The ultimate northern Italy itinerary

The heel of the boot may get all of the guidebook attention but it’s Italy’s shaft (that’s real boot terminology, boys!) that will have savvy travellers wolf-whistling with glee. Travel through ancient towns that inspired Shakespeare, lake resorts that intrigue Clooney and mountain ranges celebrated by UNESCO, pausing beside any expanse of water – from Lake Garda to the Mediterranean – to sip espresso or a glass of locally produced red. See what has us all excited with our ultimate Northern Italy itinerary below.

Tailor Made Journey

Tailor-Made Italy: The Vatican to Venice

On a privately guided journey that reveals Italy's splendours at their most compelling, enjoy a special early entrance to the Vatican, view the artistic treasures of Florence, learn about an art restoration project and sample Italian cuisine with tastings in Tuscany and a food tour in Venice.

Venice | Photo: Bethany Beck

The best time to visit Northern Italy

Having an idea about what you’re planning to do will help make trip planning Italy vacations simple. For skiing in the Dolomites, mid-December to mid-March marks the high season (with February and March bring the most powdery snow), while everyone else seeking a bit of sun along the Riviera should come towards the height of summer. Other times to consider are late summer and fall, specifically for wine lovers who can appreciate the region’s vineyards as the grapes ripen into Harvest season.

While summer certainly comes hottest and busiest, the shoulder months from April to June and September to October are great choices for mild temperatures and less intense crowds. From June onwards, peak season is in full swing until September when the cooling rains come like clockwork to wash the tourists away.

Bear in mind that the national holidays may also affect your travels, specifically in the latter weeks of August when the majority of Italians leave their respective cities en masse for summer vacation. Besides causing closures of restaurants, hotels and shops in the cities, tourist hubs like Venice and the Riviera heave with visitors and aren’t recommended. At the opposite end of the scale, beach destinations come mostly shuttered in the winter months between November and February.

Venice | Photo: Igor Oliyarnik

Photo: Ruben Hanssen

How to get around Northern Italy

With a rental car and navigation system, Northern Italy opens up like an old flame keen to tell you they still love you. One of the best places to rekindle the romance is at Milan Malpensa Airport where you can rent a manual vehicle with little effort (automatics are available but less so). While easier to reach remote areas, some say that Italy is much less stressful without a car, and instead recommend swapping the traffic-clogged roads in favour of efficient trains and subway services.

Driving in Milan and other big cities is not advised, but rather you can take a train to Milan’s Central Train Station, one of the main transport hubs connecting Italy’s major cities. If trains sound good, book in advance on the official Trenitalia website for peak time departures, validating station-bought tickets at the machines before boarding to save yourself a fine. As well as trains, Italy’s ferries will also come in handy to reach various towns in and around Lake Como and Cinque Terre, but be sure to check the schedule so that you don’t miss the last ferry back.

Como, Italy | Photo: Mariya Georgieva

Mr. Hudson highlight image

Lake Como ferries travel reliably from town to town, though private boat tours are also offered allowing you to stop at any of the historic palaces and gorgeous villages that edge the shore

1. Milan

Milan rolls out in Art Deco styles and futuristic builds right from its central station, exciting visitors with world-class art and impressive history spanning Caesar, Napoléon, Austro-Hungarian and Mussolini rule. Melding its artistic heritage with contemporary culture, Milan is a place where old masters inspire new and creativity thrives. Showcasing this is La Scala opera house, open since 1778 and now hosting the city’s vibrant music scene. Walk through the corridors of Milan’s best art galleries and museums to see the works of Da Vinci and the greats, though elsewhere, all you have to do is look up to see how the space is evolving in the 21st century, with architecture from the likes of Zaha Hadid, Daniel Libeskind and César Pelli.

A business-focused city, Milan’s suits come more fashionable than most, dressed in Armani and working for tech hubs such as Google, Alibaba and Apple. To unwind after the working week, stylish Milanese visit design exhibitions to stay ahead of the curve, such as the Triennale or other major tradeshows and fairs, like Salone Internazionale del Mobile and Fuorisalone. Outside of design festival season, locals and tourists alike may relax over at the branded spas, hotels, bars and cultural centres curated by Italy’s most famed fashion houses. As for the food, Milan goes highbrow with rich dishes such as cotoletta (golden, buttered veal) and saffron infused risotto, marrying both Mediterranean produce with French and central European cooking styles. See our full Milan gay travel guide for more.

Photo: Mariya Georgieva

Navigli District, Milan | Photo: Cristina Gottardi

2. Lake Como

Tranquil centrepiece of a 4,000-person Italian village named Bellagio, Lake Como is perhaps one of the most picturesque day trips out of Milan. Drive just 1 hour (70 kilometres via State Highway 36) or take a train to Varenna from the Lombardy capital to find this gem of a lake, shielded by the Alps and edged by countless charming villages and towns. From Varenna, ferry across the lake to Bellagio to uncover the tiny streets of its old town, particularly Via Giuseppe Garibaldi where cute bistros, leather good stores and ancient churches are frequented by well-dressed visitors who often end up at Villa Melzi Gardens for sunset.

Though you may feel envy over all the Ferraris revving through the streets, the ultimate way to travel North Italy lakes is by water. Lake Como ferries travel reliably from town to town, while private boat tours allow you to stop at any of the historic palaces and gorgeous villages that edge the shore. Of the best stop-offs, there’s the Punta Spartivento lookout in the centre of the Lake, followed by Villa del Balbianello and its gardens. Hikers and mountain bikers can also look beyond the towns and into the Alps to satisfy adventure cravings among more of the most beautiful lakes in Italy.

Photo: Mikita Yo

Lake Como | Photo: Lewis J Goetz

3. Verona

Famed among North Italy cities is the Shakespearean city of Verona, where we lay our scene some 160 kilometres from Milan (170km from Bellagio). After two hours on the A4 Highway or by direct train from Milan, you’ll arrive in Verona ready to make mischief in the bustling centre. Verona can seem a bit kitschy to some, especially for its love-themed attractions, such as the Casa di Giuletta, a site depicted as the Capulet family home in Shakespeare’s Romeo and Juliet, specifically Juliet’s balcony which now serves as a place for visitors to scrawl messages of love and take romantic photos.

Beyond that, however, there’s plenty to see among Verona’s piazzas and lanes, such as Verona’s architectural wonders, starting at the 1st-century amphitheatre and stretching out to the various churches and bridges traversing the Adige River. Wine and dine yourself into the Renaissance with regional produce from Veneto at top restaurants in Verona, later moseying the fine art galleries or cruising around nearby Lake Garda.

As well as Verona restaurants, to experience authentic food culture while in Verona it’s to market you must go, chiefly Piazza Brà at the Arena di Verona and Piazza delle Erbe where merchants ply their wares as they have for centuries. The medieval Lamberti Tower is another key landmark on the map of Verona Italy, located to the east side of Piazza delle Erbe and allowing elevated views over the whole city

Verona | Photo: Maksym Harbar

Verona | Photo: Alessandro Carrarini

4. Lake Garda

Not far from Verona is another of the beautiful lakes worth a spot on your North Italy itinerary, known as Lake Garda and accessible by car (30 minutes) or by train (20 minutes). Peschiera del Garda and Desenzano del Garda are two of the closest stations, seeing around 7 percent of all Italy’s tourists who alight to find the lake. Busy though it may be, Lake Garda makes for serene vacations, based right in the middle of three separate regions; Lombardy, Trentino Alto-Adige and the Veneto. Because of its location, Lake Garda is both culturally diverse and filled with a great many wilderness trails leading though the mountains and valleys also home to the best Northern Italy wineries.

To the north, resorts such as Riva del Garda and Torbole are chiefly presided over by German and Austrian travellers, while to the south, French and Italian families take up space in the farmhouses of Valtenesi and spa towns of Sirmione and Bardolino. Go between camps to get a taste of the distinct atmospheres, finding common ground in history at the UNESCO site of Peschiera del Garda, famed for its medieval fortress. Sustainability could also be the bridge, leading citrus lovers of all nationalities to the Limonaia Pra de la Fam in Tignale to explore a stylish eco museum based within a lemon-tree house.

Lake Garda | Photo: Blaz Erzetic

5. Venice

A sure stop on every Northern Italy tour is Venice, a floating city linked by a series of canals and waterways, familiar to postcards sent the world over. A 1-hour drive from Verona (parking in Mestre and taking the ferry across) or a direct train to the main station of Santa Lucia, Venice will astound with its fine array of Gothic and Renaissance architecture, while, on the ceilings of these beautiful basilicas and palazzos, you’ll find works by some of human history’s most revered artists. Start with a simple stroll down avenues lined with enticing art galleries presenting any era you can think of. And then, after getting your bearings, sign up to a Venice guided tour or go solo with a museum pass and transportation pass that will allow access into the main museums and use of public transport.

Of the sites to tick off your Venice Italy itinerary are the Rialto Bridge, the Jewish Quarter, Palazzo Ducale and the adjacent Basilica di San Marco, the last two with vast courtrooms and even an underground prison dating back to the 9th century. With little time to lose, jet over the waterways by vaporetto (aka water bus), to explore San Giorgio Maggiore, a small island known for a church designed by Piadino which boasts sweeping views across Venice from its bell tower. On the other side of the island lies the Vatican’s Biennale pavilion park, featuring 10 chapels designed by 10 of the world’s top architects, soon to be exhibited around the world. Other water taxi rides worth having is to Murano for a glimpse at glass production history, attending glass workshops and shopping, or to Burano to switch glass making for lace manufacturing and fish mongering among brightly-coloured homes on the water’s edge.

Stop at Torcello island to greet its eight permanent residents and walk the wildlife reserve, before heading back to Venice proper for the Peggy Guggenheim Collection to satisfy our cravings for modern art. Otherwise, Fondazione Querini Stampalia house museum offers up a look of 20th century noble life designed by Carlo Scarpa, getting more of his work at the Olivetti Showroom on Piazza San Marco if so wishing. Though Venice nightlife pales in comparison to nearby Padua, there’s still a fair few bar and club options around the main university and student area of Campo Santa Margarita. See more of the city’s wonders with our Venice travel guide.

Photo: Ingeborg Gartner Grein

6. Padua

Another of Italy’s cities inspiring ol’ Bill Shakespeare is Padua, Venice’s loud, party-loving neighbour. Less than an hour from Venice, the city-state of Padua goes medieval with Italy’s second-oldest university and market piazzas all about. Though Padua has its share of fascist-era architecture and military history, it is now very much a youthful city, made up of fun-loving students and industrial workers. Party with the local community at bars, clubs and world-famous saunas across the city, where the gay scene beats Venice’s hands down.

7. The Dolomites

Human culture may dominate Italy’s cities but it is nature that presides over the rural north, the Dolomites mountain range in particular. Making up the eastern Alps on the border to Austria, the Dolomites are labelled a UNESCO Heritage Site and a prime destination for skiing, hiking and mountain biking in the right season. At the centre of it all is Alpe di Siusi (or Seiser Alm to the Germans), an ideal base with hotels, B&Bs and apartments close to over 300 kilometres of hiking trails which wind through the glorious pastures of Italy’s highlands. For those who aren’t driving, an alternative base could be that of Cortina d’Ampezzo, reachable by both bus and train and home to the best hot chocolate in the world in hiking distance from Lake Misurina and the best peaks. Hire a guide to hike the wilderness safely throughout spring, summer and fall, but, as December approaches, skiing becomes the go-to activity, closely followed by spa visits and even cooking classes.

At certain times of the year you can see something unexpected in the Dolomites, notably in October when traditional farmers drive cattle to new stables during Almatrieb or when music resounds over the hills during the arts and performance festival of Silenzi d’Alpe.

Dolomites, Italy | Photo: Joshua Earle

Photo: Stefano Bazzoli

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Making up the eastern Alps on the border to Austria, the Dolomites are labelled a UNESCO Heritage Site and a prime destination for skiing, hiking and mountain biking in the right season

8. Portofino

Last on our itinerary is Portofino, providing 2 or more restful days along the Italian Riviera coast. To reach Portofino, head back through Milan and continue south via the A7, racking up around 177 kilometres before arriving at your Portofino resort. Of the many Portofino villas and hotels that await, Belmond Hotel Splendido comes right on the bay with its own seafood-heavy restaurant (like many delicious Portofino restaurants) – La Terrazza – ready to showcase the best Ligurian food in Northern Italy. After lunch, move along the harbourside to the lighthouse for stunning Mediterranean vistas, swimming in Paraggi Bay or hiring a yacht for fun at sundown. If time allows, consider a diving excursion or boat ride to San Fruttuoso, a neighbouring village known for its ancient abbey, also stopping at the 14th century fortress of Castello Brown on the way.

A popular Riviera town, Portofino sees an influx of rich and famous visitors each year, many of whom reside in Portofino apartments based way up on the hills, coming down at dinnertime to eat at Ristorante Puny, one of the best restaurants in Portofino.

Portofino | Photo: Kristine Tanne

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Dolomites, Italy | Photo: Joshua Earle

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