Liberty villas in Milan. Mahogany boats on the lake.

A private driver meets you at Milan Malpensa or Linate airport and takes you to a boutique hotel in the centre of Milan. The afternoon is free. Before dinner you stop at Camparino in the Galleria, an Art Nouveau bar with a view of the Duomo and an early home of the Campari and soda. Dinner is at Trattoria alla Pesa, a traditional Milanese table in a former customs weigh-house.

Stay in Milan · Private airport transfer · Aperitivo at Camparino · Welcome dinner

A private guide takes you inside the Duomo and up to its rooftops, among the spires and the gilded Madonnina. From there you cross the Galleria Vittorio Emanuele II, known as Milan's drawing room, and pass La Scala. Piazza dei Mercanti, the medieval centre of the city, gives a quiet pause before Santa Maria presso San Satiro, where Bramante painted a false choir that looks deep in a church with almost no room. Later you see Leonardo's Last Supper in its timed slot at Santa Maria delle Grazie in the refectory where Leonardo painted it. Football fans can add a behind-the-scenes visit to San Siro, with the locker rooms, the players' tunnel and the pitch.

Stay in Milan · Private guide · Duomo and rooftops · Last Supper · Optional San Siro visit

With a private guide you walk Via Montenapoleone, the heart of Milan's fashion district, and step inside Palazzo Morando, an 18th-century mansion furnished with period pieces. Via della Spiga and Piazza San Babila follow, past the flagship stores of the Italian fashion houses. A stop at Cova, open since 1817, gives a pause for pastries. The tour ends at a wine bistro in the centre, where a sommelier leads a tasting of wines from different regions of Italy and explains the grapes and the winemaking traditions behind them.

Stay in Milan · Private guide · Fashion district · Pastry stop at Cova · Wine tasting with a sommelier

The morning starts at Porta Venezia with a guide who knows which doors open. On Via Malpighi, Casa Guazzoni and Casa Galimberti show the Milanese Liberty style, with floral façades and coloured ceramics. Along Corso Venezia you enter Palazzo Castiglioni to see its grand staircase and rooms from the Belle Époque. The highlight is Villa Necchi Campiglio, built between 1932 and 1935 by Piero Portaluppi, where the interiors, the garden and the 1930s pool show how Milan's industrial families lived. After lunch you visit the workshops of Milanese craftspeople, from hand-bound books to bespoke leather goods, and the courtyards and cloisters that the guide knows best. A professional photographer can join the afternoon as an optional addition.

Stay in Milan · Private guide · Palazzo Castiglioni · Villa Necchi Campiglio · Artisan workshops · Optional photographer

Your driver takes you from Milan to Tremezzo, on the western shore of Lake Como. You walk its narrow streets and waterfront before boarding for your private boat. Then you visit Villa Carlotta, a neoclassical villa with works by Canova, Hayez and Thorvaldsen and gardens that run down to the water. The boat continues to Bellagio, at the point where the three branches of the lake meet, with time to walk its cobbled lanes before your driver takes you to your hotel on the lake.

Stay on Lake Como · Private transfer · Boat across the lake · Villa Carlotta · Bellagio

Your private driver-guide takes you north into Valtellina, the Alpine valley between the Rhaetian and Orobic Alps. At the Centro del Bitto in Gerola Alta you walk through the casera, built beside the Bitto stream, where around 3,000 wheels of Storico Ribelle age in cool mountain air, and you taste three different vintages, some aged up to ten years. Lunch is a traditional set menu with polenta taragna, local cold cuts and more of the cheese. In the afternoon a family winery on the terraced slopes pours Valtellina Superiore, the Nebbiolo of the Alps, before the drive back to the lake.

Stay on Lake Como · Private driver-guide · Storico Ribelle cellar and tasting · Traditional lunch · Valtellina winery

Today has no schedule. The morning starts slowly, with the lake outside the window. You can walk the lakefront, spend an hour at the hotel's spa or pool if it has one, or sit at a lakeside table for a long lunch of lake fish. If the mood changes, your advisor can arrange a table, a boat or a visit at short notice.

Stay on Lake Como · Free day

Breakfast, then a private transfer to Milan Malpensa or Linate, or to your next destination.

Private airport transfer