1 The path to Rome

Arrive at the Eternal City on the Via Francigena, the medieval pilgrim route from Canterbury to Rome. Alternative Travel Group (tel: 01865 315665) offers 18-day trips, covering the final 170 miles from Siena to Rome on foot. The price for next year is around pounds 2,750 per person, based on two sharing and including transfers, hotel accommodation, all meals, wine and guides. Flights are extra. Departs April, May, September.

2 Venice unmasked

For next year's Carnival, from 24 February to 7 March, Magic of Italy (tel: 0181-748 7575) is offering three nights in the Hotel Canaletto for pounds 395 per person, based on two sharing, including flights, transfers and b&b. Alternatively, Prestige Promotions (tel: 01442 879000) has a three- night break for pounds 1,699, including flights, gondola transfer, five-star accommodation and a ticket to the masked ball at the Doges' Palace. Departs 2 March.

3 Cultural Bologna

Medieval Bologna is one of the nine European Cities of Culture for 2000, and is celebrating with events ranging from a jazz festival to a Cezanne exhibition. Citalia (tel: 0181-686 5533) has two nights in February for pounds 199 per person, based on two sharing, including flights from Stansted and b&b in a three-star hotel.

4 Agroturismo

Live like the Blairs on a romantic Tuscan estate, surrounded by endless vineyards and olive groves. Italian Chapters (tel: 0171-722 9560) is offering a week at Casetto di Volpaia, which sleeps eight, for around pounds 1,350 between January and March. Flights and car hire are extra. Alternatively you can drive yourself there from the UK. To check out this and other villa properties take a look at www. villarentals.com.

5 Cook Italian

Italian chef Susanna Gelmetti runs cookery courses in Umbria, Apulia and on the Amalfi coast between April and October. Book through Italian Cookery Weeks (tel: 0181-208 0112). A seven-night trip is pounds 1,199 per person, based on two sharing, including flights, transfers, accommodation, all meals and wine, tuition and excursions.

6 In vino veritas

Visit the wine estates of north-east Italy on a six-day tour with Arblaster & Clarke (tel: 01730 893344). The tour, led by Master of Wine Jane Hunt, features tastings of wines produced at a monastery and costs pounds 1,079 per person, based on two sharing, and including flights, transfers, hotels, and dinners with wine.

7 Winetrail

Combine wine-tasting with an active holiday. Winetrails (tel: 01306 712111) offers self-guided walks through the vineyards of Umbria and other regions. An eight-day trip to the Cilento region, south of the Amalfi coast, costs from pounds 795 per person based on two sharing, including half-board accommodation in hotels and country inns, walking notes and maps, and wine-tastings along the way. Flights and rail transfer are extra, but can be arranged.

8 Cycle across Italy

Bike Tours (tel: 01225 310859) has a 15-day cycling trip from Ravenna to Rome, crossing the Apennines and staying in Perugia on the way. You cycle around 45 miles a day, so need to be fit. The cost of pounds 895 per person, based on two sharing, includes half-board accommodation, route notes and mechanical support, plus transport of bikes to Italy. Travel on Eurostar can be booked for around pounds 250 return. Departs 27 May.

9 The Dolomites

The Tirolean region bordering Austria is a place of thick forests, jagged mountains, and pretty Alpine villages. From January to March, Inntravel (tel: 01653 629010) is offering a week at the Posthotel Lamm, a 200-year-old inn on a village square, from pounds 548 per person, based on two sharing and including flights to Verona, rail and taxi transfer, and half-board accommodation. Cross-country and downhill skiing are available on the Seiseralm, the largest snow-covered plateau in Europe.

10 Florence in the winter

Winter is the best time to visit Florence, when the crowds thin out and the queues for the Uffizi are bearable. Between January and March, Kirker Holidays (tel: 0171-231 3333) is offering three nights b&b at the Pitti Palace Hotel, beside the Ponte Vecchio, for pounds 348 per person, based on two sharing, including flights to Pisa plus rail and transfer.

11 Roman archaeology

Andante Travels (tel: 01980 610555) specialises in archaeological tours in Italy, including Pompeii, Sicily and the Valley of the Tiber. Their eight-day Latium tour, departing 17 April, takes in the ancient sites south of Rome, such as Hadrian's villa at Tivoli. The cost of pounds 1,195 per person, based on two sharing, includes flights, transfers, all meals, wine with dinner, entrance fees, lectures and accommodation in a restored medieval castle.

12 Venice revisited

Among the art tours offered by Martin Randall Travel (tel: 0181-742 3355) is a seven-day trip to Venice, seeking out hidden treasures in the old Jewish quarter and the outlying islands, and visiting chapels and monasteries which are not normally open to the public. The price of pounds 970 per person, based on two sharing, includes flights, transfers by water taxi, accommodation, three dinners with wine, all entrance fees, local transport and the services of guest lecturer Dr Michael Douglas-Scott.

13 Painting

Vallicorte is a group of Tuscan farmhouses in the hamlet of Compignano, where John and Berenice Bonallack run houseparty-style courses for small groups. Book through Anglo-Italian Study Tours (tel: 0171-916 7323). An eight-day landscape-painting trip, departing 5 May, costs pounds 865 per person, based on two sharing, including accommodation, most meals, wine, four days of painting with tuition, and excursions to Florence and Lucca. Flights are extra but airport transfers are included.

14 Opera

JMB Travel (tel: 01905 425628) specialises in opera and can arrange tickets for all the leading opera houses of Italy, including La Scala. Each August, the Adriatic resort of Pesaro stages a Rossini festival in honour of its famous son. A three-night trip in August costs pounds 739 per person, based on two sharing, including flights to Bologna, b&b in a four-star hotel, and best-category tickets for two performances.

15 Football

Visit the great stadiums of European football, such as the San Siro in Milan or Turin's Delle Alpi, on a weekend football break with Italiatour (tel: 01883 623363). A two-night trip to Turin on the weekend of 11-12 December costs pounds 359 per person, based on two sharing, and includes flights, accommodation with breakfast, and tickets for Juventus v Inter Milan.

16 Learn Italian

If you want to brush up your Italian, try one of the two-week courses in Siena offered by Euro-Academy (tel: 0181-686 2363). The pounds 245 price includes 40 hours of tuition, at all levels from beginners. Half-board accommodation in a family home is also available at pounds 340 for two weeks, and there is the option of a cookery course in the evenings. Flights are extra.

17 Puccini's Lucca

Discover the charming Tuscan city where Puccini was born. Every summer there is a lakeside Puccini festival. Magic of Italy (tel: 0181-748 7575) offers three nights b&b at the Villa La Principessa, set in private parkland outside Lucca, from pounds 475 per person based on two sharing, and including flights. Bookings for the Puccini festival can be made through Andante Travels (tel: 01980 610555) or JMB Travel (tel: 01905 425628).

18 Village with a view

Vacanze in Italia (tel: 08700 772772) features self-catering holidays in the fortified village of Portovenere, on the Ligurian Coast, in an apartment sleeping six in a 19th-century villa overlooking the bay for pounds 746 for a week in May, including car hire from Genoa or Pisa airports. Flights are extra.

19 Capri

On a self-guided walking holiday with Headwater (tel: 01606 813367), you can avoid the crowds by day and explore Capri town in the evenings when the day-trippers have left. The price of an eight-day trip starts at pounds 525 per person, based on two sharing, including flights, transfers, b&b and walking notes. Departures on selected Saturdays beginning 11 March.

20 Volcanoes in Sicily

Hike to the top of three living volcanoes, including Etna on an eight- day trip with Explore Worldwide (tel: 01252 760000). The cost of pounds 639 includes flights, transfers, boat travel, accommodation in hotels and mountain refuges, and some meals. No single supplement but expect to share a room.

21 Sardinia

Explore some of the wildest countryside in Europe on an eight-day guided walking trip with Alternative Travel Group (tel: 01865 315678). Walks are between five and 12 miles daily, mostly on mountain tracks, and the price is around pounds 995 per person, based on two sharing, and includes transfers, accommodation, and all meals with wine, including huge picnic lunches. Flights are extra.