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Tuscany Travel Tips From Local Experts

Danielle Strayer Last Updated: May 25, 2025

Home > travel-blog > Podcast > tuscany > Tuscany Travel Tips From Local Experts

French People Arr. Rude Podcast Show Notes

S1, E12: Land Scam, Vertical Feud, Buried Pride, Real Excalibur

In this episode of French People Arr. Rude, Sean and Brandon expose Italy’s most romantic region. If you picture Tuscany as one giant postcard of vineyards and terra-cotta farmhouses, you’re right on track—but there’s more. Tune in and read these Tuscany travel tips to sip the best wine, find hidden farm stays, and learn how a medieval rooster decided half the wine map.


What We Cover in This Episode

  • Tuscany Stereotypes
  • Get to and Around Tuscany
  • Where to Stay
  • What to Eat
  • Best Vineyards
  • 72-Hour Tuscany Itinerary

Resources Mentioned in This Episode

  • How to Book the Best Agriturismo
  • Where to Stay in Tuscany
  • Best Wine Tours in Tuscany
  • Top Things to Do in Tuscany
  • Chianti Wine Tour from Florence
  • Italy Trip Planning Resources
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🎧 Listen on Spotify

Tuscany Travel Tips – Podcast Show Notes

Segment 1: Tuscany Stereotypes

Beautiful rolling hills of Tuscany
  • Everyone owns a vineyard: True. Vineyards are everywhere, often owned by families who’ve worked the land for generations.

  • They have the best wine in Italy: Not necessarily true. Tuscany has some of the best—Super Tuscans, Vino Nobile, and Brunello—but “the best” is a personal call.

  • Chianti is the best wine in Tuscany: False. Chianti is the most famous, but many locals prefer Brunello or Vino Nobile.

  • Beautiful hilltop towns everywhere: True. Tuscany is full of charming hilltop towns connected by quiet roads that beg for a countryside drive.

  • Everything looks like Under the Tuscan Sun: Kind of true. Rolling wheat fields, terracotta roofs, vineyards in perfect rows—it’s real. Rose bushes at the end of vineyard rows serve as early disease detectors.


Interessante Fact: The black-rooster seal on a Chianti Classico bottle traces back to a crooked medieval rooster race that let Florence grab prime wine land overnight.

👉 Want a deep dive into local wine culture? Join our Chianti Wine Tour from Florence.

Segment 2: Getting to & Around Tuscany

Women standing by jeep in Tuscany
  • By Train: You can take a train to Florence, Siena, or other major towns, but to truly explore, you’ll need a car.

  • By Plane: Fly into Rome for international flights, then take a train to Florence or Siena. Florence’s airport is nice, but domestic only.

  • By Car: Ideal way to get around Tuscany. Rent a car in Florence or Siena to avoid Rome’s chaotic traffic.

  • Driving Tips: Roads are scenic and mostly quiet. Use a GPS, and don’t count on reliable cell service in the hills.

Interessante Fact: The Sacred Forest of La Verna makes a peaceful detour between Rome and Tuscany. It’s said St. Francis of Assisi received the stigmata here.

Segment 3: Where to Stay in Tuscany

Below are our favorites mentioned in the Tuscany travel tips podcast episode. For more, check out our Where to Stay in Tuscany guide.

Agriturismo in Tuscany, a favorite mentioned during our Tuscany Travel Tips podcast episode
Agriturismo in Tuscany
  • Agriturismo: The real Tuscan experience. These farm stays legally must produce agricultural goods. Expect vineyards, views, and homemade meals.

  • San Gimignano Area: Good for everyone. Central, scenic, and full of charm.

  • Val d’Orcia (Montalcino, Pienza): For wine lovers and romantics. Cypress-lined roads, endless vineyards, and unforgettable views.

  • Chianti Region: Forested hills, iconic wineries, and villages like Greve and Radda. Great for day trips.

  • Siena: A bit bigger, with train access and great restaurants. Walkable, medieval, and perfect if you don’t want to drive every day.

Interessante Fact: Siena residents once buried city treasures under the streets to spite Florence during a siege. Some claim the loot is still down there.

Segment 4: What to Eat

Snap a pic of this list, you’ll want it on hand when you sit down.

Bistecca alla Fiorentina, a favorite mentioned during our Tuscany Travel Tips podcast episode
Bistecca alla Fiorentina
  • Crostini con pâté di fegato: Chicken liver pâté on toasted bread

  • Salsiccia e stracchino: Creamy cheese and sausage on rustic toast.

  • Bruschette al lardo e rosmarino: Rosemary and lardo over grilled bread.

  • Ribollita: Hearty white bean and bread soup.

  • Pici Pasta: Hand-rolled, thick pasta—perfect with truffle or ragu.

  • Pappardelle al cinghiale: Wide noodles with wild boar sauce.

  • Pappa al pomodoro: Tomato and bread soup.

  • Bistecca alla Fiorentina: Rare, thick-cut T-bone steak grilled over fire.

  • Cinghiale (wild boar): Often braised with herbs and red wine.

  • Cantucci & Vin Santo: Almond cookies dipped in dessert wine.

Segment 5: Where to Eat & Our Favorite Vineyards

Patio of Agriturismo Villa di Sotto overlooking a Tuscan vineyard, a favorite mentioned during our Tuscany Travel Tips podcast episode
Agriturismo Villa di Sotto

Here’s our Tuscany travel tips for where to eat:

  • At your agriturismo: Homemade meals, no menu needed.

  • Certaldo Alto: A quiet hilltop town with excellent local cuisine.

  • Montalcino & Pienza: Top-tier wine and food pairing options.

  • San Gimignano: Great lunch spots and streets made for strolling.

Favorite Vineyards:

Fattoria dei Barbi in Tuscany, a favorite mentioned during our Tuscany Travel Tips podcast episode
Fattoria dei Barbi

Call or book ahead to ensure the winery is open for tastings.

  • Tignanello: Super Tuscan legend, popular for a reason.

  • Tenuta Casanova: Upscale yet rustic, homemade pasta, and wines not sold anywhere else.

  • Poggio di Sotto: Modern, gorgeous views, and well worth scheduling in a long afternoon for.

  • Fattoria dei Barbi, Casanova di Neri, Banfi: All worth a stop in Brunello country.

👉 Learn to make Tuscan classics yourself during a Florence cooking class.

Segment 6: 72-Hour Tuscany Itinerary

Day 1: Hit the Highlights in Florence

Statue of David
  • Arrive and see the Accademia, Uffizi, and the Duomo on a guided tour.

  • Grab an iconic affogato (gelato and espresso) at Vivoli il Gelato.

  • Evening spritz at Volume Bar in Piazza Santo Spirito.

Day 2: Into the Countryside

Visit the San Gimignano, a favorite mentioned during our Tuscany Travel Tips podcast episode
San Gimignano
  • Pick up your rental car and head to wine country.

  • Visit Tenuta Casanova for wine and lunch.

  • Stop in San Gimignano to wander medieval streets.

  • Drive into Val d’Orcia and stay in Montalcino or Pienza.

Day 3: The Grand Finale

Leaning Tower of Pisa
Leaning Tower of Pisa
  • Morning: Head to Siena to see the striped Duomo and grab coffee near Piazza del Campo.

  • Afternoon: Explore Montepulciano’s underground wine cellars.

  • Optional detour to Pisa for the Leaning Tower photo-op.

  • Last dinner at a countryside agriturismo, paired with a bottle of wine or two.

👉 Let someone else do the planning by joining our Florence Day Trip to Tuscany: Siena, San Gimignano & Winery Lunch.

Pitch us on your story by emailing Press@thetourguy.com

Catch Up On Previous Episodes of French People Arr. Rude

Europe Travel Update 2025
Rome Travel Updates & Things to Know for 2025
Italy Travel Tips from Local Experts
Amalfi Coast Travel Tips From Local Experts
Naples Travel Tips From Local Experts
Puglia Travel Tips From Local Experts
London Travel Tips From Local Experts
Best Beaches in Italy Travel Tips From Local Experts

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