The Ultimate Jetset Guide to Tuscany
Ah, Tuscany. Dreamy, lush rolling golden hills, gravel roads lined with Cyprus trees, olive groves, and quintessential Tuscan countryside towns. Top it all off with pasta, farm-fresh Italian food, and wine, LOTS of wine. A Tuscan holiday is hard to beat. AND hard to plan!!!! Which is where I come in with this ultimate guide to Tuscany.
When it came to planning our trip to Tuscany, I was overwhelmed. There are SO many areas of Tuscany to choose from, where do I even begin? So I thought I’d make a post for you all to make your travel planning process much more seamless!
Table of Contents
The Basics of Tuscany
One of the biggest misconceptions about Tuscany is that it is a smaller area or town. But let me assure you – it is anything but small! Tuscany is a whole REGION that includes favorites like Florence, Pisa, Siena, San Gimignano, Montepulciano, Livorno, Lucca, and several other dreamy Italian towns. Many people think of places like Florence being entirely separate from Tuscany, but it is all within the same area!
The northern part of Tuscany is where you can find cities like Florence and Pisa, which is where many people choose to go sightseeing or kick off their trip. But, don’t get too caught up in the city, when you think of the “quintessential Tuscan experience,” you are probably thinking of southern Tuscany! This area has medieval castles, ancient villages, and those picture-perfect green valleys (such as Val d’Orcia). This is where time seems to slow down… and where you can truly kick back, relax, and enjoy the authentic Italian lifestyle! There is also coastal Tuscany which is dreamy, too!
Tuscany is gorgeous. Quiet, serene, peaceful. The vibe here completely embodies the Italian term “Il Dolce Far Niente” – the sweetness of doing nothing. Tuscany is best enjoyed (like most things in life) by taking it in slowly. Don’t make too many plans. Savor it.
How to Get to Tuscany
I recommend flying into either Florence or Rome. Florence is convenient if you want to either start or end your trip by sightseeing in northern Tuscany! Rome is south of Tuscany, so this would be most convenient if you are either doing both Rome and Tuscany in one trip or if you plan to spend your time only in southern Tuscany.
Sightseeing in Northern Tuscany – Florence, Pisa, Siena, and More
How to Get Around in Tuscany
Should you rent a car in Tuscany? This is a question many travelers find themselves asking! Put simply, you will either need to rent a car or book a car service for your trip!! Public transportation is not the best way to get around Tuscany. We rented a car for our trip!
Renting a Car in Tuscany
If you choose to rent a car, you will need an international driver’s license. You can easily get this from AAA – no need for an extra driver’s exam! Once you have this permit, you will be able to freely drive throughout Tuscany. Just keep a few of these tips in mind:
- Blue lines mean that you have to pay for the parking spot.
- White lines are for residents only, so you will get a fine if you park here.
- Most rental cars in Italy are manual, so if you need an automatic car, you will need to specify this when renting, and rent this well in advance as they are limited (they are also more expensive).
- Italian drivers drive super fast, so don’t worry if they are passing you! Just let them around you and drive at whatever speed makes you most comfortable.
Where to Stay in Tuscany
When deciding where to stay, this guide to Tuscany will help you. You must first decide what kind of experience you want to have. Like any other location, Tuscany has some absolutely stunning hotel and resort properties to offer. However, if you are looking for a more quiet, authentic experience in southern Tuscany, you may opt for what is called an “agriturismo”, or a private villa!
The Best Hotels and Resorts in Tuscany
Most hotels in Tuscany are located within its smaller villages. This isn’t the best situation for parking, so if you rent a car, be aware that you will likely have to park outside of the town center as in-town spaces are for residents only. Personally, I wouldn’t even bother with renting your own car. You can easily book a car service and avoid all the hassle! Here are some of the places I would most recommend staying in Tuscany. Check out all the best hotels for a complete guide to Tuscany.
Borgo San Pignano
- Grand estate luxury of a five-star resort meets holistic spa
- Michelin starred restaurant
- Handmade furniture and original decor
- Wine list with 500 labels from Tuscany/other regions in Italy
Check rates for your dates here
Villa San Michele, Belmond Hotel
Photo courtesy of Villa San Michele
- Located in hilltop with panoramic views of the city and Arno Valley.
- Historical architecture set in a 15th-century former monastery with Renaissance architecture and original frescoes
- Elegant rooms and suites with modern amenities.
- Beautifully manicured gardens, providing a serene and picturesque environment
- Spa services, outdoor heated pool, and fitness facilities for relaxation and rejuvenation
- Unique experiences like cooking classes, art tours, and wine tastings
- Popular venue for weddings and special events, offering a romantic and historic setting
- Personalized concierge services, private transfers, and tailor-made excursions
- Part of the prestigious Belmond hotel collection, known for exceptional service and luxury experiences
Check rates for your dates here
Castello de Casole, Belmond Hotel
Photo courtesy of Castelloo de Casole
- Luxurious rooms and suites with classic décor and modern amenities.
- Michelin-starred restaurants serving traditional Tuscan cuisine.
- Extensive collection of Tuscan wines with exclusive tastings.
- Spa with a range of treatments and outdoor pools.
- Elegant venues for weddings and events.
- Art and cultural tours to nearby historic sites.
- Eco-friendly practices and organic gardening.
Check rates for your dates here
Villa Lecchi Hotel Wellness & Tuscan Retreats
Photo courtesy of Villa Lecchi Hotel
- Tuscan villa designed for tailored journeys
- High standards of customer service
- Bright Tuscan design
- Historic country chateau
- Vineyards, vegetable gardens, and olive groves
- Infinity pool overlooking the hills of Tuscany
Check rates for your dates here
Il Borro Ferragamo Hotel
Photo courtesy of Il Borro Hotel
- 11 luxury villas (3 – 6 bedrooms)
- Elegant interiors
Check rates for your dates here
Hotel II Pelicano
Photo courtesy of Il Pelicano
If you’re looking for COASTAL Tuscany, Il Pelicano is your SPOT. This is the dreamiest, most incredible hotel on the coast of Tuscany that will take your breath away.
- 5-star hotel
- Former love nest and social club of an American socialite and British aviator
- Glamorous and slightly retro
- Discreet luxury
- Spa with a sea view
Check rates for your dates here
Fonte Verde Resort
Photo courtesy of Fonte Verde
- Situated in an ancient village famous for thermal baths
- Prestigious luxury hotel
- Holistic center and most up-to-date thermal treatments
- 8 pools
Check rates for your dates here
Castello di Spaltenna Resort & Spa
Photo courtesy of Castello di Spaltenna
- Surrounded by lush landscapes
- Countryside retreat
- 5-star resort
- 37 rooms
Check rates for your dates here
Le Fontanelle
Photo courtesy of Le Fontanelle
- Originally an ancient Tuscan estate
- Renovated and opened in 2006
- Designed in traditional style
- 5-star boutique resort
- Winery onsite
Check rates for your dates here
Renaissance Hotel Marriott
Photo courtesy of Renaissance Hotel Marriott
- Spectacular valley views
- Wineries and shops nearby
- Surrounded by 1,700 acres of landscaped grounds
Check rates for your dates here
Rosewood Castiglion del Bosco
- A historical estate set on a 5,000-acre land with village, vineyard, and castle ruins
- Features a private 18-hole golf course set within the estate
- Offers elegant suites and villas with private pools, blending rustic charm with modern luxury
- Home to a renowned Brunello di Montalcino winery, offering wine tastings and tours
- Full-service spa with holistic treatments, fitness center, and outdoor infinity pool
- Wide range of activities including cooking classes, truffle hunting, horseback riding, and hot air balloon rides
- Kid-friendly amenities and programs, including a children’s club and family activities
- Part of the esteemed Rosewood Hotels & Resorts, known for exceptional service and bespoke luxury
Check rates for your dates here
The Best Villas to Stay in Tuscany
Villa Vignalunga
Villa Vignalunga is a luxurious Tuscany villa featuring an infinity pool that offers stunning views of the Tuscan countryside. This villa has it all, with 4 spacious bedrooms perfect for large families or a group of friends of up to eight. The villa’s classic Tuscan vibes will definitely take your breath away. Booking starts from $1,171 per night, and you’ll have everything from a fully equipped kitchen, a game room, a pool, outdoor space, family and pet-friendly amenities, full air conditioning and wifi at your disposal. Trust me, you’ll never want to leave!
Villa La Lavandaia – Borgo Pignano
This is the villa where we stayed while at Borgo Pignano, and we LOVED it. Truly a magical experience – and you have all the perks of being at a luxury hotel, while having your own tucked away privacy in the villa (and a private pool) looooved this spot.
Podere Manafiore
Step back in time at Podere Manafiore, a charming historical villa with a swimming pool that screams rustic elegance. With 6 cozy bedrooms, this 7104.2 sq. ft. villa is ideal for a family reunion, a group trip with friends, or a retreat. Imagine waking up to the sound of birds chirping and enjoying breakfast on the patio, or enjoying a late afternoon swim with views of the lush Tuscan landscape. This gem offers a unique combination of traditional Tuscan architecture—think exposed wooden beams and stone walls—and modern amenities. Price starts from $1,456 per night. It’s pure bliss wrapped in history!
Bellvilla by OYO Villa Acqua
This cozy villa features 6 bedrooms and 4 apartment rooms, a private pool, and 6500 sq. m. garden of roses, rosemary and lavender! Imagine lounging on the terrace, cocktail in hand, with the Tuscan hills as your backdrop. It’s the perfect place if you want to feel the traditional charm of Italy’s country side, and with a price range starting from $982 per night, it’s an experience worth every penny!
![Holiday Home Exterior [summer]](https://media.vrbo.com/lodging/102000000/101570000/101565100/101565056/3a38b23d.jpg?impolicy=resizecrop&rw=1200&ra=fit)
Villa Irmina
Villa Irmina is a picturesque villa that you often see on postcards. This enchanting two-story Tuscan country house is surrounded by meadows and rolling hills, making it the perfect escape from the hustle and bustle. With 6 delightful bedrooms, free Wi-Fi, and a warm, welcoming vibe, it’s everything you’ve dreamed of and more. The architecture is authentically Tuscan, with charming rustic touches that give it a cozy, lived-in feel. Staying here starts at $1,997 per night where you have 2 kitchens, a pool table, a fitness room, an outdoor pool with a beautifully-manicured garden overlooking the hills. What could be better!
Argiano Private Villa
Another luxurious Tuscan stay is this private villa at Argiano. This stunning villa, perfect for up to 10 guests, boasts 5 elegant bedrooms, a private pool, and expansive patios where you can bask in the glorious Italian sunshine. Average booking per night starts at $1,250, offering complete amenities like air conditioning, a well-equiped kitchen, private pool, patio and breathtaking views!
Dimora Buonriposo Pienza Country House
Escape to the serene countryside at Dimora Buonriposo Pienza Country House. This charming retreat features 5 bedrooms and a picturesque setting that will make you feel like you’ve stepped into a postcard. Enjoy the peace and tranquility of the Tuscan landscape, with all the comforts of home including a fully equipped kitchen, cozy living spaces, and stunning outdoor areas with a price averaging at $3,144 per night.
The different regions of Tuscany
Val d’Orcia
This area is one of the most popular areas to visit and stay in Tuscany. Val d’Orcia is filled with museums, ancient abbeys, and castles for the history buffs as well as quaint farmhouses, quiet countryside, stunning sunsets, and some of the best wine in the world for those looking for a taste of Italian R&R. Imagine rolling hills dotted with cypress trees, charming medieval villages like Pienza and Montalcino, delicious farm-to-table Italian food, and WINE. This area is perfect for leisurely strolls through quaint streets, visiting ancient abbeys and castles, and unwinding in rustic farmhouses.
Florence
Florence is the pulsating heart of Tuscany and the birthplace of the Renaissance. This vibrant city is an art lover’s paradise with iconic historical landmarks like the Duomo, the Uffizi Gallery, and the Ponte Vecchio bridge. Lose yourself in the world-class art collections, stroll through the historic streets, and indulge in the city’s exquisite cuisine. Florence’s lively atmosphere, rich history, and stunning architecture make it a must-visit destination for any traveler.
Pisa
While Pisa is globally renowned for its iconic Leaning Tower, the city offers much more than just this famous landmark. The Piazza dei Miracoli is home to other architectural marvels like the cathedral, baptistery, and cemetery, all showcasing exquisite medieval craftsmanship. Wander through Pisa’s charming streets, explore local markets, and soak in the youthful energy of this university town. Pisa effortlessly combines historic allure with a vibrant contemporary vibe.
Siena
Stepping into Siena feels like traveling back in time. This enchanting city is known for its medieval brick buildings, the stunning Piazza del Campo, and the thrilling Palio horse race. Siena’s historic center, a UNESCO World Heritage site, features the magnificent Siena Cathedral and the towering Torre del Mangia. Enjoy wandering through narrow alleys, discovering hidden courtyards, and sampling traditional Tuscan dishes in cozy trattorias.
San Gimignano
San Gimignano, often dubbed the “Medieval Manhattan” for its striking skyline of towers, is a perfectly preserved gem from the past. Stroll along cobblestone streets, visit frescoed churches, and relax in picturesque piazzas. This small walled village offers a delightful escape with its rich history and breathtaking views of the surrounding countryside. Make sure to try the local Vernaccia wine while you’re here!
Montepulciano
Perched high on a hilltop, Montepulciano is a paradise for wine enthusiasts and history buffs alike. The town’s Renaissance architecture is complemented by ancient wine cellars producing the celebrated Vino Nobile di Montepulciano. The charming main street leads to the impressive Piazza Grande, surrounded by elegant palaces and churches. Montepulciano’s panoramic vistas, cultural richness, and culinary delights make it an unforgettable destination.
Livorno
Livorno is a bustling port city known for its seafood, historical fortifications, and picturesque canals. The city’s vibrant waterfront, with its mix of traditional fishing boats and modern yachts, offers a unique coastal charm. Livorno’s culinary scene is a seafood lover’s dream, with local specialties like cacciucco, a hearty fish stew. Enjoy the relaxed pace of this coastal gem, explore its diverse neighborhoods, and take in the stunning sea views.
Lucca
Encircled by well-preserved Renaissance walls, Lucca is a city of timeless elegance and charm. The historic center boasts cobblestone streets, grand piazzas, and beautifully preserved churches. The tree-lined promenades atop the city walls provide scenic walking routes with views over Lucca’s rooftops. Key highlights include the Guinigi Tower, the Cathedral of San Martino, and the unique oval Piazza dell’Anfiteatro. Lucca’s laid-back ambiance and rich cultural heritage make it a delightful spot to explore at a leisurely pace.
Guide to Florence
Florence is the perfect place to start your Tuscan adventure. Picture yourself sipping on a glass of Chianti while gazing at the Ponte Vecchio, or getting lost in the masterpieces of the Uffizi Gallery. Florence is where history meets modern Italian flair, and it’s absolutely magical.
I’d recommend kicking off your trip in Florence before heading to the more remote, countryside areas of Tuscany! This city is not just a destination; it’s an experience that will leave you enchanted and craving for more. Trust me, Florence will steal your heart.
Where to Stay in Florence
We stayed at the St. Regis Florence and it was a dream! This luxurious hotel, set in a historic palace, offers breathtaking views of the Arno River and is just a short walk from everywhere you want to see in Florence. The location is amazing, and the room was SO cool! I also loved the bar + restaurant – highly recommend for a luxurious place to plop your bags while you explore the city!
or a VRBO like this with stunning views of the city
What to Do in Florence
Florence is a treasure trove of art, history, and culture. Here are some must-see attractions:
Explore Il Duomo
The Florence Cathedral, known as Il Duomo, is a stunning architectural marvel – sooo beautiful! Climb to the top of Brunelleschi’s Dome for breathtaking panoramic views of the city.
Visit the Uffizi Gallery
The Uffizi Gallery is home to an incredible collection of Renaissance art, featuring masterpieces by Botticelli, Michelangelo, and Leonardo da Vinci. Plan your visit to avoid crowds and take a guided tour for an enriched experience.
Visit the Accademia Gallery
No visit to Florence is complete without seeing Michelangelo’s iconic statue of David! The Accademia Gallery also houses other important works of art, making it a must-visit museum.
Visit the Palazzo Vecchio – The Palazzo Vecchio is Florence’s town hall and a symbol of the city’s political power. Take a guided tour to explore its richly decorated rooms, secret passages, and the impressive Salone dei Cinquecento.
Where to Eat in Florence
Florence boasts a fantastic culinary scene. Here are some of the best restaurants:
THIS WAS THE BEST GELATO of my trip!!!! Please go here. It’s soooooo good (and worth the line!)
Ciro & Sons
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For the BEST pizza (and great gluten-free pizza in Florence if you have anyone gluten-free in your group!). This family-run restaurant offers a warm atmosphere and delicious, authentic pizzas. The crust is perfectly crispy, and the toppings are fresh and flavorful.
Bambi Trippa e Lampredotto
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For authentic Tuscan sandwiches, try this popular local market spot with their traditional Lampredotto or the Trippa or their Polpette di bollito!
La Buchetta
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Grab some budget-friendly bites made from high-quality Italian produce from this popular local restaurant. Must try dishes are Bistecca alla Fiorentina or their hand-rolled truffle pasta, a gnocchi or a Florentine steak with wine!!
L ‘Angolo del Gusto
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Eating out with family? Try L’Angolo del Gusto, a cozy, family-friendly restaurant in Florence known for its friendly service and delicious Tuscan food. People have rave about their homemade pasta and perfectly cooked steaks and tagliatelle with truffle!!
Trattoria ZaZa
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Famous for its Florentine steak, this restaurant also serves a variety of classic Tuscan dishes in a lively, rustic setting. It’s a great spot for a hearty meal after a day of sightseeing.
Enoteca Pinchiorri
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A Michelin-starred restaurant known for its extensive wine list and exquisite Italian cuisine. The tasting menus are highly recommended if you’re in the mood to splurge.
Il Latini
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A bustling trattoria known for its hearty Tuscan fare, the bistecca alla Fiorentina is a must-try if you want to try authentic bistecca paired with a good bottle of Chianti!
Osteria Francescana
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If you want something more luxurious, this three-Michelin-starred restaurant is a gastronomic experience you won’t forget. Their dishes are works of art with classic flavors.
The Best Things to Do in Tuscany
Wine Tasting
A guide to Tuscany is not complete without the best wine spots to go!!! There are two main wine regions in the southern part of Tuscany, which is where most people choose to go: Montepulciano and Montalcino. Each winery in Tuscany has microclimates within them, so every winery is truly so different. Unlike some other areas known for wine, there are hundreds of wineries in Tuscany, so it is absolutely impossible to visit them all, or even all of the regions, in one trip! Wherever you do go, you MUST have reservations as most wineries in Tuscany are smaller and do not allow walk-ins (some even close down for the day if they do not have any appointments set up).
Casa Lucii
This was one of the highlights of our trip – wine tasting at a historic family-run winery inbetween Siena and Florence called Casa Lucii.
Antinori Chianti Clasico
This is the one winery I was told you HAVE to visit – and, alas, it was too full when we went – so if you can snag a reservation, go for it!!!! It’s supposed to be amazing.
Avignonesi
One of Italy’s oldest wineries, dating to the mid-16th century, Montepulciano’s Avignonesi is a great one to visit.
Carpineto
Delicious wines and a beautiful, expansive property in the hills of Tuscany!
Castello di Ama
Book ahead, as this one gets filled up quickly, and plan a few hours for a tour and tasting at this grand estate near Siena in a charming village!
Hot Springs
This valley is known for its hot springs, like the Saturnia Tuscany hot springs – one of the most well-known thermal baths in the world. If you are looking for a quieter, less crowded experience, head to either Bagno Vignoni or Bagni di San Filippo.
Enjoy High-Quality Food
Incredible food to pair with the stellar Italian wine? Say less!! This region of Tuscany is known for its high-quality food items such as cheese, extra virgin olive oil, saffron, mushrooms, truffles, and more. Many people immediately think of pizza and red sauce when they think of Italy, but the southern part of Italy has a ton of different cuisines! Here, you will experience more beef, truffles, and heavy creams and sauces.
A few of my favorite spots to check out:
- Ristorante La Terrazza is a super romantic spot that will make you feel like you are in a movie!
- Ristorante Fonte Alla Vena is a Michelin-starred restaurant that will have you wanting to come back every night.
- Ristorante Taverna Barbarossa has the best truffle pasta! Oh, and they also have views of where they filmed The Gladiator. So cool!!
Explore the Towns
Each town within Tuscany has something unique to offer its visitors. And they’re all SO cute and fun to walk around.
Do a Cooking Class
When in Tuscany, taking a cooking class is a must-do experience!! Learn from local chefs and home cooks and prepare authentic Tuscan dishes using fresh, local ingredients. I love doing a pasta cooking class where you’ll prep everything (including the pasta and sauces) from scratch.
We did this one with Ariana while we were staying at Borgo Pignano! If you are staying in that area of Tuscany, I highly recommend! Tell her Jetset Christina sent you!
Tips for Traveling to Tuscany With a Baby
By now, you guys know that I am allllll about traveling with your baby in tow! Travel has taken on a whole new meaning for Kenny and me now that we have the opportunity to share it with our son and see the world through his eyes. It is truly an incredible experience that I think all parents should go for!! If you are traveling to Tuscany with a baby, here is what you will need:
- UppaBaby Minu Stroller – This is a lifesaver!!! The storage at the bottom is so nice (way better than the Doona IMO for European cobblestones!).
A good baby carrier
If your baby is smaller or you use a carrier a lot at home, you’ll also use a baby carrier! This one or this one are my favorites.
A pack n’ play
If you’re staying in hotels, you don’t need to pack a pack n’ play for sleep (just make sure they have a crib available for you ahead of time). But, if you’re staying in a villa without a crib, a pack n’ play is a must! We researched a bunch of different brands but ended up picking the Baby Bjorn pack and play because it seemed to be the easiest to set up and take down while being really sturdy and lightweight for travel! It has its own bag, so we check it as a bag when traveling with it.
Portable Sound Machine
This portable sound machine is one of my baby ESSENTIALS.
The Slumberpod
Ok so we didn’t start using the slumberpod until Harrison was about 1 year old but it is a GAME-CHANGER. It’s basically a (breathable) portable tent that goes over your pack n’ play to create blackout darkness for the baby/toddler, allowing you to be in the room when they’re napping and not disturb them, and allowing them to get better sleep on vacation! it’s a MUST!!! We don’t travel without it.
Italy outfits for baby – of course!
These lemons are a must!
the cutest lemon print boys hawaiian shirt!
What to Pack for Tuscany
First things first, don’t forget a good power converter for Europe!
What to Wear: Exploring Tuscany
You’ll want to break out your best earth-toned outfits and bright whites for daytime in Tuscany. Depending on the time of year, it can be hot in the summers and cools off in the late fall and winter! But since most people visit Tuscany in the summer and fall, I’ll highlight my favorite warm-weather Tuscany outfits here.
Dinners in Tuscany outfits
With the restaurants in Tuscany being as jaw-droppingly beautiful as they are, you are going to want to look the part! Here are my favorite outfits for a dinner in Tuscany!
my favorite heels right now! So comfortable and go with everything – they’re the perfect pair to pack with you!
Poolside in Tuscany outfits
Wedding in Tuscany Dresses
If you’re heading to a wedding in Tuscany, chances are the dress code is somewhere between Vineyard chic and semi-formal or black tie optional, here are my favorite looks for a beautiful Tuscany wedding.
Tuscany Outfits For Him
