A Journey Through Italy Travel Package

Our Customized Journey Through Italy Travel Package takes you to Tuscany, Montalcino, Rapallo, Portofino, Milan and Lake Como.

11-Day Journey

Your Journey

Personalized journeys by our travel designers from start to finish


Our travel designers have been around the world and back again

Peace of Mind

Our team is available 24/7/365 before, during and after your journey

What's Included in your Journey through Italy Travel Package

  • 3 x nights’ accommodation in Montalcino, Tuscany
  • 3 x nights’ accommodation in Rapallo, Portofino
  • 1 x night accommodation in Milan, Italy
  • 4 x nights’ accommodation in Como, Lake Como
  • Seamless private ground transfers as noted in the itinerary
  • All tours and excursions as noted in the itinerary
  • All breakfast, lunch and dinner mentioned in the itinerary
  • Concierge Service Abroad
  • 24/7 on call service with Crawford Concierge during your trip
  • Sightseeing tickets and entrance fees where mentioned in the itinerary

Your Journey through Italy Travel Package Itinerary

(All itineraries can be customized to your preferences).


Day 1-3 Montalcino, Tuscany, Italy


Your journey through Italy travel package begins in Montalcino, Tuscany, Italy. 

Castello di Velona Resort, Thermal Spa & Winery is an historical property, a renovated fortress dating back from the XIth century, located on a hilltop overlooking the entire Val d’Orcia, in Tuscany.

Located 8 km from Montalcino, the castle overlooks the peaceful Val d’Orcia, a landscape of olive trees and vineyards which produce the world-famous wine Brunello of Montalcino. From the Castello di Velona, you will be able to visit the famous towns of Siena, Pienza, Montepulciano, San Quirico d’Orcia, Bagno Vignoni as well as the extraordinary beautiful Abbeys of Sant’Antimo and Monte Oliveto Maggiore.

ACTIVITIES in Montalcino, Tuscany, Italy

  • Relax in the warmest thermal waters of the Val d’Orcia (suggested upon arrival)

The OLISPA is a true oasis of wellness and relaxation where one can fully regenerate its body, mind and spirit. Distributed over an area of 1500 sq. the OLISPA comprises five elegant treatment rooms with view of the Val d’Orcia, Wet Area with two Turkish baths, a panoramic sauna, ice fountain and the emotional showers that stimulate all senses through aromatherapy and chromo therapy.

  • DINNER RECOMMENDATION:  Dinner at the Restaurant Settimo Senso (Optional: Not included)
    Four courses dinner (menu items priced by weight are not included), beverage not included.

A journey through flavors and memories of traditional Tuscan and Italian cuisine

A refined cuisine, but inspired by the Tuscan culinary tradition Set in the new wing of the Castle, the elegant Settimo Sensorestaurant has a panoramic terrace facing west overlooking the most beautiful view of the Val d’Orcia. From here, at sunset it is possible to enjoy a unique panorama that acts as a natural setting for romantic dinners and special events.

Chefs Riccardo Bacciottini and Alfano Giuseppe propose a sensory journey through traditional Italian and Tuscan cuisine, recalling the ancients with skill and creativity. flavors of this land. Among our gastronomic proposals you will find a selection of carefully selected meats from all over Europe.

Each course is accompanied by fine wines, among which the Rosso and Brunello di Montalcino of Castello di Velona are produced in the 5 hectares of vineyards of the homonymous farm.

  • Private tasting in the dark of wine, paired with olive oil, cheeses and honey.

Walk through the vineyards and find out why Brunello di Montalcino is so special and famous.

Private Blindfolded Organic Wine & Olive Oil, Cheese & Honey Pairing

  • Lunch and tasting in Castello’s San Gimignano Winery

The best way to discover the secrets of the Tuscan traditions and famous wines. Private transfer, Lunch and Wine Tasting in San Gimignano Winery – in the center of the vineyard, under the gazebo.

  • DINNER RECOMMENDATIONS: Dinner – You can choose one. (Optional: Not Included)

Il Silene 1 Michelin Restaurant

Ristorante Silene has over a hundred years of history. It started out as a tavern, later becoming a restaurant; in the last twenty years it has completed its natural course by way of gourmet cuisine.

Chef Roberto Rossi:

“I’ve always loved playing with paradox in this authentic corner of Tuscany. I welcome tradition while going against the grain. I adapt the traditional recipes of my land to the times. I don’t begin from a technique established in advance but instead use different approaches for each recipe, because I know exactly what nuance of taste I want to achieve.

I’ve developed an international reputation without a social media account. My dishes are elegant in their simplicity. I like creating good taste with the wisdom of an old farmer”.

Gabbiano 3.0 Michelin Restaurant

Gabbiano 3.0 is the new chapter of a 13-year success story: the story of the young entrepreneurial initiative linked to the love for the territory of Riccardo and Marco Tomi, cousins and partners, founders of the well-established bathhouse, pizzeria and lounge complex Cafe.

Marco and Riccardo Tomi:

“I was born in Tuscany in 1991. My journey into the world of cooking starts right from my land. In 2016 my first Michelin Star at the La Leggenda dei Frati restaurant in Florence. My journey continues in Veneto, in Treviso, at the helm of the Villa Selvatico Restaurant.

At the end of 2019 I return to Tuscany, in the Maremma, where my new adventure begins, with my cousins Tomi, at the gastronomic Gabbiano 3.0.”

  • Private Tour to Siena

Combine three of Italy’s most vital delights—wine, landscapes, and history—on this tour of the 15th-century Castello Tricerchi Montalcino wine estate. Discover 600 years of history, including the chapel, the vineyards, and the cellars.

Round off your visit with a tasting of three signature wines—Brunello di Montalcino, Rosso di Montalcino, and a Toscana IGP—paired with delicious local nibbles.


Day 4-6 Portofino


Excelsior Palace Hotel in Rapallo is the only 5-star luxury hotel on the Portofino Coast. Located in a privileged position, 2km from Santa Margherita Ligure, facing east on the bay of Rapallo and west on the coast of Portofino.

Since the early 1900s it has been the symbol of the “Dolce vita”, which has conquered the international elite, thanks to its natural beauty and its legendary art of hospitality.



  • Full Day Private Boat Charter

Meet your Captain (my Captain) for a private day on the water. Spend the day on exploring the sights near Portofino. Some stops include Santa Margherita, which features colorful houses and decorative churches; Abbazia di San Fruttuoso, where you can swim and snorkel and stop for lunch; and the fishermen village of Camogli where you can try the focaccia bread.

Stop At: Portofino – During the tour, dock in the port and take a break for a pleasant free walking tour. The most famous Italian village in the world. Do you want to miss the opportunity to walk to the place where many celebrities spent their holidays?

Stop At: Camogli – During the tour dock in the port and take a break for a pleasant free walking tour. Walk in a true village of fishermen between the colors and scents of Liguria. Try the real focaccia!

Stop At: Abbazia di San Fruttuoso – This is a beautiful corner of our region; it’s perfect for swim and snorkeling to discover the under water statue of Jesus and for an amazing break for lunch time. Lunch time not included on the rate. The visit to the Abbey is not included on the rate.

Stop At: Santa Margherita Ligure – During the tour dock in the port and take a break for a pleasant free walking tour. Santa Margherita embodies the spirit of a completely relaxing holiday. Colored houses, decorated churches, trendy clubs, good restaurants and much more. 

  • Beach Day at Bagni Fiore Beach Club

Make a splash at Portofino’s most exclusive Beach! Brigitte Bardot. Maria Callas. Elizabeth Taylor. We’ve lost count of the Hollywood icons that have graced the sandy shores of Bagni Fiore.

Nestled in Paraggi and framed by crystal blue water, the bay is off limits to boats, allowing guests to luxuriate in total tranquility. Combining historic charm with a touch of exclusivity, this is where landscape and service combine to heady, sun-splashed effect.


A Journey through Italy Travel Package 1

Day 7 Milan, Italy


For over a century, this building was the private home of the Ranza family: four generations of entrepreneurs. Now this residence opens its doors as a boutique hotel with uniquely Milanese hospitality.

Its 43 rooms welcome guests in a quiet, elegant setting. The atmosphere is classic Milan–spare, practical, and ideal for welcoming those travelers seeking to explore the Lombard capital.



  • Private Fashion Tour

Learn about the world’s premier fashion capital on this private tour through Milan’s fashion district. Explore the Navigli district and explore its canals and discover a few hidden, fashion gems like local artisan boutiques as well as big-name designer stores while learning about the fashion industry from your informative guide.

    • Discover local artisan boutiques and learn the different styles of the city
    • Learn about the history of fashion while perusing through designer stores
    • Take a fashion walk through Milan with an expert style guide during this private tour experience.
    • Visit concept stores, vintage ateliers, and exclusive boutiques.
  • Private Last Supper Experience
Your private tour will take you to the worldwide famous Last Supper by Leonardo da Vinci. Your guide will take you on a journey through the discovery of one of the most important artworks in History. Get to know Leonardo and his mind in a unique way with the insight that only a guide can provide.
The Last Supper inside visit duration will be 15 minutes. The Last supper is not only one of the most Iconic Leonardo Da Vinci’s painting, it is also am Art History altering event and an extremely moving piece that only a chosen few can have the chance of visiting. due to its delicate nature, only a limited amount of people can see it every day. All the secrets and history will be unveiled on this unique experience, the tour can take you to the church of Santa Maria delle Grazie and its cloister.
  • Duomo + Terrace Inside Out: Skip the Line Private Tour

Milan’s soaring Duomo is a symbol of the city and one of its most popular sights, but the long line to enter can cut into your sightseeing time. Save hours with fast-track admission and delve into the long history and striking architecture of this Gothic cathedral with a guided tour. Cap off your visit with a stop on the panoramic terrace to take in bird’s-eye views over the city’s rooftops.

  • Avoid a long wait to enter Milan’s Duomo with a skip-the-line ticket
  • Visit with a guide for insights into the cathedral’s complex architecture
  • Access the panoramic rooftop terrace to snap photos of Milan from above
  • Enjoy the personal attention and relaxed pace of a private tour

Day 8 – 11 Como, Italy


When it was built in 1898, this remarkable property was named “Grand Hotel Plinius”; the engineer Giuseppe Salvioni drew the original project whilst the young architect Federico Frigerio designed the magnificent decoration of the top floor.

A majestic palace on the lakefront, featuring the Belle Epoque style and modern comforts, made it stand out amongst the other hotels in the city.

Como was slowly discovering its call for tourism, but sadly the two World Wars took place and the hotel closed and re-opened several times. It underwent renovation and was taken over by different owners. In 1992 the name changed to “Palace Hotel” and increased its room capacity by adding the adjacent wing – the Pianella – and also opened the Congress Centre. Since 2005 the hotel is managed by the renowned group of Villa d’Este.

Today, the two styles of the Palace Hotel perfectly combine past and present, with a glance into the future.



  • Private Boat on the Lake with my favorite Captain

Lake Como is among the most scenic of Italy’s northern lakes, lined with historic villas and gardens. With this boat tour and your Captain, admire sights that are inaccessible by ferry or car and enjoy the flexibility of a private experience. Set off from Como to cruise past Villa del Balbianello and Villa Carlotta, snap photos of Tremezzo and stop in Bellagio for lunch and shopping and get a glimpse of the lake’s island and waterfall.

  • Private Cooking Class in the home of a local

Lake Como has always been a popular retreat for aristocrats and the wealthy since Roman times, and offers many artistic and cultural gems. Famous people have or have had homes on the shores of Lake Como as it is widely regarded as one of the most beautiful lakes in Europe.

Foreigners like to experience the Dolce Vita on the lake by enjoying simple things, that most of the times we take for granted, such a cappuccino, an aperitivo in the piazza or on a terrace overlooking the lake, a cooking class with a local chef, health coach and food writer.


Italy and many other Mediterranean countries have big street markets. They are part of the culture and are held 2 or 3 days every week, usually in the morning.

The market experience is a stimulating assault on the senses: the smell of herbs and spices, fresh seafood, fresh cheese – not to mention the dozens of rows of colorful produce! Last but not least, you will experience the cultural flavor of how Italians interact when they go to the market.

With your the author and chef you be taught lessons on traditional Italian cuisine but with a modern twist – nutrition, history, culture and language – a culinary experience. 


The lesson will include a “stuzzicante” and rich aperitif with prosecco. Hands-on cooking class preparing a first, second course and dessert. A brief discussion about the origins and nutritional properties of each of the foods will be included as well.

After the lesson we can enjoy the food prepared with red or white wine. Water and digestive are included. The lesson usually lasts about 4 ½ hours.

Return Home with Memories that Last a Lifetime

Contact your Travel Designer

lisa crawford
Lisa Crawford

Luxury Travel Advisor, Founder, and CEO

Contact Lisa Crawford today at 954-456-0419 

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