The Perfect Week in Tuscany

An itinerary that provides a perfect mix of countryside, small towns, vineyards and city

Journeying through Tuscany is an adventure on just about any foodie’s bucket list.

Journeying through Tuscany is an adventure on just about any foodie’s bucket list. We all wish we could go "Under the Tuscan Sun" and stay for months, but most likely you have roughly a week to take in the sights, sounds, smells, and most importantly, tastes of this unforgettable Italian region. So, we’ve laid out an itinerary that provides a perfect mix of countryside, small towns, vineyards and city.

Pienza/Val D’orcia
Look no further than Aziz Ansari’s Italian episodes of "Master of None" to get a feel for the magical Val D’orcia area. Within this breathtaking, cypress-lined region sits the UNESCO World Heritage town of Pienza. One day in this easily walkable town, and you’ll feel like you know the everyone personally. The historic architecture is stunning, the markets are full of local pecorino cheese, and the food couldn’t be better.

If it’s good enough for Chris Martin of Coldplay, it’s good enough for us. La Bandita Hotel is the manifestation of a film-like dream: An international music executive (John Voigtmann, formerly of MTV) gets sick of his overworked life, moves to the Italian countryside with his wife, and opens a hotel. Since that epiphany, the Voigtmanns have built two properties to perfection — their original countryside location and La Bandita Townhouse in the center of town. The hotel is a seamless blend of history (a former Renaissance convent) and modern amenities like Nespresso coffee machines and fancy toiletries. The common area is decorated by gold records of Voigtmann’s, and allows guests to gather and drink wine according to the “honor system.” It kind of feels like a fancy hostel for grownups. The on-site restaurant is excellent as well — any dish with truffles here is a win.

la bandita room

La Bandita

Also in Pienza, Idyllium is a new outdoor cocktail bar with arguably the most amazing views in all of Tuscany. Their creative recipes, historic location, and hip vibe offer the best of both Old World and New.

Italians don’t take their organic certifications lightly, and nowhere is this epitomized more than at the magical organic farm of Podere Il Casale. The farm’s cheese is known as the best in the region, and they also make their own wine, honey, olive oil and produce — all 100 percent organic — a tireless, expensive, and serious accreditation. Sandra, the adorable, knowledgeable, hands-on owner; came to Italy from Switzerland decades ago and turned a flailing farm into today’s multi-purpose destination. A tour is fun and fascinating, but a long, relaxed meal and cheese tasting with wine, taken on the farm’s magnificent patio overlooking the pilgrimage road below (where "Gladiator" was filmed) is an absolute must.

If you’re looking for heaven on earth, you’ll find it at Locanda Dell’Amarosa hotel in the Sinalunga region. The valley is scattered with medieval homes and farms; and the centuries-old property used to house a significant church. The grounds of the uber-romantic hotel are laid out in a unique style, various brick and stone buildings surrounding a large courtyard. Here, guests can relax as they sip aperitifs and smell the ever-present lavender and jasmine.

locanda dell'amorosa

Locanda dell'Amorosa

The 27 double bedrooms and suites all have an charming Old World, almost B&B vibe (if your B&B was five-star and surrounded by vineyards). The rooms’ large windows and wooden doors swing out to serene, majestic views of the vibrant grounds and neighboring hills. The large pool, surrounded by bouquets of flowers, is a rarity in these parts, and makes for a nice break in the hotter months.

locanda dell'amorosa room

Locanda dell'Amorosa

Because the hotel is in the country, it works out well that the on-site dining options are top-notch. You’ll find yourself stopping by the Osteria Wine Bar often; the delicious cocktails and local wines, paired with snacks that seem to appear from nowhere, make for the perfect afternoon respite or evening extension.

The restaurant is not merely a hotel “add-on”; rather, it’s a recently opened second location of the much-loved Lo Zafferano. The dining experience here takes the hotel from exceptional to truly astounding (actress Michelle Williams recently stayed and dined on-site). The young chef, Johnny Goga, is something of a wunderkind. He serves up expert, unique delights like cold potato soup with tomato confit, ricotta and mint; beef tartar with dehydrated eggs; veal cooked low and slow with zucchini cream and mashed potatoes; and fresh lavender ice cream. Each dish is colorful, flavorful, and aromatic, yet none are overdone.

Just around the corner from the hotel is a secret so well-kept from American tourists that we were almost hesitant to share it. La Toraia is a regional farming company specializing in the famed, 2,200-year-old Chianina cattle. A breed of all-white cow, the Chianina are known for their size and flavor. The company’s colossal Sinalunga property — located in the 16th-century village of Tenuta la Fratta, hosts an agritourismo (a farm/hotel hybrid), an event space and a restaurant where you’ll have the most unforgettable burger of your life. Dine indoors or “outside” in their acrylic, boxed-in patio as you view the sprawling estate. The menu is simply meat plates, cheese, a pasta or two, and burgers; the star of the show. Don’t waste your appetite on pasta, it’s not worth missing one single bite of these juicy burgers, served fresh from the farm with toppings like truffle, eggs, and bacon.

Siena is an adorably quaint city that makes for an excellent short stay or day trip (you may have seen Kate Hudson Instagramming about it this summer). Known as the “little sister” of Florence, Siena has a specific vibe all its own. Between its San-Francisco-like hills, its medieval brick buildings, and its famed Piazza del Campo — which hosts the twice-yearly Palio horse race, there is much that makes this destination unique. This cathedral is one you can spend hours in –— the entire floor is decorated by marbled works from masters, and the central stained-glass round window (made in 1288) is mesmerizing. View the whole church from above on the “Gates of Heaven tour.

The pizza in Siena is great, but wild boar is the signature dish. Try it in a pasta, preferably the pappardelle from the prominent restaurant Osteria Le Logge.

When in Tuscany, wine is always at the top of the mind. There are many vineyards to choose from, but our favorite is Querceto di Castellina. This organic vineyard and agriturismo has been family-owned since 1945 and houses a 600-year-old main building. The winery has achieved the highest ranking of Chianti (Chianti Classico DOCG), as well as organic certification (no sulfurs, no pesticides, and three years of “clean” soil). The elder matriarch of the house — the original owner’s daughter — cooks unbelievable meals for visitors every single day. We are still dreaming about her lasagna with zucchini, pumpkin and gorgonzola, paired with the “Laura” — a soft, fruity Chianti named for her. The estate is breathtaking, and the wine is nothing short of divine — they also have merlot, sangiovese, a white blend and a rose. Take a tour, book a stay in one of their charming suites, come for a special event or simply experience a wine and food tasting; this is one you’ll never forget.

Take a shortcut to the vineyards in the ancient, underground wine cellars of Montelcino and Montepulciano. The latter, an adorable hillside town, is known for its famed, eponymous red wine — Vino Nobile di Montepulciano. Some of the best and oldest cellars include Talosa (directly under the town’s central piazza), Ercolani (which serves an excellent accompanying cheese platter), or the famed Cantine De’Ricci — commissioned by the noble Ricci family.

Orvieto (day trip)
While not technically in Tuscany, the city of Orvieto in neighboring Umbria is only 45 minutes away, and it is one of the most delightful and underrated cities in Italy. The origins go back to the Etruscan civilization (i.e. the ninth century BC), and the whole city can be explored in a day. Book a tour with Lucianna of Umbria in Tour. She knows everyone and everything and can show you all the secrets, such as the underground caves that run throughout the city. The region is known for its crisp, eponymous white wines, which are a nice break from the reds of Tuscany. The central duomo (or cathedral) is truly remarkable. The Gothic façade, which took almost 300 years to build, is considered a masterpiece of the Middle Ages, and is arguably the most significant church exterior in all of Italy. Be sure to pick up some ceramics here — they make for an excellent gift.

We won’t bore you with the given spots of Florence — the duomo, the Uffizi, the Academia/the David, the Pitti — but we can recommend touring just one or two to avoid over-stimulation (and lines).

If you want to indulge, there is one clear choice for lodging — the newly re-opened Hotel Savoy, a Rocco Forte property. This 125-year-old hotel in the heart of Florence recently underwent a six-month renovation and collaboration with Emilio Pucci, resulting in a contemporary, colorful and utterly chic property.

Hotel lobbies are not usually a exciting places, but this one — with its high ceilings, Pucci-decorated nooks, and paintings by Luca Pignatelli — is an area you’ll want to spend time in. The interiors, led by Olga Polizzi — eldest daughter of Lord Forte, and younger sister to Sir Roccco — are nothing short of spectacular. The guest rooms, patricularly the suites, are undoubtedly the most gorgeous in the city. The suites offer views of either the historical Piazza della Repubblica or the duomo, and are equipped with gorgeous linens, bright, soundproof windows, and chic Italian furnishings like Il Bronzetto tables, chairs, mirrors and pieces from Chelini Firenze workshop. Even the fitness center, with machines outfitted in Ferarri leather, is swanky.

hotel savoy suite

Hotel Savoy

The hotel’s bistro-style restaurant, Irene, and its accompanying bar have been at the top of the Florence “food-chain” since they opened a few years ago. Head of food Fulvio Pierangelini is known for his two-Michelin-starred restaurant Gambero Rosso, while head chef Giovanni Cosmai has cooked in some of the world’s most important kitchens. The menu is ever-changing, but favorite staples include the gorgeous octopus, beetroot, and radicchio salad; the lobster linguini, the raw amberjack on Himalayan salt with Sicilian pesto and lemon sorbet; and the aromatic saffron risotto with asparagus, shrimp and pistachio. Craft cocktails are a cannot-miss.

Hotel Savoy Irene

Hotel Savoy

As for the rest of your culinary adventures, there are two stops that must be on your list. The first is Cucina de La Garga, from renowned chef Alessandro Gargani. Alessandro learned techniques from his famous parents (mother Sharon Oddson, a beloved cookbook author and chef, and father Giuliano “Il Garga,” a chef/painter/restaurateur), but he’s made his own way as an adult — featured on the "Today Show"; "Diners, Drive-Inn and Dives"; and even as a contributor to The Daily Meal.

Even though the kitchen is helmed by one of the city’s best talents and has served celebrities far and wide, the experience feels like you’re in someone’s warm, eclectic, home. The walls are ornamented with colorful paintings by patriarch Il Garga, and the open kitchen makes for a great show. The food is an expert blend of traditional and modern. Twists like citrus and avocado give a distinct edge to dishes like the house-favorite Insalata Del Garga — a nice influx of crisp vegetables (which is surprisingly hard to find in Italy); and the signature Tagliatelle del Magnifico — fresh fettuccine with orange and lemon zest, mint and Parmigiano in a creamy brandy sauce. Classic Tuscan dishes are never far from mind — the Garganelli Al Sugo Delbabbo, a penne with Alessandro’s father’s “secret meat sauce recipe,” is one of the best pasta dishes you’ll try in the whole city.

For a casual, memorable, and delicious meal, Borgo Antico is a special experience. This mostly outdoor café is located across the river from the main parts of Florence (you can walk over the famed Ponte Vecchio) in an area known as the Left Bank. Situated in the Piazza Santo Spirito — a square around a church of the same name — the restaurant exudes serenity and charm. Order some pizza (the best we found in the city) and some wine, and just relax for hours. They also have an impressive weekend brunch that draws many locals from the surrounding, less-touristy areas.


  • If you like to map out trips with a travel agent (and if you’ve never done that before, this is a good time to try), Susan Ward of Custom Travel Advisors is the absolute Italy expert. She knows everyone and can suggest the best drivers, itineraries, tour guides, travel tips, etc.



Some meals and travel costs that are the subjects of this story were provided at a discounted rate to the contributor.