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  • Home
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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 6,300 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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    • 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.
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  • Page 16 of 240 Experienced Travelers Trips in Italy with 6,348 Reviews

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    Italy Experienced Travelers Trips: Venice To Florence Cycle

    Venice to Florence Cycle

    4.6
    Our recent bike trip from Venice to Florence was terrific. Viewing the countryside by bike was fun. Each days ride was different. I thought day 2 was the hardest. My sit bones were very sore despite the bike shorts. it was a bumpy gravel long ride. Day 3 and on out got easier.
    Bicycle toursCity sightseeing
    Tour Type
    Private Tour
    Accommodation
    Hotel, Hut
    Age Range
    18-99 yrs
    Operated in
    english
    Destinations
    Florence, Venice, Mestre, Chiogg
    Florence, Venice, Mestre, Chioggia, Adria, Comacchio, Ravenna, Brisighella
    View Tour
    Italy Experienced Travelers Trips: Highlights Of Matera And Apulia Private Tour

    Highlights of Matera and Apulia Private Tour

    5
    Private Tour around Apulia and Matera beyond our expectations .Very good the Hotel in Matera, Dimora di Metello..but also Tenuta Monacelle near Alberobello. Great local guide and meals. I only think you should had add an extra day in Apulia, 5 days are not enough. Anyway excellent tour and service. Very good value for money
    Sightseeing ToursFood tours
    Tour Type
    Private Tour
    Accommodation
    Hotel
    Age Range
    20-99 yrs
    Operated in
    english
    Destinations
    Matera, Puglia, Polignano A Mare
    Matera, Puglia, Polignano A Mare, Alberobello, Monopoli, Bari
    View Tour
    Italy Experienced Travelers Trips: Upgraded - Walking Italy: Rome & Umbria

    Upgraded - Walking Italy: Rome & Umbria

    4.3
    A very pleasant and enjoyable holiday with great accommodation, views ,walks and guides. Enrico our rep was fantastic. Friendly, funny and engaging. A brilliant ambassador for EXPLORE. Would have no hesitation in going with them again. Thank you.
    Walking toursCity sightseeing
    Tour Type
    Small Group TourSmall group tours usually have 8-12 participants and maximum up to 18 travelers
    Accommodation
    Hotel, Resort
    Age Range
    16-99 yrs
    Operated in
    english
    Destinations
    Rome
    Rome
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    Italy Experienced Travelers Trips: St Francis Way: Rieti To Rome

    St Francis Way: Rieti to Rome

    4
    This was a wonderful walk through the Italian landscape following quiet trails peppered with villages and ancient hilltop towns. The walking provides a sense of achievement with occasional long days and steep rocky trails.
    Trekking and Hiking
    Tour Type
    Private Tour
    Accommodation
    Hotel
    Age Range
    18-99 yrs
    Operated in
    english
    Destinations
    Rome, Rieti, Poggio San Lorenzo
    Rome, Rieti, Poggio San Lorenzo, Scandriglia, Nerola, Sabina, Monterotondo
    View Tour
    Italy Experienced Travelers Trips: Jewels Of Italy By Rail

    Jewels of Italy by Rail

    5
    Three of us girlfriends decided it was time for an Italian cultural recharge, and we picked the rail tour to hit the highlights with ease. We explored Rome and saw the Coloseum as we opted for an optional tour. Florence was also beautiful. Venice was pure magic. Our shared gondola ride under the Bridge of Sighs (with just six in the gondola) felt cozy and unforgettable . We spent afternoons discovering boutique shops and colorful squares. For us, this tour struck the perfect balance. Relaxed evenings with wine and laughter. The train travel was a breeze, everything was well-coordinated.
    Train toursSightseeing Tours
    Tour Type
    Small Group TourSmall group tours usually have 8-12 participants and maximum up to 18 travelers
    Accommodation
    Hotel
    Age Range
    8-99 yrs
    Operated in
    english
    Destinations
    Rome, Florence, Venice
    Rome, Florence, Venice
    View Tour
    Italy Experienced Travelers Trips: Discovery Of Italy: 8 Days

    Discovery of Italy: 8 Days

    5
    I have had the wonderful pleasure of touring with you, the tour was well executed. The experiences are amazing and very unique. So much fun and I will tour again. I will recommend.
    Cultural, religious and historic sites
    Tour Type
    Group Tour
    Accommodation
    Hotel
    Age Range
    1-99 yrs
    Operated in
    english
    Destinations
    Rome, Florence, Venice, The Vati
    Rome, Florence, Venice, The Vatican, Assisi, Montepulciano, Siena, Tuscany, Bologna, Padua
    View Tour
    Italy Experienced Travelers Trips: Cycle The Via Francigena - Siena To Rome

    Cycle the Via Francigena - Siena to Rome

    4.5
    The Via Francigena is well signed and has a lot of different scenery, wheat and hazelnut farms, forests old towns etc and great different accommodation each night.
    Bicycle tours
    Tour Type
    Private Tour
    Accommodation
    Hotel
    Age Range
    18-99 yrs
    Operated in
    english
    Destinations
    Rome, Siena, San Quirico d'Orcia
    Rome, Siena, San Quirico d'Orcia, Radicofani, Bolsena, Viterbo, Sutri, Formello
    View Tour
    Italy Experienced Travelers Trips: Country Roads Of Italy, A Women-only Tour

    Country Roads of Italy, a Women-Only Tour

    4.7
    It was great traveling with other women. I felt some days were too busy, especially the miles we went one day for 45 minutes at a spare. Really enjoyed the meals.
    Adventure
    Tour Type
    Group Tour
    Accommodation
    Hotel, Villa, Resort
    Age Range
    5-99 yrs
    Operated in
    english
    Destinations
    Rome, Venice, San Gimignano, Luc
    Rome, Venice, San Gimignano, Lucca, Parma, Sorrento, Todi, Perugia, Florence
    View Tour
    Italy Experienced Travelers Trips: Italian Wonders: Venice To The Amalfi Coast

    Italian Wonders: Venice to the Amalfi Coast

    5
    Our family of 5 adults recently went to Italy on a 9 day trip to Venice, Rome and Sorrento(Amalfi Coast) with private tours, fast train travel, door to door drivers, and great accommodations; which was all set up by Michael. Michael was very responsive to my communications, very helpful with trip suggestions to make the trip better, and just overall a great travel planner! I was nervous at first, because I have never completely booked a vacation online without ever meeting the travel planner, but it all worked out great! We were completely happy with everything about our trip, and will definitely reach out to Michael again when we travel to Italy! There were a couple of small issues that arose over the duration of the trip, but they were handled quickly and without further problem to us. So all was good. Our private tour guides in Rome, Ornella; and Roberta in Pompeii were incredible. Our Venice tour guide, Cynthia, was awesome too, she did a great job! We did a full day 8 hr tour in Rome of the Colosseum and Vatican, and I would recommend splitting that to two half days if you have the time. It was awesome, but a bit much for one day!! Also, we had a full day Amalfi Coast tour by van, with great driver Antonio, which was supposed to go to Positano, Amalfi, & Ravello, but because the traffic is so bad on the roads, there wasn't time to make it to Ravello. So, I recommend either going by boat, which we hear is faster, or allow more time if you want to see all three villages. Again, a great trip for the memory books! Thank you MIchael and all of the local operators who worked to make our trip such a success!!
    City sightseeing
    Tour Type
    Group Tour
    Accommodation
    Hotel
    Age Range
    7-99 yrs
    Operated in
    english
    Destinations
    Amalfi Coast & Campania, Venice
    Amalfi Coast & Campania, Venice, Naples, Florence, Rome, The Vatican, Sorrento, Amalfi
    View Tour
    Italy Experienced Travelers Trips: Via Francigena: Ivrea To Pavia

    Via Francigena: Ivrea to Pavia

    4
    Journey through the plains and ancient hamlets of northern Italy on the "Via Francigena: Ivrea to Pavia" walking tour. Over eight days, this self-guided package leads travelers from Ivrea, across Piedmont’s rice fields—transformed into shimmering "chequered seas" in spring—to the vibrant university town of Pavia. Spot herons and egrets, wander past castles, and savor the artistic wealth and lively student culture that define the region’s towns. The unique selling point: experiencing the living traditions and natural diversity of the Italian Camino’s less-trodden northern sections, all while enjoying comfortable accommodation and seamless logistics.
    Walking tours
    Tour Type
    Private Tour
    Accommodation
    Hotel
    Age Range
    18-99 yrs
    Operated in
    english
    Destinations
    Lombardy & the Lakes, Pavia, Ivr
    Lombardy & the Lakes, Pavia, Ivrea, Viverone, Santhia, Vercelli, Mortara
    View Tour