Umbrian Hill Town Exploration Tours

Come spending a lovely hour tasting fresh and fragrant products of the Umbrian gastronomy, and then lose yourself among the spectacular images, colors, scents and fragrances of our beautiful countryside.. all in complete safety and while still respecting the fundamental measures of social distancing! You will enjoy of a fantastic view of the valley of Assisi and you will be free to walk in the middle of organic vineyards and centuries old olive groves and breath pristine Umbrian air!

Join us on our Traditional Walking Food Tour in Perugia, where we'll take you to at leaast 4 of the city's best food stops and embark on a new culinary adventure. Explore the city's vibrant food scene as we take you to the best local eateries, trattorias and gelaterias. From trying Umbrian bread, “torta al testo”, cured meats and cheeses to indulging in local and traditional pasta and gelato or pastries, you'll get to taste the flavors of Perugia like never before. Immerse yourself in the city's rich culinary culture and history as you walk through the picturesque streets of the Umbrian town.

Orvieto is one of the most memorable hill towns of Umbria. Easy to reach by train from Rome or Florence, the city is located on a stunning steep hill made of tufa volcanic rock overlooking the charming “Paglia valley” below. Your walk in the city centre will take you to see Etruscan remains, the ruins of the city’s medieval fortress and of course the famous Duomo.

The tour starts from your hotel, a chance to spend a delightful day out of Rome to visit Umbria, one of the most picturesque regions of Italy rich in vineyards, olive trees and the famous hilltop villages. One of the most famous is Assisi, an UNESCO World Heritage Site. The mystic town of Saint Francis, surrounded by its ancient walls, was built on the green slopes of Mount Subasio and with its colorful houses of stone, narrow streets, flowering balconies and noble palaces provide beautiful views for memorable pictures (do not forget your camera). An interesting visit to St. Francis Basilica, with its early Renaissance masterpieces by Giotto and Cimabue, and the Basilica of Santa Maria degli Angeli. Time for lunch in a typical restaurant (optional) and then the tour continues to Orvieto, where you can admire a masterpiece of Gothic architecture with a glistening façade of stained glass, mosaics and sculptures. Soak up Orvieto’s charm and explore the city center and then Back to Rome.

Perugia is the capital of Umbria and one of the local hill towns. It is a city full of charme and history. With your private guide you will walk along its city wall dating from the Etruscan age, get lost in the symbols carved by Nicola and Giovanni Pisano's into the Fontana Maggiore and find yourself fascinated by the many layers of the Rocca Paolina.

Book our wine tasting and typical lunch (or dinner) at Enoteca Properzio, one of the best wine bars and wine stores in Italy.

Nestled in the picturesque hills near Lake Trasimeno, just a few kilometers from Perugia, this family-run winery offers a captivating wine-tasting experience that captures the essence of Umbrian tradition and innovation. For over a century, the family has been dedicated to cultivating vines, olives, and grains with deep respect for nature and the land. Today, the estate spans 12 hectares of meticulously tended vineyards, focusing on sustainable practices and producing a diverse range of red and white wines, including Merlot, Sangiovese, Cabernet Sauvignon, Grechetto, Chardonnay, and Trebbiano Toscano. Visitors can explore the sun-drenched vineyards and the historic barrel cellar, where wines are carefully aged in French oak barrels. The tasting experience includes six wines, thoughtfully paired with bruschetta drizzled with local olive oil and a curated selection of regional cheeses and cold cuts.

Guided by a local expert, your tour begins in the winding streets of Assisi, where the soul of the town is revealed through its stone houses, ancient archways, and scenic views of the Umbrian countryside. As you wander through the town, the guide shares captivating stories of Assisi’s rich history, from its Roman roots to its transformation into one of Christianity’s most important pilgrimage sites. Throughout the tour, your guide weaves together the threads of Assisi’s past and present, revealing how St. Francis’ legacy continues to shape the town’s identity today. Whether you are visiting Assisi as a pilgrim, a history enthusiast, or simply a traveler in search of beauty, this walking tour is a meaningful way to explore one of Italy’s most treasured towns.

Leave the hustle of the city behind and discover a quieter, more authentic side of Italy. This private day trip takes you away from the crowds and into the refined calm of Umbria a region of soft hills, stone villages, and timeless beauty. Your driver-guide will pick you up at your hotel in Rome in a comfortable, air-conditioned minivan. Sit back and relax as the landscape changes and the pace slows. Your first stop is Orvieto, a charming hilltop town with Etruscan roots and peaceful streets. Enjoy a traditional lunch, prepared with care by local "grandma" using family recipes. After, you’ll arrive in Assisi, birthplace of Saint Francis. Here, the air is still, the stones are pink, and the silence speaks. Explore the elegant basilica, stroll through quiet lanes, and soak in the views of olive groves and distant hills. Throughout the day, you’ll travel in comfort, with full flexibility and thoughtful guidance. No rush, no crowds just the essence of Italy, beautifully revealed.

Escape into the heart of Umbria on a small-group wine tour through Montefalco and Bevagna, where rolling hills, medieval villages, and endless vineyards set the stage for a day of indulgence. Known as the “land of Sagrantino,” this region is Italy at its most authentic—slow rhythms, passionate winemakers, and flavors that stay with you long after the last sip. You’ll visit two family-run wineries, walking among the vines and cellars as the owners share their stories and pour their signature wines, from bold Sagrantino DOCG to elegant Montefalco Rosso. Between tastings, sit down for a scenic winery lunch of seasonal Umbrian dishes—farm-to-table recipes paired with organic wine, served with views across the valley. With small groups (max 8 travelers) and pickup available on request, this experience combines the comfort of a guided tour with the intimacy of a day spent as a guest, not a tourist. It’s more than a tasting—it’s a journey into Umbria’s soul. ⸻

This is the best tour of Orvieto! Take your time to get amazed by the facade of Orvieto's Cathedral, one of the most beautiful churches in the world. Explore the hand-made tunnels of an underground area of the city and see the memories of the ancient Etruscan civilization. Walk along the impressive medieval walls and stop at the viewpoints to admire great panoramas of the countryside.

Visit the highlights of Orvieto, one of the oldest settlements in Italy, famous for its breathtaking cathedral. Learn about the spectacular Signorelli's frescoes and get amazed by this reinassance masterpiece. Admire the panoramas of the countryside from the viewpoints and see the pictoresque medieval district of the town. Discover another Orvieto exploring the underground area. Taste some typical food and wines in a local restaurant overlooking the cathedral. Go with a private car to the unique hilltown of Civita di Bagnoregio, take some pictures from the famous viewpoint and walk the bridge to reach the beautiful small city center.

Enjoy as much as possible your time in Italy and visit one of the most beautiful regions of Italy, Umbria. Your private english speaking driver* will drive you and your party through perched towns and across the beautiful italian countryside (visiting the most beautiful of them, Orvieto). After crossing the Tiber river, you will get to Orvieto. After visiting Orvieto, your private driver will continue driving through vineyards and ancient villas until you arrive to the city of Assisi. Very well known after Saint Francis, the city has a lot of attractions. You will get to know the history and secrets of Assisi with a private tour guide during 2 hours, Saint Claire, from where you can enjoy stunning panoramic views of the Umbrian countryside, as well as the old city center of Assisi. Due to the Jubilee, some monuments may be under restoration. Please pay attention to any messages we may send regarding potential changes.

Explore the enchanting cities of Cortona and Montepulciano during your transfer from Assisi (or Perugia) to Florence with our experienced driver and uncover the hidden gems of Tuscany! Immerse yourself in a full-day trip through the iconic landscape of rolling hills, cypress-lined avenues, and medieval hilltop towns, while enjoying delightful wines. We will pick you up at your location. Our first stop is Cortona, a picturesque Etruscan town at 600 meters above sea level, offering stunning views of the valley and Lake Trasimeno. Cortona is also famous as the setting of the beloved film Under the Tuscan Sun. For lunch, our driver will recommend a place for you to eat. Next, we’ll visit Montepulciano, where we'll explore the city and visit two Historic Cellars. See colossal oak barrels holding Vino Nobile di Montepulciano DOCG, followed by a wine tasting and explanation of its unique characteristics. In the afternoon, we will drop you off in Florence at your destination.

Take the worry out of your arrival or departure from Florence city orAirports with private transfers to hotels in the Umbrian  towns of Assisi or Perugia area. Relax as you drive through the garden of Italy.