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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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    • Build a personalized Italy trip for mature travelers?

    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
    • Elena Kyrimi - Italy Tours Expert
      Elena KyrimiTravel Expert in Greece & Italy
    • Danilo Catania - Italy Tours Expert
      Danilo CataniaTravel Expert in Italy
    Start planning your Trip
    Recommended by
    • BBC
    • Independent
    • Lonely Planet
  • Duration
    1 day26 days
  • Departures
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  • 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.
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    USD 112USD 18,045
    • Showing 1 - 10 of 240 results
    Italy Experienced Travelers Trips: Via Francigena: Pontremoli To Lucca

    Via Francigena: Pontremoli to Lucca

    3
    Discover Tuscany’s hidden corners with the "Via Francigena: Pontremoli to Lucca" walking tour. This eight-day self-guided journey guides travelers from Pontremoli’s castle-dotted hills to the walled city of Lucca, taking in the lush landscapes of Versilia and the artistic hub of Pietrasanta. Enjoy the option to swim along sandy beaches, explore ancient workshops, and stroll through some of Tuscany’s most captivating old towns. The unique selling point: the blend of coastal and countryside walking, punctuated by lesser-known cultural gems and authentic regional hospitality. Ideal for those who want to experience a quieter side of the Italian Camino.
    Trekking and Hiking
    Tour Type
    Private Tour
    Accommodation
    Hotel
    Age Range
    18-99 yrs
    Operated in
    english
    Destinations
    Tuscany, Lucca, Pontremoli, File
    Tuscany, Lucca, Pontremoli, Filetto, Aulla, Sarzana, Massa, Camaiore
    View Tour
    Italy Experienced Travelers Trips: Cycle The Full Via Francigena - Aosta To Rome

    Cycle the Full Via Francigena - Aosta to Rome

    4
    Experience the thrill of cycling across Italy’s historic heartland with the 'Cycle the Full Via Francigena - Aosta to Rome' tour. Perfect for experienced travelers and seniors seeking moderate activity, this 24-day self-guided journey stretches from the alpine St Bernard Pass to the Eternal City. Pedal through the Po River plain, Tuscan vineyards, Umbrian hills, and along ancient Etruscan roads, discovering towns like Parma, Lucca, Siena, and Viterbo. Along the way, savor regional delicacies, sample local wines and cheeses, and revel in the ever-changing scenery. The USP of this bike trip is its comprehensive route—offering a rare opportunity to cycle the entire Via Francigena, blending cultural depth and culinary adventure from the Alps to Rome.
    Bicycle toursExplorer
    Tour Type
    Private Tour
    Accommodation
    Hotel
    Age Range
    18-99 yrs
    Operated in
    english
    Destinations
    Rome, Turin, Piedmont & Valle d’
    Rome, Turin, Piedmont & Valle d’Aosta, Aosta Valley, Aosta, Berceto, Aulla, Massa, Lucca, San Miniato Alto, San Gimignano, Siena, San Quirico d'Orcia, Radicofani, Bolsena, Saint Bernardo Pass, Viterbo, Sutri, Formello, Verres, Viverone, Vercelli, Vigevano, Pavia, Piacenza, Parma
    View Tour
    Italy Experienced Travelers Trips: Lake Como Rambling

    Lake Como Rambling

    4
    Picture yourself rambling along the shores of Lake Como, where deep blue waters meet soaring alpine peaks and historic villas line the banks. The 'Lake Como Rambling' tour is an 8-day self-guided walking adventure crafted for those who appreciate both natural splendor and cultural refinement. Starting and ending in Lake Como, this trip weaves through charming towns such as Como, Breglia, Bellagio, and Varenna. Walks are designed to showcase the region’s diverse scenery, from lush meadows and manicured gardens (thanks to the lake’s unique microclimate) to panoramic hillside paths. Ferries connect you to different shores, adding variety and a touch of old-world glamour. Delve into the region’s storied past, where Roman villas gave way to grand Victorian hotels, and enjoy the mild climate that allows tropical and temperate plants to flourish. Each evening, unwind in carefully selected accommodations and savor the region’s renowned cuisine. The unique selling point of this tour package is the opportunity to explore Lake Como’s beauty both on foot and by boat, offering a flexible, moderate trekking experience that blends relaxation with discovery. Ideal for travelers who seek a balanced getaway in one of Italy’s most picturesque locales.
    Walking tours
    Tour Type
    Private Tour
    Accommodation
    Hotel, Villa, Hut, Resort
    Age Range
    18-99 yrs
    Operated in
    english
    Destinations
    Lake Como, Como, Breglia
    Lake Como, Como, Breglia
    View Tour
    Italy Experienced Travelers Trips: Rome, Florence & Tuscany Family Adventure

    Rome, Florence & Tuscany Family Adventure

    5
    Hi Stefania! Sorry to take so long to write back. It has been crazy trying to get back into the swing of things at work after that trip. Italy was amazing!! We absolutely loved it! As for feedback on the trip, we really don't have anything that was negative. We loved everything that was planned! We especially loved how you planned the sites that we went and how the pattern flowed (not sure if you did it on purpose but we think so). Also, thank you for being very accessible to us during the whole planning of the trip. You helped put us at ease and it was very reassuring that we chose the right company. That is all that I can given you that might be considered constructive. The rest I could say would just be compliments on everything else. If I can think of anything else that I think is useful I will definitely email you. Hope all is well, Jane P.S. - Does your company only provide trips for Italy or other countries as well, just wondering for the future :)
    Food tours
    Tour Type
    Private Tour
    Accommodation
    Hotel
    Age Range
    6-99 yrs
    Operated in
    english
    Destinations
    Rome, Florence, Tuscany, San Gim
    Rome, Florence, Tuscany, San Gimignano, Chianti, The Vatican
    View Tour
    Italy Experienced Travelers Trips: Christmas In Italy: Rome To Venice

    Christmas in Italy: Rome to Venice

    Imagine celebrating Christmas surrounded by Italy’s most iconic sights, each one aglow with festive lights and the warmth of the holiday season. The Christmas in Italy: Rome to Venice tour is a 9-day small-group trip that starts in historic Rome and winds through Montepulciano’s rolling hills before ending in enchanting Venice. Stroll through cobblestone streets lined with artisan markets, experience the grandeur of the Roman Colosseum, and sip mulled wine as you take in the Ponte Vecchio and Venice’s magical canals. The itinerary is rich with cultural experiences, local flavors, and festive cheer, making it the perfect way to experience Italy’s beauty with a seasonal twist. This tour package stands out for its unique blend of sightseeing, cultural immersion, and holiday spirit—ideal for travelers who want to see Italy at its most enchanting and create holiday memories that will last a lifetime.
    Explorer
    Tour Type
    Small Group TourSmall group tours usually have 8-12 participants and maximum up to 18 travelers
    Accommodation
    Hotel, Villa
    Age Range
    12-100 yrs
    Operated in
    english
    Destinations
    Rome, Venice, Montepulciano, Florence
    Rome, Venice, Montepulciano, Florence
    View Tour
    Italy Experienced Travelers Trips: Highlights Of Italy

    Highlights of Italy

    Let Italy’s timeless wonders sweep you away on the "Highlights of Italy" tour, a nine-day journey from Rome to Venice. This adventure immerses you in the heart of Italy’s history, art, and flavors—stand in awe of Rome’s ancient ruins, get lost in Florence’s Renaissance masterpieces, and soak up the romance of Venice’s canals. Indulge your senses in Montepulciano, savoring regional wines and culinary delights. With a perfect mix of guided sightseeing and free time, this trip is ideal for those who want to experience Italy’s highlights at a comfortable pace. The unique selling point is the tour’s comprehensive blend of iconic sites and gastronomic pleasures—delivering the essence of Italy in one unforgettable package.
    Explorer
    Tour Type
    Small Group TourSmall group tours usually have 8-12 participants and maximum up to 18 travelers
    Accommodation
    Hotel, Villa
    Age Range
    12-100 yrs
    Operated in
    english
    Destinations
    Rome, Venice, Montepulciano, Florence
    Rome, Venice, Montepulciano, Florence
    View Tour
    Italy Experienced Travelers Trips: Cycling Lake Garda By E-bike

    Cycling Lake Garda by e-bike

    It's no surprise that Lake Garda is northern Italy's most popular destination. Full of beauty and history, lush green hills frame the clear waters as each point around the lake has its own unique character and charm. We have chosen the southern tip of the lake as our base, perched on the edge of the Mincio River. Our routes take you through diverse landscapes and towns around Lake Garda and along the river, on both the Lombardy and Veneto sides of the water. Cycle through vineyards, medieval towns, and along the famous Sirmione peninsula with its ancient castle. There's plenty to see along the way as you can visit UNESCO Heritage sites, Roman ruins, and of course, relax lakeside. There are also opportunities to sample the local wines in Bardolino and Valpolicella, regarded as some of the country's finest reds.
    Bicycle tours
    Tour Type
    Private Tour
    Accommodation
    Hotel
    Age Range
    12-99 yrs
    Operated in
    english
    Destinations
    Lake Garda, Bardolino, Borghetto
    Lake Garda, Bardolino, Borghetto, Lombardy & the Lakes, Sirmione, Mantua
    View Tour
    Italy Experienced Travelers Trips: The Amalfi Coast Walk

    The Amalfi Coast Walk

    Step into the timeless beauty of Italy’s Amalfi Coast, where dramatic cliffs meet shimmering seas and centuries-old villages beckon with charm. 'The Amalfi Coast Walk' is a 9-day moderate trekking tour designed for experienced travelers eager to explore both the iconic sights and hidden corners of this legendary region at their own pace. Your self-guided private trip begins along the elegant terraces of Ravello, home to the ethereal gardens of Villa Rufolo and Villa Cimbrone. The route winds through the pastel hues and vibrant beaches of Positano, before leading you to the secluded shingle coves of Marina del Cantone—places few tourists ever find. The trek culminates in Sorrento, perched on a cliff with sweeping views of Vesuvius, providing a spectacular base for optional excursions to Pompeii, Herculaneum, Capri, or Ischia. Along the way, you’ll encounter authentic moments: farmers harvesting olives, fishermen tending their boats, and panoramic vistas from the famed Path of the Gods above Positano. The unique selling point of this tour package is its perfect balance of celebrated highlights and off-the-beaten-path discoveries—crafted for those who value independence, cultural depth, and breathtaking landscapes. With accommodations, transport, and meals included, all you need to do is lace up your boots and let the Amalfi Coast’s magic unfold.
    Trekking and HikingHoneymoon
    Tour Type
    Private Tour
    Accommodation
    Hotel, Villa, Resort
    Age Range
    13-99 yrs
    Operated in
    english
    Destinations
    Amalfi Coast & Campania, Sorrent
    Amalfi Coast & Campania, Sorrento, Amalfi, Positano, Marina Del Cantone
    View Tour
    Italy Experienced Travelers Trips: Local Living Italy - Tuscany San Gimignano

    Local Living Italy - Tuscany San Gimignano

    If Tuscany has ever called your name, this is your chance to answer. For seven days, you’ll settle into a charming farmhouse in San Gimignano — your home for the week and your base for exploring the heart of central Italy. Wake up to vineyard views, stroll medieval streets, and soak up sunsets over rolling hills, all at a pace that feels truly local. With free days to embrace the countryside or head out on day trips to Florence, Siena, and Volterra, this isn’t just a visit — it’s living Tuscany, one unforgettable day at a time.
    Local culture
    Tour Type
    Small Group TourSmall group tours usually have 8-12 participants and maximum up to 18 travelers
    Accommodation
    Hotel
    Age Range
    12-100 yrs
    Operated in
    english
    Destinations
    Florence, San Gimignano
    Florence, San Gimignano
    View Tour
    Italy Experienced Travelers Trips: Premium Puglia

    Premium Puglia

    Puglia, Italy’s best-kept secret, invites you to discover its sun-drenched coastlines, ancient wonders, and architectural gems on the "Premium Puglia" tour. This 8-day small group adventure winds from Bari to Naples, offering easy-paced exploration ideal for seasoned travelers and seniors. From the charming port of Bari to the trulli dwellings of Alberobello and the sassi cave homes of Matera, each destination unveils a new facet of the region’s rich history and culture. Stay in a former palace in Nardo and explore the legendary ruins of Pompeii, all under the guidance of local experts. What truly distinguishes this tour package is the opportunity to experience Puglia’s understated beauty with insider access—enjoying local cuisine, staying in unique accommodations, and traveling with knowledgeable guides who bring the region’s stories to life. For those who crave authentic Italian adventure without the crowds, this journey through Puglia is a revelation.
    Explorer
    Tour Type
    Small Group TourSmall group tours usually have 8-12 participants and maximum up to 18 travelers
    Accommodation
    Hotel
    Age Range
    15-99 yrs
    Operated in
    english
    Destinations
    Bari, Naples, Polignano A Mare
    Bari, Naples, Polignano A Mare, Nardò, Matera
    View Tour

    Page 18 of 240 Experienced Travelers Trips in Italy with 6,348 Reviews

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