10 Beautiful Places to Discover on a Tuscany Family Vacation

For a first-time Tuscany family vacation, iconic cities like Florence and Pisa usually top the list of must-sees. But if you’ve already explored some of the more popular sites and want to go deeper, the region has plenty of smaller and more obscure gems to seek out. Whether you’re looking to relax amid the cypress-dotted countryside, walk along pristine stretches of coastline or meander through peaceful hill towns, Tuscany offers countless ways to connect with its rich traditions and one-of-a-kind landscapes.

With tips and insight from our preferred Italy travel partner as well as our expert Advisor team, here are our top 10 recommendations for families looking for a new way to experience all that Tuscany has to offer.

Towns and Regions Not to Miss on a Tuscany Family Vacation

Cortona and Arezzo

Nestled close together in southeastern Tuscany, Cortona and Arezzo both offer a rich blend of history, culture and kid-friendly experiences. Cortona, charming and relaxed, includes sites such as the MAEC Museum, a treasure trove of Etruscan and Roman artifacts, as well as the medieval Convento delle Celle monastic complex nearby. Parents can enjoy wine tastings in surrounding vineyards while little ones play, and you’ll also find abundant hiking trails, olive groves and agriturismos that host family cooking classes and farm animal experiences.

In less-traveled Arezzo, the Basilica of St. Francis is home to the fresco cycle known as The Legend of the True Cross by Piero della Francesca — a must-see for art and history lovers. If you’re there on the first Sunday of the month, don’t miss the monthly antiques fair, which draws thousands of visitors hunting for collectibles and curiosities.

TIP: Both towns are convenient to Siena, one of Tuscany’s most iconic medieval cities — its car-free historic center, Piazza del Campo, makes it easy for kids to explore. Ascend the Torre del Mangia for panoramic views and learn about the famous Palio horse race at the museums housed in each contrada, or district, represented in the race. Although we don’t often recommend the Palio itself for kids due to the heat and the crushing crowds, we’ve arranged for families to watch from the comfort and safety of private balconies; reach out to our CB Travel Advisor team for info.

Viareggio and Livorno

The beach might not be the first thing that comes to mind when you think of Tuscany, but the coastal areas provide a wealth of seaside experiences. Viareggio and Livorno are excellent, more local alternatives to better-known beach towns like Forte del Marmi. About half an hour’s drive west of the pretty medieval town of Lucca, Viareggio’s accessible shores, great walking spots and vintage seaside lidos make it ideal for younger kids. Attractions like the Pineta di Ponente, a forest park with bike rentals and pony rides, as well as the Museo del Carnevale, which showcases the town’s celebrated carnival floats year-round, are worth exploring if you need a break from sand and surf.

South of Viareggio, the port town of Livorno offers ancient canals, lively markets and ferry access to farther-flung destinations such as Sardinia and Corsica. Visit the Aquarium of Livorno as well as the Terrazzo Mascagni, a promenade with sea views and great running space for kids.

Maremma

Often referred to as the “Wild West” of the Tuscan region, Maremma straddles the point where the rolling hills meet the Tyrrhenian Sea, creating ruggedly beautiful scenery that combines the best of the countryside and the beach. It’s ideal for those seeking adventure — hiking through the forest, cycling along scenic trails and boat trips along the coast are readily available. The Maremma beaches are secluded and accessible by foot or boat, and the area’s local wildlife, charming villages and coastal views combine for a slower-paced trip.

At Maremma’s heart is the capital, Grosseto, a cozy walled town that serves as a gateway to local beaches, national parks and farms. Pitigliano stands out with its dramatic cliffside setting and ancient Etruscan pathways, while Castiglione della Pescaia offers a seaside escape with medieval streets and pristine beaches. Families can explore Etruscan ruins or bike through the unspoiled Parco Naturale della Maremma, which also includes a miles-long stretch of coastline.

TIP: This region is home to two of our favorite destination-worthy luxury properties: a clifftop retreat and a small-town escape that both lie along the Argentario coastline, renowned for its dramatic cliffs and crystal-clear waters. Our Advisors can help you book as well as design a full itinerary for your time in the area.

Chianti

The Chianti region south of Florence is a natural pairing for travelers seeking iconic rural scenery, vineyards, picturesque towns and, of course, world-class wine and local cuisine. Laden with boutique wineries such as those in Chianti Classico and Bolgheri (the birthplace of Super Tuscan reds like Bolgheri Sassicaia and Bolgheri Ornellaia), this area offers fabulous private vineyard tours and and tastings, many of them kid-friendly. Beyond wine, medieval hill towns like Greve and Castellina give visitors a glimpse into what life here was like in the past and offer delicious local produce, such as olive oil, honey and cheeses.

Punta Ala and Porto Ercole

Situated along the southern Tuscan coast, Punta Ala and Porto Ercole offer a wonderful seaside experience for families who prefer a quieter stay and fewer crowds. Punta Ala has a calm, sandy beach with family-friendly restaurants and water sports of all kinds; just south, Porto Ercole is a picturesque harbor town backed by fortress ruins, ideal for scenic boat outings and day trips to nearby coves. With ample sailing, kayaking and other seaside pursuits, this is the place to be if you want to spend much of your time amid the waves.

Pienza

Pienza is one of the prettiest hill towns in the idyllic Val d’Orcia, renowned for its stunning views and native Pecorino cheese (you can even smell its pungency as you stroll!). The winding streets are lined with inviting markets and specialty shops that brim with fresh regional produce and artisanal goods, reflecting the essence of Tuscan cuisine — perfect for foodie families. For a truly immersive experience, consider joining a guided market tour that culminates in a hands-on cooking class or touring a local cheese farm, where you’ll discover the time-honored techniques and traditions used to craft each wheel of Pecorino.

TIP: Agriturismos are a dime a dozen in the Tuscan countryside, but it’s important to choose one of exceptional quality that suits your family’s needs. Read our guide to agriturismos with kids, then get in touch for booking help.

Elba

Accessible via a one-hour ferry from the port city of Piombino, the isle of Elba is full of tucked-away beaches, hiking trails and seaside towns like Portoferraio and Capoliveri. It’s an excellent option for active families: You can ride a cable car up Monte Capanne, the highest peak on the island, for sweeping vistas over the Tuscan Archipelago; head to Biodola Beach to snorkel and scuba dive; or rent kayaks to paddle among the sea caves along the coast.

For a bit of history, visit Villa dei Mulini, where Napoleon lived during his exile, or explore the hilltop fortress of Volterraio to delve into Elba’s layered past. Nature lovers can follow scenic trails through the Mediterranean scrub to secluded coves like Cala dei Frati or the pebbled beach of Sansone, both ideal for a quiet afternoon swim. In the evenings, stroll the harbor promenades of Porto Azzurro or Marina di Campo before you settle in at a trattoria for freshly caught seafood and locally made Aleatico wine.

San Quirico d’Orcia

At the center of the Val d’Orcia just a short drive from Pienza, San Quirico d’Orcia is an ideal home base for families looking to explore southern Tuscany. The town is charming and easy to walk around, offering shaded gardens like the Renaissance-era Horti Leonini and storied treasures such as the 8th-century Collegiata di San Quirico church. Just outside San Quirico, the Cappella della Madonna di Vitaleta stands amid gently sloping fields, its postcard-perfect setting making it one of Tuscany’s most photographed spots.

The nearby hamlet of Montalcino is best known for its Brunello di Montalcino wine, which parents can sip at local wineries like Tornesi or Castiglion del Bosco; round out the day by exploring Montalcino’s 14th-century fortress, wandering the historic center and churches, and visiting nearby Sant’Antimo Abbey for a peaceful retreat into the past. Or dip into the thermal baths of Bagno Vignoni, which harken back to Roman times.

Cinque Terre

Although the Cinque Terre is technically in Liguria, the area sits a stone’s throw from the Tuscan border, within day-trip distance from the northern part of the region. These five colorful seaside villages — Monterosso al Mare, Vernazza, Corniglia, Manarola and Riomaggiore — offer incredible cliffside views, colorful harbors and coastal walking trails. You can travel between them via train or book a boat tour with stops along the way. Note, the villages are tiny and often burst with crowds during the peak summer season, so we prefer visiting in spring or fall when you’re likely to have more breathing room.

Norcia

Like the Cinque Terre, Norcia isn’t actually in Tuscany; it’s just beyond the border in Umbria, tucked into a valley at the foot of the Sibillini Mountains. Still, it makes for an easy and rewarding excursion, roughly a two-hour drive from Siena and the southern reaches of Tuscany. This quiet town is a haven for food lovers, famed throughout Italy for its rich gastronomic heritage, and in summer, brilliant wildflowers carpet the high plateau of Castelluccio di Norcia, an appealing backdrop for hiking and picnicking.

Norcia’s name is synonymous with norcineria (the traditional art of pork butchery and charcuterie) and its cured meats, particularly wild boar sausages and prosciutto, are legendary. So too are Norcia’s black truffles, foraged from the surrounding forests, and the tiny, flavorful Castelluccio lentils grown nearby. Get immersed in this deep-rooted food culture through hands-on truffle hunts, visits to local farms and kid-friendly cooking classes focused on Umbrian fare.

Relevant Links:

Browse all accommodations and destinations in Italy on Ciao Bambino

52 things to know before traveling to Italy with kids

1 to 2 weeks in Italy: The best itinerary for families

10 tips for traveling to Italy with kids

Essential tips for a Tuscany farm stay with kids

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Our 6 favorite things to do in Siena, Italy with kids

Editor’s note: This post was accurate when published. We advise checking independently for the latest information and updates. Ciao Bambino does not accept responsibility or liability for any errors or omissions in, or for any actions taken based on, the information presented.