All Star Italy Luxury Tour: Milan, Como, Tuscany & Amalfi

The tour begins with your arrival at the Milan Malpensa airport. You’ll be greeted by a representative who will provide a private transfer from the airport to your hotel. Perfectly situated in the city center, your five-star hotel offers Old World charm and elegant atmosphere combined with modern comforts. You’ll be staying in a spacious suite that is decorated in the plush 19th-century Lombard style with sumptuous fabrics and a sleek marble mosaic bathroom.

In the afternoon, you’ll have free time to begin exploring Milan, a center of finance, banking and fashion. This historic city has Italy’s most ornate Gothic cathedral, which has a dazzling facade of elaborate spires and Gothic gargoyles. This must-see site overlooks the beautiful Piazza del Duomo where crowds gather on their way to see opera at the nearby La Scala theater. Tonight you’ll have a delicious welcome dinner at your hotel.

Today you’ll have a chance to experience the bustling fast-paced city of Milan. Your guided tour includes a private museum visit with VIP entrance so that you can skip the lines. After lunch, you’ll be introduced to the fashionable clothes that Milan is famous for. Many people visit Milan just to go shopping. Milan has attracted Europe’s best-dressed people since the Middle Ages and today it's an international center of fashion, with most Italian designer brands based here. You’ll have the option of having a special shopping experience: a private trunk show at Gucci or another designer label brand.

Today you’ll travel from Milan to the romantic Lake District of Northern Italy. After breakfast at your hotel, you’ll set off for Lake Como, a lovely lake resort with inspiring views of the snow-kissed Swiss Alps. Far away from the chaos and bustle of Italian cities, the Lake District is a place where you can truly relax. In the afternoon, admire the scenery on a private boat tour around Lake Como. You’ll depart from the dock of one of the elegant lakeside hotels in Bellagio, and then cruise to a small fishing village. You’ll visit the famous historic villas and their gardens, including Villa Carlotta, the Villa Cipressi, and the Rockefeller Foundation Villa Garden.

After your all-day tour, you’ll travel to Florence by private transfer. Check into your luxury suite and enjoy dinner at the hotel.

Rise after a restful night’s sleep in Florence, one of Italy’s most beautiful Renaissance cities. Today you’ll discover the city on a guided walking tour that covers all the must-see sites, including the magnificent Duomo that took six centuries to complete. You’ll also have a chance to linger at the Piazza della Signoria, the city’s main square where locals gather to converse and enjoy an espresso. Here you’ll also find elegant cafes with great cappuccinos and the finest designer boutiques, full of the latest Italian fashions. The tour also includes a private visit to the Uffizi Museum with VIP entrance so you get to skip ahead of the long lines. For lunch, experience a typical meal at a traditional Florentine trattoria. In the afternoon, it’s time for a shopping spree on Via Tornabouni, Florence’s most glamorous fashion street where you can shop at Armani, Gucci, and Prada.

Today is a full day of sightseeing at two of Tuscany’s most important cities. You’ll start in Pisa, famous for its leaning tower. Your tour guide will take you to visit the beautiful Piazza dei Miracoli and a cathedral near the tower. Then you’ll stroll along the tranquil Arno River towards the University of Pisa, founded in 1343, which makes it one of the oldest universities in the world. You can feel the history as you walk around the ancient courtyards and old stone buildings.

Next stop is Lucca where you’ll have lunch and then take a guided tour. Lucca is truly a gem of a city with history dating to ancient times. Most of the sites are still perfectly intact, including the medieval walls. The bustling center of Lucca, the circular Piazza dell'Anfiteatro, was built around the original Roman amphitheater. It also has a fascinating cathedral featuring a unique mix of architectural style as well as precious paintings and sculptures.

Travel from Florence to Siena, where you’ll begin your discovery of another region in Tuscany. You’ll take a private sightseeing tour through the Chianti wine region, starting with Greve. The largest city in Chianti, Greve has a bustling town square with a vibrant market. Next stop is the Podere La Capella Winery, a privately owned estate winery. Enjoy a private lunch at the owner’s home and a wine tasting of the estate’s Chianti, Chianti Reserve, and prestigious super Tuscans wines. This special program is organized just for this tour and is not open to the general public.

After the fantastic lunch and wine tasting, you’ll tour the vineyard estate. This renowned winery produces outstanding wine and exports globally. Podere La Capella even supplies wine to the Vatican as the family that owns the winery has a long-standing connection with the Holy Church. The fascinating history makes this winery tour a standout experience. After a scenic drive through the Chianti region, you’ll return to Siena in the evening.

Just when you thought it couldn’t get any better, you’re dazzled with another once-in-a-lifetime experience. Travel through the Tuscan countryside in style as you spend the day driving around in a luxury sports car, either Ferrari or Porsche, with an instructor and lead driver. You’ll travel through beautiful, off-the-beaten-path roads in Tuscany. The landscape is untouched by modernity, with its gentle rolling hills lined by cypress trees. Along the way you’ll see tiny medieval villages at the top of the hills. Many of the villages are surrounded by protective walls that deterred invaders during the Middle Ages.

During your scenic tour, you’ll stop for an incredible gourmet lunch and be introduced to some local cuisine. Continue through Chianti until you return to Siena for dinner. After dinner is a private visit to the Palio Museum where you’ll learn about the city’s famous horse races.

Spend the day touring the region in Tuscany that produces the most prestigious red wine in Italy. The guided tour is led by an expert sommelier. Your first stop is in Montalcino, a medieval hilltop town with spectacular views of the surrounding vineyards. The area around Montalcino produces exceptional wine known as Brunello di Montalcino, considered the finest Italian red wine. Then you’ll visit the city of Cal D’Orcia for wine tasting and lunch. You’ll also visit the Fattoria dei Barbi wine estate, an award-winning winery owned by the Colombini family, descended from an ancient and distinguished Sienese line.

Your next stop is Montepulciano, another Tuscan hill town. Stroll through the pleasant medieval streets where cars aren’t allowed. Visit the notable Duomo of Montepulciano and the impressive Renaissance palaces where nobles once lived. Wine tasting is at one of the acclaimed wineries near Montepulciano. Here you’ll sample the world-famous Vino Nobile di Montepulciano, one of Italy’s classic red wines.

Take a scenic drive from Siena through the sunny and spectacular Amalfi Coast. Your destination today is the incredible archaeological site of Pompeii. This ancient Roman town was frozen in time in 79 AD after a volcanic eruption buried the city, and it wasn’t rediscovered until the 18th century. As Pompeii has been slowly uncovered, the discoveries have unveiled a fascinating look into the ancient world. Enjoy an insightful guided tour of the site.

As you walk through the ruins, you’ll get a look at everyday life two millennia ago! You can see where ancient vineyards produced fine wine, visit the amphitheater where plays were performed, and see the well-preserved sauna where cubbyholes for towels are still visible. After your tour, you’ll be transferred to Positano on the Amalfi Coast.

Get ready for the most amazing driving tour of your life! The incomparable Amalfi Coast is a place of dramatic scenery that will dazzle, delight, and inspire you. It’s a dizzying ride around the twists and turns. The road stretches for about 50 kilometers along steep mountains that drop off sharply into the sea. Stop at viewpoints to soak up the seaside air and panoramic views. The Mediterranean Sea sparkles in the distance with its deep blue serenity. Visit the picturesque villages that are tucked away in the mountains along the Amalfi Coast.

The town of Amalfi was once the base of a maritime empire, while Ravello is a lush cliff-top paradise with elegant villas and verdant flowering gardens. The driving tour concludes in time for lunch in Positano. The afternoon is at your leisure to explore Positano or just to bask in the sun.

Sail away in style to the glitzy Island of Capri. Your motor yacht will pick you up in Positano for a sensational day of sailing and sightseeing at this jet-setting destination. Surrounded by the mesmerizing Mediterranean Sea, Capri is a stunningly beautiful place and a glamorous playground for the rich and famous. Your yacht tour will take you around the island and to the numerous grottos, including the famous Blue Grotto. You’ll also visit an exclusive beach club where you can take a dip in the sea, sunbathe on a comfy lounger, and enjoy a gourmet lunch at the water’s edge. The club offers excellent food, and they serve a legendary iced sangria that is made from chilled white wine and island peaches. Your excursion includes a guided walking tour of the island. Explore the island’s lovely villages, stylish cafes, and upscale boutiques.

You’ll have dinner at an elegant restaurant set in beautiful gardens. The restaurant serves sublime Mediterranean cuisine, especially seafood, gourmet pizzas and traditional dishes that are typical of Capri. After dinner, check out the nightlife at that fashionable Anema e Core Taverna, a club that has great live music. The club is hidden in the center of Capri and is usually missed by tourists. Dance the night away and then return by yacht to Positano.

Today you’ll have free time to discover the enchanting village of Positano. This photogenic town is dotted with little whitewashed and pastel houses clinging to a cliff overlooking the Mediterranean Sea. As you walk through the town’s narrow medieval streets, enjoy the sweeping panoramic views at every turn. Visit the cathedral with its unique majolica decorations, typical of the area. Stroll past whitewashed houses covered with vibrant bougainvillea to find colorful artisan ceramics shops, boutiques selling lemon products, and tiny trattorias. Walk down the steep steps of the town’s “main street” until you reach a beautiful protected beach. You can continue walking along the beach or stop and rent a private lounger to sunbathe. This gorgeous secluded setting is a wonderful escape from everyday life.

You have another full day to savor the beauty and relax in Positano. One of the highlights of this tour is tonight’s dinner at a Michelin-starred restaurant. Part of a prestigious Relais & Châteaux property, the restaurant is decorated in bright Mediterranean colors and has a warm, romantic atmosphere. The refined and elegant cuisine is an expression of the region’s history and land. Each dish is made from exceptionally fresh ingredients, such as vegetables grown in the hotel gardens, estate olive oil from the property, and local meat and cheeses produced nearby. The flavors are exquisite, and the presentation is impeccable.

The restaurant also has a wine cellar that was built in a pre-Roman era tunnel. There are over 25,000 bottles of the finest quality wines that pair perfectly with the restaurant’s gourmet cuisine. Savor an exquisite meal accompanied by wonderful wines in a memorable setting with personalized service. After dinner, you’ll take a private tour of the restaurant’s wine cellar and then return to Positano.

The tour concludes this morning as you leave the Amalfi Coast on a private transfer to the Naples airport. It’s time to say goodbye to this gorgeous area of the world, but you’ll return home with incredible memories of your amazing experiences!