Tuscany
Overview

Legend has it there exists a wondrous place of rolling golden hills, endless shopping opportunities, and vast vineyards where wine is cheaper than water. This magical place is real. This place is called Tuscany. Seriously though, in this enchanting region between Florence and Rome, you can actually buy a bottle of Merlot cheaper than a bottle of Fiji. Now that’s amore. It is a wine-taster’s paradise, particularly in the fall harvest season, and what’s more is that as you travel from town to town and vineyard to vineyard, you’ll not only be absorbing fermented grapey goodness, but also rich Tuscan culture resonant of the Renaissance era. This region is stunning—there’s a reason it inspired much of Michelangelo’s masterpieces. You can see some of the most famous works of these renowned artists throughout the medieval towns and charming piazzas scattered throughout. Beyond, Tuscany has inspired a new wave of artistic prowess by the names of Gucci and Ferragamo, among others (fashion is art. Inarguably). This is la dolce vita at its best.

Italians are inherently chic, therefore the only way to get mistaken for a local (and not a leftover Kimye wedding guest) is by stepping up your sartorial game. Tailoring is key, and wrinkle-free fabrics will have you feeling up to par. Packing tip number one is to layer up. From sightseeing in Florence to strolling Siena, you’re sure to encounter varying temps and terrain that require outfit versatility. Think skinny J Brand jeans and Prada riding boots for a day at the vineyards, with splashes of rich colors in your top, sweater, or accessories to pop amid the gorgeous light that Tuscany is known for. A pair of tortoiseshell sunnies should complete the look. For daytime, we love a fitted, floral dress a la Stealing Beauty. When out to dinner or wine bar-hopping in town, go for a flirty dress and sturdy shoes (cobblestones!) like those to-die-for Valentino brocade floral booties paired with an Iro black leather moto jacket to add some edge. A boho suede Chloe mini will inject some softness into the look as well. Main takeaway is that mostly anything goes in terms of trends, just keep the materials sleek and the looks chic (as always) and bring a layer along to beat the briskness. Whatever vacation style you pack along with you, once you’ve had your first day of perusing artisanal shops, and sipping Sangiovese beneath the cypress trees, you’ll be hooked. Take us back under the Tuscan sun!

Stay

Where to stay

Indulge

Indulge

WINE 'N DINE 

First things first, you may want to bring an extra suitcase (or buy a cute new one there) to house the bottles on bottles of Tuscan wine, balsamic, and maybe even olive oil, that you will undoubtedly want to take home with you, and if you're maybe feeling nice, you'll share with your friends.   Best place to sample flavors and buy the bottles? The wineries, duh. Castello Banfi is so vast you may want to dedicate a whole weekend to this gorgeous family-owned vineyard in Montalcino (we’re talking 7,000 acres here). Sample their syrahs and merlots, but don’t leave without a bottle of their award-winning Brunello. If Chianti is your thing, or even if it isn’t, visit Barone Ricasoli winery, where Barone himself created the first Chianti ever in 1872. He’s kind of a big deal. Close(ish) by, in the Chianti Rúfina region, you can find Marchesi de Frescobaldi Castello di Nipozzano, a charming winery best known for their mormoreto. If you’re anything like us and crave all things elite and exclusive, than you’ll have to score a bottle of Italy’s most sought after wine—Sassicaia. Lucky for you, the original and only producer of this delicious blend is located right in Tuscany at Tenuta San Guido, where Sassicaia used to just be the personal wine of the estate owner (Mario Incisa della Rocchetta) until he released it to the public in 1971. You’ll have to drop 60 euro as an entrance fee to the tour, but think of it as a cover charge to Tuscany’s most exclusive dance club and it’s totally worth it. Others include Biondi-Santi, Tenuta Il Greppo, Azienda Agricola Montefioralle, and Avignonesi.

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Obviously the food in Tuscany is amazing because, well, Tuscany is in Italy and needs no explanation. There’s pasta, there’s pizza, there’s great fish and meats, and there’s wine (which btw is cheaper than water). Eating at any restaurant in this region should satisfy any gourmand, but a few favorite must-try's in Tuscany are as follows...

If you’ve ever wished you had a quintessential Italian mamma that lives for cooking, Da Delfina is a solid substitute with an elegant twist, offering Tuscan specialties in a charming old stone farmhouse with a vast terrace overlooking Buontalenti’s Medici villa, all complete with crisp tablecloths and bow tied waiters. This one is so authentic you’ll have to ditch your precious plastic for the evening—cash only!

For more Tuscan classics and gorgeous views, consider Il Canto Del Maggio, set on a hilltop surrounded by the Arno Valley. The food is local, rustic, and delicious, and while the dining is indeed fine, don’t feel the need to dress too fancy (a flowy dress with wedges is a safe bet). The restaurant at il Falconiere twinkles with the only Michelin star of the Arezzo province. Expect high quality (local) ingredients and service that call for a high quality ensemble.

For great cuisine and Chianti at great value, head over to La Bottega in the charming wine village of Volpaia where you can head straight to dinner in your denim (your nice denim, however…) after a day of vineyard exploration. For those of you who prefer to subsist primarily on a diet of fermented grapes, La Torre Di Gnicche is one of the best wine bars and eateries in Arezzo. The small establishment in Arezzo features simple long wooden tables aside walls lined with over 800 wine bottles to choose from. Don’t get us wrong, they’ve got great crostini and delicious hot dishes too, it’s just really a no-miss for true wine-lovers.

Named for its talented head chef, Ristorante Walter Redaelli offers an award-winning epicurean experience (with seasonal ingredients coming from the restaurants own garden) in a romantic 18th century redbrick villa, candlelit by night. Ditch the kids and wear something sexy and sophisticated; this one is for date night.

And finally, no trip to Tuscany is complete without at least one meal (we had 3 our last trip) at Osteria le Logge, housed in a former pharmacy in Siena… Don’t miss the prosciutto or the spinach and ricotta cheese ravioli or anything with pasta in it!


NIGHTLIFE

If you don’t slip into a food and wine coma circa 11pm, first of all, we’re impressed. Second of all, you should check out the many dive bars, lounges, and night clubs that Tuscany has to offer for a night on the town (and where you can finally ditch your chunky walking boots for some swanky heels). Pop by Un Tubo, a wine bar and music club with contemporary design in a medieval space and the latest add-on to Siena's party scene. If you’re looking to mingle with the locals, Caffé del Corso in Siena is a popular bar among savvy Italianos socializing into the morning hours. End your trip with elegant after dinner drinks at SaporDivino, the wine bar at the Grand Continental Hotel in Siena, featuring live piano performances and a well-stocked liquor collection (great whiskey, if you’re all wined-out). 

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Explore

Explore

Drink wine and lots of it. So much of it that we’ve got a whole winery section later on, so for now we’ll skip to sightseeing. You can kill two birds with one stone with sightseeing and wine at the stunning Castello Di Brolio, a castle of breathtaking architecture in Chianti that housed the Ricasoli family for 800 years and is now the famous home to a lotta delicious wine. Foodies will love a special experience at the all too yummy Antica Macelleria Cecchini butcher tavern in Chianti, famed for its succulent regional bistecca alla florentina.  Better yet, learn how to craft your own Tuscan specialties through a Tuscan cooking class, like the 3-hour afternoon class at the Villa Dianella in the heart of Tuscany or the Il Falconiere cooking school  (though there are many cooking class options by region Chianti… Montalcino… Montepulciano… Cortona). You can burn it off later with a scenic Tuscan bike tour.

We also cannot get enough of the romantic idea of ballooning over this beautiful region… Or if you want the real local experience, take a trip to Tuscany in July & August during the Palio Races in Siena...  and if you don’t come back we'll just come visit!

SHOP

Where to Shop

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October is prime time in Tuscany because its harvest season aka best time for wine. Now with the euro so low, shopping pit stops to search for the outfits, to pour the wine in at home are completely necessary. When there is discount Prada, Saint Laurent, Lanvin, Balenciaga, and the holy grail of discounts, Tom Ford, a girls gotta speak up which is why we are telling you RUN don’t walk to the Mall Outlet which is right in Tuscany, 30 minutes outside Florence.

Head to the picturesque town of Siena, which basically is to Tuscany as Madison Avenue is to NYC. In other words, the shopping here is the best ever and you’ll leave with heaps of heavy shopping bags and a much lighter wallet. Fioretta Bacci is a darling Sinna shop where Bacci herself works on giant looms at the back, weaving wool, mohair, linen, cotton and silk on-site into sweaters and jackets in a vast array of vibrant colors, because honestly rainbows are for feeling, not for tasting. Both Cortecci and Dolci Trame are best visited with a rich companion who will buy you stuff as it houses the finest luxury labels and some extra cool jewelry we might add (just swipe the card and don’t look back…). 

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For a lifetime pair of handmade Italian shoes, visit Alessandro Stella’s shop for unmatched craftsmanship and quality. Once you’ve accumulated a full Italian wardrobe, you can transition to home goods, like embroidered linens, curtains, and sheets at Antiche Dimore, as well as other housewares made by Sienese artisans..  As we all know, shopping is basically cardio so once you’ve worked up an appetite head to Mercato, the open air market open every Thursday and Sunday that sells the freshest Tuscany produce, where you can munch on juicy fruits and other snacks. Lucca is another great town for shopping in Tuscany (it is also home to beautiful Renaissance structures and more rich history, but def wait to take pics until you’ve purchased the perfect outfit to fit the scenery). Mode Mignon is your one-stop, high-end designer shop, with big brands like Miu-Miu, Jil Sander, and Tod’s—among others.

In the town of Anghiari, you can find luscious handcrafted fabrics, tablecloths, towels, curtains, and sofas created at Busatti, renowned for historic weaving methods. There is no better time for antique shopping than at Fiera Antiquaria, an antique fair held every first Sunday of the month in Piazza Grande in Arezzo

And of course, you can’t return home without some delectable Chianti to take you back to your wondrous vacation, so stop by de La Cantina Di Greve (located at 2 Galleria delle Cantine) for some of the good stuff. If you need to tell yourself, you’re only buying four bottles because some will be gifts for friends/family back home, go right ahead.

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