Best of Tuscany: 4 Days in Chianti Dream Wine Region

Check in at Borgo San Felice, a breathtaking medieval village estate and working winery tucked into the Chianti hills, where centuries-old stone buildings have been transformed into one of Tuscany's most romantic retreats.

We recommend settling into your room, then spending the afternoon wandering the property's cobblestone lanes before unwinding poolside as the golden Tuscan light sets in.

In the early evening, enjoy an on-property wine tasting at the estate's own winery, where you'll sample wines made from grapes grown right on the surrounding hillsides. Cap off the day with dinner at Poggio Rosso, the hotel's Michelin-starred restaurant, where traditional Tuscan cuisine is elevated with modern technique and impeccable presentation—the perfect way to begin your trip!

Start the morning with breakfast at the hotel before heading out for a full-day gourmet Chianti tour, a fully guided experience that immerses you in the countryside surrounding Borgo San Felice.

Over roughly six hours, you'll visit a working farm and wine cellar, taste estate-pressed olive oil and artisan cheeses, and sit down to a leisurely lunch, all included as part of the tour.

We recommend returning to the hotel afterward for some well-earned rest, giving yourselves 1.5–2 hours by the pool, on the terrace, or in your room before heading out again for the evening.

Dinner is at Le Pietre Vive in Castelnuovo Berardenga, a farm-to-table gem in the Sienese valley known for its garden setting, seasonal local ingredients, and standout dishes like knife-chopped beef tartare, homemade pici pasta, and osso buco.

Spend the day exploring Siena, one of Italy's most magnificent medieval cities—a car-free hilltop gem built in warm terracotta brick and centered around the Piazza del Campo, one of the greatest public squares in the world.

Start the morning with a cappuccino at a terrace café on the Piazza del Campo, then head to the Siena Cathedral (Duomo), allowing 1–1.5 hours to take in one of Italy's most breathtaking cathedrals.

Stop by Antica Drogheria Manganelli 1879 on Via di Città for panforte, ricciarelli, and local olive oils and wine to bring home.

Then enjoy lunch at Osteria Le Logge, a celebrated Sienese restaurant steps from the Campo known for its quaint dining hall and classical upstairs room.

In the afternoon, unwind with a couples massage at the Botanic Spa, set beneath original oak beams in the estate's former olive oil press, then enjoy an optional glass of Prosecco on the terrace as golden hour light falls over the vineyard.

Round out the day exploring Villa a Sesta with dinner at Ristorante Enoteca Villa di Sotto, a charming family-run spot with a panoramic terrace, simple and tasty specialties, and plenty of vegetarian and gluten-free options.

Start the day with a Brunello cooking experience that pairs a small-group cooking class with a tour of vineyards and a 13th-century castle that's been in the same family for seventeen generations. On a panoramic terrace kitchen, you'll learn to prepare classic Tuscan dishes like tagliatelle with Tuscan sauces and braised beef, pairing each course with local wines for lunch, before touring the castle grounds and wine cellar.

Afterward, spend some time exploring Montalcino, a perfectly preserved medieval hilltop town and home to Brunello di Montalcino, one of Italy's greatest wines. Wander the charming streets, then consider stopping at Enoteca La Fortezza inside the town's 14th-century fortress for a guided Brunello tasting on the ancient ramparts, with sweeping views over the Val d'Orcia—one of the most atmospheric wine experiences in all of Tuscany.

Close out the evening at Castello di Brolio, a dramatic medieval Ricasoli castle and estate—the grounds are free to explore, with sweeping views from the ramparts and the chance to pick up a bottle of Chianti Classico Riserva at the estate shop.

Dinner is at Osteria di Brolio, set at the foot of the castle with a panoramic outdoor terrace and an exceptional seasonal Tuscan menu.