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From destination advice to how to maximise your budget, our expert answered your questions on travelling to Italy in 2026.
That’s all for today’s Q&A. Thanks to those of you who sent in a question. You can head to the comments section for all of our expert’s answers.
You can catch up on the Travel series here for Greece, Spain or France.
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Kathryn Moorebick asks: “I’m looking for a villa with a pool in Tuscany for a multi-generational holiday in July which is less than an hour from the airport and ideally within walking distance of a small town or village with a restaurant. Any recommendations?”
“Ciao Kathryn! My go-to villa resource is Trust & Travel (and their higher-end Excellence Villas for a splurge). They have a wide-ranging portfolio with lots of options that have been personally vetted by the owner Katharina, and a very responsive staff that will work hard to match you with a great property.
“I have recommended them scores of times over the years; they have a concierge service included with their higher-end villas that is a lifesaver for planning a multi-generational trip.
“As far as the area, you will probably be looking at either Chianti (an hour from the Florence airport) or the stretch between Lucca and the Tuscan coast (an hour from the Pisa airport); the former has more options near towns and villages while the latter has more affordable prices.”
Robert Marsden
“My wife and I plan in June/July to take our car and tour France down to the Mediterranean where we have friends and then to Italy, Tuscany. Once in Tuscany we would like a week staying on a vineyard which has a restaurant and good wine and is close to public transport to access the major cities. 
“Whilst touring our aim is to book the next day’s accommodation online. What advice do you have regarding finding good-quality accommodation? We toured around France a couple of years ago and used the internet to book last minute accommodation and bluntly the choice and quality was appalling. We don’t want to book up a series of hotels months in advance because this takes away spontaneous decisions – if we like a place why not stay a day or two before moving on? Cost per night is a consideration so five-star hotels are out and we prefer good homely food and comfortable lodgings.”
“Ciao Robert! I actually find that Booking.com is a great way to find accommodations in Italy (I’m not getting a commission from them, I promise). The vast majority of Italian hotels, B&Bs and apartments are listed, and if you play around with the filters a bit, you can really narrow your search to exactly what you are looking for. I generally filter for options rated nine or above, click the amenities I am specifically interested in (breakfast included, for example, or a pool), then I go directly to the map and poke around to see what’s available. Tick the box to show only available properties to clean up the map view a bit, then favourite the few that catch your eye. Read the reviews carefully (I have uncovered details like low water pressure or lots of stairs from scanning the reviews) and always try to contact the property directly to book, since they will often match or beat the rates on Booking.com or throw in perks like a spa admission or upgrade.”
Amanda JM asks: “Could you please recommend a lovely restaurant in Rome which does the matched wines thing? We’re going there on our honeymoon later in the spring so would like a memorable meal as part of the experience. Thank you.”
“Ciao Amanda! And congratulations on your nuptials – Rome is the ideal destination for a romantic honeymoon. I would definitely steer you towards a rooftop dining experience with a view for your special meal.
“Some of my favourites include Settimo (overlooking Villa Borghese), Aroma (overlooking the Colosseum), Imàgo (overlooking the Spanish Steps), and Terrazza Les Etoiles (overlooking St. Peter’s).
“All of these are fine-dining establishments that generally offer fixed menus with wine pairings; some also offer à la carte options but may not have wine pairings to go with. Italian sommeliers are excellent resources, so don’t be shy to ask for recommendations.”
Gwilym Joseph asks: “Off to Calabria oin May, any particular places one should look out for in this region?”
“Ciao Gwilym! Oh, so happy to hear that you are headed to unsung Calabria! It’s a fabulous region that continues to fly under the radar. Of course you’ll be visiting Tropea. If the weather is fine, do book a boat trip along the Costa degli Dei (Coast of the Gods. Need I say more?) to Capo Vaticano. 
“You’ll also want to visit the charming seaside towns of Pizzo and, farther south, Scilla and Chianalea. Reggio Calabria is a bit of an assault on the senses, but it is home to the fabulous Riace Bronzes in the archaeological museum to tick your culture box. 
“The Sila National Park is ideal for hiking excursions; I would book a hiking guide to help navigate the trails without the stress of trying to decipher the signage and maps. Cosenza is nearby, with its UNESCO-listed cathedral and authentic atmosphere. 
“Finally, if you’d like to head east to the Ionian coast, Isola Capo Rizzuto has some of the most beautiful (and protected) beaches in Italy, and you’ll have them virtually to yourself!”
Peter Smith would like recommendations for the special occasion: “Hi, we are going to Puglia in September to celebrate our 50th wedding anniversary with another couple also celebrating their anniversary. We will stay in Martina Franca. Two questions: can you recommend a good restaurant for our celebration dinner (utilising a taxi), and general advice on places to visit, (we will hire a car).”
“Ciao Peter! Martina Franca is an ideal base because you’ll have the Val d’Itria and Salento both within striking distance. For a special dinner, I have often sent travellers to the lovely Masseria Croce Piccola for their vineyard wine-tasting dinners. It’s a rustic, open-air meal but with authentic dishes and unbeatable, family hospitality.
“For something more upscale, Ostuni has great dining. I love Osteria del Tempo Perso. As far as places to visit, you have the best of Puglia within striking distance: Alberobello and Locorotondo, Ostuni, Monopoli and Polignano, the olive farms and wineries of the Val d’Itria, and even Matera across the border into the region of Basilicata. Also, don’t sleep on Lecce, one of my favourite cities in Italy!”
Kath Herleva asks: “[I’m a] single mum with two children aged five and six. We’re not a sit by the pool kind of family – and the kids would love to see some culture – but also have to be realistic with their ages and parenting solo. What could be a child friendly first intro to Italy? My late husband and I (their Dad) honeymooned in Rome so I’d love Italy to be part of their growing up story.”
“Ciao Kath! Italy is a fabulous spot for kids, with its pizza-and-gelato meals and traffic-free squares for kicking around a ball. The first thought that came to mind is Siena, in Tuscany. This hill town is just big enough to have a bit of culture but also just small enough to be safely walkable; its main Piazza del Campo is closed to traffic and the de facto football pitch for local kids.
“The town is also well-connected to Florence by train for a day trip (or arrival/departure flights) or you can rent a car to explore the surrounding Chianti villages and countryside. My favourite spot to send families in Chianti is the Chianti Cashmere goat farm for a farm experience and lunch; a hands-on pasta-making class at an area farm would also be a fun activity for you and the kiddos.”
Richard Conry is looking to arrange his first family ski holiday.
“As children neither my wife nor I went on skiing holidays. As far as I can see it’s more of a secret society than a holiday, and trying to work out where to take three children (12, 10 and eight, boy, girl, boy) that caters for absolute beginners and also females with a tendency for cold white fingers seems really difficult! We are finally in a position where we could afford a break, albeit probably the cheaper/mid range of the market, but it seems hard to navigate the many options. The children are very intrepid and keen, we’re all quite sporty, but the wife insists a hot tub might be necessary to help her commit to finally going on a “cold holiday”! Any help appreciated, thank you!”
“Ciao Richard! We have taken our kids skiing since they could barely walk, and there are lots of great options for families who want to keep the budget in check. My first suggestion is Madonna di Campiglio in the Brenta Dolomites, just north of Lake Garda.m The town itself is charming and full of nice shops and eateries to break up the skiing, while the runs in the area resorts of Madonna di Campiglio, Pinzolo and Folgarida-Marilleva will keep skiers of all skill levels happy. Avoid the pricey hotels in Madonna di Campiglio and instead check out the apartment offerings in neighbouring Folgarida (free ski buses run between the two towns), and be sure to purchase your family ski passes online in advance for discounts. 
“The area also offers promotional weeks with perks such as ski passes included in hotel bookings. Enroll in ski school each morning so everyone can hone their skills with certified instructors – we always opted for group classes for the kids so they could connect with other young skiers and my husband and I would splurge on a private instructor for an hour in the meantime. The closest airports are Verona, Bergamo and Milan; the FlySki Shuttle coach runs directly from these airports (and the Trento train station) to the town centre for seamless logistics.”
Rachel Garnett wants to treat her daughter to an Italian getaway: “Looking for recommendations for a post-GCSE holiday treat with my daughter, just the two of us – thinking of Sorrento, any tips welcome!”
“Ciao Rachel! Sorrento is a great base for exploring some of southern Italy’s highlights (think Pompeii, Mt. Vesuvius, the Amalfi Coast, and Capri), but brace yourself for crowds in June when the cruise season is in full swing. 
“The Circumvesuviana train is an easy way to travel between Sorrento and Naples/Pompeii/Herculaneum; choose the Campania Express, which runs on the same line but is a tourist route that only stops at the stations nearest the main attractions. 
“Buses run between Sorrento and the Amalfi Coast, but I would opt for the ferry to avoid getting stuck in the famously tangled traffic along the single coastal road. I would also take the time to visit Capri (again, be prepared for crowds), but plan to spend most of your time on a boat tour of the island rather than on land, where the throngs can really overwhelm. 
“Finally, take a pizza-making class while there! You will be in the birthplace of true ‘pizza napolitana’ and it’s a fun, hands-on mother-daughter activity to break up the sightseeing.”
John and his wife want to book a holiday in Sicily.
“My wife and I are 77 and 82, we live in Sussex and are both retired. The idea is to keep an eye on the weather and just jump on a flight from Gatwick to wherever we think we’ll get a few days of sun, in winter or early spring. Can you advise on hotels and nice places to visit in southern Italy and Sicily? We know the area quite well. We’ve been to Naples, Sorrento, Positano, Tropea, Ostuni in Puglia, Cefalu, Palermo and Taormina in Sicily.”
“Ciao John! It looks like you’ve been using your retirement time wisely, as you’ve already covered some of my favourite spots in southern Italy on previous trips. There are direct routes from LGW to Catania, so you could easily hop on a flight and then head south along Sicily’s eastern coast about an hour to Syracuse. This seaside city has excellent ancient ruins, great architecture, and wonderful cuisine. My go-to hotel is the Algilà in the Ortigia old town. If the weather is fine, you can take a boat tour of the nearby coastal caves or explore the protected Plemmirio promontory and its beaches just south of the city. Otherwise, head inland to the UNESCO-listed Noto valley to marvel at its ornate baroque churches and palaces.
“Puglia is tricky to reach from Gatwick, as flights to Bari and Brindisi are seasonal. However, direct flights to Naples depart in winter and early spring, an easy gateway to Capri or Ischia by ferry. These two islands teem with tourists in the high season, but are a delight to visit before the throngs descend. Just keep in mind that choppy seas can lead to cancelled ferries, so plan to spend your final night on the mainland so you don’t end up missing your return flight home.”
Reader Karen Diver asks: “I’m 58 and live in Lancashire. I’m a tax professional. Is it possible to rent an affordable holiday home in the Italian alps so we can take our dog? Is it a dog-friendly area? My small rescue dog is 14 and blind but still active.”
“Ciao Karen! Yes, of course, the Italian peaks are very dog-friendly, and there are lots of areas where you can find affordable holiday lets. I assume you are looking to visit in summer, because the winter snows and frigid temperatures will be tough on an elderly pup, while the cool mountain air is a welcome relief come July. 
“To keep the rental costs down, I would steer away from high-end areas such as Cortina just north of Venice or Alta Badia and the Val Gardena in South Tyrol. Instead, try lesser-known areas that are just as pretty, such as the Val di Funes or the Val di Fassa. Here, you’ll find plenty of self-catering apartments or simple agriturismi (farm holidays) that allow pets and have easy access to easy trails. You’ll probably need to rent a car for the duration of your stay, since getting around the smaller towns by public bus can be a hassle, and be prepared for seven-day minimum rental periods (often Saturday to Saturday or Sunday to Sunday).”
Peter Avery asks: “We’ve done a lot of Italy but never the lakes, partly because there is so many of them to choose from. Where would you recommend for a lakes novice. We are looking for something reasonably upmarket but not ridiculous.”
“Ciao Peter! The lakes are among the most beautiful destinations in northern Italy, but of course that means crowds and sky-high prices in the summer season. I would steer clear of Lake Como for your first trip, unless you are planning to visit in early spring or late fall when the crowds abate.
“Instead, consider Lake Maggiore (from Milan) or Lake Garda (from Milan or Venice). On Lake Maggiore, base yourself in Stresa if you’ll be getting around by public transportation (there is a ferry stop and train station).
“On Lake Garda, Sirmione is the biggest transport hub but also very crowded in high season, so opt for Riva del Garda on the northern reaches of the lake and get around by ferry. Both offer splendid vistas, lots of trails to explore, pretty towns with villas and gardens, and ferry and train connections for easy logistics.”
Robert asks: “We live near Cambridge. I’m 62 and a retired senior IT executive and my wife is 64 and a retired midwife.
“We are planning to visit Rome in September but would prefer not to fly. What is the best alternative way to travel? We are also thinking of travelling on to visit Perugia after staying in Rome for about four nights, then onto Ljubljana for another week touring/walking around the lakes.”
“Ciao Robert! Trains are a great way to get around Europe and Italy, and you can take the Eurostar from London to Paris, then a high-speed train from there to Milan, where you’ll change for Rome. You will probably have to overnight in either Paris or Milan, however, so build that extra night into your itinerary. There are direct regional trains from Rome to Perugia several times a day, and the trip takes about two-and-a-half hours. To get to Ljubljana for your next leg, plan to take the train from Perugia to Trieste (you’ll change in Florence and Venice along the way), then the direct train to Ljubljana. The trip will take you a full day and you’ll want to make sure you have plenty of time to make your connections along the way!”
Our first question is from Gary Edwards who is looking to book in a ski trip.
“Hi, myself and my wife are planning a ski trip which will be mainly alpine skiing but also incorporate some ski touring. For the touring element, we are looking for scenic hikes rather than accessing back country skiing. Our touring so far has been limited to skinning up the side of the piste but we are looking for something more interesting. We may not have a car so the touring routes need to be accessible from the resort. We generally like resorts above 1500m that are within two hours of a major airport. Can you please suggest a European resort that hits the mark? Thanks!”
“Ciao Gary! Italy is hosting the Winter Olympics in just a week, and the ski resort of Livigno (aka Little Tibet) is having its moment in the spotlight. This massive resort area near the Italy-Switzerland border sits at 1800m – so snow is pretty much guaranteed – and it’s known for both its downhill runs and ski touring trails that cover 150 square kilometres of pristine peaks. The network of chairlifts and cable cars is robust, and the town is served by a free bus line to get skiers between the different lifts. The only catch is that this winter wonderland is about four hours from the Milan and Bergamo airports, so a bit farther than you’d like to travel. That said, the Livigno Express coach connects these transport hubs directly to the town, so you don’t need to fuss with rental cars or multiple train or bus connections. To get your bearings, I suggest you hire an Alpine guide for a day: Outventure Livigno has a great team of experienced and licenced guides and instructors to explore safely.”
This Q&A will be getting underway in just 15 minutes. Telegraph Travel expert Rebecca Winke is on hand to answer your questions and give you tips on how to plan a brilliant holiday in Italy.
Rebecca writes about Italian travel, culture and cuisine. She has been based in central Italy for more than three decades, and has written for numerous print and online travel publications on topics ranging from luxury hotel openings to underdog wine comebacks. 
Are you planning a holiday to Italy in 2026? Leave your questions in the comments and our expert will reply to you from 12pm today. 
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