Your Ultimate Tuscany Travel Guide: From Truffles to Chianti
Where Flavor Meets Slow Living
Few places capture the heart (and appetite) quite like Tuscany. Rolling hills, cypress-lined drives, and long lunches that linger until sunset — Tuscany isn’t just a destination, it’s a way of life.
Confession time: Italy wasn’t always at the top of my travel list. I know, shocking — a foodie and a wine lover admitting that! But when my best friend and I made a pact to celebrate our 40th (shhh, that part stays between us) with a trip to Tuscany, everything changed.
Sipping Chianti beneath olive trees, the evening breeze dancing through the vineyards, I realized what everyone meant when they said Tuscany stays with you. It’s not just the food or the wine — it’s the pace, the people, and the way life feels beautifully unhurried.
I want you to experience the same magic I did — the authentic, flavor-filled Tuscany beyond the guidebooks. This post will give you a perfect starting point for planning your own journey, from truffle hunts to Chianti tastings.
✨ Want to take it a step further? My Tuscany Digital Travel Guide & Itinerary includes a full curated itinerary, my favorite restaurants, winery recommendations, and hidden-gem stays — designed to help you experience Tuscany the Road & Table way.
{Hey there! Just a heads-up—some of the links on this site are affiliate links, meaning I may earn a small commission if you make a purchase (at no extra cost to you!). These earnings help fuel my adventures, allowing me to travel more, discover incredible food experiences, and bring you even more exciting content.}
When to Visit Tuscany
Timing in Tuscany is everything — the way the light hits the hills, the rhythm of the vineyards, the scent of truffles drifting through autumn air. I mean the truffles......Sorry, I got distracted...Anyway, each season offers its own flavor, and choosing the right one can completely shape your experience.
Spring (April – June)
Wildflowers bloom across the countryside, vineyards wake from winter, and café terraces fill with locals and travelers alike. It’s warm enough for enjoying lunches outside and cool enough to wander medieval hill towns without the crowds.
Road & Table Tip: May is prime time for vineyard picnics and early summer cooking classes.
Autumn (September – November)
If you’re visiting for truffles, wine harvests, and cozy slow evenings, this is your season. HMMM, my kind of season... The air turns crisp, olive harvests begin, and every village seems to host a festival celebrating food, wine, or both.
Summer (July – August)
Tuscany in summer is long golden days, slow lunches, and evenings that stretch late into the night under twinkling lights. But let’s be honest —
it’s hot.
When we visited in
July, we got lucky with a small break from the heat, but most days are toasty, and the midday sun can be intense. While the evenings cool off beautifully and make for dreamy dinners outside, if you don’t love the heat, consider another time of year.
Road and Table Tip: For a true local feel, escape to smaller towns like Anghiari or Pienza and skip the mid-day rush in Florence. Plus the heat and the city....let's just say it's a lot!
Winter (December – March)
Winter is Tuscany’s best-kept secret. The tourists are gone, the prices drop, and you can have Florence’s art galleries (almost) to yourself. It’s also the best time to cozy up with hearty Tuscan dishes like ribollita or pici cacio e pepe.
No matter when you go, Tuscany rewards those who slow down and savor.
Tuscany Region Breakdown: Where to Stay & What to Expect
Chianti Classico
Best for: Wine lovers, scenic drives, romantic countryside stays
Vibe: Rolling vineyards, cypress trees, stone villas, and the iconic “Under the Tuscan Sun” feel
The Chianti region is pure Tuscany — all sun-soaked vineyards and long lunches under vine-covered pergolas. Towns like Greve in Chianti, Radda, and Castellina are filled with wineries, farmhouses, and small trattorias that serve local wines right from the source.
Road & Table Book Club Pick: Want to be inspired and dream about Tuscany? Read:Under The Tuscan Sun
Val d’Orcia
Best for: Photography lovers, peaceful escapes, wine and cheese trails
Vibe: Storybook views, golden hills, and postcard-perfect villages
Val d’Orcia is Tuscany.....think Pienza, Montepulciano, and Montalcino. It’s quieter, more rural, and deeply rooted in food and wine culture (hello, Brunello di Montalcino and pecorino from Pienza).
Arezzo & Anghiari
Best for: Hidden gems, market lovers, wine, foodies and art enthusiasts
Vibe: Medieval charm, antique markets, authentic local life
This corner of eastern Tuscany feels undiscovered — and that’s exactly why I love it. Arezzo hosts one of Italy’s best antique fairs, while Anghiari is all winding lanes, artisans’ workshops, and views that make you want to stay forever.
Road & Table Pick: Anghiari feels like stepping back in time. It’s the perfect base if you love slow mornings, farmers markets, and fewer tourists.
Where to stay: Buccia Nera (35 minutes from Arezzo) A family-run wine estate and agriturismo set among rolling vineyards and olive groves. Offers charming farmhouse apartments, a pool, and on-site wine tastings for a relaxed countryside escape.
Get all the inside scoop to Anghiari and Arezzo with my Tuscany Travel Guide: Arezzo & Anghiari Culinary Itinerary!
🏙️ Florence (Firenze)
Best for: Art lovers, culture seekers, and aperitivo enthusiasts
Vibe: Renaissance grandeur meets modern café culture
Florence is Tuscany’s beating heart — a city where Michelangelo, espresso, and aperitivo all belong in the same sentence. Stay here for a night or two to immerse yourself in the museums and piazzas, then escape to the countryside for a slower pace.
Road and Table Tip: If standing in long museum lines isn’t your idea of vacation bliss, skip the long museum lines and visit the Medici Palace instead. It’s quieter, beautifully preserved, and filled with stunning artwork, frescoed halls, and secret courtyards — a glimpse into Florence’s Renaissance splendor without the crowds.
Lucca & Pisa
Best for: Family-friendly stays, cycling, and classic sightseeing
Vibe: Elegant, laid-back, and easily accessible
Lucca’s city walls are made for biking — a perfect way to take in the view while enjoying a gelato stop (or three). Pisa, of course, has its famous Leaning Tower, but beyond that, it’s a charming riverfront city with a growing culinary scene.
Siena & San Gimignano
Best for: History lovers, architecture buffs, and those chasing that “classic Tuscany” feel
Vibe: Medieval charm, piazza life, and sweeping vineyard views
Siena is a stunning mix of Gothic architecture and Tuscan warmth, while nearby San Gimignano offers one of the best skyline views in Italy — all those medieval towers rising from the hills.
Maremma & the Tuscan Coast
Best for: Off-the-beaten-path travelers, beach lovers, and wine with a sea breeze
Vibe: Wild coastlines, olive groves, and seaside villages
The Maremma region is Tuscany’s wild side — part countryside, part coast, and all authenticity. Think long beaches, seafood feasts, and boutique stays hidden among olive trees. Towns like Bolgheri are known for their “Super Tuscan” wines, while Castiglione della Pescaia brings a coastal charm that pairs perfectly with a glass of Vermentino.
Eat & Drink: A Foodie’s Map of Tuscany
If Tuscany had a love language, it would be food. Every meal here tells a story — of family, land, and centuries of flavor perfected with simplicity. From earthy truffles to full-bodied Chianti, Tuscany invites you to slow down, savor, and experience the region one bite (and one sip) at a time.
Truffle Heaven: San Miniato & Mugello
There’s a certain magic in following a truffle dog through the forest, the earth rich with scent, the anticipation building until that small, precious treasure is unearthed.
Tuscany’s
San Miniato and
Mugello regions are truffle country, especially in autumn when the air turns crisp and the white truffles make their grand appearance.
Many local farms offer guided truffle hunts followed by rustic, home-cooked meals — think tagliolini tossed in butter and shaved truffle, paired with a glass of local wine.
✨ My Tuscany Travel Guide: Arezzo & Anghiari Culinary Itinerary includes trusted truffle-hunting experiences and the trattorias that serve these treasures the authentic way.
Chianti & Beyond: Wine Regions You Can’t Miss
No trip to Tuscany is complete without time among the vines. The Chianti Classico region, stretching between Florence and Siena, is the heart of Tuscan wine culture — rolling hills, centuries-old estates, and family-run wineries where tasting feels more like being welcomed home.
But don’t stop there. Venture beyond Chianti into Montepulciano, known for its velvety Vino Nobile, and Montalcino, home of the world-famous Brunello. Smaller producers here often offer intimate tastings, personal stories, and bottles you’ll never find on U.S. shelves.
Farm-to-Table Tuscany: Local Markets & Cooking Classes
Food in Tuscany starts at the market. Wander through Florence’s Mercato Centrale, where locals shop for pecorino, fresh pasta, and baskets of sun-ripened produce. Or visit Arezzo’s weekly market, where the air is thick with the scent of herbs, cheese, and fresh bread.
For a deeper taste of the culture, join a cooking class in a farmhouse kitchen — learning how to roll out pici by hand or prepare bruschetta over open flame. These experiences connect you to Tuscany in the most delicious way possible.
If your planning a trip to Arezzo get my Anghiari and Arezzo Itinerary.
Tuscan Classics You Can’t Miss
Every region has its culinary icons, but Tuscany’s dishes are a masterclass in rustic perfection.
- Tagliata di Manzo – Grilled steak drizzled with olive oil and rosemary.
- Pici Cacio e Pepe – Hand-rolled pasta tossed with pecorino and black pepper.
- Ribollita – Hearty vegetable and bread soup, rich with olive oil.
- Cantucci with Vin Santo – Almond cookies dipped in sweet dessert wine to end your meal on a warm note.
These dishes embody everything that makes Tuscany unforgettable — simplicity, seasonality, and a whole lot of love.
🍷 Want restaurant recommendations? Inside my Tuscany Travel Guide: Arezzo & Anghiari Culinary Itinerary— includes my favorite hidden trattorias, wine tastings, and foodie stops
Tuscany Itinerary Snapshot
If you’re anything like me, Tuscany isn’t just a destination — it’s an experience you want to live, not just visit. Whether you have a few days or a full week, this snapshot itinerary gives you a taste of the Road & Table way to explore: equal parts food, wine, slow mornings, and unforgettable views.
✨ For a complete 8-day digital itinerary — including hidden-gem stays, Road & Table–approved dining, attractions and more — find it all inside my Tuscany Digital Travel Guide: Arezzo & Anghiari Culinary Itinerary
Day 1 – Market Morning & Tuscan Pantry
Ease into slow living with a visit to local markets and charming alimentari shops. Stock up on fresh olive oil, cheeses, and local wines for the week ahead.
Day 2 – Truffles & Twilight in Arezzo
Follow a truffle dog through the forest, enjoy a truffle-infused lunch, then spend your evening in Arezzo sipping wine and dining under the stars.
Day 3 – Olive Oil, Nature & Michelin Nights
Tour family-run olive presses and taste liquid gold straight from the source. Relax in the countryside before indulging in a Michelin-starred dinner.
Day 4 – History & Culinary Heritage in Anghiari
Explore medieval streets, browse artisan shops, and eat at farm-to-table restaurants. and stroll the village as the sun sets behind the hills.
Day 5 – The Wine Road
Sip your way through Tuscany’s iconic vineyards — from Chianti Classico estates to Brunello tastings.
🍷 Extend Your Stay
Add extra days to explore Florence, Siena, or the Tuscan Coast — or let me design a custom 7- or 8-day itinerary with private tastings, hidden-gem stays, and driver arrangements.
Bringing Tuscany Home
One of my favorite parts of traveling is finding ways to bring a little piece of that place home —
not through souvenirs, but through
flavors, stories, and simple rituals that make travel feel alive long after the suitcases are unpacked. The heart of
Road & Table is creating
travel-inspired moments that connect us to the world through food, wine, and story.
- When I can’t be in Tuscany, I recreate it in my kitchen with my Ricotta Gnocchi with Gorgonzola Cream and Pears, inspired by candlelit dinners under olive trees.
- Join my Journey & Bites Newsletter for Italian-inspired recipes, upcoming travel stories, and behind-the-scenes glimpses from my culinary adventures.
- Don’t miss the Wanderlust Reads Book Club, where each month’s pick pairs perfectly with a destination — from Tuscan vineyards to Parisian cafés and seaside escapes.
Plan Your Road & Table Journey
Ready to turn your Tuscan daydream into reality?
My Tuscany Digital Travel Guide has everything you need to plan your perfect trip — from truffle hunts to Chianti tastings, boutique stays, and restaurant recommendations.
Prefer to have it all done for you? Inquire about my Custom Curated Itinerary Services or my full booking services and travel the Road & Table way.
© Jamie Cassidy and Road And Table, 2023. Unauthorized use and/or duplication of this material without express and written permission from this site’s author and/or owner is strictly prohibited. Excerpts and links may be used, provided that full and clear credit is given to Jamie Cassidy and Road and Table with appropriate and specific direction to the original content.
