240+ Experienced Traveler Trips in Italy - Curated Adventures

Accommodations

BudgetSimple stays with essential amenities. Typically guesthouses, hostels or hotels rated below 3 stars — clean, no-frills, and great for value-conscious travelers.
Mid-rangeComfortable and reliable 3-star stays. Expect private rooms, en-suite bathrooms, and solid amenities — a great balance between comfort and cost.
PremiumUpscale 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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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 GalassiTravel Expert in Italy
Elena KyrimiTravel Expert in Greece & Italy
Danilo CataniaTravel Expert in Italy

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Recommended by

Venice to Rome by Rail + Sorrento and the Amalfi Coast

(1 review )

No booking fees

Best price guaranteed

Italy by rail offers a journey of timeless allure. On this 14-day adventure from Venice to Sorrento, with stops in Rome, Florence, and the Amalfi Coast, travelers experience the country’s iconic sights through a blend of city sightseeing and coastal exploration. The tour is tailored for those who appreciate a moderate pace, combining the freedom of train travel with guided discovery. Wander Venice’s romantic canals, browse Bologna’s bustling food markets, and marvel at Florence’s architectural masterpieces. Two full days in Rome allow deep dives into the Colosseum and Roman Forum. The sun-drenched Sorrento Peninsula awaits, with optional excursions to Capri and walks along the scenic Path of the Lemons. Pompeii’s legendary ruins and the dramatic silhouette of Mount Vesuvius complete the experience. This trip’s unique selling point is its seamless integration of Italy’s urban grandeur and coastal serenity—all connected by the comfort and efficiency of rail travel. It’s a tour package designed for those who want to see it all, at just the right pace.

City sightseeing

Tour Type

Small Group Tour

Accommodation

Hotel, Resort, Villa

Age Range

16-99 yrs

Operated in

english

Destinations

Venice, Sorrento, Maiori, Amalfi

Venice, Sorrento, Maiori, Amalfi, Bologna, Pisa, Rome, Naples

Duration14 days

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Via Francigena: Pontremoli to Lucca

(1 review )

No booking fees

Best price guaranteed

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

Duration8 days

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Cycle the Full Via Francigena - Aosta to Rome

(1 review )

No booking fees

Best price guaranteed

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

Duration24 days

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Highlights of Italy

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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 Tour

Accommodation

Hotel, Villa

Age Range

12-100 yrs

Operated in

english

Destinations

Rome, Venice, Montepulciano, Florence

Duration9 days

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Cycling Lake Garda by e-bike

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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

Duration7 days

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The Amalfi Coast Walk

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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

Duration9 days

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Local Living Italy - Tuscany San Gimignano

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Best price guaranteed

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 Tour

Accommodation

Hotel

Age Range

12-100 yrs

Operated in

english

Destinations

Florence, San Gimignano

Duration7 days

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Premium Puglia

No booking fees

Best price guaranteed

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 Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Bari, Naples, Polignano A Mare

Bari, Naples, Polignano A Mare, Nardò, Matera

Duration8 days

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Premium Sicily

No booking fees

Best price guaranteed

Sicily’s sun-drenched coasts, ancient mosaics, and volcanic landscapes await on the "Premium Sicily" tour, tailored for experienced travelers and seniors seeking comfort and depth. Over 10 leisurely days, your small group will be guided by a local expert through Palermo’s ornate palaces, Siracusa’s marble-lined lanes, and the wine-rich region of Marsala. Venture beyond city walls to the slopes of Mount Etna, Europe’s largest active volcano, and savor Sicily’s culinary treasures with a hands-on cooking class—think Genovesi pastries, arancini, and classic cannoli. What truly sets this tour package apart is its exclusive experiences, including a luxury countryside Feature Stay, offering authentic local charm in serene surroundings. With all logistics—accommodation, meals, and transport—carefully arranged, this sightseeing trip promises a relaxed yet immersive exploration of Sicily’s unique blend of history, culture, and gastronomy.

City sightseeingAdventure

Tour Type

Small Group Tour

Accommodation

Hotel, Resort

Age Range

15-99 yrs

Operated in

english

Destinations

Palermo, Catania, Marsala, Agrig

Palermo, Catania, Marsala, Agrigento, Siracusa

Duration10 days

Premium Walking & Hiking on Italy's Amalfi Coast

No booking fees

Best price guaranteed

Lace up your hiking boots and set your sights towards the spectacular Mediterranean horizon. This seven-day Premium walking and hiking trip on the Amalfi Coast features the best of the short hikes in the area, and is a nature-lover’s dream! Walk the crater rim of the Mount Vesuvius volcano, say Buongiorno to local farmers along the Pathway of the Gods, take in sweeping panoramic views from the Path of the Lemons, and catch a ferry to the glamorous island of Capri. Then, visit Pompeii to explore the preserved ruins and learn about the history of the area. Spend two nights in in a clifftop hotel, soak up sunsets, eat your weight in delicious Italian food (carbs, anyone?) and get active in one of the most beautiful parts of Italy, if not the world.

Trekking and Hiking

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

15-99 yrs

Operated in

english

Destinations

Naples, Capri, Sentiero Degli De

Naples, Capri, Sentiero Degli Dei, Amalfi

Duration7 days

Experienced Traveler Trips in Italy

Build a personalized Italy trip for mature travelers?

Page 15 of 185 Experienced Travelers Trips in Italy with 5,461 Reviews

Venice to Rome by Rail + Sorrento and the Amalfi Coast

Via Francigena: Pontremoli to Lucca

Cycle the Full Via Francigena - Aosta to Rome

Highlights of Italy

Cycling Lake Garda by e-bike

The Amalfi Coast Walk

Local Living Italy - Tuscany San Gimignano

Premium Puglia

Premium Sicily

Premium Walking & Hiking on Italy's Amalfi Coast

Page 15 of 185 Experienced Travelers Trips in Italy with 5,461 Reviews

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Experienced Traveler Trips in Italy

Build a personalized Italy trip for mature travelers?

Page 15 of 185 Experienced Travelers Trips in Italy with 5,461 Reviews

Page 15 of 185 Experienced Travelers Trips in Italy with 5,461 Reviews