WeGalavant’s Insider’s Guide to Tuscany

Tuscany is all about slow travel, with rolling countryside, hilltop towns, and long lunches. In Siena, Montepulciano, and Montalcino, you’ll find medieval streets, world-class wine, and a pace that encourages wandering. Neighbouring Umbria shares the same scenic charm but feels a bit more under-the-radar, with towns like Assisi and Spello offering fewer crowds and plenty of character. 

This region appeals to couples, food and wine travellers, or anyone craving the countryside over city buzz. Expect days filled with wine tastings, farm-to-table meals, and drives through postcard-worthy landscapes. Read on to find out where to sleep, eat, and visit across the smaller towns in Tuscany.

Need to know

Book reservations in advance for popular restaurants, winery tastings, and small-group experiences, especially from May through October. Not only is it peak travel season, many places will operate at limited capacity to preserve quality. Be mindful of local customs, dressing modestly in churches and embracing the unhurried pace of meals. Regions are very safe, but it’s still smart to keep an eye on bags in busy squares. Note that many shops and restaurants close for a few hours in the afternoon. Italy also runs on the 24-hour clock.

Currency: The Euro (EUR) is used everywhere. Credit cards are widely accepted, though small trattorias, farm stands, and markets may prefer cash. ATMs are easy to find in all towns.

Languages: While English is spoken in hotels, restaurants, and attractions in larger cities, Italian is likely all you’ll hear in smaller towns and rural areas. Knowing some basic Italian phrases will go a long way, starting with a friendly “buongiorno” during the day or “buonasera” in the evening.

• Key phrases: ciao (hello / goodbye), arrivederci (goodbye), scusi (excuse me / pardon), grazie (thank you), per favore (please), sì / no (yes / no).
  

Airports: Flying into the region means you’ll most likely fly into Rome’s Fiumicino Airport (FCO), Florence Airport (FLR), or Pisa International Airport (PSA). Rome has nonstop international flights to most major US gateways, like New York, Atlanta, Chicago and Los Angeles. There are lots of connections to European hubs from both Florence and Pisa airports, including London, Paris and Amsterdam.

• Siena: Siena’s closest airports are Florence or Pisa, about 1.5 to 2-hours away by car.
• Montepulciano and Montalcino: Both towns are tucked deep into the Tuscan hills, but the closest major airport is Florence (about 1.5 to 2 hours away).
• Umbria: The closest major airport is Rome, about a 2-hour drive to central Umbria. Florence is a convenient option for towns in northern Umbria, however.
  

Transportation: The most convenient way to explore this region is by renting a car, especially if you plan to visit other towns and countryside wineries. Private transfers can also be arranged for  a stress-free way to arrive in comfort.

• Siena: Siena’s historic center is mostly pedestrianized, so expect to park outside the city walls. It is also connected by rail to cities like Florence, Pisa, and Rome. 
• Montepulciano and Montalcino: Expect scenic, small country roads.
• Umbria: Roads are quiet but can be winding. There’s also decent train access between larger towns like Perugia, Spoleto, and Assisi, though smaller villages do require a car.
  

Best time to visit: Tuscany is a great year-round destination, but spring (March to May) and fall (September to October) are the best times. Warm days, fewer crowds, and the countryside is either in full bloom or harvest mode. Summer (June to August) brings festivals and energy, along with the heat and higher prices. The winter months (November to March) are cooler and quieter, great for exploring cities like Florence and Siena without the crowds.

Ideal length of stay: Five to seven nights is the perfect amount of time to balance exploring the area and unwinding with a glass of wine.

Signature dishes: 

• Siena: ribollita (hearty soup with bread and vegetables), panforte (spiced fruit and nut cake), and garlic tomato pici (simple pasta with garlic and tomato).
• Montepulciano: pici with pork ragu (thick pasta with pork or meat sauce), crostini with chicken liver (toast with savory spread), and cantucci with vin santo (almond cookies dipped in sweet wine).
• Montalcino: tagliatelle with wild boar (rich, meaty pasta dish), aged pecorino cheese (served plain or with honey and truffles), and delizia amalfitana (custard pie with pine nuts).
• Umbria: strangozzi with truffle (handmade pasta with local black truffles), porchetta (slow-roasted pork with herbs), and torta al testo (flatbread filled with sausage, cheese, or greens).
  

What to wear: Days are warm, so stick to breathable linens and cotton. Wear comfortable shoes for cobblestones and hill towns. Evenings call for effortless and relaxed tailoring, flowy dresses, and leather sandals. A light jacket or wrap is smart for cooler evenings.

Where to stay in Tuscany and Umbria

Image courtesy of COMO Castello Del Nero

Siena

Siena leans into the drama, and that’s what makes it unforgettable. Its medieval roads wind like a maze, leading straight to the Piazza del Campo, home to the legendary Palio horse race. The cathedral stuns with black-and-white marble, the energy is fiercely local, and the whole city feels like a love letter to its past. Sip a glass of Chianti as the sun dips over terracotta rooftops before retiring to one of these favorite places to stay.

COMO Castello Del Nero: Spa serenity and sleek design in a 12th-century castle. This decadent estate blends medieval character with COMO’s signature wellness-forward vibe. Clean-lined rooms, countryside views, and world-class massages await.

• Our perks include a £75 hotel credit, complimentary airport transfers, daily breakfast, an upgrade, and extended check-in/out whenever possible.
  

Hotel Borgo San Felice: A wine-lover’s dream in a beautifully restored medieval countryside hamlet. Old-world charm with polished, five-star comfort alongside morning walks through olive groves, it’s a top choice for romantic getaways.

• Our Perks include a £75 hotel credit, daily breakfast, an upgrade, and extended check-in/out whenever possible.
  

Borgo Pignano: Gardens and rolling hills surround this restored 18th-century villa featuring sustainability in a way that feels deeply authentic. You’ll find Farm-to-table meals, horseback rides through wildflower fields, and an infinity pool carved into the hillside.

• Our Perks include a £75 hotel credit, daily breakfast, an upgrade, and extended check-in/out whenever possible.
  

Montepulciano and Montalcino

Image courtesy of Rosewood Castiglion del Bosco

If you’re into bold reds and postcard-perfect views, Montepulciano and Montalcino are a dream duo. Montepulciano brings Renaissance flair, with hilltop streets, stone piazzas, and wine bars pouring Vino Nobile on every corner. Montalcino feels a bit more rustic, sun-drenched, and it’s also the birthplace of Brunello. Together, they offer a slower, richer slice of Tuscany.

Rosewood Castiglion del Bosco: Equal parts rustic charm and polished style on a 5,000-acre private estate. Sprawling villas with private pools, a Brunello-producing winery, cooking school, and even a private golf course make this retreat a unique choice.

• Our perks include a welcome amenity, daily breakfast, an upgrade, and extended check-in/out whenever possible.
  

Lupaia: This charming farmhouse-turned-storybook-hideaway delivers big on atmosphere. Stone walls, wood-beamed ceilings, candlelit dinners, and sweeping views of vineyards and olive groves. It’s upscale but unpretentious, with standout service, and an intimate feel.

• Our perks include a £35 hotel credit, daily breakfast, an upgrade, and extended check-in/out whenever possible.
  

La Bandita Townhouse: Stylish but low-key, this former convent turned chic boutique hotel blends 500-year-old stone walls with mid-century furniture and art books. This vibe is laid-back and contemporary, effortlessly cool without trying too hard.

• Our perks include a welcome amenity, daily breakfast, an upgrade, and extended check-in/out whenever possible.
  

Umbria

Image courtesy of Reschio Hotel

Umbria is its own region just next door to iconic Tuscany. This is central Italy at its most timeless, with rolling hills, morning mist, and stone towns that feel untouched by modern life. Wander through Assisi or Orvieto, linger over truffle pastas in family-run trattorias, and soak up a slower, earthier rhythm. 

Reschio Hotel: A restored 10th-century estate turned design-forward retreat off-the-beaten-path, every corner feels curated but never staged. The suites are moody and cinematic, the spa is inside an old wine cellar, and the vibe is quiet luxury with a rustic soul.

• Our perks include a £75 hotel credit, Nature-related experience for specific suites, daily breakfast, an upgrade, and extended check-in/out whenever possible.
  

Borgo dei Conti Resort: This 17th-century villa in the countryside features sprawling grounds, old-world charm, and modern comfort, plus world-class service. There are spacious rooms, indoor and outdoor pools, and curated experiences like truffle hunting.

• Our Perks include a £75 food & beverage credit, daily breakfast, an upgrade, and extended check-in/out whenever possible.
  

Vocabolo Moscatelli Boutique Hotel & Restaurant: Authentic and relaxed, this boutique hotel is cozy and welcoming. The rooms are comfortable and inviting, the restaurant serves up delicious regional dishes, and peaceful surroundings provide a perfect backdrop.

• Our perks include a welcome amenity, daily breakfast, an upgrade, and extended check-in/out whenever possible.
  

History and culture

Tuscany’s history reads like a living museum, layered with stories that still shape the region’s spirit today. Tuscany was home to the Etruscans, an advanced, pre-Roman civilization known for their mysterious tombs, intricate metalwork, and early belief in divination. Their legacy lingers in towns like Volterra and Cortona, home to ancient walls and archaeological sites. Tuscany then rose to global prominence during the Renaissance, when Florence became a creative powerhouse under the Medici family, who funded the works of Michelangelo, Botticelli, and Leonardo da Vinci. This era not only shaped Western art but also embedded a deep reverence for beauty, balance, and intellect into the Tuscan identity. 

Today, that cultural pride shows up in everyday rituals, from the local passeggiata (evening stroll) to seasonal festivals tied to harvests, saints, or historic rivalries. Siena’s Palio horse race, for instance, is deeply rooted in neighborhood rivalry with centuries of pride behind each colorful contrada flag. In rural areas, time-honored traditions remain, like truffle hunting, olive oil pressing, and winemaking. Even the Romanesque churches, medieval towers, and Renaissance piazzas remain central to local life, hosting everything from open-air markets to processions and community gatherings. For travelers, Tuscany offers more than views, it offers a connection to a culture where history, beauty, and ritual are still very much alive.

Cultural celebrations & events

• Settimana dei Musei (Tuscany-wide, March): A culture lover’s dream with free museum entry and special exhibits across Tuscany.
• Cantine Aperte (Tuscany & Umbria, last weekend of May): Wineries throw open their doors for a weekend of tastings, cellar tours, and live music.
• Infiorata di Spello (Umbria, June): For one weekend, Spello’s streets bloom with elaborate floral carpets made entirely of petals.
• Umbria Jazz Festival (Perugia, mid-July): One of Europe’s top jazz events. Big names, balmy nights, and a buzzy crowd make it a fun side trip from southern Tuscany.
• Palio di Siena (Siena, July 2 & August 16): A no-holds-barred horse race in full medieval regalia with fanfare, flag-throwing, and local pride. Book early, it fills up fast.
• Sagra del Tordo (Montalcino, last weekend of October): Archery contests, feasts, and pageantry take over this hilltop town during its annual festival.
  

What to do in Tuscany and Umbria

From hilltop strolls and wine tastings to hands-on cooking classes and centuries-old cathedrals, Tuscany and Umbria are made for slow, immersive travel.

Siena

• City center: Start in the Piazza del Campo. Grab a coffee at a sun-drenched café, take in the sights of daily life, then climb the Torre del Mangia for sweeping views across terracotta rooftops and rolling hills beyond.
• Duomo di Siena: Step inside the Duomo di Siena, a Gothic marvel of black-and-white marble, soaring arches, and masterpieces by Donatello and Michelangelo. Don’t miss the Piccolomini Library or its frescoed Renaissance ceiling.
• Santa Maria della Scala: Explore Santa Maria della Scala, a former hospital turned cultural hub with layered exhibits that reveal Siena’s medieval roots and artistic heart.
• Cooking class: Roll up your sleeves at a cooking class in the countryside. Hand-rolled pici pasta, Chianti sips, and recipes passed down through generations.
• Via Francigena pilgrimage trail: Walk or e-bike a stretch of the Via Francigena pilgrimage trail. You’ll wind through olive groves, vineyards, and timeless villages that feel a world away from modern life.
  

Montepulciano

• City center: Stroll Montepulciano’s cobbled lanes lined with Renaissance palazzi, wine bars, and sweeping views over the Val di Chiana.
• Wine tasting: Head underground to taste Vino Nobile in centuries-old cellars, often paired with local cheeses and stories that bring the town’s winemaking past to life.
• Torre di Pulcinella: Climb the quirky Torre di Pulcinella for a bird’s-eye view and catch the Punch automaton ringing the town bell.
• Local food: Settle into Piazza Grande for hand-rolled pici and truffle dishes, best enjoyed with a glass of red and a front-row seat to Montepulciano’s timeless charm.
  

Montalcino

• Wine tasting: Sip Brunello at renowned estates like Biondi-Santi and Casanova di Neri, where tastings come with vineyard strolls and cellar tours.
• City walls: Walk the ramparts of the 14th-century Fortezza di Montalcino for panoramic views over the vine-covered hills.
• Abbey of Sant’Antimo: Visit the serene Abbey of Sant’Antimo, a Romanesque masterpiece where cypress trees frame the stone façade and Gregorian chants occasionally echo through the nave.
• Vineyard trails: Hike or bike through Montalcino’s vineyard trails, with olive groves and golden hills unfolding at every turn.
• Chapel Vitaleta: Pause at the Chapel Vitaleta, a lone stone church on a cypress-lined ridge, one of the Val d’Orcia’s most iconic photo moments.
  

Umbria

• Towns: Wander the hill towns of Spello, Assisi, and Perugia. Cobblestone streets lead to artisan studios, cozy cafés, and boutiques stocked with handwoven linens, ceramics, and small-batch olive oil.
• Local traditions: Experience local craft and cuisine by touring a cashmere atelier in Bevagna, shaping clay in Deruta, or rolling out pasta in a farmhouse kitchen using garden-fresh truffles and herbs.
• Unique adventures: Go truffle hunting with a seasoned guide, take a hot air balloon ride above vineyards, or sip bold reds and crisp whites in Montefalco and Orvieto.
• Seasonal offerings: In late spring, catch the blooming wildflower fields of Castelluccio di Norcia, then end your day with a golden-hour stroll through olive groves or a quiet glass of wine with a view.
  

Where to eat in Tuscany and Umbria

These standout restaurants blend tradition, creativity, and a deep sense of place. Here’s where to eat across Tuscany and Umbria.

Siena

• Ristorante Enoteca Del Duca: Refined Tuscan plates and an impressive wine list served just outside the city walls in a romantic, quietly elegant space.
• Campo Cedro: A minimalist, modern twist on Tuscan flavors with hyper-local ingredients and a cool, low-key vibe.
• La Taverna di San Giuseppe: Hearty classics like wild boar ragù and hand-rolled pici served in a cozy 13th-century cellar with deep roots and deeper wine.
• Arnolfo (Colle di Val d’Elsa): A two-Michelin-Star tasting menu experience where Tuscan ingredients meet creative finesse, worth the detour.
• Tre Cristi: Siena’s oldest fine dining spot, known for elegant seafood and old-world charm in a quietly luxurious setting.
  

Montepulciano

• Ristorante Daria: A warm, family-run spot in Montepulciano serving Tuscan comfort food.
• Sette Di Vino: A cozy enoteca known for local wine flights and small plates of cured meats, cheeses, and regional bites.
• Dopolavoro La Foce: An elegant farm-to-table restaurant on a historic estate, ideal for a long lunch with garden views.
• Porta di Bacco: A relaxed osteria blending tradition and creativity, with handmade pastas and seasonal ingredients in a rustic-modern space.
• Osmosi: A Michelin-noted dining experience where inventive tasting menus and regional wines elevate classic Tuscan flavors.
  

Montalcino

• Tenuta Le Potazzine: A Brunello estate pairing elegant wines with farm-to-table dishes for a full countryside dining experience.
• Ristorante Il Leccio: A cozy, family-run favorite serving rich Tuscan classics like wild boar stew and roast lamb with Brunello by the glass.
• Osticcio: A sleek spot where organic, seasonal ingredients meet modern Tuscan cooking and sweeping vineyard views.
• Tenuta di Sesta: Scenic and serene, this winery pairs panoramic views with fresh regional fare and standout Brunello pours.
• Locanda Demetra & Montalcino Cooking School: A hilltop hideaway where cooking classes turn into intimate feasts of handmade Tuscan dishes and local wine.
  

Umbria

• Ristorante Vespasia: A Michelin-Starred gem in Palazzo Seneca, serving refined Umbrian dishes like black truffle pasta and slow-roasted lamb, all sourced locally.
• Apollinare: Set in a 12th-century stone building, this cozy favorite blends Umbrian tradition with modern flair in a candlelit, intimate space.
• Locanda del Capitano: A quiet village escape known for its elegant farm-to-table menus that spotlight the best of seasonal Umbrian produce.
• L’Acciuga: Perugia’s cool-kid favorite, serving bold, produce-driven plates and natural wines in a sleek, sustainable setting.
• Enoteca Properzio: A charming, family-run enoteca where Umbrian wines shine alongside beautifully executed regional classics.
• Casa Vissani: Umbria’s ultimate splurge, with theatrical plating, bold flavors, and a cellar fit for a celebration.
• Lungarotti Winery: A must for wine lovers, taste Rubesco reds, stroll the vines, and explore Torgiano’s wine museum all in one visit.
  

Add-on destinations

If you want to expand your trip, these spots make for easy additions. Each one offers a different side of Italy, from hidden gems to cultural powerhouses.

Brunello di Montalcino Region (30 minutes from Montalcino): A must for wine lovers. Spend the day sipping Brunello at family-run vineyards in the postcard-worthy countryside.

Lucca (1–1.5 hours by car or train): Quiet charm, leafy promenades, and a slower pace. Rent a bike and loop the Renaissance walls before settling in for a lazy lunch.

Pisa (1–1.5 hours by car or train): Come for the Leaning Tower, stay for the river views, university-town buzz, and surprisingly pretty piazzas.

Florence (1–2 hours by car or train): Art, architecture, and Aperol. Florence packs in Renaissance treasures, high fashion, and enough cultural hits to fill days.

Rome (2.5–3 hours by train or car): End or begin your trip with the Eternal City’s mix of ancient ruins, chaotic beauty, and unforgettable pasta.

Milan (3–4 hours by train): Chic, fast-paced, and surprisingly artistic. A good base for exploring northern Italy, with easy hops to Lake Como or the Alps.

If not Tuscany…

If you’ve done Tuscany and want that same mix of charm, wine, and countryside magic with a fresh twist, consider these destinations:

Provence, France: Lavender fields, hilltop villages, and rosé-filled afternoons. It’s slower, sun-soaked, and every bit as dreamy as Tuscany.

Bordeaux, France: Vineyards for days, a polished food scene, and grand châteaux dotting the countryside. Big wine energy, with a French accent.

Madeira, Portugal: All dramatic cliffs and lush green hikes, this island is like Tuscany meets Jurassic Park, but with wine.

Istria, Croatia: Rolling hills, truffle pasta, and coastal towns kissed by the Adriatic. It’s like Tuscany, but with sea breezes and a Croatian twist.

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