Take Me To 05.17.2022

Your Ultimate Month in Italy

Intro Stay Highlights itinerary

There are private tours of Italy that are simply about checking the boxes. And then, there are customized itineraries tailored to your tastes at every single stage; we’re here to provide inspiration for the latter.

Italy continues to garner a top spot on the extensive list of SmartFlyer clients’ most in-demand international destinations. Between its rich culinary history, diverse landscape, and unparalleled hospitality, this special country has something for every type of traveler. And whether this is your first or fifteenth trip out to Bel Paese – translated as “beautiful country”– we crafted this thirty-day journey to spark a conversation with your SmartFlyer travel advisor about how we can help to curate your next visit.

This private tour of Italy offers a sampling of our most beloved properties across the country. Similar to how they didn’t build Rome in a day, you can’t see the entire country…even in a month! But, we’re going to try anyway. Our itineraries are highly-customizable to fit your travel needs and scarce availability. We recommend starting planning approximately one year in advance for summer in Italy. So whether you’re looking for the ultimate month-long escape or will simply glean portions of this as inspiration, let’s work together to choose your own adventure.

Contributed By



Thirty days

We Love it For

Couples or friends looking to be completely immersed in Italy's rich history and culture

Trip Style

An elegant tasting menu through Italy’s highlights

Agent Notes

We encourage you to take your time during this trip; while it’s tempting to fill your schedule, Italy is a destination where fully embracing “il dolce far niete” (“sweetness of doing nothing”) is rewarded. Feel free to relax and fully take in the country’s stunning sights and dine in the countless eateries in between.


SmartFlyer Picks

The Bulgari Hotel Milano

On a private street in downtown Milan, The Bulgari Hotel Milano is positioned in a tastefully renovated 18th-century Milanese palazzo. This five-star hotel is situated in the cultural and commercial heart of a city that hides delightful and unexpected courtyards and green spaces behind its austere façades. Nowhere is this more evident than the hotel’s 4,000-square-meter private garden – a natural extension of the nearby Botanical Garden – where it acts as a restorative oasis of serenity and relaxation in the midst of Milan’s busy pace.


Grand Hotel Tremezzo

An iconic family-owned and female-managed property, Grand Hotel Tremezzo is an art-nouveau hotel sitting on the western shores of Lake Como. With views spanning the waters towards Bellagio and the Grigne mountains, the hotel invites guests to lay out along the shorelines and be treated to their renowned hospitality. The property only continues to garner attention in its 110 years and counting; its pool sunk within the Lake for a water-on-water effect is a unique calling card.


Portrait Firenze

Portrait Firenze, owned by the Ferragamo family, provides a fashionable and luxurious space while overlooking the iconic Ponte Vecchio on the Arno. A perfect mix of classic and contemporary, Portrait Firenze offers a distinguished and unique style to guests. Views of the river and Florentine countryside serve as an ideal home base both to explore bustling Florence as well as cozy up and watch the city come to life from your window. Guests receive preferential access to Ferragamo-owned stores and museums.


Borgo Santo Pietro

Guests are welcomed to this 800-year-old villa by a drive lined with Cypress trees, rolling hills for as far as the eye can see, and a garden stocked with different species and fragrances. Borgo Santo Pietro's spirit of collaboration and deep-rooted wellness permeate the estate, where the Michelin-starred chef works with farmers and culinary gardeners to craft dishes using tailor-made ingredients, an onsite skincare laboratory produces the hotel's natural amenities with ingredients harvested from the farm, and the Borgo spa blends freshly picked seasonal plants and healing herbs into purifying tisanes and therapeutic treatments.

Courtesy of Pellicano Hotels
Courtesy of Pellicano Hotels
Courtesy of Pellicano Hotels
Courtesy of Pellicano Hotels
Courtesy of Pellicano Hotels

Hotel Il Pellicano

Located on the Tuscan coast, the hotel’s central building and cottages are surrounded by centuries-old olive trees set in an extensive garden. Guests will relish the chance to spend time on the water thanks to a lift to the private cove with direct access to the sea where they can relax, water-ski, or swim in the heated seawater swimming pool. The PELLICLUB Health & Beauty and the boutique offer the chance to sink into wellness or shop from a well-curated selection of national and international items. There’s also a state-of-the-art gym and tennis courts for active guests.


Hotel de La Ville

One of the newest additions to the Rome hotel scene, the Hotel de la Ville is ideally located atop the Spanish Steps with a glamorous rooftop bar and a fresh cocktail program. The property’s 104 rooms and suites are filled with playful, contemporary furniture and sumptuous fabrics that draw influence from the era of the Grand Tour. With traditional wooden floors, elegant marble bathrooms, and wonderful views over via Sistina and the rooftops of the Eternal City, Hotel De La Ville promises to be an artistic and timeless choice in Rome.


Palazzo Avino

Known as the “Pink Palace”, this intimate hotel was once a 12th-century private villa for an Italian noble family. Tucked away in the medieval hilltop village of Ravello, this well-appointed property is an ideal introduction to the Mediterranean side of Italy. The hotel rooftop features a magnificent sun terrace with hydromassage plunge pools. There’s also an outdoor swimming pool whose terraces enjoy stunning views over the coast. The property boasts a serene outdoor gym and a full-service spa complete with a sauna, steam bath, and hydrotherapy pool. One of the most popular attractions at the hotel is its new private "Clubhouse by the Sea" beach club as well as its boutique, The Pink Closet.


Le Sirenuse

Step deeper into local life on the Amalfi Coast with a stay at Le Sirenuse. The property is an 18th-century palazzo converted into a five-star, family-owned and operated hotel, located in the heart of Positano. Facilities include its iconic heated swimming pool open, fitness center with a new spa, indoor and outdoor bar, and Michelin star restaurant serving local specialties. All rooms are decorated with a combination of antique and contemporary furniture, contrasting cool whitewashed walls and floors are covered with colorful tiles from Vietri. Most rooms have a balcony or terrace overlooking the azure sea with the gentle soundtrack of waves.



  • Learn the art of Italian fashion side-by-side with an atelier on a private guided tour through their workshop Day 1-4
  • Discover the magic of Lake Como aboard an exclusive Venetian water limousine as you explore the historic Villa del Balbianello Day 5-8
  • Take a tour of the Gucci Garden, complete with access to their exclusive one-of-a-kind boutique Day 9-12
  • Journey Tuscany via private bike tour for sweeping views of Val D'Orcia Day 13-15
  • Enjoy oceanside reprieve at the understated, star-studded Bar Roberto Day 16-18
  • Gain early access to the Eternal City's legendary monuments and attractions Day 19-22
  • Shop through the impeccably curated "Pink Closet" boutique collection Day 23-26
  • Indulge in a romantic candle-light dinner at sunset, indulging in champagne and oysters at La Sponda Day 27-30


1-4 Milan, Italy
Sink into chic with Milan Style

Begin your private tour of Italy with a flight into the city of Milan. While you won’t see the capital included in every private tour of Italy as it is often passed up for Rome or Venice, hear us out. Milan offers a blend of old and new with sights that pay homage to the Renaissance in equal numbers to spots that are all about cutting-edge fashion, art, and design. Our favorite way to get started on arrival day is not with a rest – though, we will be sure to secure you an early check-in at Bulgari Hotel Milano – but by getting out to explore on foot. We love pairing travelers with a guide for a historical walking tour to see sights like Sforza castle and the iconic Duomo. If you’re up for it, climb all the way to the terrace; we promise the view is worth the jetlagged effort.

As you dive into subsequent days in this fashion mecca and the country’s center for commerce, you’ll discover that Milan is a big city that still feels like a small town. Outside the main piazzas, you’ll find quaint neighborhoods lined with cobblestone streets, cafés, and antique shops where everyone seems to know one another. Suppose you’re after an unforgettable art experience. In that case, your SmartFlyer travel advisor can work with Bulgari Hotel’s concierge team can arrange for guests to enjoy a private viewing of Leonardo Da Vinci’s Last Supper, one of the most iconic paintings in the world. We can even arrange for private dining beneath the work at the Refettorio di Santa Maria delle Grazie.

…all about cutting-edge fashion, art, and design.

Step into fashion artistry within the Quadrilatero D’Oro or Golden Quad with couture in Montenapoleone, including Armani, Ferragamo, Prada, and Gucci. Then, head to the small unique shops of the Brera. A beloved experience offered by SmartFlyer travel advisors centered in the city’s fashion district; we can arrange for a private, behind-the-scenes trip into an atelier’s workshop where you’ll speak with the designer before watching them hand stitch a garment! So authentically Italian.

5-8 Lake Como, Italy
Luxuriate in Lake Como

After a few days to acclimate to the time zone and explore Milan, it’s time to head to the Lake District. With a private tour of Italy, the transfers can either be by a professional driver or a sleek rental car. It’s up to you! Either way, enjoy the superbly scenic drive to Lake Como where you’ll check into Grand Hotel Tremezzo. This iconic property features two waterside crowning jewels: the T Beach and T Marina. T Beach is a white sand beach that lines the lake and opens up to a floating pool suspended over the lake’s natural waves. We recommend recharging from your travel day here and spending some time at their chic Pommery Pop champagne bar.

After taking the night to settle into your terrace suite, wake up and board one of two boat experiences on the T Marina. Batt – named after the hotel’s forefather Giovanni Battista Mallone – is styled as a classic Venetian water taxi. Alternatively, Ruy is a veritable water limousine from 1961 that was lovingly restored at the Ernesto Riva shipyard. Choose one of the two to sail out to the gorgeous Villa del Balbianello, a historic villa built in 1787 known for its elaborate terraced gardens. If you’re craving adrenaline though, then work with your SmartFlyer advisor to book a spot on their hydroplane. This excursion takes you across the area’s three lakes – Como, Lugano, and Maggiore – as well as the highest tips of the alps.

…wake up and board one of two boat experiences on the T Marina.

The history of this 110-year-old family-owned property long ago cemented Grand Hotel Tremezzo as a grande dame. Designed to please the most discerning global traveler, the De Santis family guided the property into the 21st century celebrating a century of charm and authentic Italian hospitality. Third-generation owner Valentina De Santis believes the secret to the hotel’s success is the staff, who are like family and, in turn, treat their guests like one of their own. Family ties are strong here and checking out will surely feel like you’re saying goodbye to a newfound family. Luckily, arrivederci means “until we meet again!”

9-12 Florence, Italy
Take a step back in time in Florence

As the sun breaks over the lake and you look back at your first week in Italy, bid farewell to Lake Como and head south to Florence. After a four-hour train ride, you’ll reach the doorsteps of Portrait Firenze. The Ferragamo family’s warm hospitality is felt throughout every design element and equally polished service. From their tables set up along the Arno for aperitivos and prime people-watching to their suites complete with stunning views of the Arno River, you’ll be hard-pressed to ever leave the hotel!

However, it wouldn’t be a trip to this Renaissance city without requisite visits to the Uffizi Gallery, Galleria dell’Accademia, and Bardini Museum (to name a few). In between museum visits, pop into Florence’s various charming cafes and iconic shopping. Combine efforts on both fronts with a special trip to Gucci Garden. This private tour brilliantly combines a walk through Gucci’s storied history with a boutique offering exclusive items not sold anywhere else in the world. Cap off your visit with lunch or even just a celebratory cocktail while you admire your purchases at Gucci Osteria, an outlet imbued with creativity brought to life by chef Massimo Bottura. If you’d like your private tour of Italy to include any VIP access to off-the-beaten-path spots, your SmartFlyer travel advisor can arrange for exclusive tours of historic Florentine homes and more.

The Ferragamo family’s warm hospitality is felt throughout…

Exploring this storied city by foot helps to strike a balance with all of the delicious bites you’ll be indulging in along the way. Consider climbing to the top of the Duomo to enjoy views of the city. Afterwards, step through Mercato Centrale and treat yourself to the bounties of fresh produce or prepared bites (did someone say arancini?) for lunch. For those with a penchant for sweets, Vivoli’s renowned gelato is just steps away. You can also visit the world-famous David at the Galleria dell’Accademia di Firenze before strolling through the most famous piazzas. Finally, close your day of sightseeing out at Palazzo Vecchio where you can access the exclusive Vasari Corridor. Florence dinner favorites include Trattoria Cammillo, Osteria della Tre Panche (truffle everything), and Cantinetta Antinori.

13-15 Tuscany, Italy
Unwind in Tuscany

After checking out of the Portrait Firenze, enjoy your private driver guide you through the hills of Tuscany, or, opt for a vintage rental car if you prefer to self-drive. For the uninitiated, this vibrant region is known as the home to some of the most sought-after vineyards in the world. Here, the charming Borgo Santo Pietro will welcome you home. Take some time to relax in the countryside as you enjoy nature’s healing properties at the Borgo Spa. You can also soak up the hotel’s tranquility in their well-appointed gardens.

It wouldn’t be a SmartFlyer-designed private tour of Italy without making sure you have a full tasting menu of Tuscany. If you’d like to journey into neighboring towns, walk through their storied streets and do some wine tasting along the way, there are ample options. A midsummer drive to Montalcino affords you both gorgeous views of the countryside and the most breathtaking sunflower fields in full bloom. Don’t forget your camera so you can snap some shots en route to tasting the spectacular Brunello wine! Alternatively, take a drive to Montepulciano and visit a historical winery in the old part of town; there are several that offer underground tours of their cellars, including a favorite called Cantina Ercolani.

…walk through their storied streets and do some wine tasting along the way…

If you’re looking to take your exploration off the ground, there are all-day private helicopter tours through the valley that will transport you to two wineries; Podere Le Ripi in the morning and Castiglion del Bosco in the afternoon, as well as a lunch at the Michelin-starred Restaurant Silene. For the fitness enthusiast, consider a guided five-hour biking tour through the Tuscan valley. Cap it off with a delicious Italian Merenda, picnic style. Your evenings back at stunning Borgo Santo Pietro will be all about enjoying their Michelin-starred spot, Meo Modo, which showcases the freshest ingredients that are organic, time-honored, and simple.

Set table for breakfast in the terrace of Suite Santo Pietro,Relais&Chateaux Borgo Santo Pietro,Località Palazzetto, Chiusdino
Set table for breakfast in the terrace of Suite Santo Pietro,Relais&Chateaux Borgo Santo Pietro,Località Palazzetto, Chiusdino
16-18 Porto Ercole, Italy
Seaside bliss at Hotel Il Pellicano

As far as bucket list hotels go, Hotel Il Pellicano certainly qualifies for itineraries to build an entire trip out of; if you’re breaking this private tour of Italy into multiple trips, you could consider flying into Rome and then just jetting out to Hotel Il Pellicano for a few nights. In this case, we’re positioning it in between Tuscany – located just an hour and a half drive away – and Rome to get you a taste of the sea breeze before rounding out your itinerary further south.

Pellicano Hotels embarked on a mission to refresh “La Dolce Vita” for a modern traveler through what they call “a more conscious approach to travel.” Here, it’s all about protecting and preserving the territories and local communities which they accomplish thanks to sharp attention to detail. Nowhere is this more clear than with their sister brand, ISSIMO. This is a true declaration of love to Italy as a collection of “Made in Italy” products, many of which are available in the property’s boutique.

Courtesy of Pellicano Hotels
Courtesy of Pellicano Hotels

The journey here is well worth it, whether that be for the terraced private beach, heated seawater swimming pool with cliff views, pleasantly spacious guest rooms, the Boutique, the Pelligrill, and the Michelin-starred restaurant Il Pellicano. Many of the rooms in the central building and cottages have entrancing views of the Tyrrhenian Sea. Make your way to the Pelliclub health and beauty facility, featuring Technogym equipment, or take a cooking class. Nights here end at Bar Roberto where piano notes drift on the night air; legends, royalty, and inconspicuous guests alike who’ve all been photographed during their stays can’t help but toast to this stunning setting.

Courtesy of Pellicano Hotels
Courtesy of Pellicano Hotels
19-22 Rome, Italy

No trip to Bel Paese is complete without a stay in Rome. Home to major sites like the Colosseum, Trevi Fountain, and the Pantheon, this place has a special spot in our team’s hearts. But, we love it for so many more reasons than historical monuments. Though, if you do wish to see those during your private tour of Italy, work with your SmartFlyer travel advisor to secure early entrance to two of the city’s most iconic landmarks: the Vatican and St. Peter’s. This is best paired with a guided tour to the Sistine Chapel where you can gaze up at the Last Judgment and the Creation of Adam without worrying about the crowds. Lastly, walk through the vast St. Peter’s Basilica, one of the largest places of worship in the world. You can also take a guided tour through the iconic Colosseum, Roman Forum, and Palatine Hill during your stay.

No trip to Bel Paese is complete without a stay in Rome.

In our view, a trip to “The Eternal City” is equally about exploring charming residential neighborhoods, weekend markets, and discovering her secret bars as it is seeing the main sights. Make sure to walk through Monti; back in ancient times, this neighborhood was the heart of Rome’s red-light district. Today, this residential area is a quiet gem sandwiched between major landmarks. Also, don’t miss out on the weekend market open every Saturday and Sunday for local artisans and designers followed by a coffee at La Casetta (or, opt for a cocktail with a side of people-watching in Piazza Della Madonna if that’s more your vibe!).

If you’re after a killer shot, arrive early to the towering green doors of the secret “keyhole” nestled in the Aventine Hill before a queue forms. Afterwards, choose between exploring the Basilica of Santa Sabina or the nearby Giardino degli Aranci. We also recommend stopping by the Orange Garden and taking a picture amongst the lines of orange trees. Close out your day with a fun dinner at Roscioli Salumeria con Cucina for their famous family-run deli meets restaurant setting; the deletable plates of cured meats and cheeses being cut before your eyes are married perfectly with their negroni. Don’t skip the house tiramisu.

23-26 Amalfi Coast, Italy

As you work towards the latter portion of your epic Italy trip, we don’t want to say we’ve saved the best for last (we don’t play favorites!). But we can assure you that this coastal component won’t disappoint. End your private tour of Italy on the fabulous Amalfi Coast, located just over three hours from Rome by private ground transfer. We love beginning our time in Amalfi with a few nights at Palazzo Avino, nestled in the quiet town of Ravello.

You’ll leave feeling like you were the only guests.

Since 1953, this quaint region has hosted a colorful range of artists and musicians from across the globe. Begin your afternoons at Ravello’s “Pink Palace” with some time relaxing by the water at Palazzo Avino’s Clubhouse by the Sea. For dinner, enjoy a candlelit dinner at Rossellini’s; the lobster and martini bar paired with a stunning view is the perfect way to close out the day. If you’re looking for something in town, head over to Cumpa Cosimo that’s just minutes away on foot.

For those who are seeking some unique pieces to bring home, a stop at the “Pink Closet,” an impeccably curated boutique born right out of Managing Director and owner Mariella Avino’s dreams. It’s both intimate and feminine with clothes and accessories compiled from attentive research. The ethos of this family-owned and run property is centered on service and with an average of two staff members dedicated to each of its 43 rooms and suites; you’ll leave feeling like you were the only guests!

27-30 Amalfi Coast, Italy

While we don’t truly believe that all good things have to come to an end (you will be back, after all), the final stop on this dolce vita tour culminates with a stay at the iconic Le Sirenuse in Positano. The Sersale family has owned this land for three generations, dating all the way back to the 19th century. But Le Sirenuse is anything but stuck in the past with its specially-curated selection of contemporary art throughout the property, from floor-to-ceiling murals to neon light art. Guests will feel like they are inside a movie set as they take in views from their balcony each morning.

Guests will feel like they are inside a movie set…

Legendary American author John Steinbeck said it best, “Positano bites deep. It is a dream place that isn’t quite real when you are there and becomes beckoningly real after you have gone.” We think Steinbeck would agree that a stay at Le Sirenuse feels incomplete without time spent on the water. Take an afternoon out at sea on their beautiful Sant’Antonio fishing boat. This is an ideal way to see the gorgeous coastline; sail out to Nerano, a seaside village whose stellar restaurants and trattorias are well-known to Amalfi Coast insiders.

Upon your return, the champagne and oyster bars at sunsets are must-tries, followed by dinner at the stunning La Sponda restaurant. The team here lights 400 candles every evening, creating the perfect atmosphere for one final romantic seaside dinner in Italy. Rest assured as you savor the final moments of your private tour of Italy that this is just one in a series of “final” nights in Italy. And when you’re ready to plot your eventual return, we’re here to help.

Book Now

Contact your SmartFlyer travel advisor to learn more about planning your epic Italian adventure.

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