Create the perfect Italy adventure that's uniquely yours! Choose from over 190 customizable tours and trips that you can tailor to fit your budget, preferred travel dates, and personal style. Whether you're seeking luxury experiences, budget-friendly options, or something in between, our flexible packages allow you to design every detail of your journey. Join 90 satisfied travelers who've crafted their ideal trips with our customizable options.
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1 day22 days
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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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Showing 1 - 10 of 183 results
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USD 27USD 9,203
Page 4 of 183 Customized Tours and Trips in Italy with 100 Reviews
Discover the Tuscan countryside and culture on this 8-day self-guided walking tour. Through the extensive footpath network of the area, roughly following the traces of the Via Francigena, one of Europe’s most important ‘highways’ in medieval times, you walk from village to village and experience a full immersion in the world-famous Tuscan landscape. The tour is perfect as an introduction to the region and a great choice for people who love museums, galleries and Gothic and Romanesque architecture. You have plenty of time to visit attractions on most of the days.
You will also have time to visit all the beautiful medieval villages and historic towns along the Via Francigena: starting from beautiful Lucca, you’ll pass through Fucecchio, San Miniato, Gambassi Terme, the stunning San Gimignano with its medieval skyscrapers and Monteriggioni, admired by Dante in his Divine Comedy. An optional detour can bring you to beautiful Colle Val d’Elsa and the tour ends in Siena, arguably the most perfectly preserved medieval town in Tuscany. This tour threads together some of the most attractive towns and villages in Tuscany in an eloquent procession.
However, the emphasis of the tour is to enjoy the countryside, the rolling vineyards, the poppies in spring and the wild cyclamen in autumn. The area north of Siena is an amazing landscape of rolling hills, alternating vineyards and forests, while cypresses line the way leading to the distant farmhouses. Walking here is an unforgettable experience and many of the views have barely changed for hundreds of years.
Accommodation and some meals are included. You spend a night in one of the best agriturismos in Tuscany, and the final night in the heart of Siena, in one of the most characteristic little hotels.
This is a moderately easy tour which is suitable for those who have some experience of walking and a good general physical condition.
Trekking and Hiking
Tour Type
Private Tour
Accommodation
Hotel, Hostel
Age Range
18-99 yrs
Operated in
English
Destinations
Siena, Tuscany, Lucca, Altopasci
Siena, Tuscany, Lucca, Altopascio, San Miniato Alto, Gambassi Terme, San Gimignano, Monteriggioni
Naples promises a city break like no other, where the spirit of southern Italy is alive in every corner. On this 4-day self-guided art and architecture tour, seniors and culture enthusiasts alike can explore the city’s rich tapestry at a relaxed pace.
Wander the lively waterfront beneath the watchful gaze of Mt. Vesuvius, then lose yourself in the winding lanes of Naples’ historic center—brimming with artistic treasures and architectural marvels. The city’s vibrant street life, delectable cuisine, and centuries-old traditions create an unforgettable atmosphere, perfect for travelers who delight in authentic local character.
Accommodation, meals, and transport are included, ensuring a stress-free experience. The unique selling point? Naples’ singular blend of history, culinary excellence, and natural beauty, making this tour package a must for anyone seeking Italy’s true soul.
Art and architecture
Tour Type
Small Group TourSmall group tours usually have 8-12 participants and maximum up to 18 travelers
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
Wander through the enchanting streets of Alberobello on this walking tour devoted to its famed trulli houses—a UNESCO World Heritage site. Your guide leads you from the Aia Piccola district through narrow alleys lined with these iconic limestone dwellings, built entirely without mortar. Along the way, step inside the church of St. Anthony, the only trullo-shaped church in the world, and explore the Sovereign Trullo, which serves as a museum showcasing early 20th-century rural life. The tour also introduces you to local crafts and offers a relaxing shopping break, giving you a taste of authentic southern Italian culture. What sets this tour package apart is its focus on the unique architecture and living traditions of Alberobello, offering a rare opportunity to explore one of Italy’s most distinctive historical towns.
Picture yourself gliding along Italy’s iconic coastline, savoring the romance and charm of Naples, Pompeii, Sorrento, and Capri—all in just five days. The "Southern Pearls (on Request)" tour invites seniors to enjoy a relaxed, self-guided art and architecture trip that begins and ends in Rome. With handpicked accommodations and transport taken care of, the focus remains on leisurely exploration.
The first half of the journey immerses travelers in history and grandeur, from the ruins of Pompeii to the bustling energy of Naples. In Sorrento and Capri, take your time to soak up mesmerizing coastal vistas. The latter part of the tour lets you unwind in Positano, offering the freedom to lounge at your hotel, wander through picturesque streets, or swim in the Mediterranean’s inviting waters.
The standout feature of this tour package is its flexibility—allowing mature travelers to craft their own pace while enjoying the best of Italy’s southern gems. Whether you’re seeking cultural richness or seaside relaxation, this trip promises a harmonious blend of both.
Craving an authentic taste of Italian culture? This four-day tour package in Bologna is an ideal choice for seniors and lovers of fine living. Uncover culinary secrets in a hands-on cooking class with a local Cesarina, savoring the flavors of traditional Bolognese cuisine. Pedal through the city’s historic streets on a guided bike tour, immersing yourself in its vibrant atmosphere and architectural beauty. The tour also whisks you into Italy’s Motor Valley, where exclusive museum and factory visits bring the legends of Ferrari and Lamborghini to life. Blending gourmet delights, cultural depth, and automotive passion, the USP of this trip is its unique fusion of food, art, and motoring heritage—all set within the charismatic charm of Bologna.
Picture yourself winding through the sun-drenched landscapes of southeastern Sicily at your own pace. The South-oriental Sicily Beauty, Self-drive trip invites seniors and relaxed travelers to embark on a 7-day journey from Catania, weaving through Siracusa, the charming village of Marzamemi, the coastal wonders of Vendicari Nature Reserve, and the baroque splendor of Ragusa.
Explore Catania’s bustling markets and baroque treasures, step back into antiquity in Siracusa, and indulge in fresh seafood by Marzamemi’s scenic harbor. Spend tranquil moments birdwatching or lounging on pristine beaches at Vendicari, then conclude your adventure among Ragusa’s storybook streets and gourmet delights.
This self-guided tour package is tailored for those who cherish independence and a leisurely pace, with the unique benefit of flexible exploration—allowing you to savor Sicily’s cultural gems and natural beauty entirely on your own schedule.
Step into the tranquil heart of Italy with the "Hilltowns of Umbria, Self-drive" tour, designed especially for senior travelers seeking a relaxed, enriching escape. Over eight leisurely days, you'll chart your own course from Spoleto to Todi, weaving through the timeless beauty of Umbria—often celebrated as the "Green Heart of Italy." This self-guided trip puts you in the driver’s seat, inviting you to savor the region’s rolling hills, medieval towns, and celebrated art and architecture at your own pace. Explore historic gems like Perugia and Orvieto, wander ancient streets, and marvel at centuries-old castles nestled among vineyards and olive groves. Each day holds opportunities to sample local wines, taste decadent chocolates, and enjoy authentic cuisine in charming, welcoming settings. Comfortable hotel stays, included meals, and seamless transport make this tour package worry-free, so you can focus on creating memories. The standout feature? The complete flexibility to craft your own adventure through Umbria’s storied landscapes, all while enjoying the ease and comfort tailored to the senior traveler.
Sardinia’s shimmering coastline and vibrant traditions await you on the "Best of Sardinia, Self-drive" tour—crafted for travelers who appreciate comfort and independence. Beginning and ending in Cagliari, this eight-day self-guided adventure lets you explore the island’s diverse landscapes at a leisurely pace, perfect for those seeking a relaxed holiday. Journey from the bustling streets of Cagliari to the historic charm of Oristano, the coastal allure of Olbia, and the medieval magic of Alghero. Along the way, revel in the spectacular beaches of Costa Smeralda, wander through ancient ruins at Nora, and savor the lively culture of Sardinia’s renowned towns. The tour package includes comfortable hotel accommodations, transport, and select meals, ensuring a smooth and enjoyable experience. What makes this trip special? The freedom of a self-drive format, allowing you to uncover Sardinia’s hidden treasures, indulge in local cuisine, and embrace the island’s unique blend of old and new—all at your own gentle pace, ideally suited for seniors.
