Smart Luxury: An Affordable Tuscany Road Trip

by  Lavanya Sunkara | Dec 5, 2017
Brolio Castle
Brolio Castle / Lavanya Sunkara

When you think of Tuscany, romantic villas and delicious wine come to mind, but there’s much more to experience in the idyllic countryside located between Florence and Siena. Stay in a farmhouse villa, visit medieval villages and castles, marvel at churches, and feast on authentic cuisine at quaint farm-to-table restaurants. Here’s a look at an affordable way to experience the charming wine region of Chianti.

Getting There

Tuscany gets packed with vacationing Europeans during summer. The best time to avoid traffic jams, long lines, and overbooked hotels is in the shoulder seasons (May and September). Airline tickets from major cities range from $500 to $700 per person. Since driving from the big cities isn’t for everyone (not to mention the high gas prices), it’s best to take trains to Siena or Arezzo from Florence/Rome and rent a car to explore the region. The best route is on ItaliaRail trains from Rome to Florence to Siena, with first class cost per ride from Rome to Florence starting at $37; from Florence to Siena from $12 per person.

Car Rental

Tuscan car rental companies have a bad reputation for losing reservations. But, a reliable source for auto rentals, provides a comparison of various vehicle rentals starting at $150 per week/$21 per day, and ensures that your car is waiting when you arrive. Pro tip: Get an International Driver’s Permit ($20) from your local AAA before leaving the States to avoid paying hefty fees if pulled over for speeding, which is heavily enforced in Italy.

La Castellina wine cellar / Lavanya Sunkara

Wine Tastings

It seems like there’s a winery every few miles on the winding roads of Tuscany, and plenty of them offer complimentary or inexpensive ($5 - $10) wine tastings, but be sure to make reservations. Only a handful of tasting rooms offer unscheduled tastings, such as Castello Di Brolio, where you can also explore the rural castle from the Middle Ages and its gorgeous grounds. Major wineries such as La Castellina have shops in towns that offer wine from self-serve dispensers, offering up to 10 tastings for €10 (or about $12 USD).

What to Do

The instantly recognizable landscapes of cypress tree-lined roads leading to hilltop villages can be seen in Chianti. The winding roads over ridges connect the villages of Radda, Greve, Castellina and Gaiole, each with its own charm offering a variety of activities. Sip sumptuous Chianti Classico at the Viticcio Winery Estate (€10 or $12 per person) in Greve and learn about the evolution of wine at the Museo del Vino. Admire the Rocca Fortress and the Church of San Salvatore in Castellina. Visit Castles of Vertine, the Meleto and Castle Brolio in Gaiole. Enjoy a lavish meal at La Vin Osteria or shop the stores alongside the maze-like streets in Radda. Walk along the top of the border walls of beautiful Monteriggioni, an adorably preserved Old World, walled Tuscan town. Nature and art lovers can explore the intimate, beautiful Chianti Sculpture Park set in the midst of vineyards in Pievasciata (for €10 or about $12 per person).

Tregole villa / Lavanya Sunkara

Where to Stay

Charming country villas with rustic decor is the norm in most Tuscan accommodations, and farmhouse lodgings are popular among visitors. Support agriturist estate Fattoria Tregole, voted no. 1 B&B on TripAdvisor in Castellina in Chianti, situated atop a hill overlooking sweeping vineyards, olive groves, and nearby estates. Tregole offers standard rooms from €130 per night (or $155). Those who want to splurge can rent a two bedroom, two bath villa with a kitchen and living room for €220 per night (or $262). A continental breakfast is included. At the onsite restaurant, indulge in a hearty four-course gourmet meal made with fresh ingredients from the farm, which costs $75 per person and includes a glass of house wine.

After a few days of cruising the winding roads, sampling the wine, and experiencing the dolce far niente (pleasant idleness) in Chianti’s darling villages, you are sure to feel refreshed--especially when you've saved so much money.

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