Le Marche Hills to Sea

  • Sample Itinerary
  • Experiences
  • Pricing
  • Featured Hotels
  • Custom Quote

Journey into the emerald hills of Le Marche where the beauty of its lush landscapes and sweeping sea views are matched only by its fine artistic traditions, historic cache and hearty flavors. A land of Renaissance dukes and painters, olive groves and wild flowers, let Le Marche inspire you at every turn.

Sample Itinerary

Day 1

Your private chauffeur will welcome you at Ancona Airport before departing for the Renaissance town of Urbino, situated high in the lush, rolling green hills of Le Marche. Arrive for check-in at your four-star deluxe hotel, a former 14th century convent, with splendid views of the Ducal Palace. Get acquainted with Urbino with the help of a local expert who will bring its history to life as you privately tour the town's medieval quarters, artistic treasures, and hidden chapels. Visit the city’s illustrious Ducal Palace with its incredible studiolo featuring impeccable intarsia and trompe l’oeil craftsmanship. Next, visit the birthplace and childhood home of the Renaissance prodigy Raphael. End your walking tour with a delicious dinner of regional specialties like braciola all’urbinate and passatelli in brodo.

Day 2

Be transported by chauffeur to rolling hillsides that overlook the Adriatic to visit Le Marche’s infamous castle of Gradara, where the power struggles of the Malatesta family came to pass. In the afternoon enjoy a typical Marchegiani lunch at an organic farm located in the countryside. Return to Urbino by chauffeur for a free evening to explore the city’s noted woodworking shops or enjoy an aperitivo in the main piazza, the perfect place to observe everyday life in Urbino.

Day 3

Set-off for a day in Le Marche’s prestigious Verdicchio wine country, located just outside of Jesi. Partake in an exclusive wine tasting of DOCG Verdicchio wines at two of the area’s most renowned wineries. In the late afternoon depart Jesi for check-in at your noble country estate nestled in the foothills of Macerata. Savor a very special dinner of ancient recipes curated and developed by the same noble family that owns the property today. Taste your way through generations of Marchegiani culinary tradition through these recipes lovingly prepared using olive oil and other ingredients produced on the estate.

Day 4

Depart by chauffeur for the hilltop seaside hamlet of Fermo, with its breathtaking coastal views and rich history. Be greeted by your local guide and learn about the storied past of this Roman colony dating back to 264 BC with an insider’s look at its ancient baths and Villa Vitale. Stop for a sumptuous lunch in the heart of Fermo before enjoying some free time to stroll through the town and shop. From Fermo, travel to the city of Macerata for a guided walking tour of some of its most beloved sights like the Sferisterio and Palazzo Ricci. Return to your country estate by private car for a free evening of relaxation at the garden pool or dining at the rustic osteria located on the premises.

Day 5

Leave the countryside of Macerata for the vineyards of Offida where you will indulge in a tasting of the area’s DOCG Offida Rosso and Pecorino wines. After your wine tasting, travel to the ancient city of Ascoli Piceno where you'll arrive for check-in at your four-star luxury hotel that was once the town chancery and a noble palace. Rest a bit, then savor a luscious meal of traditional dishes from the area like olive ascolane, coniglio al forno, and vinci grassi.

Day 6

Today your local expert will guide you on a private exploration of Ascoli Piceno to discover the city’s medieval walls, beautifully preserved towers, ancient Roman bridge, and elegant cloisters. Stop for lunch at a historic osteria before continuing your guided walk with a visit to the city’s extraordinary archaeological museum to learn about the area’s ancient Piceni civilization. End your afternoon with an espresso and sweet confection at the famous Caffe Meletti, founded by the region’s premiere anisette producer.

Day 7

Following breakfast and check-out, you'll depart Ascoli Piceno via chauffeur, in preparation for your return flight or the next leg of your adventure.

Experiences We Recommend

  • Privately guided architecture tour of Urbino's Palazzo Ducale and its famed trompe l'oeil studiolo
  • Art history focused visit of the birth home of painter Raphael
  • Visit of 12th century castle of Gradara
  • Visit to small batch winery in Jesi specialized in premium DOCG Verdicchio
  • Countryside lunch at organic farm specialized in its own olive oil production
  • Guided exploration of former Roman colony of Fermo dating back to 264 BC
  • Winery visits and tasting at boutique producer of Offida Pecorino DOCG vintages
  • Cooking class of traditional Marchigiana fare at a local restaurant in Ascoli Piceno
  • Tasting of traditional anisette at historic cafe
  • Guided history tour along Ascoli Piceno's medieval walls and ancient Roman bridge


The minimum trip length for a CountryBred Encounter is 5 Days/4 Nights

Pricing for our Italy Encounters begins at:

  • $850-$1,000/per person, per day* based on double occupancy and a travel party of two
Small group pricing available for travel parties of four or more

*The final price of your custom tour will be determined by your travel party size, departure dates, trip length, amount of meals included, percentage of guided time requested, cities chosen in your itinerary and signature CountryBred excursions selected. This sample itinerary can also be crafted for solo travelers.

Encounters Include

  • Stays at five & four-star boutique luxury hotels
  • Chauffeured transport for touring & transfers
  • Private touring with professional local guides
  • Engaging activities led by cultural experts
  • Signature experiences with insider access
  • Regionally authentic dining
  • Traveler Welcome Package
  • Taxes & base gratuities

Read Client Reviews

  • Gay B.

    Alentejo to Lisbon
    Above and beyond our expectations for an amazing well organized adventure for 26!!
  • Mark W.

    From Castilla to Basque Country
    Our third CountryBred travel experience guided us through the rich cultural history, food, wine & unique culture throughout central/northern Spain. Our selected experiences coupled with the region/city ambassadors throughout our trip were exceptional and made our experience GREAT! (hotels too!)
  • Barbara R.

    Getaway to Tuscany and Northern Italy
    CountryBred thought of every detail for our trip. We didn't have to think about or worry about anything because they had it all covered by professionals every step of the way. From the chauffeurs, to the private boats, to the ambassadors who were extremely knowledgeable and spoke good English, to the amazing hotels, to the selection of restaurants and wines...WOW!

Crafting the Experience

Experiential travel takes time, passion and local ingredients to make something truly special.

Read more


We turn travel inspiration into unforgettable journeys. Begin the trip design process by filling out the form below and a CountryBred specialist will contact you to get your next great adventure underway.


  • CountryBred Encounters begin at $750-$1,000/per person, per day
  • The minimum trip length for a CountryBred Encounter is 5 Days/4 Nights
  • All CountryBred Encounters are land touring experiences only and do not include airfare
  • Groups of four or more are eligible for small group pricing


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