Italy is one of the most popular travel destinations in Europe and is by-far one of the most traveled places by several Luxury League agents. From the idyllic countryside of Tuscany, and the historical sites of Rome and Pompeii, to the canals of Venice and beaches of the Amalfi Coast, Italy is a wanderlust’s dream. Luxury League member, Kathryn Scarborough of Engel & Voelkers Austin, is a long-time traveler to “Bel Paese” and has shared her insider tips for creating the luxury Italian vacation of your dreams. 

Starting in Rome and ending in Milan, Kathryn will take us on a once-in-a-lifetime, two-week tour of her favorite stops in Italy. 


Rome is one  of the easiest access points for international travelers and is Kathryn’s recommended first stop on your Italian holiday. There is a lot to see and do in the Eternal City, so you will want to be strategic in your planning to ensure you see all of the historical highlights. 

Upon your arrival, book a panoramic driving tour of the city. This is one of the best ways to see all of the major highlights. You can enjoy a beautiful view of the city from Gianicolo  or the Aventine. You might also visit some of the key squares of the city such as Piazza Venezia, Piazza di Spagna or Piazza del Popolo. A stop in Centro Storico, the historic center of Rome, is full of stunning Baroque architecture and art, as well as city squares that are both charming and magnificent. You can take a break at one of the outdoor cafés that overlooks the Pantheon or make a pit stop for gelato. 

On day two, plan for a full day of tours to experience the rich history of Rome. There is no better way to see it all than by a  private, guided tour to see historical highlights including the Colosseum, the Roman Forum,  the Catacombs and Basilica of San Clemente.

The final day in Rome includes special access (prior to opening to the general public) and a three-hour private, guided tour to the  Vatican Museums, Sistine Chapel and St. Peter’s Bisilica. At the conclusion of your tour, if you’re up for the challenge, there are 320 steps from the base of the dome at St. Peter’s up to the cupolo. The view of the city from this vantage point is worth the journey.

Kathryn’s Pro Tip: You will need a minimum of 3 nights in Rome to best experience all the city has to offer. 


En route to Capri, our next stop is Pompeii. The ancient Roman city was buried under ash, sand and pumice following the massive eruption of Mount Vesuvius in 79 A.D., and was preserved by debris for hundreds of years. 

During a two-hour tour, your guide will take you to witness the remarkable basilica that was once a justice palace, the forum and the well-maintained large and small theaters. You will also visit a bakery where you can still see the stone mills and an oven. Next, you could visit one of the amazingly preserved private homes in Pompeii.. What is so remarkable about the ruins of Pompeii is the incredibly complete, fresh, vivid and intimate insight they give us into the daily life of a Roman city at the height of the Roman Empire. 

Following lunch, venture to the public hydrofoil in Naples to start on your 50-minute journey to the island of Capri. 

Next stop. Mediterranean paradise AKA Capri. 


After a few full days of sightseeing it is time to kick back and relax on the Isle of Capri. Take in the stunning view from the top of Monte Solaro, which is reached by chairlift from Anacapri. Anacapri is known as the island’s “second city” and is much more relaxed than Capri. Check out the shops on Via Camerelle in Capri and visit L’Arte del Sandalo Caprese di Antonio Viva in Anacapri for handmade sandals. Eat lunch at a cafe and perhaps enjoy a glass of limoncello. Fun fact: Italy is the world’s largest producer of lemon. 

If you’re looking to escape the other visitors on the island, check out the immaculate Gardens of 

Augustus, which affords great views of the Faraglioni Rocks jutting up from the sea off the far side of the island. Looking for a workout?  Visit and hike the ruins of Tiberius’s Villas. 

Now it’s time to head to the Amalfi Coast. Kathryn and her crew travel along the coast on a private, 40’ sports yacht passing close by the Faraglioni Rocks and making a pit stop at the Blue Grotto along the way. 

To visit the Blue Grotto, you must exit your private boat and  board smaller rowboats operated by locals. The grotto opening is just six feet high by six feet wide, and sea conditions can prevent access. Just keep in mind the grotto attracts crowds, so feel free to ask your captain to visit another, less crowded spot such as the Green Grotto! 

On the way, make a stop for a dip in the Med if you like or consider stopping for lunch at a beach club/restaurant such as Conca del Sogno. Proceed across the open sea a short distance to the Amalfi Coast and cruise along the coast (more amazing panoramas to enjoy). You can elect to cruise through the Galli Islands located just off the Amalfi Coast. End this fabulous cruise at the dock of Amalfi where you can arrange private transfer up the mountain to the elegant mountaintop village of Ravello. 


The elegant mountaintop town of Ravello oozes luxury. Relax on property on the terrace or by the pool to take in the views of the Gulf of Salerno. Visit the gardens of Villa Cimbrone or Villa Rufolo and browse the shops. Enjoy lunch on the terrace of Villa Maria hotel and  limoncello on the main square in front of the Duomo. 


You can’t visit the Amalfi Coast without making a stop in Positano. The jumble of buildings cascading down to the beach is quite remarkable. There are some shops worth checking out and plenty of restaurants to consider. 

Kathryn’s Pro Tip: The small town can get crowded. Have lunch high above Positano in Montepertuso which offers great views of the coastal town.  The best time to visit Positano is after 5:00 p.m. after many day trippers have departed. 


Travel by railway from Ravello to Florence for the next stop on your adventure. Enjoy lunch on your own and then embark on a walking tour that combines rich art history with historical context. Visit  L’Accademia (founded in the nineteenth century to house Michelangelo’s magnificent statue of David) and study five other sculptures by Michelangelo– the four unfinished Prisoners and St. Matthew – along with another must-see, Giambologna’s Rape of the Sabines. Next, stroll  through the medieval, cobblestone streets to admire Piazza Signoria and its open-air collection of original statues. 

On your first full day in Florence, consider kickstarting things with a hike up to Piazzale Michelangelo or the Basilica of San Miniato for an outstanding view of the Renaissance and Medieval skyline of the city. You might also check out the boutiques on the fashionable Via Tournabuoni and the fun San Lorenzo Street Market, a great spot for small items and gifts. In San Lorenzo, you might venture into the wonderful Mercato Centrale food market. 

Pro Tip in Florence: Not all gelato is created equal. Geletaria La Carrai at Via de Benci, 24 is a can’t-miss gelato stop. 

Siena, Monteriggioni and the Tuscany Countryside

With Florence as your home base, venture out for a day of  beautiful scenery and several hours in Medieval Siena, a favorite of the small cities in all of Italy. Start your visit to Siena in the fan-shaped main square, Piazza del Campo, the site of the Town Hall, the largest Gothic civic building in Italy (climb the Mangia, the town hall tower, for exceptional views following your tour). 

Located 20 minutes from Siena, the tiny hilltop village of Monteriggioni is one of the best-preserved medieval communities in all of Tuscany. Kids particularly love to walk two sections of the fully intact walls. You might walk through vineyards and olive groves, learning about sharecropper’s traditions. You’ll enjoy panoramic views in the gorgeous area around Monteriggioni. 


After departing Florence, take a one hour and 50 minute train ride to Milan.  Milan is the second-most populous city proper in Italy after Rome and has been recognized as one of the world’s four fashion capitals (along with London, New York and Paris). 

Shop on your own or arrange to have a private driver escort you and your bags around the city. The best spot is The quadrilatero d’oro, or “the golden quadrilateral” consisting of four thoroughfares full of luxurious shops: Via della Spiga, Via Montenapoleone, Via Alessandro Manzoni, and Corso Venezia. There’s also Corso Vittorio Emanuele II which connects Piazza Duomo to Piazza San Babila. There you’ll find a range of boutiques and shops as well as the luxury department store, La Rinascente.

Lake Como

Enjoy your last day in Italy before departing Milan by exploring one of the most beautiful mountain lakes in the world, Lake Como, by lake cruiser. Make a stop for lunch on your own in the enchanting lakeside village of Bellagio. Enjoy a guided stroll of the lovely village after lunch then continue your voyage, perhaps cruising past George Clooney’s three villas as well as other magnificent private villas of Como. 

If you’d like, make a stop at Villa Balbianello. The highlight is the panoramic terraced garden dominated by the elegant “loggia” with three arches rising on the highest point of the promontory. 

The number one pro tip from Kathryn is to hire a reputable, experienced travel specialist that can customize an itinerary specific to your interests and budget. She personally recommends Austin-based, Amanda Watkins Travel to curate a once-in-a-lifetime Italian adventure.