The Elsewhere Guide
Tuscany, Italy
Rolling hills, Chianti, and the most painted landscape in history
In the rolling hills of Tuscany, where cypress trees punctuate the horizon and vineyards stretch as far as the eye can see, luxury is not just a lifestyle but an art form. Here, ancient villages whisper tales of the past, and the art of living is perfected in every glass of Chianti and every bite of truffle-laden pasta. This is Tuscany at its most glorious, where every moment is an indulgence in beauty and taste.
Visit in late spring or early fall when the landscape is lush and the weather is warm, yet comfortably mild, perfect for vineyard tours and al fresco dining.
Where to Stay
Aman Venice
Florence
A historic palazzo on the Grand Canal, Aman Venice offers unparalleled luxury with frescoed ceilings and private gardens.
Why we love it: Its private access to the canal offers the most exclusive way to experience Florence.
Belmond Castello di Casole
Casole d'Elsa
Nestled in a 4,200-acre estate, this 10th-century castle blends Tuscan charm with modern luxury and breathtaking views.
Why we love it: The estate's expansive vineyards and olive groves provide a true Tuscan retreat.
Rosewood Castiglion del Bosco
Montalcino
An idyllic country estate offering rustic charm, with suites and villas surrounded by vineyards and forests.
Why we love it: Their private Brunello di Montalcino wine tour is an unforgettable experience.
Seven Days in Tuscany
Florentine Beginnings
Champagne breakfast at Caffè Gilli, a Florentine institution since 1733.
Florence
💡 Try their signature pastries for a sweet start.
Private tour of the Uffizi Gallery guided by an art historian.
Florence
💡 Focus on the Renaissance masterpieces for an enriching experience.
Lunch at Enoteca Pinchiorri, a three-Michelin-starred gastronomic delight.
Florence
💡 Reserve a table with a view of their wine cellar.
Stroll through the Boboli Gardens, a masterpiece of Italian garden design.
Florence
💡 Don't miss the Porcelain Museum inside the gardens.
Dinner at Osteria Francescana, renowned for its avant-garde Italian cuisine.
Modena
💡 Book months in advance for a chance to dine here.
Florence is best explored on foot; wear comfortable shoes.
Tuscan Vineyards and Villages
Breakfast at La Terrazza at Belmond Castello di Casole, with views over the vineyards.
Casole d'Elsa
💡 Enjoy the freshly baked focaccia with local olive oil.
Private vineyard tour and tasting at Antinori Chianti Classico.
Chianti
💡 Ask to try their exclusive vintages not available for sale.
Lunch at Ristorante Albergaccio di Castellina, known for its traditional Tuscan fare.
Chianti
💡 Request a table on the terrace for panoramic views.
Explore the medieval village of San Gimignano with a private guide.
San Gimignano
💡 Sample the local Vernaccia wine, a white variety unique to the area.
Dinner at La Bottega del Buon Caffè, a Michelin-starred farm-to-table restaurant.
Florence
💡 Their tasting menu is a must-try for the full experience.
The Chianti region is perfect for scenic drives; consider hiring a vintage car for the day.
Art and Artisan
Breakfast on the terrace of Rosewood Castiglion del Bosco.
Montalcino
💡 Their fresh ricotta and honey is a local favorite.
Exclusive pottery workshop with a local artisan in Montelupo.
Montelupo Fiorentino
💡 Create your own piece to take home as a unique souvenir.
Lunch at Il Falconiere, a Michelin-starred restaurant set in a historic villa.
Cortona
💡 Their wine-pairing menu is highly recommended.
Visit the Museo dell'Opera del Duomo for a glimpse of Renaissance art.
Florence
💡 The museum's rooftop offers stunning views of the city.
Dinner at La Pergola, set in a historic palace offering exquisite Italian cuisine.
Rome
💡 Their truffle dishes are legendary.
Today is a blend of hands-on experiences and high culture, ideal for art lovers.
The Essence of Siena
Breakfast at Hotel Certosa di Maggiano, a serene retreat just outside Siena.
Siena
💡 Try their homemade jams with fresh Tuscan bread.
Private tour of Siena's historic center, including the stunning Duomo.
Siena
💡 Visit the Piccolomini Library for its breathtaking frescoes.
Lunch at La Taverna di San Giuseppe, known for its hearty Tuscan dishes.
Siena
💡 Their ribollita soup is a local favorite.
Explore the medieval streets of Siena and shop for local crafts.
Siena
💡 Look for hand-painted ceramics and leather goods.
Dinner at Ristorante Campo Cedro, offering panoramic views of the Tuscan countryside.
Siena
💡 Their wine list features exclusive Tuscan labels.
Siena's charm is in its medieval architecture and vibrant culture, best explored leisurely.
Truffles and Treasures
Breakfast at Borgo Santo Pietro with its farm-to-table ethos.
Chiusdino
💡 Their yogurt and berry compote is a fresh start.
Truffle hunting experience with a local expert and his trained dogs.
San Miniato
💡 Wear comfortable shoes for the forest terrain.
Lunch at Il Piastrino, featuring dishes with freshly foraged truffles.
Pennabilli
💡 Their truffle risotto is unparalleled.
Visit the Leaning Tower of Pisa and the Piazza dei Miracoli.
Pisa
💡 Climb the tower for a unique perspective of the city.
Dinner at Da Caino, a two-Michelin-starred restaurant in a charming village.
Montemerano
💡 Their seasonal menu showcases the best of Tuscan produce.
San Miniato is Italy's truffle heartland, offering a truly unique culinary experience.
Coastal Charms and Culinary Arts
Breakfast at Hotel Il Pellicano, with spectacular sea views.
Porto Ercole
💡 Their fresh fruit selection is unbeatable.
Explore the picturesque village of Portofino with a private guide.
Portofino
💡 Stop by the Castello Brown for panoramic views.
Lunch at Ristorante Puny, known for its Ligurian seafood.
Portofino
💡 Their spaghetti alle vongole is a must-try.
Relax on a private yacht cruise along the Tuscan coast.
Porto Ercole
💡 Bring a camera for the stunning coastal vistas.
Dinner at La Pineta, a Michelin-starred restaurant with beachfront dining.
Marina di Bibbona
💡 Their catch of the day is always a fresh choice.
The Tuscan coast offers a serene escape with its azure waters and charming harbors.
Tuscan Farewell
Breakfast at the terrace of Villa Cora, overlooking the Boboli Gardens.
Florence
💡 Their cappuccino is a perfect final touch.
Private tour of the Accademia Gallery to see Michelangelo's David.
Florence
💡 Visit early to avoid the crowds.
Lunch at Trattoria Sostanza, a Florentine favorite for bistecca alla fiorentina.
Florence
💡 Their butter chicken is another highlight.
Shopping at the luxury boutiques on Via de' Tornabuoni.
Florence
💡 Look for handcrafted leather goods as a memento.
Farewell dinner at Cibreo, an iconic Florentine restaurant.
Florence
💡 Their tasting menu is a journey through Tuscan culinary traditions.
End your Tuscan journey with a memorable day in Florence, savoring its art, culture, and cuisine.
The Table
Restaurants that define the destination.
Enoteca Pinchiorri
✦✦✦For an unparalleled dining experience with a legendary wine list.
Osteria Francescana
✦✦✦A culinary pilgrimage for modern Italian cuisine.
Il Falconiere
✦A serene setting in a historic villa with exquisite Tuscan dishes.
Da Caino
✦✦For its creative use of local ingredients in a charming village setting.
La Pineta
✦Beachfront dining with a focus on fresh seafood.
Cibreo
An iconic institution offering a true taste of Florence.
Trattoria Sostanza
Known for its bistecca alla fiorentina and historic charm.
Ristorante Albergaccio di Castellina
For its authentic Tuscan dishes and scenic views.
Make It Extraordinary
Experiences beyond the obvious.
Private Vineyard Tour at Antinori Chianti Classico
Explore the renowned Antinori estate with exclusive tastings of their finest wines.
Truffle Hunting in San Miniato
Venture into the woods with a truffle hunter and his dogs, followed by a gourmet truffle lunch.
Hands-On Pottery Workshop in Montelupo
Craft your own ceramic masterpiece with a local artisan in this historic pottery town.
Private Yacht Cruise along the Tuscan Coast
Sail the azure waters in luxury, with stops at secluded beaches and charming coastal towns.
Exclusive Uffizi Gallery Tour with an Art Historian
Delve into the world of Renaissance art on a private tour tailored to your interests.
Shopping Spree on Via de' Tornabuoni
Discover luxury fashion and artisanal treasures on Florence's premier shopping street.
Tuscany is a land where time slows down to the pace of a leisurely meal, where every glass of wine tells a story, and every sunset over the rolling hills is a masterpiece. Embrace the art of living, Tuscan style, and let the region's beauty, culture, and flavors linger in your memory long after you leave.
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