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Experienced Traveler Trips in Italy

Discover Italy through the eyes of experienced travelers with over 240 carefully curated tours. Featuring in-depth cultural experiences, authentic local connections, and sophisticated itineraries designed for discerning travelers, rated by more than 6,400 experienced adventurers.

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    Design a fully customized Italy trip with a local travel expert who understands what experienced travelers seek. From immersive cultural experiences and curated stays to flexible pacing and exclusive access.

    • Alessandra Galassi - Italy Tours Expert
      Alessandra GalassiTravel Expert in Italy
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      Elena KyrimiTravel Expert in Greece & Italy
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    Start planning your Trip
    Recommended by
    • BBC
    • Independent
    • Lonely Planet
  • Physical Rating
  • Departures
  • Tour Types
  • Accommodations
    • Simple stays with essential amenities. Typically guesthouses, hostels or hotels rated below 3 stars — clean, no-frills, and great for value-conscious travelers.
    • Comfortable and reliable 3-star stays. Expect private rooms, en-suite bathrooms, and solid amenities — a great balance between comfort and cost.
    • Upscale 4-5 star hotels and lodges. Enjoy high-end service, refined comfort, and premium locations — ideal for travelers seeking extra indulgence.
  • Activities
  • Guide Types
  • Duration
    1 day26 days
  • Destinations
    • Showing 1 - 10 of 240 results
  • Price
    USD 112USD 18,045
  • Start & End Location
    • Italy Experienced Travelers Trips: Backroads To Venice

    Backroads to Venice

    4.7
    A most enjoyable, at times challenging experience since we did the whole trip on conventional bikes. The bikes were in good condition, the chosen hotels were good, and the special app made navigation easy. We were lucky with the weather; I would have hated to do some of the gravel/dirt road stages in the rain.
    Bicycle tours
    Tour Type
    Private Tour
    Accommodation
    Hotel, Villa
    Age Range
    18-99 yrs
    Operated in
    english
    Destinations
    Venice, Trentino-South Tyrol, Do
    Venice, Trentino-South Tyrol, Dolomites, Bolzano, Trento, Peschiera, Verona, Vicenza, Padova, Mestre
    View Tour
    Italy Experienced Travelers Trips: Classical Sicily

    Classical Sicily

    4.7
    Excellent itinerary, competent and resourceful leader, good guides, comfortable transport.
    Cultural, religious and historic sites
    Tour Type
    Small Group TourSmall group tours usually have 8-12 participants and maximum up to 18 travelers
    Accommodation
    Hotel, Villa, Resort
    Age Range
    16-99 yrs
    Operated in
    english
    Destinations
    Syracuse, Sicily, Giardini Naxos
    Syracuse, Sicily, Giardini Naxos
    View Tour
    Italy Experienced Travelers Trips: Via Francigena: Orvieto To Rome

    Via Francigena: Orvieto to Rome

    4.6
    I did Orvieto-Roma with my dog Ariel and we both had an amazing time. The organisation was impeccable, the accommodation was good and the app fantastic: even for somebody like me who gets lost all the time!
    Walking tours
    Tour Type
    Private Tour
    Accommodation
    Hotel
    Age Range
    18-99 yrs
    Operated in
    english
    Destinations
    Rome, Orvieto, Bolsena, Montefia
    Rome, Orvieto, Bolsena, Montefiascone, Viterbo, Vetralla, Sutri, Campagnano Di Roma, Isola Farnese, Piazza San Pietro
    View Tour
    Italy Experienced Travelers Trips: Gran Paradiso Guided Hike

    Gran Paradiso Guided Hike

    5
    We booked a 7 day trip with U-Tracks, with the ultimate goal of summiting Gran Paradiso. We were a group of 11 work colleagues who annually take on a charity event with this being the selected even this year. I must admit the trip was spectacular. the 6 day 'approach' to gran paradiso was varied in the way of physical challenge and then scenery. our guide - max was first class. he was able to assess the group and maintained a superb pace to keep us all moving. this was the first time we had taken on something as demanding as this (the final day in particular). The last day summit of gran paradiso was physically challenging but not technically (the very final summit section becomes technical but very well managed). the whole trip was fantastic from start to finish. I would 100% recommend and use again.
    Walking tours
    Tour Type
    Small Group TourSmall group tours usually have 8-12 participants and maximum up to 18 travelers
    Accommodation
    Hut
    Age Range
    18-99 yrs
    Operated in
    english
    Destinations
    Lyon, Refuge De L Archeboc, Rifu
    Lyon, Refuge De L Archeboc, Rifugio Federico Chabod, Refuge Bezzi, Refuge Benevolo, Rifugio Savoya, Rifugio Vittorio Emmanuele II, Bourg
    View Tour
    Italy Experienced Travelers Trips: A Taste Of Tuscany - Hilltop Towns And Vineyards

    A Taste of Tuscany - Hilltop Towns and Vineyards

    4.8
    Trip was excellent. Tour Guide, Gus, was fantastic, very knowledgeable, great communicator, and made sure all of our needs were met. Food and wine tour could not have been better. Never really liked many wines but the tastings proved me wrong. The agricultural farms were great and the food fresh and abundant. Villages were quaint. Castle was very interesting - 34 generations living in it and continuously running a vineyard and producing wine since 1141 is unbelievable! Looking into another food tour in another country. Gave accommodations less rating because hotels were in old buildings and they made due with space available: 1) First 2 nights in Hotel Bologna, the room was very, very small and had 2 twin beds aligned in tandem against one wall - would not have fit any other way, 2) Hotel Le Cisterna, last 3 nights, walls were so thin we could hear every word people next door said.
    Wine tasting toursFood tours
    Tour Type
    Small Group TourSmall group tours usually have 8-12 participants and maximum up to 18 travelers
    Accommodation
    Hotel
    Age Range
    16-99 yrs
    Operated in
    english
    Destinations
    Pisa
    Pisa
    View Tour
    Italy Experienced Travelers Trips: Via Degli Dei: Bologna To Florence

    Via Degli Dei: Bologna to Florence

    4.8
    The Via Degli Dei is a fantastic walk - 2 great Italian cities and stunning landscapes every day which made the tough climbs worthwhile. They dealt with everything once we arrived, the accommodation was good and varied which added to the appeal of the trip. It's helpful to have some basic Italian as a couple of places did not speak English but everyone was so friendly. Will use them again - we are already planning next year's trip!
    Walking tours
    Tour Type
    Private Tour
    Accommodation
    Hotel
    Age Range
    18-99 yrs
    Operated in
    english
    Destinations
    Florence, Bologna, Sasso Marconi
    Florence, Bologna, Sasso Marconi, Monzuno, Bruscoli, San Piero A Sieve, Olmo, Fiesole
    View Tour
    Italy Experienced Travelers Trips: Portofino And The Cinque Terre

    Portofino and the Cinque Terre

    5
    Great scenic walking with demanding ascents and descents but comfortably within the capability of a walker used to the Fells. The organisation was excellent and everything worked seamlessly. The hotels were all good although the quality of the restaurants in the villages was mixed with good and bad experiences from what was recommended. A great week.
    Walking tours
    Tour Type
    Private Tour
    Accommodation
    Hotel
    Age Range
    18-99 yrs
    Operated in
    english
    Destinations
    Cinque Terre and Liguria, Liguri
    Cinque Terre and Liguria, Liguria, Bonassola, Genoa
    View Tour
    Italy Experienced Travelers Trips: Puglia Guided Walk

    Puglia Guided Walk

    5
    I would highly recommend this trip. It covered all the interesting areas in Puglia. Our guide Gabriele was fantastic, he went over and beyond what was expected, he made the trip entertaining and enjoyable for everyone with his stories and knowledge of Italian culture. Everyone in our group got along well which helped to make the trip a pleasure. From the food, drinks, to the execution of our activities, it was all a memorable experience. Great time of year in May to see the many wildflowers and greenery in the Italian countryside. Thanks.
    Walking tours
    Tour Type
    Small Group TourSmall group tours usually have 8-12 participants and maximum up to 18 travelers
    Accommodation
    Hotel
    Age Range
    18-99 yrs
    Operated in
    english
    Destinations
    Matera, Lecce, Ostuni, Alberobello
    Matera, Lecce, Ostuni, Alberobello
    View Tour
    Italy Experienced Travelers Trips: Via Francigena: Southern Tuscany From Siena

    Via Francigena: Southern Tuscany from Siena

    4.4
    Having worked with them on a trip in Northern Italy last year, I was confident they would deliver a great experience. They did. From the quality of the hotels, included meals, the navigation app used down to the distances covered each day, everything was well thought out and first rate. Along the way I met other walkers who’d used other companies. Every single one had a complaint about the company they used. I had no complaints and recommended them repeatedly along the route. I’m already making arrangements for an Italian walk next year with this company.
    Trekking and Hiking
    Tour Type
    Private Tour
    Accommodation
    Hotel
    Age Range
    18-99 yrs
    Operated in
    english
    Destinations
    Rome, Siena, Lazio, Lucignano D
    Rome, Siena, Lazio, Lucignano D Arbia, Tuscany, San Quirico d'Orcia, Castiglione D Orcia, Radicofani
    View Tour
    Italy Experienced Travelers Trips: Highlights Of Puglia

    Highlights of Puglia

    4.5
    It was a great trip. The tour leader was fantastic and the itinerary so interesting. I like holidays to be a discovery and it certainly was. The food in Italy is also gorgeous.
    Food tours
    Tour Type
    Small Group TourSmall group tours usually have 8-12 participants and maximum up to 18 travelers
    Accommodation
    Hotel
    Age Range
    16-99 yrs
    Operated in
    english
    Destinations
    Bari, Lecce, Matera, Alberobello
    Bari, Lecce, Matera, Alberobello, Otranto
    View Tour

    Page 12 of 240 Experienced Travelers Trips in Italy with 6,401 Reviews

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