Timeless Tuscany: A Curated Travel Guide

Icon Share

SHARE

Advisor - Angela Hope
Curated By

Angela Hope

  • Food & Wine

  • Luxury Travel

  • Slow Travel

  • Tuscany

  • Relaxation

Advisor - Timeless Tuscany: A Curated Travel Guide
Curator’s statement

Tuscany holds a special place in my heart because it captures everything I love about travel: slow, intentional living; stunning landscapes; and a deep appreciation for food, wine, and culture. Whether you’re wandering through medieval hill towns, sipping Brunello straight from the vineyard, or watching the sunset over golden fields, it feels like stepping into a dream. It’s a place I return to in my mind often, and one I believe everyone should experience at least once.

The Fora Difference

Book with Angela to access exclusive perks and experiences on your trip.

Icon Travel Perks
Killer perks

Free upgrades, spa credits and more—we got you

Icon Recommendations
Personalized recs

Customized travel planning for your style

Icon Inside Knowledge
Insider knowledge

Expert advice from people who’ve actually been there

Where to stay in Tuscany

Unlock perks by contacting Angela to book your trip.

Things to do in Tuscany

  1. Wine tasting in Montalcino & Montepulciano: Explore world-renowned wineries producing Brunello and Vino Nobile - take a private tasting tour, stroll through the vineyards, and enjoy wine paired with local pecorino and olive oil.

  2. Explore the hilltop towns of Val d’Orcia: Visit beautiful towns like Pienza, San Quirico d’Orcia, and Bagno Vignoni. These villages offer stunning views, artisan shops, and that peaceful, timeless charm Tuscany is known for.

  3. Truffle hunting in the Tuscan woods: Join a local guide and their truffle dog to forage for seasonal truffles, then enjoy a rustic lunch with what you find.

  4. Stay at a countryside villa or agriturismo: Book a few nights at a villa surrounded by olive groves and vineyards. These stays give you a true taste of rural Tuscan life with homemade meals, sweeping views, and total relaxation.

  5. Visit Siena’s historic Piazza del Campo: Walk the cobbled streets of Siena and marvel at its grand, shell-shaped square - home to the famous Palio horse race. Climb the Torre del Mangia for panoramic city views.

  6. Take a cooking class with a local chef: Learn how to make fresh pasta, Tuscan ribollita, or tiramisu in a hands-on class. Many are hosted in private homes or on farms, making the experience feel intimate and authentic.

  7. Relax in natural thermal baths: Unwind in Tuscany’s natural hot springs, like Saturnia or Bagni San Filippo.

  8. Tour the Chianti wine route (Via Chiantigiana): Drive (or hire a driver) along this scenic wine road, stopping at charming towns like Radda, Castellina, and Gaiole. Each has its own wineries, enotecas, and rustic trattorias.

  9. Watch the sun set over the cypress-lined roads: Nothing beats the magic of golden hour in Tuscany. Head to spots like the Chapel of Vitaleta or the rolling hills near Monticchiello to soak in the landscape as it glows with warm light.

Places to eat & drink in Tuscany

  1. Osteria Le Logge – Siena: A cozy yet refined osteria steps from Piazza del Campo, known for its seasonal Tuscan dishes and extensive wine list. The interiors feel like an elegant private library.

  2. La Bottega del 30 – Castelnuovo Berardenga (Chianti): This Michelin-starred restaurant in a tiny Chianti hamlet offers a warm, romantic setting and a creative take on Tuscan classics, with impeccable service from a husband-and-wife duo.

  3. Meo Modo by Jean-Luc Lefrançois – Borgo Santo Pietro, Chiusdino: A two-Michelin-star experience in a luxurious countryside estate, offering farm-to-table tasting menus with ingredients sourced directly from the estate’s own gardens.

  4. Osteria Acquacheta – Montepulciano: Beloved for its massive, perfectly cooked bistecca alla Fiorentina, this no-frills osteria is a local favorite. Expect a lively, rustic atmosphere and hearty portions of classic Tuscan fare.

  5. La Porta – Monticchiello: With breathtaking views of the Val d’Orcia, this romantic spot is known for dishes featuring truffle, pecorino, and local saffron. Ideal for sunset dinners on the terrace.

  6. La Grotta – Montepulciano (San Biagio): Set in a Renaissance-era building across from the stunning San Biagio church, this upscale restaurant is ideal for a refined lunch or dinner with handmade pastas and excellent wines.

Need to know

  • Slow down: Tuscany is all about slow living—long lunches, lazy afternoons, and spontaneous stops in charming villages. Don’t overpack your itinerary— leave room to just wander and soak it in.

  • Make wine tasting reservations in advance: Especially during peak months, many wineries require bookings for tastings or tours. Plan a few days ahead of time to secure a spot.

  • Avoid Sundays for shopping & sightseeing: Many shops, restaurants, and even gas stations close or have limited hours on Sundays, particularly in smaller towns. Plan accordingly or use it as your day to relax.

For more inspiration and insider recommendations, visit our Tuscany page.

Advisor - Angela Hope

Travel Advisor

Angela Hope

Get in touch with Angela

Did you like this guide? Reach out to customize and book your own experience. Or, just to chat about travel in general.

You can expect a response from Angela within 1–2 business days. You’ll also be subscribed to our traveler newsletter (you can unsubscribe at any time).

We use cookies to enhance the user experience. Read our Privacy Policy here.