Itinerary
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Small group of 6 people | $5900 per person
6-13 September 2026
Do you know about Valtellina?
Probably not. it’s Northern Italy’s best-kept secret.
This hidden Alpine gem offers stunning landscapes, world-class wines, and authentic mountain adventures far from the crowds. -
Day 1
Begin your journey with a warm welcome in Valtellina. Enjoy a traditional dinner at a local restaurant, savoring regional dishes and fine wines in a relaxed setting. It’s a chance to get to know one another and preview the experiences that await in the days ahead.
Included: Dinner and accommodation.
Activity level: Easy -
Day 2
After a relaxing breakfast with breathtaking mountain views, we’ll visit the heroic terraced vineyards of Valtellina, a UNESCO-recognized landscape where Nebbiolo grapes thrive on steep mountain slopes. You’ll tour the vineyards and the cellars of Cantina Menegola, learning about traditional winemaking methods before enjoying a tasting of their exceptional wines crafted from centuries-old vines.
Included: Breakfast, guided winery tour with wine tasting and light lunch, dinner, and accommodation.
Activity level: Easy -
Day 3
Today we set out on a tour of Lake Como aboard a classic wooden boat. Take in the stunning views of towering mountains and charming lakeside villages while experiencing the lake’s timeless beauty from the water. From this peaceful vantage point, we’ll discover hidden corners and unique perspectives that can only be seen from the lake itself.
Included: Breakfast, boat tour with wine and light charcuterie, dinner, and accommodation.
Activity level: Easy -
Day 4
Today, we’ll visit the Storico Ribelle dairy, home of the historic Bitto cheese, for a guided tour and tasting. Surrounded by the beauty of the alpine valley, you’ll discover traditional cheese-making methods and enjoy the rich flavors that define this remarkable local specialty.
Included: Breakfast, guided dairy visit, cheese and wine tasting, dinner, and accommodation.
Activity level: Easy -
Day 5
Today, enjoy the Bernina Red Train, a UNESCO World Heritage route through the stunning Swiss Alps. Upon reaching Poschiavo, you can take an optional hike around the beautiful mountain lake or relax with a meal at one of the village’s charming restaurants, surrounded by nature. This journey perfectly blends impressive engineering with breathtaking alpine scenery for an unforgettable experience.
Included: Breakfast, train ride, dinner, and accommodation.
Activity level: Easy -
Day 6
Embark on a scenic hike through the Italian Alps in Bormio, often referred to as a hike paradise due to its vast network of trails and breathtaking landscapes. Afterward, unwind at Terme di Bormio’s Bagni Vecchi, a historic thermal spa since Roman times. Rejuvenate in natural hot springs and ancient stone structures. This adventure combines physical challenge with relaxation, tailored to your fitness level. Enjoy breathtaking views and rejuvenate your body and mind.
Included: Breakfast, guided hike, spa entrance, dinner, and accommodation.
Activity level: Moderate -
Day 7
Embark in a scenic hike into the breathtaking Parco Nazionale dello Stelvio. This national park is one of Italy's oldest, established in 1935, and is renowned for its stunning alpine landscapes, including glaciers, alpine pastures, and diverse wildlife. This evening offers a chance to reflect on the adventures we've had and the experiences we've shared.
Included: Breakfast, guided hike, dinner, and accommodation.
Activity level: Easy -
Day 8
On our final day, after a relaxed breakfast together, we’ll share our goodbyes and reflect on the memories created throughout the journey. Guests are then free to depart at their leisure, whether heading to the airport or continuing on to their next destination.
Included: Breakfast
Activity level: Easy
Restaurants and Accommodations
Throughout the journey, accommodations will be in carefully selected alpine-style hotels, rich in character and charm, offering comfort, warmth, and an authentic sense of place. Evening dinners will be hosted in traditional local restaurants, where regional cuisine and welcoming hospitality create a refined yet genuine cultural experience.
As a longtime customer of Andrea, I always wanted to explore the wineries in Northern Italy and meet producers of his exceptional wines. So, last Spring, I spent 10 days having Andrea as a guide visiting several wineries, meeting producers, snow hiking in a beautiful mountain near Swiss Alps, it was an amazing experience! It would have never been possible without Andrea. Strongly recommended.
-Mitsuo
I’ve been a customer of Andrea’s for the past five years. While I will truly miss his exceptional wines, I’m excited about his new venture. Andrea’s passion and attention to detail are remarkable. We look forward to using this service for our next trip to Italy..
-Warren
Andrea helped my wife and me plan an amazing trip to Italy last summer, connecting us with local wineries, restaurants, and charming B&Bs we wouldn’t have found otherwise. The highlight was visiting Menegola Winery, where Walter spent two full days showing us around and sharing the unique long history of his family on this beautiful land. We tasted his great wine and hiked all over the vineyard with him while he told us the history. And we capped it all off with an incredible meal at his amazing restaurant which had the best Risotto we ever had. The recently built luxurious accommodations on the vineyard hills gave us an unbelievable view from the bed to an amazing National park across the valley. Truly unforgettable. Highly recommend this service provided by an extremely authentic guy (Andrea) who knows some of the the most beautiful hidden secrets of Italy!
-Joe
This is a picture we took from Walters B&B during our Trip
