Italy is a destination that's made for slow, month-by-month discovery.

From the snow-capped Dolomites in January to the sun-drenched shores of Lake Como in August, every corner of the country offers something unique as the seasons shift.

Whether you’re drawn to ancient ruins and UNESCO World Heritage sites, or prefer lazy afternoons on the sandy beaches of Southern Italy, this guide will help you time your trip just right.

Along the way, we’ll take you to cities steeped in rich history, towns brimming with Renaissance art, and landscapes so diverse they feel like multiple countries in one.

What's more, we’ve paired each destination with a handpicked luxury stay to seriously enhance your experience, wherever you choose to go.

“Italy’s charm lies in its diversity and seasons. I’ve carefully chosen each destination and luxury stay in this guide to showcase its unique character — from vibrant cities to tranquil coastlines — ensuring you experience the authentic warmth, history, and beauty that make Italy a place you’ll want to return to time and time again.”

Alice, Europe Product Manager

Alice, Europe Product Manager

1. January: Dolomites

  • World-class skiing without the crowds

  • High-altitude dining done properly

  • A slower, more elegant winter escape

Dolomites, Italy

Best known for their jagged peaks and UNESCO-listed beauty, the Dolomites offer a very different kind of Italian winter. In January, when the snow is fresh and the crowds are few, it’s all about crisp mornings on the slopes and long, leisurely lunches in the sun.

Alpe di Siusi is a standout — Europe’s largest high-altitude plateau, known for its wide-open pistes, scenic cross-country trails and cosy mountain huts serving hearty South Tyrolean dishes with a side of spectacular views.

This isn’t a place that shouts. Charming villages like Castelrotto and Siusi feel rooted in tradition, with chalet hotels, herbal-infused spa rituals and menus that draw on the alpine larder — think speck, mountain cheese and elderflower syrups. There’s beauty in the big views — pink-tinged peaks at dusk, meadows buried in snow — but also in the pace of it all.

Off the slopes, it’s all horse-drawn sleigh rides, forest walks and that quiet kind of après-ski where you sip wine by the fire rather than dance on tables. For a winter escape that blends elegance with ease, and skiing with soul, the Dolomites in January are hard to beat.

Where to stay?

Hotel: COMO Alpina Dolomites

COMO Alpina Dolomites

Perched on the Alpe di Siusi plateau, COMO Alpina Dolomites is an uber-stylish retreat surrounded by dramatic mountains and wide-open skies. This sleek stone-and-timber hideaway offers a front-row seat to one of the quietest corners of the Dolomites — a place for skiing, snowshoeing or simply savouring the stillness that comes with fewer crowds.

Inside, interiors are calm and considered, all soft wood, earthy tones and vast windows framing the peaks. The COMO Shambhala spa delivers serious switch-off time, while evenings unfold fireside with hearty mountain flavours and local wine. Combining wellness with wilderness and a striking contemporary design, this is alpine living at its most refined.

2. February: Venice

  • Carnival season with masquerade balls

  • Famous landmarks without the crowds

  • Atmospheric in winter: misty mornings & golden light

Venice is an enchanting Italian city, unlike any other — a labyrinth of narrow alleys leading to hidden squares, cosy cafés, and centuries-old churches. Visiting in February means experiencing this unique city at its most atmospheric, with fewer crowds and a mysterious, misty charm that feels straight out of a storybook.

The city’s heartbeat is the Grand Canal: a shimmering waterway lined with grand palazzos that whisper tales of Venetian nobility and maritime glory. Along its winding route, you’ll find St Mark’s Basilica soaring above the famous square, the ornate Doge’s Palace steeped in history, and the iconic Rialto Bridge bustling with passers-by.

There’s no better way to soak it all in than on a guided tour, where a knowledgeable local brings the city to life — uncovering not just the iconic landmarks, but also those tucked-away gems you might otherwise miss.

Whether you glide through the canals on a gondola or stroll the vibrant streets, Venice feels like a living museum, every corner offering a picture-perfect moment enhanced by the soft winter light of February. After a day exploring, unwind at a waterside café, sipping a warming spritz as the sun sets over the lagoon.

Where to stay?

Hotel: The Gritti Palace, a Luxury Collection Hotel

The Gritti Palace, a Luxury Collection Hotel

Once the private residence of Doge Andrea Gritti, this 15th-century palazzo on Venice’s Grand Canal is now a masterpiece of restored opulence. The Gritti Palace, a Luxury Collection Hotel blends Murano chandeliers, Rubelli silks and antique furnishings with modern comforts, offering 82 uniquely styled rooms and suites — some named after illustrious guests like Hemingway and Guggenheim.

During your winter getaway, savour refined Venetian cuisine at Club del Doge, unwind at the Sisley Paris spa or learn Italy's culinary secrets at the Gritti Epicurean School. With its prime San Marco location and rich heritage, the Gritti Palace epitomises timeless Venetian elegance.

"Staying at The Gritti Palace was like stepping into a Venetian painting. Overlooking the Grand Canal with uninterrupted views towards the lagoon, its location is unmatched. Watching the sun rise over the water from my window was a moment I’ll never forget – pure Venetian elegance, right at the heart of it all." — Alice, Europe Product Manager.

3. March: Rome

  • Mild weather and fewer crowds at iconic sites

  • Spring blooms brighten up the city scenery

  • Local life buzzes back at cafes & bars

Rome, Italy

March is a wonderful time to experience the Eternal City at its most atmospheric. With the soft light of early spring casting a golden glow over its ruins and rooftop terraces, Rome reveals a quieter, more romantic side before the summer crowds descend.

You can wander cobbled streets and piazzas with ease, uncovering layers of ancient history without the rush — from the imposing Colosseum to the crumbling majesty of the Roman Forum, where wildflowers begin to bloom between centuries-old stones.

Italy’s capital city feels more intimate in March. Locals reclaim the cafés and fountains, and there’s space to pause by the Trevi Fountain without the usual bustle, tossing a coin into its waters to ensure your return to Rome — or so the legend goes. Alfresco lunches return as the temperature gently rises, and the city’s many gardens — from the Villa Borghese to the Orange Garden on the Aventine Hill — begin to stir into life.

This is a Rome of soft jackets, early evening aperitivi and spontaneous detours down ivy-draped alleyways. It’s the perfect month to fall in love with the city all over again — or for the very first time.

Where to stay?

Hotel: Hotel de la Ville, a Rocco Forte Hotel

Hotel de la Ville, a Rocco Forte Hotel

Overlooking Rome’s iconic Spanish Steps, Hotel de la Ville, a Rocco Forte Hotel, offers an irresistible blend of classic Italian grandeur and contemporary flair. Housed in a refurbished 18th-century palazzo, this refined property features beautifully designed interiors — think antique furnishings, dazzling chandeliers and ornate stone balconies.

Enjoy Michelin-standard dining at Mosaico or rooftop cocktails with panoramic views at Cielo Bar, while the Irene Forte Spa provides a tranquil sanctuary with Sicilian-inspired treatments.

Located in the heart of Rome’s historic centre, just moments from landmarks like the Trevi Fountain and Via dei Condotti, it’s the ideal base for exploring Rome in style.

4. April: Florence

  • Admire Renaissance art without the usual crowds

  • Enjoy alfresco dining in vibrant piazzas

  • Browse markets bursting with fresh produce

Florence, Italy

In-the-know travellers flock to Florence in April, when the city shakes off winter’s chill and bursts into life. Steeped in history, Florence is a living gallery of Renaissance masterpieces, from Michelangelo’s David to Botticelli’s Birth of Venus, all nestled within its historic buildings. The city’s lively piazzas — Piazza della Signoria and Piazza del Duomo among them — buzz with locals enjoying café culture and street performers.

Spring is also market season, and Florence’s bustling markets, like San Lorenzo, brim with fresh produce, leather goods and handcrafted souvenirs. Wander through Mercato Centrale, where the mingling aromas of fresh bread, rich espresso and Tuscan herbs invite you to pause and indulge.

April’s mild weather also lends itself to alfresco dining and long, leisurely strolls along the Arno, where you can admire the Ponte Vecchio’s picturesque architecture without the summer crowds. With fewer tourists and an air of renewal, Florence truly feels like the beating heart of Italy in spring.

Where to stay?

Hotel: Portrait Firenze

Portrait Firenze

Set along the Arno River with unbeatable views of the Ponte Vecchio, Portrait Firenze blends mid-century glamour with its Florentine heritage.

Owned by the Ferragamo family, this boutique hotel comprises just 37 suites designed by Michele Bönan, featuring warm wood tones, vintage photography, and Carrara marble bathrooms. Floor-to-ceiling windows frame the river, while discreet kitchenettes and curated bookshelves add a homely touch.

The Lifestyle Team at the hotel can also craft bespoke experiences for you during your stay — from private museum tours to Vespa rides through the city. After a day exploring, head downstairs to Caffè dell’Oro, where modern Italian dishes are given a global twist and served on the riverside terrace, where you can watch the world drift by as you dine.

With its central location and thoughtful touches throughout, Portrait Firenze is a stylish, intimate base for discovering Florence’s art, fashion, and culture.

Feeling inspired by this article so far? Keep reading for more, or speak to our team to start planning.

As a reminder, your Inspiring Travel holiday will always include:

  • All flights with premium lounge passes at UK airports
  • VIP meet & greet service at departure
  • Private transfers to and from your hotel
  • Personal concierge service throughout
  • 24/7 assistance when travelling
  • The first-hand knowledge of our team

Peter

Travel Specialist

I'm here to tailor-make your perfect holiday. Give me a call and I'll use my expertise to create your personalised experience.

5. May: Tuscany

  • Perfect weather for scenic drives and countryside strolls

  • Local cuisine is at its freshest with spring produce

  • World-class wine tasting minus the summer crowds

Tuscany, Italy

Come May, Tuscany is at its most glorious. The rolling hills are lush and green, dotted with vineyards, olive groves and poppy fields in bloom — a picture-perfect backdrop to days spent exploring the region’s rural beauty. With the summer crowds still a few weeks away, the pace is unhurried, and the weather is just right for scenic drives through the Tuscan countryside or lazy afternoons by a hilltop pool.

This is also the moment when Tuscany’s local cuisine truly shines. Seasonal produce fills the markets, from artichokes and asparagus to cherries and broad beans — all making their way onto menus in traditional trattorias and family-run osterias. Al fresco dining becomes a daily ritual, best paired with a crisp local white or a bold Chianti Classico.

Of course, no trip here is complete without wine tasting. May is a fabulous time to visit the region’s celebrated vineyards, where cellar doors open to sun-dappled terraces and passionate winemakers are keen to share their craft with the first visitors of the season.

Whether you’re wandering medieval towns like San Gimignano or sipping something special in a rustic winery, Tuscany in May feels like the real Italy — warm, welcoming, and wonderfully indulgent.

Where to stay?

Hotel: Castel Monastero

Castel Monastero

Tucked away among the Chianti vines in the majestic Ombrone Valley, Castel Monastero is a beautifully restored 11th-century hamlet surrounded by stunning landscapes of vineyards, olive groves, and cypress-lined hills.

This remarkable property offers an authentic slice of Tuscan countryside hospitality. The hotel’s wine cellar is a standout, showcasing local vintages from nearby estates, while Tuscan cuisine is elevated in the hands of expert chefs at Contrada restaurant, which received its first Michelin star back in 2024.

Days here are delightfully unhurried — immerse yourself in a cooking class, unwind in the 1,000-square-metre spa, or explore the region with guided tours, golf, polo, or even truffle hunting. This is Tuscany at its most indulgent!

"Castel Monastero is perfectly placed for exploring Siena, just a 30-minute drive through the Tuscan countryside. On our visit, we had a guided tour of the city and learned all about the Palio – Siena’s legendary bareback horse race, held each summer in Piazza del Campo. It’s not just a race, but a centuries-old tradition of fierce local pride, passion and pageantry." — Alice, Europe Product Manager.


Drive through the rolling hills of Tuscany and beyond with the help of our podcast

6. June: Portofino

  • Warm, sunny days — perfect for harbour strolls

  • Fewer crowds in the villages for a laidback vibe

  • Fresh seafood and al fresco dining

Portofino, Italy

Portofino has long been the Italian Riviera’s crowning jewel, a once-sleepy fishing village that’s quietly become the playground for elite travellers. Since the 1950s, it’s drawn a glamorous crowd — from Hollywood stars to European aristocrats — all captivated by its colourful harbour and narrow streets lined with luxury boutiques and seafood trattorias.

June is the ideal time to visit, when the crowds are lighter, but the village is alive with sunshine and the scent of the sea. Spend your time savouring fresh seafood and local wine on a waterside terrace, before taking a sunset stroll through Portofino’s maze of narrow streets.

For a true taste of the Italian Riviera lifestyle, head to one of the harbour bars where the vibe is relaxed but undeniably stylish. Whether you’re cruising along the coast or simply soaking up the village’s quaint charm, Portofino in June is the epitome of sophisticated coastal living.

Where to stay?

Hotel: Splendido, A Belmond Hotel, Portofino

Splendido, A Belmond Hotel, Portofino

Perched high above Portofino’s glittering harbour, Splendido, A Belmond Hotel, Portofino is an icon of the Riviera. Originally a 16th-century Benedictine monastery, it has evolved into one of Italy’s most celebrated luxury retreats. The hotel’s hillside location offers sweeping views of the Ligurian coastline, while its lush gardens and Mediterranean-style terraces provide a seriously serene escape.

Inside, the hotel exudes understated glamour, with rooms and suites adorned in soft pastels and featuring private balconies. Foodies will love it here, as you can feast on exceptional Ligurian cuisine at La Terrazza, the hotel's main restaurant, or if relaxation is on the cards, the Dior Spa has got you covered with a range of treatments inspired by the region's abundant natural beauty.

7. July: Amalfi Coast

  • Sunny days made for boat tours on the Mediterranean

  • Long, alfresco lunches with fresh seafood & sea views

  • Cliffside villages come alive with culture & colour

Amalfi Coast, Italy

The Amalfi Coast in July feels like a postcard come to life. This stretch of Southern Italy is famed for its steep cliffs draped with terraced vineyards and lemon groves, tumbling down to meet the shimmering Mediterranean Sea. Small fishing villages like Positano and Amalfi buzz with energy, their narrow streets winding past pastel-hued houses and bustling piazzas.

A boat tour is the best way to take it all in — from hidden coves and secret beaches to the dramatic coastline dotted with villas that cling precariously to the cliffs. Onshore, fresh seafood is the star of the show. Local restaurants serve the catch of the day with views of the infinite blue sea, where the fresh flavours of the Mediterranean marry perfectly with traditional Italian ingredients.

Despite the summer crowds, the Amalfi Coast manages to keep its easygoing ambiance. Evenings bring the smell of salt air mingling with garlic and herbs as diners gather to enjoy the local cuisine beneath fairy-lit terraces. In July, this part of Southern Italy feels vibrant, alive and utterly irresistible.

Where to stay?

Hotel: Caruso, A Belmond Hotel, Amalfi Coast

Caruso, A Belmond Hotel, Amalfi Coast

Set 1,000 feet above the Mediterranean in Ravello, Caruso, A Belmond Hotel, Amalfi Coast is a former 11th-century palace turned cliffside sanctuary. Its standout feature is its showstopping infinity pool, seemingly suspended between sea and sky, offering panoramic views of the Amalfi Coast.

The hotel's terraced gardens are a fragrant mix of lemon trees and roses, leading to frescoed halls and vaulted suites that retain their historic grandeur. Dining at the al fresco Belvedere Restaurant is another 'must do' while staying here, where Neapolitan cuisine is crafted from fresh, local ingredients.

In July, Caruso offers complimentary boat tours along the coast, so you can explore the region's hidden coves and charming seaside towns, like Positano, at your leisure.

8. August: Italian Lakes

  • Swim in crystal-clear lakes beneath alpine peaks

  • Explore elegant villas with manicured gardens

  • Enjoy sunset aperitivi with stunning lake views

Italian Lakes

Set against the foothills of the Alps in Northern Italy, the lakes of Como and Garda offer a cool, refined escape from the August heat. This is a land of extraordinary natural beauty — where cypress-studded hills meet glistening waters, and boats skim across mirror-still surfaces beneath pastel-coloured towns.

It’s little wonder the scenery has drawn artists, writers, and filmmakers for centuries — including George Lucas, who famously chose Lake Como as a filming location for Star Wars: Attack of the Clones.

Lake Como, with its winding shoreline and elegant villas with botanical gardens, has long been a magnet for discerning travellers. Many arrive by boat, hopping between hillside towns like Bellagio and Varenna, or pausing for gelato along flower-lined promenades. Further east, Lake Garda is bigger and a touch more playful, with medieval castles, cable cars and lakeside markets.

In both regions, the views are nothing short of spectacular — whether you’re sipping espresso by the water or swimming with the mountains at your back. And while the days are wonderful for exploring, there’s no rush. Life around the lakes moves at its own pace — slow, scenic, and sophisticated. August never looked so good.

Where to stay?

Lake Como:

Grand Hotel Tremezzo

If it's refined Italian hospitality you're looking for, then look no further than Grand Hotel Tremezzo.

Grand Hotel Tremezzo is a showstopper on Lake Como’s western shore, offering Art Nouveau glamour and cinematic views across the water to Bellagio. Days here are spent floating in the resort's famous 'Water on Water' lake pool, wandering manicured gardens or soaking up the mountain backdrop from the T Spa. Inside, it’s all gilded mirrors and velvet armchairs — an opulent base for exploring Northern Italy’s breathtaking landscapes.

Lake Garda: Lefay Resort & Spa Lago di Garda

Lefay Resort & Spa Lago di Garda

Lefay Resort & Spa Lago di Garda is a rare find — a luxury sanctuary set above the lake’s sparkling waters. Surrounded by fragrant olive groves and lush woodlands, it boasts mesmerising views of Lake Garda and a 4,300-square-metre spa dedicated to relaxation and wellbeing.

Plus, with two exceptional Mediterranean restaurants and a strong commitment to sustainability, Lefay combines luxury, nature, and wellness like no other hotel on Lake Garda!

"Lefay Resort Lago di Garda is one of the most breathtaking places I’ve ever experienced – the scent of lemon trees, the stillness of the lake below, and infinity pools overlooking the mountains. It’s the ultimate retreat for serenity, scenery and soul-soothing luxury." — Alice, Europe Product Manager.

9. September: Sicily

  • Soak up the late-summer sun, sans the crowds

  • Ideal time of year for hiking Mount Etna & nature trails

  • Enjoy a street food tour in Palermo without the queues

Sicily

Sicily’s magic lingers long into September, when the summer crowds thin out and the island’s natural beauty and old-world charm take centre stage.

The sea is still warm enough for swimming, so you can hop between white-sand beaches and rocky coves on the west coast, or sail out to the Egadi Islands for a snorkelling fix. Inland, the landscape is dramatic — especially around Mount Etna, Europe’s largest volcano, where hiking trails weave through surreal lava fields and wineries dot the foothills.

Palermo, the regional capital, is a chaotic feast for the senses — and best explored on a street food tour. Expect deep-fried arancini, sizzling panelle, and sweet cannoli served with stories passed down through generations.

For something wilder, head to Madonie National Park, where scenic trails wind through ancient villages, oak forests, and limestone peaks. Or Zingaro Nature Reserve — located on the coast between San Vito Lo Capo and Scopello — where you'll walk through fragrant Mediterranean scrub to discover secret beaches.

Sicily in September feels balanced — warm but not sweltering, vibrant but not chaotic. It's when the island's wild beauty, layered history, and unique culture come together in the most rewarding and enjoyable way.

Where to stay?

Hotel: San Domenico Palace, a Four Seasons Hotel

San Domenico Palace, a Four Seasons Hotel

Perched on a cliff above the Ionian Sea, San Domenico Palace, a Four Seasons Hotel is Sicily’s most iconic stay — a 14th-century monastery transformed into a luxurious hotel in the heart of Taormina.

Here, you can soak in the infinity pool with Mount Etna on the horizon, wander lemon-scented cloisters, and savour Michelin-starred dining at Principe Cerami. Its cinematic allure was showcased in series two of HBO’s The White Lotus, but the real magic lies in its serene gardens, impeccable service, and awe-inspiring views, which are around every corner.

With Taormina’s ancient Greek theatre and stylish boutiques just a short stroll away, this is a stay that feels both deeply Sicilian and seriously special.

10. October: Puglia

  • Wander sun-kissed cliffs and secret coves in peace

  • Harvest season means fresh food & local wine tasting

  • Perfect weather for exploring hilltop villages & trulli houses

Puglia, Italy

Tucked into the heel of Italy’s boot, Puglia is a well-kept secret worth uncovering. October brings calm — the crowds fades, the sea stays warm, and the sun casts a honeyed glow over olive groves and weathered villages. Dramatic cliffs and rugged landscapes stretch alongside hilltop towns that gaze out over the shimmering Adriatic, creating a place of natural contrasts and quiet wonder.

Puglia is also a treasure trove of captivating towns: whitewashed Ostuni, with its labyrinthine lanes; baroque Lecce, often dubbed the 'Florence of the South'; and Alberobello, famous for its storybook trulli.

The food is rustic, honest, and utterly delicious: think orecchiette pasta, creamy burrata and just-caught seafood served with a drizzle of local olive oil. And with harvest season in full swing, October is ideal for sampling the region’s wines straight from the source.

Puglia’s wonders are quiet but deeply felt — this isn’t just a place to visit, it’s a place to sink into. And in autumn, it’s nothing short of enchanting.

Where to stay?

Hotel: Borgo Egnazia

Borgo Egnazia

Borgo Egnazia is a modern classic: a reimagined Puglian village set between ancient olive groves and the Adriatic Sea. Built from creamy local stone, its candle-lit alleyways, bougainvillea-draped courtyards and piazza feel timeless, though the resort itself is just over a decade old.

Rooms and villas are styled with rustic elegance, while the Vair Spa offers treatments inspired by regional rituals. Dining is another highlight — from the Michelin-starred Due Camini to the traditional flavours of La Frasca. It's a property that embrace's Puglia's poetic, old-world essence, but in the most polished way possible. 

11. November: Verona

  • Fewer crowds at iconic sites like Juliet’s House

  • Cosy cafés and trattorias are ideal for autumn evenings

  • Enjoy opera and art in an intimate, festive atmosphere

Verona, Italy

Often overshadowed by Italy’s bigger-hitting cities, Verona is a revelation — and November is the best time to discover it. With the summer crowds gone and the mist curling over the Adige River, this romantic city takes on a dreamlike quality. Fewer visitors mean you can linger longer at the best historical sites, from the ancient Roman Arena to Juliet’s famous balcony, without jostling for space.

The city’s compact centre is easily explored on foot, so lace up your comfiest shoes for a gentle walking tour through cobbled lanes and picturesque piazzas. You’ll pass medieval churches, Renaissance palazzi, and quiet courtyards that feel frozen in time. Café terraces stay open late into autumn, so you can indulge in a spot of people-watching too, over a rich Italian coffee. 

Verona also shines when it comes to culture: in November, theatres and galleries come to life with concerts and exhibitions. And then there’s the food. This is truffle season in Northern Italy, and restaurants serve comforting risottos and rich pastas that set you up well for the crisp evenings.

Verona in November is slower, softer, yet still culturally vibrant — a city that rewards those who venture beyond the usual and visit outside the peak season.

Where to stay?

Hotel: NH Collection Palazzo Verona

NH Collection Palazzo Verona

Just steps from Verona’s Roman Gate and a short stroll from Juliet’s House, NH Collection Palazzo Verona puts you right at the heart of the city's most famous attractions. This restored 14th-century palazzo houses its own museum, complete with ancient mosaics and ruins beneath your feet. Rooms are stylish yet understated, while the restaurant serves authentic Italian cuisine in an elegant dining room.

Order a cocktail in the Lobby Bar and you’ll be treated to a surprise gourmet canapé — a little extra indulgence to end the day. With major sights on your doorstep, there's no better base for exploring Verona on foot.

12. December: Milan

  • Shop chic boutiques lit up for the festive season

  • See da Vinci’s Last Supper at Santa Maria delle Grazie

  • Warm up in cool restaurants serving Northern Italian comfort food

Milan, Italy

Milan may be Italy’s fashion capital, but come December, it takes on a different kind of glamour. Lights drape the grand facades of the Duomo and Galleria Vittorio Emanuele II, while locals and visitors dip in and out of chic boutiques, stocking up on seasonal gifts and winter staples. Panettone lines the shelves of every pasticceria, and aperitivo hour takes on a festive twist with mulled wine and rich northern fare.

Beyond the shopping and cool restaurants, there’s culture in spades. Santa Maria delle Grazie is quieter in winter, giving you space to really take in da Vinci’s The Last Supper. Contemporary art spaces like Fondazione Prada and Pirelli HangarBicocca provide a sharp contrast to the Renaissance treasures.

Milan in December isn’t showy — it’s stylish, yes, but also grounded in tradition. It’s a city where you can see world-class art, sip something strong in a snug bar, and watch the city light up under a wintry sky.

Where to stay?

Hotel: Portrait Milano

Portrait Milano

Step through the grand Baroque gateway into Portrait Milano, a sanctuary of style tucked within a 16th-century former seminary. Overlooking the elegant Piazza del Quadrilatero — the largest square in Milan’s famed fashion district — this refined retreat blends heritage with high design.

Interiors by Michele Bönan pair warm woods and plush textures with bathrooms lined in gleaming Italian marble, while original monk’s drawings recovered from the vaults offer a quiet nod to the building’s past.

Downstairs, Beefbar Milano serves up a bold menu of gourmet street food and haute cuisine, rounding off an effortlessly chic stay in Italy’s style capital.

Top tailor-made Italy holiday ideas

Don't limit yourself to just one of Italy's most beautiful spots - our Travel Specialists can tailor your own bespoke itinerary, so you can get the most out of your holiday.

Inspired to explore Italy all year round?

Whether you’re a history buff drawn to ancient archaeological sites, a sun-seeker dreaming of beautiful beaches, or simply planning your next unforgettable Italy holiday, there’s a perfect place to visit in every season.

From the snow-capped Dolomites in winter to the vibrant Amalfi Coast in summer, Italy is a year-round masterpiece waiting to be explored.

Our Travel Specialists know the best places to visit in Italy throughout the year and will tailor every detail to suit your travel style. So, whether it’s a cultural city break, a foodie escape, or a scenic coastal retreat, we’ll craft an itinerary that’s uniquely yours.

Speak to one of our dedicated Travel Specialists to start planning your bespoke Italy holiday, or browse our full collection of luxury escapes, cultural tours and tailor-made experiences.

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