Couples Journey through Italy Travel Package

Our Couples Journey through Italy Travel Package includes Tuscany, Portofino, Milan and Lake Como

10-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

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

What's Included in your Couples Journey through Italy Travel Package

  • 3 x nights’ accommodation in Tuscany, Italy
  • 3 x nights’ accommodation in Portofino, Italy
  • 1 x nights’ accommodation in Milan, Italy
  • 3 x nights’ accommodation in Como, Italy
  • Seamless private ground transfers as noted in the itinerary
  • All tours and excursions as noted 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 Couples Journey through Italy Travel Package Itinerary
(All itineraries can be customized)

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Day 1-3 Tuscany, Italy


Your Italy Travel Package starts now! 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.

The only Thermal Castle with its own Brunello di Montalcino wine and olive oil from Organic Agriculture.


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

Option 1: 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”.

Option 2: 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 Tuscan Tour

Meet your driver in the lobby of Castello di Velona.

Today’s private tour begins with sight-seeing experience (with wonderfully scenic drives through the val d’Orcia) to visit the Unesco-protected town of Pienza (and the smaller and very characteristic town of Monticchiello.

After you will enjoy a visit to the farm with a guided tour of the dairy process to learn more about the local Pecorino sheep cheese production) followed by lunch. The lunch always includes vegetables, extra virgin olive oil, grains (to make the break and pasta) and wine from the farm.

In the afternoon, you will travel to the hilltop town of Montepulciano. This is quite a big town with lots of things to see and boutique shops of local crafts. Included is a cellar tour in an historic cellar and tasting.

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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.

Excelsior Palace Portofino Coast is honored to be voted a 2021 I Prefer Members’ Choice Award Winner.
Out of more than 650 independent hotels around the world, we were chosen as one of the top hotels in Europe.

This award is a testament to our commitment to deliver on the I Prefer Hotel Rewards promise of discerning standards and memorable, personalized service during each stay.
With over 3.8 million members, I Prefer Hotel Rewards remains the world’s largest points-based loyalty program for independent hotels. We are proud to serve these members and provide exceptional experiences to every guest, every stay.

Splendid setting for weekends and for holiday stays, Excelsior Palace Hotel five-star luxury hotel Rapallo devotes special attention to lovers of excellence, welcoming its guests in the exclusive Beach Club with the only two infinity pools facing the sea in the Costa di Portofino, one of which is equipped with hydromassage beds.

A fantastic Spa and a suggestive gym overlooking the sea will be available for those who want to indulge in moments of relaxation and well-being.

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  • 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.

Couples Journey through Italy Option 2 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.

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  • Best of Milan Private Walking Tour

Meet your guide in the lobby of your hotel.

Discover the secrets of Milan’s historical centre on a customized 3-hour walking tour, and enjoy the personalized services of a private guide. Ideal for those who have already taken an historical tour of the city center’s main sites, this walk will take you to some of the city’s more hidden locations. Your guide will reveal hidden secrets about the streets of Milan. Hear fascinating stories about the art and architecture of the city as you dive down narrow streets and hear about the people that used to live there. Listen to sometimes funny, and sometimes tragic, tales to get an alternative perspective of Milan.

  • Private Last Supper and Duomo Experience and Milan City App

Fill your day with art, and see Leonardo da Vinci’s The Last Supper and the Duomo Cathedral in Milan with a skip-the-line ticket. The biblical scene painting has become one of the world’s most famous pieces of art. So skip past the long lines of people waiting to see it, and head straight inside the UNESCO-listed Church of Santa Maria delle Grazie where the work of art sits for an up-close look at the masterpiece itself. Our licensed tour guide will then lead you to discover the Duomo, one of the most iconic building of Milan and the fourth largest Cathedral in Europe. Fall in love with its gold plated statue of the Madonnina and see the true symbol of the city.

  • Entrance ticket to Leonardo da Vinci’s Last Supper and the Duomo di Milano 
    • Bypass the queues with a skip-the-line entrance ticket
    • Get close-up to Leonardo’s masterpiece inside a Dominican convent
    • Hear some of the mysteries related to the mural and the biblical scene that it depicts
    • Discover the Duomo with a licensed guide
    • Get access to a useful Milan App with additional information and services
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Day 8-11 Como, Italy


A new boutique hotel has born, from a complete renovation of the clerical buildings facing the Como Cathedral with 14 rooms and 5 suites.

The essence of the work we have done is captured in the search of design, in the furnishing and materials all rooms have a very high level of soundproofing and beds with patented technologies to ensure the maximum comfort.

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  • Dinner at on the terrace at Platano at Villa d Este

This restaurant offers a simple and refined cuisine in an informal atmosphere.

Platano also boasts an unmistakable view that will satisfy your desire to relax while you enjoy a classy but not demanding menu, accompanied by wines of absolute value.

  • The Grandeur Of Como: Villa Olmo and Brunate Funicular

Enjoy a full day tour discovering Italy’s silk capital, Como. Our favourite guide will disclose the history of the landmarks of the main town of the lake, where major silk producers built their factories and famous inventor Alessandro Volta was born. After strolling through the historic centre among ancient buildings and local workshops, we will head to the majestic Villa Olmo.

Next head to the Funicolare Como-Brunate where you will take the funicular and enjoy breathtaking views over lakes and mountains below.

  • 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.

  • 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.


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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