How To Plan Your Ultimate Tuscany Food And Wine Lovers Road Trip

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If you love Tuscany, food and wine, then this road trip is a must for you.

Have you always wanted to go on a road trip through Tuscany? Have you ever thought about driving from Florence to Pontassieve, Pontassieve to Poppi, Poppi to Arezzo, Arezzo to Siena, Siena to Chianti, Chianti to Colle di Val d' Elsa, and Colle di Val d' Elsa to Florence? Sounds like a grand road trip right?

Tuscany roadtrip distance

This round-trip driving itinerary through Arrezzo, Siena, and beyond begins in Florence and offers a glimpse of the unique communities which make up the heart of this renowned region.

Explore Florence
The restaurants of Florence have everything a food and wine-lover could wish for, and it is perhaps fitting to start your roadtrip with a leisurely day or two spent exploring this fantastic city.

This is a great way to ease into your Tuscany roadtrip, recover from any jet-lag you may be experiencing, and feel refreshed before you hit the road to explore the Tuscan countryside.

Tuscany rooftop restaurant

Some restaurants worth checking out include La Bottega del Buon Caffe and Il Palagio (excellent destinations for traditional Italian fare if fine-dining is what you're after), or Sandwi Chic, Il Bufalo Trippone, or Panini Toscani if you're on a budget and want something delicious, yet casual.

Lo Sverso and Note di Vino are notable wine bars in the city, and La Terrazza Lounge Bar offers beautiful views of the river from their outdoor terrace if you're looking for a way to unwind, enjoy some wine and drink in the Florentine atmosphere!

Explore Pontassieve
Pontassieve is the confluence of the Arno and Sieve rivers and is a short drive in your Florence rental car, and when you arrive you'll be rewarded by a variety of high-quality watering holes and fine-dining eateries.

Tuscany rooftop restaurant

Ristorante Al 588 is one such favorite. It's a hidden gem and when you arrive you'll feel thankful. Expect fantastic service!

Looking for casual dining in Pontassieve, Italy? Experience Italy's version of fast food at a Pancia Piena, or snag a pizza or authentic pasta dish at Ristorante Pizzeria Acone. In fact get two pizzas if you're in Italy! A short drive north and you'll find the historic Nipozzano Castle and estate, which is the perfect location to taste the lovely Frescobaldi wines.

Explore Poppi
To get from Pontassieve, follow SR70 east - a beautiful drive through Borselli, Concuma, and Scarpaccia. Once you arrive you can make a stop at Brancaia winery for a tasting before dinner (it is recommended that you register in advance).


After your tasting (and perhaps purchasing a bottle of Chianti for a picnic later in the trip), visit Il Capanno, a restaurant which offers fabulous, authentic food with a casual atmosphere.

What we love about this well-reviewed restaurant, nestled in the trees in Casentino is that there's plenty of room outside to stretch your legs and enjoy a walk before or after dinner.

If you're looking for something more formal, Osteria il Porto and La Torricella offer well-appointed dining rooms and excellent service. Note that Osteria il Porto is slightly more upscale, so you may want to clean up a bit for dinner.

Explore Arezzo
Hopefully, you enjoyed your visit to Poppi and you're ready to continue your Florence roadtrip to the next destination.

From Poppi, travel south on SR 70 through Bibbiena, Rassina, and Capolona toward the heart of Arezzo. The wonderful part about this trip is that it's flexible - we've outlined a general circuitous route for you, but if you spy a shop, restaurant or village which you'd love to explore, by all means, turn off and take a detour anywhere in Arezzo Province.

Arezzo Province

Park your Arezzo car rental and explore this historic destination. The Town Hall (Palazzo del Comune), Cattedrale di San Donato, and Monumento a Francesco Petarca are all worth visiting, and after you've walked the city and worked up an appetite for more authentic Italian cuisine, enjoy Le Chiavi D'Oro, Ristorante Dario e Anna, or Saffron (high end) or grab a sandwich at Panini&Co or Dal Moro (and keep exploring!).

Explore Siena
If you're a fan of medieval architecture you will enjoy visiting Siena. When you arrive in Siena (just over an hour by car), be sure to visit the Siena Cathedral, Biblioteca Piccolomini, and take time to walk the Piazza del Campo. Each of these landmarks will inspire you with the rich history of the city, and lend balance to the rural vistas you've enjoyed all day.

Arezzo Province

If the timing is right and you're planning to stay in Siena for any length of time, plan to have breakfast at Antica Salumeria Salvini. You can thank us later. If it's dinner in Siena, it has to be Ristorante PorriOne - refined dining and an excellent selection of wine.
Castellina In Chianti

Explore Castellina In Chianti
Your roadtrip is coming to an end, but don't worry because you still have a couple beautiful places to visit.

Head north from Siena (enjoying a beautiful drive). Your next stop is in Chianti, Italy where you can tour the beautiful old Church of Saint Saviour, and perhaps spend the night in Hotel Villa Casalecchi - a 4-star destination with rooms that typically run about $100 a night.

Castellina in Chianti

After you're checked in, why not indulge in some Italian comfort food (and wine) at Osteria Pastececi da Sonia; a beautiful restaurant that offers a nice change of pace from the other eateries we've recommended. If possible, dine outdoors!
Colle di Val d'Elsa

Explore Colle di Val d'Elsa And San Gimignano
After your stay in Castellina, head west for the final destinations of your trip (before returning to Florence). Today you'll explore Colle di Val d'Elsa (a stunning location in the province of Siena, Italy), and nearby San Gimignano.

In Colle di Val d'Elsa be sure to visit Il Baluardo where you'll get your bearings of the historic city with a panoramic view (perfect place for photos), the Palazzo Campana, and dine at the Officina della Cucina Popolare, Arnolfo, or (more casual), Ristorante Pizzeria il Torrione.

Colle di Val d'Elsa

While exploring nearby San Gimignano, why not take a walk in the Riserva Naturale di Castelvecchio, or if you're looking for something different visit the Museo della Tortura (Torture Museum).

If you're looking for a unique way to spend your final night in Italy, there are numerous farm stay options, which are sure to delight with a truly unique Tuscan experience. Poderi Arcangelo Agriturimo San Gimignano. There are numerous fine options in the area which range from posh to rustic.

Back To Florence
From San Gimignano, drive north to return to beautiful Florence where you'll drop your rental car at Florence Airport.

If you enjoyed a farm stay and depart northern Siena in the morning, try to arrange an evening flight so you have one final day to enjoy Florence. We find that after driving the Tuscan countryside and exploring the region, you'll appreciate the city, even more, when you return and begin to feel like a local.

Florence Italy

There are plenty of art museums you could visit before lunch while they're not crowded and then dine at Enotria, enjoying a glass of wine or two to relax you before your long flight home.

Looking for other things to do in Italy? Check out our other Drive to Discover guides where we explore the best road trips in Italy including a The Ultimate Italian Road Trip Escape, an Amalfi Coast itinerary and a guide to UNESCO sites surrounding Venice.

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