphill, you’ll eventually reach the Santa Margherita Sanctuary, and just beyond it, the Fortezza del Girifalco, where the views stretch across the valley below. Just outside the town walls, the elegant Santa Maria delle Grazie al Calcinaio church is another beautiful stop, adding to the peaceful atmosphere that makes Cortona such a special place to stay.

Monastero di Cortona Hotel & Spa – $$$

Monastero di Cortona Hotel & Spa is one of the most unique places to stay in Cortona, set inside a beautifully restored historic monastery. This elegant property blends centuries of history with modern luxury, offering incredible views over the Valdichiana valley and easy access to the town’s charming piazzas and restaurants.

The hotel’s interiors feel refined yet peaceful, with spacious guest rooms featuring elegant décor, air conditioning, flat-screen TVs, minibars, and free Wi-Fi. Many rooms overlook Cortona’s rooftops or the surrounding countryside, adding to the sense of staying somewhere truly special.

One of our favorite features is the rooftop garden, where you can relax while taking in the incredible valley views. There’s also a full spa on-site, perfect for winding down after a day wandering the steep cobbled streets. Prices typically range from about €300 to €1,000+ per night, depending on when you go.

Hotel San Michele is another fantastic historic stay right in the heart of Cortona’s old town. Housed in a beautifully restored 15th-century palace near Piazza della Repubblica, this elegant hotel offers classic Tuscan charm with comfortable rooms and easy access to Cortona’s restaurants, shops, and scenic viewpoints.

Hotel Villa Marsili – $$

Set within Cortona’s historic walls, Hotel Villa Marsili is a charming boutique hotel known for its incredible panoramic views over the Valdichiana. Housed in an elegant 18th-century residence, this charming hotel combines historic character with warm hospitality and Lake Trasimeno in the distance.

Inside, the property still showcases original architectural details, including frescoes that date back to a 14th-century church that once stood on the site. Guest rooms are comfortable and thoughtfully designed, with air conditioning, flat-screen TVs, minibars, and free Wi-Fi, creating a relaxing retreat after a day exploring Cortona’s steep cobbled streets.

We especially enjoy the peaceful garden spaces and cozy sitting rooms with fireplaces, which make perfect spots for a quiet afternoon tea or evening drink. Depending on your room choice, prices typically range from about €120 to €480 per night.

For a smaller, more intimate stay in Cortona, Casa Ambra is a charming guesthouse located in the heart of the historic center. The family-run property is just steps from Piazza della Repubblica and offers comfortable rooms with a welcoming local feel.

Hotel San Luca – $

Hotel San Luca is a great value stay located right in Cortona’s historic center, making it easy to explore the town’s charming streets, piazzas, and restaurants on foot. Tucked along the edge of the hilltop town, the hotel also enjoys fantastic views across the surrounding countryside, adding to the relaxed Tuscan atmosphere.

One of the highlights here is the panoramic terrace, where you can take in valley views while having a morning coffee or evening drink. The hotel also features a small gym set on the covered terrace, so you can still enjoy the scenery while staying active during your trip.

Guest rooms are comfortable and classically styled, with air conditioning, satellite TVs, minibars, and free Wi-Fi throughout the property. Prices typically range from about €80 to €200 per night, depending on the room and season.

If Hotel San Luca is sold out for your travel dates, Hotel Italia Cortona is also a great spot right in the heart of the historic center. Set inside a historic 13th-century mansion, this hotel is known for its rooftop terrace with panoramic views stretching across the Val di Chiana valley and toward Lake Trasimeno.

Just outside the town walls, Villa Santa Margherita offers a peaceful setting surrounded by gardens and beautiful countryside views. This elegant villa-style hotel provides spacious rooms and a quiet atmosphere, yet is only a short walk from Cortona’s historic center.

Related Read: Looking for something more unique? Check out our guide to the best vineyard hotels in Tuscany, featuring boutique stays, luxury estates, and unforgettable countryside views.

Top Activities to do in Tuscany

Now that you’ve picked out the best area and hotel for your Tuscan adventure, you can plan the rest of your trip. Regardless of whether you choose to stay in a city or a quaint country town, there is plenty to do! Of course, expect to do some wine tasting, but we’ve also included epic activities like a hot air balloon ride, a horse-drawn carriage, and a chance to sharpen your cooking skills!

• Take a day trip to wine region – If you don’t have time to stay in the countryside, Florence is a great hub for a day trip. We loved this full-day tour, which took us to Pisa, Siena, and San Gimignano to experience small towns, cobblestone streets, and some amazing wine tasting!

• Learn how to make authentic pasta – If you travel like us, you travel for the food! So booking this pasta-making class was an easy addition to our Florence itinerary. We had so much fun learning the techniques to perfect our ravioli, but eating it was the best part!

• Float over Tuscany – Seeing Tuscany on this hot air balloon ride from Siena was absolutely magical for us. Drifting over vineyards, stone villas, and cypress-lined roads at sunrise felt like something out of a painting. The experience ended with a sparkling wine toast and breakfast, which made the morning even more special.

• Visit a local organic winery near Siena – This small-group wine experience at Azienda Agricola La Lastra offers an inside look at winemaking from vine to bottle. Walking through the vineyards, touring the cellar, and tasting four organic wines paired with a light Tuscan lunch made this one of our favorite relaxed activities near the city.

• Ride in a horse drawn carriage through Lucca – This carriage ride is the best way to see Lucca! The town is overflowing with history, and this makes it easy to see more and save your feet. Plus, it doesn’t get more romantic than a horse drawn carriage!

Thanks for reading!

We had been eager to visit Tuscany, and once we finally did, it was worth the hype! This region is stunning, full of history, and even better – amazing wine! Regardless of whether you stay in the convenient base of Florence or are looking for a quiet getaway amongst vineyards, you can find the right option for your travel style. Be sure to book your hotel well in advance, as the best ones book out early!

Before you go, check out all of our Europe blogs. As long-time travelers, we love helping others plan their bucket-list trips. Here are a few helpful articles as you plan your Italy getaway. Cheers!

25 Best Things to do in Italy

Renting a Car in Italy: 16 Things to Know + My Personal Tips

Where to Stay in Siena, Italy: 3 Best Areas & Hotels

Where to Stay in Sardinia, Italy: 5 Best Areas & Hotels