Tuscany Without Crowds

Best time to visit
August, September, October, November

Rolling vineyards, rose-tinted sunsets, Renaissance refinement and so much history…the only things not to love about Tuscany are the crowds. With so much to offer this is deservedly one of the world’s most famous travel destinations.

Coronavirus cases in Tuscany have stayed low throughout the pandemic, but the current climate means very few people are traveling. You can visit Tuscany in 2020, explore the famous highlights, and not need to battle through the tour bus crowds.

Italy is open to visitors from Europe, Canada, Australia and a handful of other countries. There is no quarantine period or need to present a negative test. With this experience you can travel safe, to attractions and accommodations with increased safety measures to prevent the virus. And you will be traveling in private, to some of the most romantic places on the planet.

Day 1 - Arrival in Florence

Superb Tuscan food is a great introduction to your time in Tuscany.

pizzeria sausage pizza in florence italy

Florence Food and Wine Tour


Surrender to new pleasures of the palate as you discover Florence’s most delicious tastes. Following your guide through the city’s streets, you will get intimately acquainted with some of Tuscany’s most distinctive dishes and wines.Tuscan cuisine mixes products from the fields, the woods and the sea. Among Tuscan wines are the world-famous Chianti and Brunello. By tasting dishes and wines — and dessert! — during a street-food tour, you will get to know the real Florence: its bustling daily life, habits, traditions and culinary pleasures locals cannot live without.

Portrait Firenze Hotel

Stay at Portrait Firenze Hotel


You can’t be better placed in Florence than Portrait Firenze Hotel. Gazing over the Arno River, a few steps from Ponte Vecchio, less than ten minutes on foot to the Duomo, Uffizi and other key highlights. Instead of Renaissance, the hotel’s interior is retro haute couture from the 1950s and 1960s. And it’s glorious, an echo of dolce vita from another time. This is a wonderfully private and low-key boutique hotel. Expect discreet pampering, floor-to-ceiling windows overlooking Florence, and a sense of escaping to a forgotten Italian era.

Day 2 - Icons of Florence

Discover the city's famous highlights and where the Renaissance started.

Florence Cityscape, Italy

Florence and Uffizi Highlights Tour


This is the day to make your art-loving heart glad. Begin by the Duomo. A gothic design and interior, a neo-gothic façade and a Renaissance dome (the largest brick dome ever built.) Then, Giotto’s bell tower, lovely in its colored marble patterns. From there you will stroll on to Piazza della Signoria, to admire many different sculptural and architectural styles in the statues and buildings.At the Uffizi Gallery, your guide will introduce you to the most prestigious collection of Renaissance paintings in the world. And your tour will end on the Ponte Vecchio — the iconic medieval bridge spanning the Arno River.There’s no dearth of things to marvel at in Florence.

Piazzale degli Uffizi in Florence at sunrise, Italy

Visit Uffizi and Accademia Galleries in Florence


In the Uffizi Gallery, your expert guide will lead you from hall to hall, introducing you to masterpieces by the greatest artists of all time. You will feel the peace that emanates from Giotto’s golden icons. You will be filled with admiration for the human genius of Leonardo da Vinci, and for the perfect technique of Raphael and Titian. And at the Accademia Gallery, among a number of other impressive statues, you will marvel at the perfect proportions of Michelangelo’s handsome David.

Day 3 - Hidden Florence Highlights

Uncover more of the Renaissance city with a private guide.

View of Florence Italy from the Boboli Gardens

Palazzo Pitti and Boboli Garden Visit in Florence


Enter Palazzo Pitti and you enter a palace that housed three dynasties of rulers. The Medici, masters of Florence. The Dukes of Tuscany, of the Habsburg-Lorraine House. And the House of Savoy — the last kings of Italy. Now, this vast palace houses five museums. The one you are visiting is the Palatine Gallery. If you love Raphael, Titian, Tintoretto, Caravaggio and Rubens — this is paradise for you. Outside, you will ramble the wide alleys of the vast Boboli gardens. Here you will find fruit groves, a miscellany of fountains and sculptures and grottos, and sweeping views of the whole city of Florence. This is truly a royal place.

Biking in Florence, Italy

Florence Bike Ride


An expert guide takes you along, showing you the great monuments of Florence and telling you their stories.You admire the immense cathedral of Santa Maria del Fiore, with its famous dome by Brunelleschi (and maybe you think of Richard Madden as Cosimo in Medici…). Then you pedal on to Piazza della Signoria and Palazzo Vecchio, once the seat of Florence’s powerful government.From there, go towards the Arno. You will cross the iconic Ponte Vecchio, and learn how this 14th-century bridge withstood even the German attacks during the Second World War.

Day 4 - Drive Through Chianti in a Ferrari

Get behind the wheel of a Ferrari and drive through glorious Chianti.

Chianti Tour in a Ferrari


Explore Italy’s most legendary region in one of Italy’s most distinctive vehicles. You will drive a Ferrari or Lamborghini across Chianti, winding through Tuscan hills of olive groves, vineyards and sunflower fields. The roads twist and turn, rise and fall. Every corner and every rise is another sublime vista. Small villages dot the route, featuring rectangular church towers and crumbling facades. Medieval castles are also abundant, contrasting the sleek red of your sports car.Stop in the hilltop town of San Gimignano, where the streets narrate tales of cobblestone and intrigue. Continue to Siena, the very embodiment of a medieval city, where the Piazza del Campo evokes 12th-century glory. Then drive through the Chianti Classico region, back to Florence upon Italy’s most famous driving route.

Villa La Massa, Aerial view, Italy

Villa la Massa


As you arrive, you can’t help but remember your silver screen idols. Cinema legends such as Richard Burton, Elizabeth Taylor and Gregory Peck once lodged at this 14th century estate.Villa la Massa allies manor stateliness and countryside charm. Your rooms are in typical Tuscan style, tempered by a touch of contemporary luxury.Admire the Chianti hills from your windows. Wander through the splendid gardens and immense park by the Arno River. Float in the pool, looking up at the blue Italian sky.  And crown your day with a riverside dinner at Il Verrocchio restaurant.

Day 5 - Meet the King of San Gimignano

Visit a fairytale hilltop town for some exclusive experiences.

San Gimignano Horseback Riding With Lunch & Wine


Ancient paths meander beneath San Gimignano’s medieval towers, through vineyards and woods and private estates.Ride in this Tuscan paradise on a horseback adventure that can be tailored to all ability levels. Inhale fresh country air and feel how tradition continues to dominate here.After riding will come the tasting, as you are guided through library reserve vintages from the vineyard’s cellar. And not just wine. But food as well, as you dine on four courses of local Tuscan cuisine, while looking over the vines.

Dining & Wine Tasting in a San Gimignano Castle Tower


On San Gimignano’s main square you will be surrounded by medieval memoirs. Your guide narrates. This town was once home to 72 medieval castle towers. Only 14 of them remain, protected as a UNESCO World Heritage Site. Only one is still inhabited. And it is the castle tower owned by your travel designer’s family.Be invited by the Giachi family. Sip Prosecco with a private view onto the busy square. Listen to operatic harp and soprano in the Central Hall. Dine on three fine Tuscan courses, as sunset colours slowly work across the sky.Sample vintage wines from the Giachi family cellars, including rare Super Tuscans and Brunello. Only guests of the Useppi Palace can access this Torre Chigi tower and you have a full evening to enjoy this exclusivity.Other San Gimignano towers are open to the public and get very crowded. You will have an evening in the town’s second highest tower, in private, living 900 years of history and culinary expertise.

Borgo Santo Pietro

Stay at Borgo Santo Pietro


Borgo Santo Pietro was a healing stopover for medieval pilgrims. Fast forward three centuries and modern souls still come for its exceptional spa and salubrious waters. The 800-year-old establishment is now a contemporary sanctuary, a hideaway in the heart of Tuscany, a boutique hotel evoking the glamour of a region. Think vintage furniture, green gardens, endless views, and a Michelin-starred restaurant doing farm to plate dining on site. And just wait to see the wine list!Borgo San Pietro remains a working estate and this adds to the authenticity. You may want to hide away here forever, enveloped by the landscapes of old Tuscany.

Day 6 - Relax and Indulge

By now you'll be fully relaxed, savouring Tuscany's rural charms.

Male truffle hunter in 20's assists his two dogs that are sniffing and digging out truffles in the woods with a wooden hoe called vanghella, Abruzzo, Italy, Europe

Truffle Hunting and Slow Cooking in Tuscany


The charming dog sniffs around expertly. Soon, close to the roots of an old oak, you will find it: the precious truffle. Feel the thrill of scouring the woods with your guide and his dog, and unearthing this hidden delicacy. Then learn how to use it, to take pasta and scrambled eggs to another level.Live authentic Tuscan moments, in the forest and in the kitchen.

Hot air balloon in Tuscany, Italy

Balloon Ride Over Tuscany


Fly over the legendary Chianti landscape, with its hilltop medieval towns, castles, vineyards, and woods. Looking down from your balloon, the olive groves' shades of silver and green appear as a veil over the silent rolling hills. In the distance you can see Florence, with the majestic Apennine range in the background. To the west, San Gimignano, Certaldo, and Volterra and the sea in the far distance, to the south, Siena and Monte Amiata.Upon descending back to earth from your aerial tour, you will enjoy a breakfast of tasty local products, made perfect by a glass of champagne.

Day 7 - Tuscan Wine Experiences

Take a fun drive in a Vespa before settling into a full day of wine tasting and romance.

Ride a Vespa in Chianti


Chianti is magical on a Vespa, a vintage Italian region complemented by vintage Italian wheels. Travel slowly along quiet, twisting roads. Admire vineyards and villages, from San Gimignano down through the backcountry.You can ride romantically, just two of you upon the roads of Chianti. It’s also possible to be accompanied by a guide or photographer as well.After whizzing around in the Vespa you will dine at a sumptuous vineyard, enjoying a classic Tuscan lunch and a full library of reserve vintages from the winery’s cellar.

Torciano Winery Full-Day Experience


So much is possible when you spend the day at a private vineyard. The Giachi family invites you into their vineyard for a day-in-the-life-style experience.Start with an introduction to truffles and go truffle hunting in the woods. Continue with an archery lesson in a private forest before a cooking class that revolves around truffle-based dishes.Lunch with wine tasting is usually served in the cellar, where you’re surrounded by rare bottles and taste from the owner’s library collection.Continue the experience by touring San Gimignano nearby, or perhaps take a helicopter tour back to your accommodation.

Day 8 - Departure