Getaway to the Italian and Swiss Alps

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

Experience the glorious landscapes of the Italian and Swiss Alps on a getaway that will take you from the enchanting banks of Lake Lugano and Lake Como to the mountainscapes of St. Moritz and the Engadine. Crown the experience with an elegant stay in Milan, where you’ll visit some of the city’s signature artistic and cultural wonders.

Sample Itinerary

Day 1

Begin your journey by arriving at Milan Malpensa Airport where you will be greeted by your private chauffeur and depart for the sophisticated Swiss city of Lugano. Arrive for check-in to your splendid five-star hotel overlooking Lake Lugano. Relax while taking in beautiful views of the lake before indulging in an elegant dinner of Mediterranean inspired creations at your hotel’s gourmet restaurant.

Day 2

Today you will discover the enchanting city of Lugano with the help of your local expert. Spend the day touring the city’s lovely pedestrian center packed with charm as you weave through the city’s historic arcades and discover Lugano’s quaint squares like the elegant Piazza Reforma and renowned shopping street of Via Nassa. Indulge in a lunch of Swiss Italian delicacies before traveling to Mt. Bre to marvel at exquisite panoramic views of Lugano and the lake.

Day 3

Delight in the unique flavors of the Ticino canton while experiencing its medieval roots. Start the day with an exclusive visit to one of the region’s most acclaimed chocolatiers where you’ll enjoy a guided tour and tasting of their fine Swiss chocolates. Afterward, travel by chauffeur to the capital of Ticino, Bellinzona, revered for its series of three medieval castles honored as UNESCO World Heritage Sites. Be welcomed by your local expert and embark on a privately guided historical tour of Bellinzona’s Castel Grande before savoring a lunch of quintessential Ticino flavors paired with the local Merlot wine, at a typical grotto (rustic tavern).

Day 4

Depart Lugano by chauffeur for the picturesque town of Gravedona, located on the northern portion of Italy's Lake Como. Set off on a private walking tour of the town, prized for its rich architecture and ancient history dating back to the Romans. Enjoy a scenic drive through Lake Como’s Alto Lago before arriving in Tirano, a mountain hamlet at the Italy-Switzerland border. Depart First Class on the Bernina Express, which will take you on a stunning train journey along the UNESCO honored Rhaetian Railway through the Albula/Bernina Landscape. Arrive in St. Moritz where your chauffeur will transfer you to your opulent five-star hotel offering stunning views over Lake St. Moritz. Savor an elegant dinner featuring traditional, local flavors at your hotel’s charming Engadine-style restaurant.

Day 5

Enjoy a day of Alpine exploration with your expert local guide, starting in Pontresina where you will take a scenic cable car ride to the Upper Engadine lakes and mountain ranges, culminating with a view from the top of Muottas Muragl. Delight in a panoramic lunch while atop the mountain before returning back down to continue your guided adventure with a visit to the lovely town of Zuoz to learn more about Graubunden’s ancient Romansch culture and language.

Day 6

Spend a leisurely free day exploring St. Moritz’s noted art galleries, designer boutiques, and esteemed Segantini museum, featuring the most comprehensive collection of works by the celebrated 19th century artist.

Day 7

Check-out and depart St. Moritz via the scenic Bernina Express for the Italian town of Tirano, where your private chauffeur will be waiting to transport you to Valtellina wine country. Indulge in a lunch of rustic Valtellinese fare featuring the region’s signature ingredients, such as pizzocheri, Bitto cheese, polenta and cured Bresaola. Next, travel to the cosmopolitan heart of Milan for check-in to your exquisite five-star hotel. Enjoy a free evening to get acquainted with the city at your leisure.

Day 8

Be welcomed by your resident expert and start the day with a privately guided visit to Milan’s Pinacoteca di Brera to admire the gallery’s Raphael, Bellini and Tiepolo masterpieces. Afterward, stop for a lunch of typical Milanese delicacies like Ossobuco and Risotto alla Milanese in the lively neighborhood of Brera, known for its distinct cafe culture and art galleries. In the afternoon visit the Duomo di Milano before enjoying a special trip to the top of the cathedral for exhilarating views of Piazza Duomo and beyond. Spend the rest of the day shopping along the Galleria Vittorio Emanuele or within the Triangolo Della Moda fashion district at your leisure.

Day 9

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

Experiences We Recommend

  • Scenic funicular ride to the top of Mt. Bre
  • Hike along the olive path with guided visit to village of Gandria
  • Lunch at a typical mountain grotto
  • Scenic boat rides along Lake Maggiore including visits of Ascona and Locarno
  • Privately guided historic tour of the UNESCO designated castles of Bellinzona
  • Scenic panoramic first class train ride on the Bernina Express railway
  • Visit of the lakes of Upper Engadine and scenic cable car ride to Muottas Muragl
  • Gourmet exploration of Valtellina inclusing visit to artisan producers of bitto cheese and bresaolo cured beef
  • Exclusive vineyard visits and premium tasting of Valtellina wines including Sfurzat, Grumello and Inferno
  • Guided art history focused visit of the Pinacoteca Brera and Da Vinci's Last Supper in Milan


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

Pricing for our Switzerland Encounters begins at:

  • $1,000-$1.300/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

  • Nini W.

    Northern Italian Alpine Sojourn
    "The experience is deep and intimate while feeling well taken care of in this special family trip. I would not work with anyone besides CountryBred."
  • 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!)

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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