Elegant Lombardia: Milan, the Lakes & Art Cities

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

Bask in the sophistication of Milan, the loveliness of the lakes, and Lombardy’s famed cities of art. From chic galleries and noble palazzi to classical theaters and Belle Epoque villas, luxuriate in the filigree facets of elegant Lombardia.

Sample Itinerary

Day 1

Your getaway through elegant Lombardia will begin with arrival to Milan Malpensa or Milan Linate Airport. Be welcomed by your private chauffeur and depart for the cosmopolitan heart of Milan. Arrive for check-in to your sophisticated city retreat, which will place you just moments from the city’s most coveted cultural treasures. Celebrate the start of your journey with an elegant dinner of traditional Milanese fare at a romantic ristorante.

Day 2

Discover the heart and soul of Milan’s historic center, starting in the the splendid Piazza del Duomo, where you’ll set off on a privately guided visit of the city’s iconic Gothic Duomo. Experience the majesty of the Galleria Vittorio Emanuele II, known for its exquisite architecture, fine shops, and bustling cafes, before visiting the medieval Piazza Mercanti. For lunch, delight in a meal of typical Lombardian specialties at a historic trattoria. End your guided day at the Convent of Santa Maria Delle Grazie where you’ll experience Leonardo da Vinci’s masterpiece, “The Last Supper”, with a reserved viewing.

Day 3

Today you will uncover Milan’s artistic riches with the help of a resident expert. Begin with a visit to Milan’s chic Brera district, known for its vibrant café culture, art galleries, and historic roots as one of the city’s oldest neighborhoods. Next, you’ll discover the superb art collection of the famed Pinacoteca di Brera, before stopping for lunch at a charming trattoria that captures the spirit of Milan’s creative energy. After lunch you’ll enjoy a unique glimpse at the golden age of Milanese Industry with a visit to one of the city’s most illustrious villa residences from the first half of the 20th century.

Day 4

Spend a full free day experiencing Milan’s premier fashion district, the Quadrilatero della Moda, which includes the famed Via Montenapoleone. A wonderland of high-end designer boutiques and chic shop windows, you’ll have free time to explore the fashion finery that is on display.

Day 5

After breakfast, depart Milan and travel to the historic city of Cremona where your resident expert will help you discover its rich fine arts traditions. Behold prized Stradivari violin masterpieces before visiting the workshop of a present day luthier. Savor a lunch of regionally inspired dishes then embark on a private walking tour of Cremona’s medieval center, stopping along the way to sample the city’s famed nougat confection, Torrone. You will travel onward by chauffeur to majestic Mantua, a Renaissance jewel perfectly preserved in time. Arrive at your luxury suite hotel, a former 12th century tower owned by a descendant of Castiglione, and nestled in the heart of the city.

Day 6

Today your local guide will take you on an intriguing walking tour of the city, an important center for art, culture and music for centuries. Visit the Ducal Palace of the noble Gonzaga family before touring Mantua’s esteemed Teatro Scientifico Bibiena, which hosted one of Wolfgang Amadeus Mozart’s earliest concerts. Enjoy a typical lunch of risotto alla Mantovana before experiencing Mantua’s Palazzo Te, celebrated for its exceptional Mannerist architecture and Chamber of Giants. In the afternoon, visit the UNESCO World Heritage city of Sabbioneta, built by the Gonzaga dynasty as an ideal Renaissance city.

Day 7

Following breakfast, depart Mantua by chauffeur for Lombardia’s sparkling wine capital of Franciacorta. Indulge in a tasting flight of Franciacorta DOCG vintages at one of the region’s most esteemed wine estates, before traveling to your sumptuous five-star wine country getaway for check-in and a free evening.

Day 8

After a leisurely morning travel to nearby Lake Iseo. Delight in free time to explore the many quaint villages that line the shores of the lake by chauffeur. Along the way, stop to enjoy lunch at an enchanting waterfront eatery.

Day 9

From the lovely landscapes of Franciacorta and Lake Iseo, you will depart for the classical sophistication of Bergamo, located at the foothill of the Alps. Arrive for check-in at your chic five-star hotel and be welcomed by your resident guide. Set off on a fascinating walking tour of “la Citta’ Alta”, Bergamo’s hilltop medieval neighborhood before embarking on a scenic funicular ride above the city to admire marvelous views of the surrounding Colle di San Vigilio. For lunch you’ll savor a meal of elegant Bergamasco fare at a beloved historic eatery

Day 10

Experience the restorative power of the famed thermal baths of San Pellegrino with a full day of spa relaxation. During your day of pampering you will have access to San Pellegrino’s beautifully refurbished Art Nouveau thermal baths and wellness center. In the late afternoon you’ll return to your hotel by chauffeur to freshen up, then in the evening, you’ll savor a sumptuous 3-Michelin star meal at one of Italy’s most acclaimed restaurants.

Day 11

Depart Bergamo for the idyllic shores of Lake Como. Arrive in one of the lake’s most scenic towns where you’ll partake in a hands-on cooking class of Northern Italian cuisine, led by a renowned local chef. Following lunch you’ll travel to your luxurious waterfront hotel for check-in and a free evening to get acquainted with your stunning surroundings.

Day 12

Journey back to the Grand Tour splendor of Lake Como through the insights of your local expert. Explore Tremezzo’s 17th century Villa Carlotta, known for its exquisite architecture and botanical gardens, before whisking away by private boat to visit the sparkling town of Bellagio with is picturesque cobblestone streets and dazzling waterfront. Dine on local charcuterie paired with regional Valtellina wines before strolling through the 19th century gardens of Villa Melzi.

Day 13

Enjoy a free day to explore the fairytale villages of Lake Como independently. At night, set off on a private evening boat ride to a romantic gourmet restaurant featuring splendid waterfront views and exceptional cuisine, and toast to your time on the lake.

Day 14

Following breakfast and check-out, depart Lake Como by chauffeur for Milan Malpensa or Milan Linate Airport, in preparation for your return flight or the next leg of your adventure.

Experiences We Recommend

  • Private shopping tour through Milan’s Quadrilatero della Moda with local fashion insider
  • Private watercolor painting class led by renowned artist on Lake Como
  • Guided visit of Milan’s Castello Sforzesco & Parco Sempione
  • Hands-on cooking class of Lombardian cuisine with acclaimed chef
  • Exclusive spa day at the famed thermal springs of San Pellegrino
  • Wine and cheese experience in the Valtellina
  • Privately guided visit of 17th century Villa Carlotta in Tremezzo


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

  • Carolyn W.

    Milan & North Italy's Art Cities
    "We experienced a little trepidation when signing up for a Country Bred travel itinerary through Italy’s Lake District, having learned of them through the Internet. We’re so glad we did—their guides, drivers, hotels, restaurants, activities were outstanding. "
  • Patricia S.

    Getaway to Lombardia & Veneto
    "I loved all the personalized, attention to the utmost perfection from CountryBred. Our group of four would love to use their services again for future travel."
  • Gay B.

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

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


What do you appreciate most when you travel? (Check all that apply)

How would you best describe your ideal travel pace?

(Early start denotes 8:30 AM; Later start denotes 10:30 AM)

What has been one of your favorite hotel stays & why?

Will you be celebrating any special occasions while on your CountryBred Encounter? (Check all that apply)

Are there any other considerations that you feel are important for us to know?