Undiscovered Central Italy: Marche, San Marino & Umbria - 8 Days

Day 2: Marche Wine Tasting Experience

Set out into the countryside today to spend the day exploring the rich winemaking traditions of Marche. Tucked between the Apennine Mountains and the Adriatic Sea, this geographically diverse region is often referred to as "Italy in miniature," with distinct microclimates and rich limestone and clay soils that produce remarkable wines. It's best known for its crisp whites, made with Trebbiano and Verdicchio grapes, though you'll also find world-class reds like the rare, floral Lacrima di Morro d'Alba.

With an expert driver and guide, you'll be free to relax and taste the many varieties, learn about the area's viticulture practices, meet wine producers, and stroll through the scenic vineyards. Stop for a traditional Italian lunch to recharge before more touring and tasting in the afternoon. At the end of the day, you'll be dropped off back at your hotel in Ascoli Piceno.

Day 3: Drive to Urbino via the Adriatic Coast

Get back on the road and drive just over two hours north to reach another Marche gem, the exquisitely preserved hill town of Urbino. Nestled high above a sloping hillside, this walled fortress was a beacon of art and learning in the 16th century, and is still home to a remarkable collection of Renaissance art and architecture. The journey there will take you up the Adriatic coastline, and you can take your time and break up the drive with stops at quiet beaches or take a slight detour to explore Ancona, a vibrant coastal city known for its fine museums and ancient Roman ruins.

When you pull into Urbino, get settled at your hotel, then get your bearings with a walk through its atmospheric, UNESCO-listed medieval center. Visit the famous Palazzo Ducale, home to the Galleria Nazionale delle Marche, and see where one of the Renaissance's greatest painters was born at the Casa Natale di Raffaello. When you've worked up an appetite for dinner, dive into the city's renowned dining scene (including 11 Michelin-starred restaurants) with local dishes like lumachelle al tartufo (unique snail-shaped pasta with a rich truffle sauce) and coniglio in porchetta (rabbit roasted with fennel and bacon).

Day 4: Day Trip to San Marino & Climb the Rocca Guaita

Journey about an hour north to spend a day in the fairy-tale mountain kingdom of San Marino. The fifth-smallest and arguably most intriguing of the world's independent countries, this ancient republic sits high in the Apennines, with a history stretching back to the fourth century CE. Join a private guide to hear stories of the small country's dramatic history as you stroll around the cobbled center, visiting Piazza della Libertà, the Basilica of Saint Marino, and other highlights.

Don't miss the steep climb to the precarious mountaintop Rocca Guaita (known as the "First Tower")—you'll be rewarded with breathtaking views of Apennine peaks and the Adriatic Sea. If you're visiting during the summer months, you'll also get to catch the famous Changing of the Guards in front of the Palazzo Pubblico. After a full day of exploring, return to Urbino for the evening and rest up; tomorrow you're off to Umbria.

Day 5: Drive to Perugia, Explore Umbria's Capital 

After a leisurely breakfast, hit the road and drive 1.5 hours southwest into the beautiful rolling landscapes of Umbria. Your route will cut through the Apennines by tunnel, and you can break up the trip with a stop in Gubbio, a spectacular medieval hill town nestled on the slopes of Monte Ingino. Your final destination is the region's lively hilltop capital of Perugia. Brimming with historic sights dating back to the Etruscans, this university town attracts students from around the world and plays host to world-class galleries and an international jazz festival.

Freshen up at your hotel, then set off to explore the medieval "Upper Town," connected to the modern city below via a series of escalators that travel up through the remains of the 16th-century fortress of Rocca Paolina. Take a self-guided ramble around the atmospheric plazas, or opt for a private tour with a knowledgeable local guide. Visit the Galleria Nazionale dell'Umbria (National Gallery of Umbria) to browse a prestigious collection of Renaissance and medieval art, or discover idyllic hidden gardens of the ancient church of Sant'Angelo.

Day 6: Perugia Market Tour & Cooking Class 

Today, you'll immerse yourself in Perugia's culinary culture with a traditional cooking class. Start with a visit to a nearby market to source locally grown ingredients, chat with local vendors, and get a glimpse of daily life in the city. Then, roll up your sleeves and help prepare a four-course meal in the kitchen of your local host. Discover the secrets of Umbrian cuisine, hear how the region has embraced the Slow Food movement, learn how to pair dishes with regional wines, and finish the day with a celebratory dinner to savor your creations.

A typical meal might start with oil and garlic bruschetta, followed by soup made with lentils grown in the heart of the nearby Sibillini Mountains. Pasta dishes are based around stringozzi, the region's version of tagliatelle, and dessert is often a type of torcolo—a medieval sweetbread unique to Perugia. Sip Umbrian wines with each course, and end the evening like a local with an espresso and an herbal digestivo.

Day 7: Free Day in Perugia: History, Art & Chocolate

Today is free to explore Perugia and its surrounding areas at your leisure. You could browse the eclectic Palazzo Baldeschi al Corso museum, whose palatial 14th-century rooms showcase art and sculptures from the 16th through 20th centuries, or stroll through souvenir and craft stalls in the bustling underground markets of the Rocca Paolina fortress. Stop by the University of Perugia, one of Italy's oldest universities, known for its beautiful courtyards and lively student atmosphere.

Spend the afternoon at Palazzo Sorbello, a 17th-century palace that preserves a precious collection of art, ceramics, books, and tapestries (don't miss the 3,000-year-old Etruscan Well hidden in the basement). If you have a sweet tooth, head to the Perugina Chocolate Factory, famous for its Baci chocolates. Here you can tour the chocolate laboratory to see the production process in full swing, before tasting various chocolates and products made on-site. Catch a sunset from Giardini Carducci, a tiny park with far-reaching views, then savor a final taste of Umbrian cuisine with dinner at a local trattoria.

Day 8: Depart Perugia

It's time to say goodbye to this special corner of Italy. After one last cappuccino and cornetti over breakfast, head to the airport, drop off your rental car, and catch your departing flight. Safe travels!

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