Renaissance and Medieval Riches of Central Italy

Renaissance and Medieval Riches of Central Italy

Your journey of historical discovery will take you through the Renaissance cities and medieval burgs of Tuscany, Le Marche and Umbria. Unearth the antiquities of Florence with the help of a local historian and examine the region’s medieval roots beneath its Renaissance gilt in Arezzo. Appreciate the Renaissance heritage of Le Marche in Urbino before relishing the medieval splendor of Umbria in Gubbio and Assisi.

Renaissance and Medieval Riches of Central Italy

Sample 8-Day Private Tour Itinerary

Florence, Arezzo, Urbino, Gradara, Gubbio, Assisi


Day 1

private_luxury_tours_florence_countrybredArrive in Florence and be greeted by your private chauffeur that will transport you to your 15thcentury villa turned four-star luxury accommodation with breathtaking city views. Meet your local expert and begin a historical walking exploration of Florence, beginning at the famed Piazza Della Signoria with its 14th century Palazzo Vecchio. Stop for an early dinner at a coveted historic restaurant located in the heart of the city’s most antique quarter.

Day 2

custom_luxury_tours_florence_countrybredStart your day with a privately guided visit to Pitti Palace, the 16thcentury home of the Medici family. During your historical examination of the Medici dynasty, you will next visit the acclaimed Uffizi museum where you can peruse the Medici family art collection showcased within the illustrious galleries of this temple to Renaissance art. Afterward, take a leisurely look at Florence’s tranquil Boboli gardens before savoring lunch at a typical Florentine trattoria located just steps from Ponte Vecchio. After your hearty meal of Tuscan classics like Bistecca Fiorentina, enjoy an afternoon to explore the city at your own pace and take part in local city life as you stroll through its iconic piazzas and passageways.

Day 3

urbino_custom_le_marche_tour_countrybredDepart the Renaissance capital of Florence for the Tuscan countryside and journey to the medieval hilltop town of Arezzo. Enjoy an insider’s look at the 16th century Medici family fortress and the city’s Piazza Grande, once the city’s most bustling marketplace. Stop for a light lunch at a historic cafe dating back to the early 1800’s and once said to be the intellectual meeting place for Arezzo’s scholars and poets. Afterward, tour the birthplace of the famed “Father of Humanism”, Petrarch. In the afternoon depart for the Renaissance jewel of Urbino situated in the lush hills of Le Marche. Arrive at your 4-star deluxe hotel with stunning views of Urbino’s Ducal palace that was once a 14th century convent. End your day with a delicious dinner of Urbino specialties like braciola all’urbinate and passatelli in brodo in the center of town.

Day 4

urbino_private_le_marche_tour_countrybredGet acquainted with Urbino with the help of a local expert who will bring the history of the city to life through its antique medieval quarters, artistic treasures and hidden chapels. Enjoy a private tour of the city’s Ducal Palace, the former home of the illustrious Duke of Montefeltro. Tour the palace’s regal chambers and courtyards, and its incredible studiolo featuring impeccable intarsia and trompe l’oeil craftsmanship. Next, visit the birthplace and childhood home of the Renaissance prodigy Raphael. Afterward, savor a rich lunch at a locally favored osteria before enjoying an afternoon to discover Urbino at your leisure.

Day 5

gradara_castle_le_marche_private_tour_countrybredToday you will journey to emerald hillsides overlooking the Adriatic to visit the infamous 12th century 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 country foothills. Return to Urbino 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 6

umbrian_countryside_custom_umbria_tour_countrybredDepart Urbino’s Renaissance elegance for the stunning mountains and serene hills of Umbria. Arrive in Gubbio, where you’ll settle into your 17th century monastery restored into a four-star luxury accommodation located in the historic city center. Enjoy a light lunch at a local’s only trattoria of typical Umbrian salumi and cheeses paired with DOCG Montefalco wine produced in the countryside surrounding Perugia. After lunch be greeted by your local expert for a historical walking tour of Gubbio stopping to admire sites such as its 14th century Palazzo dei Consoli, one of Italy’s most beautifully preserved public halls, and the city’s 12th century Duomo. In the evening return to your hotel and rejuvenate amidst its lush grounds stopping at its Monasticum Convent Pharmacy to discover traditional homeopathic products and elixirs then feast on an elegant dinner of Umbrian regional cuisine in a historic restaurant.

Day 7

umbria_tour_italy_countrybredSet-off for the day to explore the UNESCO honored Basilica of St. Francis in Assisi and its exquisite Giotto frescoes with the guidance of a local art expert. Afterward stop at an agriturismo countryside farmhouse for a lunch featuring estate produced olive oils and wine before making your way to Deruta to learn about the ancient art of maiolica ceramic making. In the evening partake in a farewell dinner at a renowned eatery located in the center of Gubbio.

Day 8

Depart Assisi for your return flight home or the next leg of your trip.

-As part of our Enriched Booking process your customized itinerary will be designed with the assistance of a CountryBred specialist.
-This trip can be specifically tailored for organizations, associations and corporate incentives.


The recommended tour length for this sample itinerary is 8 days/7 nights with pricing options beginning at $5,400/person based on double occupancy. Please note that the “Share Bred With Friends” preferred pricing program will be applied to 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.

Included in this sample CountryBred Encounter are:

  • 7 Nights at CountryBred approved, four-star boutique accommodations
  • Deluxe and/or Superior room stays
  • Private luxury chauffeur for all intercity travel, day trips and excursions
  • Airport / Train station transfers with baggage assistance
  • Private touring with professionally licensed local guides and cultural experts
  • Flexible guided time with local experts based upon your preference
  • 3 Gourmand dinners
  • 5 Regionally authentic lunches
  • Exclusive wine tastings
  • Archeologist led visits of ancient sites
  • Daily breakfast
  • Museum tickets & entrance fees
  • All gratuities & taxes
  • Traveler welcome package including customized Culture Guide
  • Please note that transfers to airports and/or train stations outside of Florence for arrival/departure, are available upon request for an additional, supplemental fee. Airfare is not included.

Featured Deluxe Hotels

Antica Torre Di Via Tornabuoni 1 ****

Antica Torre di Via Tornabuoni 1 is a historic property dating back to the 13th century, located in the heart of Florence. Initially built by the Guelf Family, the medieval palace served as the residence of some of Florence’s most noble families from the 14th through 18th centuries, including the Ruggerini and Gianfigliazzi. In the early 20th century the palace played host to a series of aristocratic Italian families and English intellectuals traveling through Tuscany, before eventually closing its doors to guests. In 2001, after a careful restoration, the palatial residence was reopened to guests as a four-star luxury hotel nestled in one of Florence’s most prized locations, adjacent to The Bridge of Santa Trinita’. A protected historic residence of Florence, the building stands today as a four-story property with its original medieval architecture carefully preserved in such details as period cast-iron fixtures, stonework and facade. A unique feature of the hotel and a delight to all guests is the hotel’s series of panoramic terraces that afford stunning views of the cupola of Santa Maria Del Fiore, the hills of Fiesole and the Arno River.

Albergo San Domenico ****

Just steps from Urbino’s Duomo and Palazzo Ducale, Albergo San Domenico is the elegant reincarnation of a 14th century convent, lovingly restored and owned by the Marcucci Pinoli family. The hotel is your perfect introduction to Urbino’s rich history, with its Roman cistern, medieval cloister and magnificent fourth floor view of the Renaissance era Chiesa di San Domenico. Enjoy an abundant breakfast in the hotel’s sunlit refettorio off of the main cloister, or an afternoon glass of Mistra in the serene courtyard. Albergo San Domenico is the perfect way to experience the town that gave us Raphael and Paolo Volponi.

Park Hotel Ai Cappuccini ****

Beautifully bringing together a rich Umbrian heritage with a distinguished medieval past, Park Hotel ai Cappuccini is an extraordinary 17th century monastery restored into a four-star luxury accommodation located in the historic city of Gubbio. Providing visitors with a careful balance between isolated tranquility and close proximity to the city center, the hotel is an oasis of countryside calm amidst the bustling activity of a historic town. From its beginnings in 1631 as a church built under the direction of the Bishop of Gubbio and its legacy as a monastery of Capuccini friars to its rebirth as a deluxe accommodation of the 1960’s and once again refurbished in the early 1990’s, Park Hotel ai Cappuccini is a unique glimpse into history through the plush setting of a modern luxury accommodation.

Encounter Something Unexpected

Experiential travel takes time, passion and local ingredients to make something truly special. When you travel with CountryBred, you can look forward to the following:

      • A personalized and private travel experience, whether you’re a solo voyager, a couple, group of friends, family or an organization


      • A well crafted itinerary that is a reflection of your cultural interests, which we bring to life through our unparalleled insider knowledge, local access and dedicated team


      • A thoughtful travel pace that leads you down roads less traveled while leaving time to enjoy the quiet moments that make for remarkable memories


      • Enriching activities that immerse you in local culture and traditions


      • Premium accommodations that are distinct reflections of the regions they reside in, with real histories and real people behind them


      • Regional ambassadors and local cultural experts that go beyond educating, to invite you into their community and introduce you to their unique corner of the world.


    • Authentic dining that ensures you enjoy the finest in regional culinary traditions from quaint family owned eateries to innovative Michelin-starred restaurants. Each meal is in itself a work of art, passionately prepared and uniquely local.


Authentic is Premium