Luxury Italy vacations


Fashion, food, wine, history, and culture – Italy has it all. Whether you’re looking to whisk your partner away on a romantic trip along Venice’s famous waterways, indulge yourself with authentic Italian food and wine in Tuscia, or simply experience some of the world’s most famous works of art, we can curate your dream Italian adventure.

Here at Out Of Office, we truly understand the world you live in, and the world you want to explore. Our attention to detail, exceptional service and deep understanding of both luxury travel and LGBTQ+ travel make us a fantastic choice for those looking for a travel experience where exclusivity meets inclusivity.

At a glance

? Don't forget that all of our itineraries are totally customized and so this is just an idea of what we can build for you.

Italy is a land of huge variety, with fascinating cities and stunning swathes of rolling countryside. Wherever you visit in the country, you can expect awe-inspiring views and tantalizing local delicacies.

Head down south and explore the charms of the Amalfi Coast, taking in Naples, Pompeii, Capri and Sorrento in one trip, or spend your Italian adventure in the country’s northern regions and join the legion of A-listers who flock to Milan and Lake Como each year.

Visit the country’s iconic cities and immerse yourself in their rich and historic culture. History buffs can head to Rome to find ancient ruins like the Colosseum and the Vatican. Art aficionados can flock to Florence to find Renaissance treasures, including Michelangelo’s David. In Venice, take a gondola ride through winding canals and find historic palazzos and picturesque bridges.

It’s no secret that one of Italy’s strongest pull factors is the country’s mouth-watering array of local and national dishes. Nowhere is more synonymous with Italian cuisines farm-to-table approach to dining than Puglia, where home cooks and Michelin-star chefs alike queue at market stalls for the day’s freshest produce.

Luxury Italy truly is a world of its own, with a caliber of hotels reserved for only the most discerning of clientele. At Out Of Office we’ve got fantastic relationships with the country’s most exclusive and sought-after properties – get in touch with one of our knowledgeable travel experts to begin planning your luxury Italian getaway.

More Trips in Italy

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Lake Como and Lake Garda
Lake Como and Lake Garda


Discover the enchanting allure of Italy’s renowned lake district on a luxurious journey to Lake Como and Lake Garda. This bespoke itinerary, curated by Out Of Office, offers an idyllic escape into the heart of Lombardy’s most picturesque landscapes. Perfect...

Italy: The Out Of Office Collection
Italy: The Out Of Office Collection


Italy has been attracting tourists ever since tourism existed in a recognizable form. You weren’t considered to be educated unless you’d seen the marvels of the ancient world in Italy, from the Roman Colosseum to the Venetian lagoon. Italy has...

The Venice Simplon-Orient-Express
The Venice Simplon-Orient-Express

Group Trip Departs: • 3rd August 2024 • 14th August 2024 • 22nd October 2024 • 1st November 2024 • 14th November 2024 • 19th November 2024 • 23rd November 2024 • 28th November 2024 • 22nd December 2024 • 1st August 2024 • 6th August 2024 • 12th August 2024 • 20th August 2024 • 1st October 2024 • 20th October 2024 • 10th October 2024 • 30th October 2024 • 5th October 2241 • 12th November 2024 • 17th November 2024 • 21st November 2024 • 10th December 2024

Embark on a timeless voyage aboard the world-famous Venice Simplon-Orient-Express, an iconic journey that blends the romance of bygone travel with contemporary luxuries. Starting in London, this enchanting overnight journey on heritage train carriages takes you through the heart of...

Venice & Croatia’s Coast
Venice & Croatia’s Coast


Carefully crafted for discerning travelers seeking the epitome of sophistication, this 13-day exclusive journey seamlessly blends the romantic grandeur of Venice’s legendary canals with the pristine natural beauty of Croatia’s sun-drenched coastline. Your adventure commences in the enchanting city of...

French & Italian Riviera Journey
French & Italian Riviera Journey


Immerse yourself in the epitome of coastal luxury on this exceptional 14-day journey through the French and Italian Rivieras. Your adventure begins in the heart of Nice, at the iconic Hotel Negresco, where the French Riviera’s elegance comes to life....

Gay Group Trip: Luxury Cruise in Italy, Sicily & Croatia
Gay Group Trip: Luxury Cruise in Italy, Sicily & Croatia

Group Trip Departs: • 14th August 2024

Spend time aboard the brand-new luxury expedition ship, the World Traveler, and enjoy a coastal tour of some of the Mediterranean’s most jaw-dropping destinations. Beginning in Venice, Italy’s northern gem, this 10-day adventure will make stops in Italy, Croatia, Albania,...

Claire. D

“Me and my wife are both history lovers, and Out Of Office created the perfect cultural trip for our interests. ”

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David. L

“We looked at a number of travel agencies before reaching out to Out Of Office- what a stroke of luck!”

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Pedro. A

“Our Italian honeymoon couldn't have run more smoothly. We only have great things to say about the Out Of Office team.”

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Our Experts

Maria Gardner

Maria Gardner

Luxury Travel Expert

"Italy is one of the best places in Europe to experience culture, food and beautiful scenery. With so much character and colour, the Amalfi Coast is a personal favourite of mine."

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Jaike Rowe

Jaike Rowe

Luxury Travel Expert

"I never get tired of planning luxury vacations in Italy. There are so many magical cities and experiences to be enjoyed. Beaches, mountains and rolling countryside, there really is something for everyone. "

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Travel Information

Italy is a wonderful and enchanting country waiting to be discovered. The word ‘romance’ originates from Rome, where ancient monuments and cobbled streets create an environment that is perfect for romantic connection. The streets are lined with beautiful buildings and practically every one bares a trace of the city’s fascinating past. Take the time to toss three coins into the Trevi Fountain; the first ensures you will return to Rome, the second means you will find romance, and the third guarantees impending marriage. It’s lovely stories and local legends like these that elevate Rome’s reputation to truly magical levels.

With so many interesting places to visit and a bounty of historical sites to explore, you’ll never have a dull moment in stunning Italy. There isn’t an ugly building in sight and regardless of your tastes, your stomach is sure to be satisfied with the many pizzerias and fine-dining restaurants. Venice is one of the most picturesque places Italy has to offer, the labyrinth of tiny canals, the floating buildings, and stunning architecture make it a fantastic place to simply wander.

In Italy, there are so many places to visit, it’s great if you are looking for a longer holiday and equally perfect for a last-minute weekend getaway. We can put a personalized itinerary together for you, enabling you to visit wherever you would like. From the beautiful coastlines of Capri, the Amalfi Coast, and Sicily to the awesome presence of Pompeii and luxury boutiques of Milan, if you’re craving a taste of Italy, get in touch today.

Visiting Italy is a must for LGBTQ+ travelers. Milan has the biggest scene, but you’ll also find many traces of LGBTQ+ history in Italy’s unrivaled artistic landscape.

LGBTQ+ Italians enjoy a host of equality and anti-discrimination laws. However, same-sex couples are not able to adopt children together, and the country recently elected an anti-LGBTQ+ government. Italy is a very religious country, but the major cities are all home to vibrant gay scenes.

Things to do in Italy

The Colosseum

The Colosseum is a must-see attraction for anyone visiting Italy. Built in 80 AD, it could originally hold up to 80,000 spectators and was used for gladiatorial contests and other public spectacles. Today, visitors can explore the ruins and learn about the history of this impressive structure. Walking through the Colosseum is like stepping back in time, with the sounds of the crowds and swords clashing almost audible as you wander through the ruins. The Colosseum also houses a museum where you can see artifacts from ancient Rome and learn more about the amphitheater’s history. Whether you’re interested in history or architecture, the Colosseum is a must-visit attraction. The sheer size and grandeur of the structure are also sure to impress, so don’t forget to bring your camera to capture the stunning views of the Colosseum and the surrounding area.

Venetian gondola ride

One of the most quintessentially Venetian experiences is taking a gondola ride through the city’s picturesque canals. As you glide through the narrow waterways and under charming bridges, you’ll be treated to stunning views of the city’s architecture and scenery. While it may seem like a touristy activity, it’s a must-do experience that offers a unique perspective on Venice. Negotiate the price with your gondolier beforehand, and consider sharing a ride with others to save some money. Whether you opt for a private or shared ride, a gondola ride in Venice is a romantic and unforgettable way to spend an afternoon or evening.

The Leaning Tower of Pisa

The Leaning Tower of Pisa is a must-see attraction for any traveler visiting the city of Pisa. This bell tower is famous for its tilt, caused by an unstable foundation. Despite its precarious lean, visitors can climb to the top for breathtaking views of the surrounding area. Just be prepared for a bit of a workout – the tower leans at a 5.5-degree angle. Don’t forget to snap a classic tourist photo of yourself “holding up” the tower. While the tower may be a bit of a tourist trap, it’s still worth a visit. The tower is a stunning example of Romanesque architecture, and the surrounding Piazza dei Miracoli (Square of Miracles) is a UNESCO World Heritage Site. In addition to the tower, visitors can also explore the nearby Cathedral of Santa Maria Assunta and the Baptistery of St. John. For a unique experience, consider visiting the tower at night when it’s illuminated and looks even more magical under the stars.

  • January

    6°C - 13°C

    January brings averages of 8°C in Rome, with around 25 mm of rainfall. Because of the colder temperatures, prices are lower so if you are looking to save money the best time to visit is during the winter.

  • February

    6°C - 14°C

    February is similar to January with temperatures averaging at around 9°C.

  • March

    6°C - 17°C

    Temperatures start to pick up a bit with the average reaching around 12°C.

  • April

    8°C - 20°C

    April is a good time to visit if you aren't a fan of hot weather but also don't want anything too cold. With averages hitting around 15°C, it brings a pleasant atmosphere with little rain.

  • May

    13°C - 24°C

    May brings warmer temperatures and also a slight increase in average rainfall (33mm). Since it is on the cusp of the summer season it is a nice time to visit if you are looking to save money.

  • June

    17°C - 29°C

    June is the start of peak season as the weather really picks up. Enjoy long hot sunny days and very little rainfall. The Amalfi Coast comes to life during the summer with temperatures averaging at 27°C.

  • July

    19°C - 32°C

    July is very similar to June, lots of hot sunshine and little to no rainfall. Again the Amalfi Coast is a fantastic place to visit as sea temperatures reach 25°C.

  • August

    18°C - 30°C

    With it still being peak season prices are high for August but in return, you get glorious sunshine and virtually no rainfall. In Rome, temperatures average at 24°C.

  • September

    16°C - 27°C

    In September, temperatures start to cool off slightly, so it would be a good time to go if you like the heat, but nothing scorching. Average rain precipitation increases to 42mm.

  • October

    12°C - 23°C

    October sees milder temperatures and around the same rainfall as September.

  • November

    8°C - 18°C

    In November daily averages in Rome drop to 13°C. Precipitation levels increase to 50mm. Average temperatures fall to 10°C in Rome.

  • December

    4°C - 15°C

    In December rainfall jumps up quite a lot to around 96mm. If you are looking for that winter festive feeling then Rome is a great destination.

If you’re dreaming of a trip to Italy, the first step is figuring out how to get there. Luckily, there are plenty of airlines that offer flights to Italy from all over the world. Some of the most popular airlines include Alitalia, Delta, American Airlines, United, and Emirates. To save money and ensure availability during peak travel seasons, it’s best to book your flights in advance. And when it comes to choosing an airport, consider flying into major hubs like Rome’s Fiumicino Airport or Milan’s Malpensa Airport for easy access to transportation options.

Traveling by train in Italy is a convenient and efficient way to explore the country. Trenitalia, the national train company, operates an extensive network that connects major cities and smaller towns. For those looking to travel quickly between major cities like Rome, Florence, and Venice, the high-speed trains, known as Frecciarossa, Frecciargento, and Frecciabianca, offer a comfortable and speedy option. Regional and local trains are also available for those looking to explore smaller towns and villages.

Before embarking on your trip to Italy, it’s crucial to determine whether or not you need a visa. Depending on your country of origin, the length of your stay, and the purpose of your visit, you may or may not require a visa. It’s important to choose the right type of visa for your specific situation, as there are various options available, including tourist, business, study, and work visas. Each type of visa has its own set of requirements and restrictions, so it’s essential to carefully review your options and select the one that best suits your needs. Our team of travel experts can assist you in navigating the visa application process and ensuring that you have all the necessary paperwork and documents for your international travel. Contact us today to learn more.

From the blog

The top places to visit in Rome, according to the locals
The top places to visit in Rome, according to the locals

A new survey of Italian locals has found that the most popular tourist attraction is the Colosseum. Over 29% of residents surveyed by a car rental company Autoclick listed the iconic and largest amphitheatre in the world as the place...

Matera: Italy's Ancient Cave City
Matera: Italy's Ancient Cave City

Matera is the 2019 European Capital Of Culture. Perched above a ravine in the region of Basilicata, it’s one of the most beautiful and enigmatic cities Europe. It’s also Italy’s best-kept secret, having only emerged as a tourist destination in...

Amalfi Coast or Cinque Terre – which is better?
Amalfi Coast or Cinque Terre – which is better?

The Amalfi Coast and Cinque Terre are two of Italy’s most popular and luxurious destinations. Both call to mind colourful buildings perched over cliffs and dreamy sunsets. Cinque Terre is located in northwest Italy on the Italian Riviera. The Amalfi...

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