Classic Northern Italy

Your Italian adventure gets underway at 6pm with a welcome drink at your hotel, having made your way over from Rome–Fiumicino International Airport (FCO), and the chance to meet your group and our Local Insider who will accompany your group throughout the trip. Dinner will be served at Ristorante Al 34, opened by Walter and Maria Luisa Casalini in 1968 and now helmed by son Nicola, whose extensive menu revolves around Italian classics such as lobster linguini and Roman meatballs. After dinner, you’ll be free to explore before turning in for the night.

The action starts with a three-hour guided bike tour through Roman antiquity (bikes, helmets and insurance are all included). You’ll pedal past landmark attractions such as the ruins of Trajan’s Market, the Mausoleum (built in 28BCE and commissioned by Augustus, the first Roman emperor), and piazzas Spagna, Navona and Venezia, before finishing near the Colosseum. Refuel over lunch at Ristorante Isidoro – the building in which it sits was a convent in the 17th century – before walking to the Colosseum, Roman Forum and Palatine Hill, all of which you can access with your pre-booked ticket. The rest of the day and the evening’s dinner venue are up to you.

Day three kicks off with a private transfer and train to Siena, one of the most important medieval cities in Tuscany. On arrival, lunch will be served in the 13th-century dining room of Gallo Nero; expect typical Tuscan dishes with locally sourced ingredients, freshly pulled pasta and homemade bread. Next, you’ll be whisked off to your hotel in the Chianti wine region; you’re free to explore by yourself for the rest of the day. You could make your way into Siena and admire the beautiful gothic Duomo di Siena, or unwind with an Aperol spritz by the hotel pool.

Go light on breakfast, because today is all about eating and drinking. Departing at 9am, you’ll be driven 45 minutes north of Siena, to a winemaking estate in the walled medieval village of San Gimignano. Tour the vineyards and olive groves, visit the cellars, then taste fresh produce on a terrace with panoramic views. Then, the main event: a rustic Tuscan lunch outdoors and a cooking class in which you’ll learn how to make tiramisu and pici pasta. Don’t worry about over-indulging – all you have to do afterwards is sit back as you are driven to your Florence hotel.

Start the morning with a walking tour of Florence. Afterwards, you can spend the day as you wish. There’s so much to explore in Florence. Beyond art, the Accademia has an extraordinary collection of instruments for music lovers, while Farmaceutica di Santa Maria Novella will entice perfume fans. Alternatively, recharge at the hotel and take a cocktail in the American Bar. You’re ideally placed for shopping and sightseeing, as the hotel is just off Via Tornabuoni, where designer stores such as Gucci and Tod’s mingle with Renaissance palaces, such as Palazzo Strozzi.

Today you’ll be whisked away in a private vehicle to Pisa, giving you the chance to see the leaning tower. Next, it’s onto the coastal resort town of Levanto, a hidden gem in the heart of the Italian Riviera with views over the leafy hillsides on the edge of the Cinque Terre National Park. Stroll down to the medieval town where pastel-coloured houses cling to the cliffside, snap those all-important photos along the promenade and enjoy an Aperol spritz at sunset. If you’re in the mood, take the chance to cool off with a swim in the Mediterranean.

The main event today is a coastal hike through the five fishing villages of Cinque Terre, a Unesco National Park. It’s a six-minute train ride from Levanto to Monterosso, from where you’ll trek 13km (8mi) along basil-strewn clifftops to Manarola, via Vernazza, Corniglia and Volastra. Drink in panoramic Mediterranean views through the pine trees. Then take the train from Manarola back to Levanto. The excursion will take about four hours, which leaves you free to explore this stretch of unspoilt coastline at your leisure. Alternatively, enjoy the coastline by train and ferry ride.

Today starts bright and early with a private four-hour transfer to the shores of Lake Como. Enjoy lunch by the lakeside and perhaps a visit to the 14th-century Como Cathedral and its 18th-century bell tower, which offers astonishing views. Next, hop on a boat where an English-speaking skipper will lead a tour of Lake Como. Sip an aperitif as you watch the sunset, and later, wander the romantic cobbled streets of Como to find a restaurant of your choice.

After a slow breakfast, it’s time to say goodbye to Lake Como. You’ll be in Milan by midday, in time to start a three-hour culinary walking tour of the economic powerhouse of Italy. Among the gastronomic treats you’ll sample are 24-month-aged Parma ham, artisanal ice cream, melanzane alla parmigiana, lasagne and mondeghili (meatballs done the Milanese way). Finish the day with a farewell dinner at 10 Corso Como, where a conservatory-style interior blends seamlessly into a secluded patio overflowing with foliage and flowers. Choose a bottle or two of Italian wine and toast an unforgettable trip with new friends.

Your trip around Northern Italy concludes with one final breakfast. Say goodbye to your group at 10am before catching your return flight home from Milan Malpensa Airport (MXP)or, alternatively, staying in Italy to explore some more. Remember: if you got a little carried away with the souvenir shopping during your trip, check an extra bag.