Luxury Italy vacations

Italy Luxury Tours & Vacations & Holidays 2025 & 2026

Proudly LGBTQ+ Experts and Welcoming to All Travelers


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 luxury trip to Italy.

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.

Why is Italy a popular luxury travel destination?

? 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 great variety, with reliable transport links making many of the hotspots easily accessible. For example, you can easily combine Venice, Verona, Florence and Lake Garda in a single trip.

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

History buffs can head to Rome to find ancient ruins like the Colosseum and the Vatican. Art aficionados can flock to Florence to see Renaissance treasures, including Michelangelo’s David. You can also explore the Uffizi Gallery, where you’ll find the world’s greatest collection of Renaissance art, most of which was created in Italy.

Italian cuisine reveals its true magic not through individual dishes but through its profound regionalism, where every province, city, and village maintains fiercely protected culinary traditions that reflect local geography, history, and culture. Travel from Bologna’s rich, egg-based tagliatelle with ragù to Rome’s simple yet perfect cacio e pepe, from Sicily’s Arab-influenced arancini to Venice’s fresh crudo preparations, and you’ll discover that “Italian food” is actually dozens of distinct culinary languages speaking through local ingredients and ancestral techniques.

At Out Of Office, we have fantastic relationships with Italy’s most exclusive and sought-after hotels – get in touch with one of our travel experts to begin planning your bespoke Italian getaway.


More Trips in Italy

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Italy’s Romeo & Juliet Trail: Verona, Venice & Florence
Italy’s Romeo & Juliet Trail: Verona, Venice & Florence

Tailor-Made Vacation

Italy is one of the most romantic destinations in the world. Shakespeare set Rome and Juliet in Verona for a reason. He probably never visited Italy but it existed in his imagination as a place of romance. With this itinerary,...

Gay Group Trip: Tuscany Explorer
Gay Group Trip: Tuscany Explorer

Group Trip Departs: • 22nd July 2025 • 5th September 2025

Stay in a 600-year old castle in Tuscany, perched on a hillside overlooking vineyards and a historic village. You’ll be exploring one of the most beautiful parts of Italy with 30 gay travelers. Sun yourself by the private pool, explore...

Bavarian Alps and Dolomites Tour
Bavarian Alps and Dolomites Tour

Tailor-Made Vacation

This bespoke itinerary invites you to discover the soul of southern Germany, Austria, and Italy, weaving together cultural treasures, natural beauty, and gourmet experiences. From the historic streets of Munich to the soaring peaks of the Dolomites, every moment has...

Naples and Amalfi Coast
Naples and Amalfi Coast

Tailor-Made Vacation

Delve into the vibrant culture and breathtaking scenery of southern Italy with this Naples and Amalfi Coast luxury vacation. This exquisite journey is a delightful exploration of the region’s rich historical tapestry, complemented by the stunning natural beauty of one...

Call Me By Your Name Filming Locations
Call Me By Your Name Filming Locations

Tailor-Made Vacation

Dive into the captivating scenes and settings of Call Me By Your Name with this bespoke Italian vacation, meticulously curated for fans of the acclaimed novel and film, as well as those who cherish Italy’s romantic allure. This journey invites...

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

Group Trip

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...

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 for Italy

General Information


Italy’s strategic position at the crossroads of Europe, Africa, and the Mediterranean has shaped it into one of the world’s most geographically and culturally diverse nations. The country stretches like a boot into the Mediterranean Sea, encompassing dramatic Alpine peaks in the north that share borders with France, Switzerland, Austria, and Slovenia, while its southern regions bask in warm Mediterranean sunshine across Sicily and Sardinia.

This remarkable topographical diversity creates distinct regional climates and landscapes: the industrial prosperity of Lombardy and Piedmont contrasts sharply with the sun-soaked olive groves of Puglia, while the volcanic drama of Mount Etna and Vesuvius offers stark contrast to the rolling hills of Tuscany and Umbria.

The country’s extensive coastlines along both the Adriatic and Tyrrhenian seas provide thousands of kilometers of beaches, from the glamorous Riviera to the dramatic Amalfi Coast, while inland regions feature pristine lakes like Como and Garda that have attracted aristocratic visitors for centuries.

Italy’s tourism industry ranks among the world’s most significant, welcoming over 60 million international visitors annually who contribute more than €50 billion to the national economy. This success stems from the country’s unparalleled concentration of UNESCO World Heritage Sites 58 in total, more than any other nation, spanning from ancient Roman ruins like the Colosseum and Pompeii to Renaissance masterpieces in Florence and Venice’s unique lagoon architecture.

Italy LGBTQ+ Rights


Italy offers a mix of progress and challenges when it comes to LGBTQ+ rights. LGBTQ+ individuals benefit from anti-discrimination laws that protect against bias based on sexual orientation and gender identity, and same-sex couples have had access to civil unions since 2016. These unions provide many of the legal rights associated with marriage, such as inheritance and hospital visitation. However, same-sex marriage itself is not recognized, and joint adoption rights for same-sex couples remain unavailable, reflecting gaps in full equality.

In recent years, the political landscape has become more conservative, with policies that complicate family recognition for LGBTQ+ individuals. This includes restrictions on surrogacy, both domestically and abroad, which have disproportionately impacted same-sex couples looking to start families. Despite these setbacks, public opinion is gradually becoming more supportive of LGBTQ+ rights, driven by younger generations and urban communities.

Northern cities like Milan, Turin, and Venice generally offer welcoming, cosmopolitan environments where same-sex couples encounter little hostility, while Rome has developed vibrant gay districts around areas like San Giovanni and Testaccio.

However, more conservative regions, particularly in the rural south, may present challenges for openly LGBTQ+ visitors. Italy’s luxury hospitality sector, particularly international hotel chains and high-end properties, maintains professional standards that welcome all guests regardless of orientation, while major cities host established Pride celebrations and maintain active gay scenes.

Visit The Colosseum

The Colosseum is Rome’s most iconic monument and one of the world’s most recognizable structures, a massive amphitheater that once hosted gladiatorial contests, wild animal hunts, and elaborate spectacles for up to 80,000 spectators during the height of the Roman Empire nearly 2,000 years ago. Built between 70-80 AD under emperors Vespasian and Titus, this architectural marvel showcased Roman engineering prowess with its complex system of underground chambers (the hypogeum), retractable awnings for weather protection, and sophisticated crowd control mechanisms that could empty the entire structure in just 15 minutes.

Today’s visitors can explore this UNESCO World Heritage site through various access levels, from standard admission that covers the main arena floor and first two tiers, to premium experiences including underground chamber tours, third-tier access offering panoramic views over the Forum, and after-hours visits that avoid daytime crowds while providing dramatic evening lighting.

Modern conservation efforts have restored sections of the arena floor, allowing visitors to stand where gladiators once fought while digital reconstructions and audio guides bring the ancient spectacles to life, though the experience requires patience for security lines and advance booking during peak season. Despite the crowds and commercialization that surround this tourist magnet, standing within the Colosseum’s weathered walls remains a profoundly moving encounter with history that connects contemporary visitors directly to the grandeur and brutality of ancient Rome.

Visit The Leaning Tower of Pisa

The Leaning Tower of Pisa may well be the world’s most famous architectural accident, a stunning white marble bell tower that began tilting during construction in the 12th century due to unstable foundation soil – transforming what should have been a straightforward religious monument into an inadvertent masterpiece that has captivated visitors for nearly 900 years.

Originally designed as the freestanding campanile for Pisa’s cathedral complex, the tower began leaning when builders reached the third floor around 1178, prompting medieval engineers to attempt corrections by making subsequent floors taller on one side, creating the distinctive curved appearance that adds to its charm today. Modern visitors can now safely climb the tower’s 296 steps to the top (limited to 30 people at a time with advance reservations essential), experiencing the disorienting sensation of walking up an increasingly tilted spiral staircase while enjoying spectacular views over Pisa’s red-tiled rooftops and the surrounding Tuscan countryside.

The tower’s location within the stunning Campo dei Miracoli (Field of Miracles) means your visit encompasses not just the famous lean, but also the magnificent Romanesque cathedral, circular baptistery with its perfect acoustics, and peaceful cemetery, all constructed from the same luminous Carrara marble that gives the complex its ethereal beauty. While the tower’s fame has made it something of a tourist circus with countless visitors posing for “holding up the tower” photos, the actual experience of standing before this gravity-defying monument and climbing through its ancient chambers remains genuinely awe-inspiring, proving that sometimes the most beautiful destinations are born from happy accidents rather than perfect planning.

Truffle Hunting in Umbria

Umbria’s misty forests conceal one of Italy’s most exclusive and secretive culinary traditions – truffle hunting with trained dogs in private woodlands that have yielded these precious “diamonds of the kitchen” for centuries. This ancient practice takes place at dawn when scents are strongest, as you follow local tartufari (truffle hunters) and their specially trained Lagotto Romagnolo dogs through oak and hazelnut groves near medieval towns like Norcia, Spoleto, and Gubbio. The experience transcends typical food tourism as you witness the remarkable partnership between hunter and dog, learning to read subtle signs in the forest floor while discovering why these ugly, aromatic fungi can command prices exceeding gold per ounce – white truffles can reach €3,000 per kilogram during peak season.

What makes Umbrian truffle hunting truly special is its authentic, family-based nature – many truffle hunters guard their secret locations jealously, passing down forest maps and hunting techniques through generations while maintaining relationships with specific restaurants and dealers. Visitors who arrange these exclusive experiences through local contacts rather than tourist operators often conclude their hunts with intimate meals in centuries-old farmhouses where the morning’s discoveries are shaved over handmade pasta, paired with local Sagrantino wines, and accompanied by stories of legendary finds and family rivalries. The combination of adventure, natural beauty, and extraordinary gastronomy creates encounters with Italian food culture that go far beyond restaurant dining, connecting travelers directly to ancient traditions where the forest’s mysteries are unlocked through knowledge, patience, and the extraordinary bond between humans and their four-legged hunting partners.

 

Weather in Italy


  • 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.

Getting to Italy


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

Amalfi Coast or Cinque Terre - which is better?
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Luxury Wine Tasting on the Amalfi Coast: The Best Vineyards to Visit
Luxury Wine Tasting on the Amalfi Coast: The Best Vineyards to Visit

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The Best Vatican Relics to Visit
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Atrani, Amalfi, or Ravello: Where to Stay on the Amalfi Coast?
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A Luxury Gay Guide to Rome
A Luxury Gay Guide to Rome

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Exploring Milan and Lake Como
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Luxury Hotels from Gay Movies You Can Visit
Luxury Hotels from Gay Movies You Can Visit

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The Best Gay Honeymoon Destinations in Europe
The Best Gay Honeymoon Destinations in Europe

Europe is an unbeatable destination for a honeymoon. It’s packed with romantic cities and towns, not to mention history. Italy alone is like an open-air museum you could spend a lifetime exploring. We have helped thousands of clients choose the...

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