Itineraries

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Italy is the most-requested destination for Virtuoso travelers, and Lily Pond Luxury is no exception. Whether you’re planning your first visit or you live la dolce vita on the regular, find some of our favorite spots to stay, play, dine and wine in Tuscany, below.

Know Before You Go

Perhaps no area epitomizes la vera Italia more than Tuscany, with its rolling green hills, and quintessentially “Italian” small towns, or its beautiful bounty of cheese, wine, olives and more.

Osteria di Passignano

Cooking school done right

But what many travelers forget is that Tuscany takes up much of central Italy, occupying nearly 9,000 square miles. That’s the size of New Jersey, or roughly the size of Israel… so planning your perfect visit requires a detailed vision for the scope and style of your travels.

Florence, the state capital and cradle of the Renaissance, is the area’s biggest draw, but you’ll find diverse and worthwhile terrain throughout the region, from the posh Forte dei Marmi to the beautifully preserved Siena, where the famous Palio horserace takes place every July and August.

But to truly enjoy Tuscany, it’s less a forced march through the Uffizi and Accademia with bits of wine and cheese thrown in for succor and more a leisurely stroll through small towns, with a great resort or villa as your home base.

For a city break/country escape, we love Castello del Nero, a 12th century restored castle turned 52-room hotel just 40 minutes south of Florence, on the outskirts of Chianti country, recently re-flagged under the wellness-oriented Como Hotels brand. The hotel offers regular shuttle service to both Florence and Siena, making a day trip possible, but not mandatory. Request suite 118, with its beautiful frescoes, or 116, with a gorgeously arched ceiling, or Room 222, which boasts a 30-square-foot rain shower with two showerheads.

While you’re in town, don’t miss a dinner or afternoon at the cooking school of Osteria di Passignano, an ancient monastery dating back to the year 395, established by the archbishop of Florence. Today, the Vallombrosan Order, a type of Benedictine monk, make excellent wine on the property. The Osteria also offers a cooking school, branded by KitchenAid, where guests learn to make traditional Tuscan fare, taste local olive oils, and, of course, sample local wine.

Il Borro

Convenient combination with Florence

Similar in vibe and proximity to Florence is Castello di Casole, a Belmond Resort, one of the largest private landholdings in all of Italy – if you’re traveling with kids, this is one of the more family-friendly high-end Tuscan options in the area.

Arguably one of the best names in Tuscan wine, Antinori is a must-stop and just an hour from Florence perfectly positioned on the highway toward Siena. You can taste your way through Chianti Classico in the impressive winery that’s been in the same family for 26 generations, since the year 1385. It’s well worth a seven-wine cru tasting, as well as lunch at the onsite Rinuccio 1180, where you’ll see 360-degree views of the surrounding countryside.

The resorts themselves are practically playgrounds for the epicurean-inclined, but for those who want something a bit more physical for their souvenirs, plan for an afternoon The Mall, an outdoor outlet mecca with more than two dozen shops, including massive outposts of Gucci, Valentino, Tods, Dolce & Gabbana, Fendi and Prada, plus other top names including Loro Piana, Moncler, Jimmy Choo, Aquazzura and more. You’ll fight your way among tour busses on a weekend, but the sale prices are often worth the crowds. Goods are usually last season, not specialty “made for factory store” varieties. If it’s just Prada and Miu Miu you’re after, travel about an hour further afield for Space, located at the Prada factory, which boasts a dedicated outlet for clothing, shoes, and bags, plus an onsite café.

For honeymooners or those who wish to truly escape from it all, Relais Borgo Santo Pietro is another excellent option, a collection of fewer than 20 rooms and suites in a 13th century villa. Bohemian meets elegant, the resort looks straight out of an Instagram dream, with its picturesque walled gardens, infinity-edge pool overlooking vineyards, and its massive “white road” driveway lined with Cypress trees. For ultimate luxury, book one of the private villas with their exclusive use walled gardens or one of two brand new suites featuring private pools.

We spent part of our own honeymoon at this gorgeous escape.

Borgo Santo Pietro

Romantic, Perfect for Honeymooners

We loved the intimate Borgo Spa, which makes its own in-house products from the herbs and animals on the property, as well as the onsite cooking school and Michelin starred restaurant Meo Modo, which dishes up the modern farm to plate fare with a dignity one wouldn’t expect in a remote countryside resort. You’ll be walking distance (or a short Vespa) from the San Galgano Abbey, home of the famed Sword in the Stone, although if you spent days lounging by the infinity pool and never left the resort, we’d hardly judge.

If you’re headed afterward to Rome, look to Monteverdi, another high design escape that mixes traditional Tuscan with a stripped-down, minimalist modern aesthetic that could look Spartan, but instead manages to strike the perfect balance between luxurious and authentic.

Side Trips

With so much to see and do, it’s hard to say what to skip because even the small villages, such as the perfectly preserved Pienza, have their charm. It’s also possible to make an easy day trip to the walled city of Lucca, an excellent and less touristy alternative to Pisa.

To skip the true tourist traps, stay away from anywhere that actively advertises its status as a restaurant not catering to locals; photos of the food on menus or a “we ship to the States” sign are dead giveaways. Also, avoid anything billed as a “wine and cheese” tour, says Marco Amorico, of Access Italy, a celebrity favorite private tour company to Oprah, Ben Stiller, President Obama and a range of top executives, as they often serve a sub-par combination of both.

Be glad to know that all of our itineraries come with optional restaurant suggestions - we’re happy to book you a table at a Michelin-starred spot or a local eatery that suits your desires.

Tuscany’s vast size and often less-than- direct roads can make getting from point A to B a bit of a trek, but still, it’s worth heading deep into the countryside for a few days of rest and relaxation.

Uri Harash, who has been guiding well-heeled travelers around Italy for his company Perfetto Traveler since 2001, says that travelers often try to pack in more than they will enjoy. Spreading your time among three or four nights at several resorts is preferred to trying for several day trips from a city home base.

Florence Explorations

Pro Tip: Book Flytographer and rise before the crowds to capture the moment. This is us, back in 2017.

For a true Italian experience, it’s also strategic to plan your trip with ample time to relax and enjoy the Tuscan scenery. A great local guide can offer a “made in Tuscany” day to show you under-the-radar finds like an authentic producer of fine cashmere, or take you to goldsmiths or leatherworkers for a one-of-a-kind piece designed just for you.

You’ll save yourself hours of searching, and enjoy an authentic local expe-rience in the process.

When to Go

Tourist season begins in earnest on Easter Weekend and runs through September, but you can avoid crowds—and most costs—by visiting early or later in the season. July and August will bring the highest prices, and the biggest crowds. May, September, and even early October are some of our favorite times to visit Tuscany, as you’ll save cost and crowds but still have gorgeous weather.

Getting Around

While the romance of driving a convertible up and down the winding Tuscan roads or around the hairpin turns of Amalfi can seem a dream, but in reality, the unmarked roads, dust, traffic, and lack of cell service can make it a nightmare.

Private is the way to go – avoid the crowds and often unpredictable trains (except the high-speed versions between major cities like Florence and Rome) by utilizing private transfers and guides.

Whether you’re a first-timer or a regular visitor, maximize your time in Italy by planning for a minimum of three nights in each destination or hotel. While you may be tempted to go, go, go, skip daily guided touring for a mix of full- and half-day excursions, as well as plenty of downtime to enjoy local café culture, relax by the pool or beach club, or explore local towns and villages.

An ideal length of the trip is anywhere from eight to 14 nights, with two to four destinations in total. Italy is also easily combined with other countries, including Greece, Monaco, France, or Switzerland.

Popular combinations in Italy include city breaks and country escapes such as Florence and the Tuscan countryside, Rome plus the Amalfi Coast, or even Tuscany and Amalfi together. Or, pair one of the destinations with an up-and-coming region, such as Forte dei Marmi, Sicily, Puglia, or Sardinia. For a family trip, try the grand tour, starting in Venice, meandering through Milan, finding fashion in Florence and then ending in Rome.

How to Get There

To begin in Tuscany, fly to Florence or Pisa, although Rome, with its direct flights, is also popular.

Even if you don’t intend to spend much time in the cities, you’ll find a night or two in Florence or Rome on the front or back end makes traveling that much easier – you’ll be easily primed for a morning return flight, and can get your quick fix of museums or designer shops.

Should you have several nights to spend in Tuscany, we’d suggest combining one or more resorts for an experience that spans several regions. In fact, for repeat visitors to the area or those staying at least a week, it’s worth considering a villa instead of a hotel for your stay.

We’re happy to source fully staffed villas for families or couples — our network extends throughout the country. These are often great options for longer stays.

Even if you don’t intend to spend much time in the cities, you’ll find a night or two in Florence or Rome on the front or back end makes traveling that much easier, as you’ll be easily primed for a morning return flight and a quick fix of museums or designer shops. Of course, either of these destinations is worth a deep dive if you haven’t already experienced them to their fullest.

For a great Florence city center hotel, try the Hotel Savoy, a Rocco Forte property that just finished up a multi-year renovation this April. It’s a convenient location (just off the Piazza della Republica and right next to the Duomo) and the décor—the perfect blend of modern chic (think: chic Ferragamo-inspired paintings shoes) and historic (the property dates to 1893)—makes it a great escape. The Lungarno property, owned by the Ferragamo family and right on the Arno, is another solid choice, as is the boutique chic Villa Cora, one of our favorites for honeymooners due to its intimate size and welcoming hospitality.

In Rome, an all-star is Hotel Eden, part of the Dorchester Collection. It’s perfectly perched on a corner in the via Veneto neighborhood, an area known for its spectacular views. Rocco Forte also boasts three great choices: Our favorite for location in Rome is the new Hotel de La Ville, near the Spanish Steps, or their all-suite Rocco Forte House.

This piece has been adapted from a story originally published in Woodbury Magazine by McLean Robbins.