There are parts of Europe where the borders feel theoretical. Northern Italy is one of them. Palm trees and lemon trees cling to the lakes while snow gathers on mountains that seem impossibly close, and somewhere beyond them Switzerland is already beginning, first in the roofs, then in the food, then in the clean cold air of the high valleys. For ten days we follow that gradual shift north, from Milan's stone and shadow to the deep blue of Como, through villages where Italy and Switzerland have spent centuries borrowing from one another, and finally over the Bernina Pass into the Engadin, where glaciers hang above dark forests and the evenings arrive with the smell of woodsmoke.

This is not a journey concerned with collecting places. It is interested in what happens between them. A train climbing slowly enough that you can watch vineyards disappear beneath the snow line. Lunch at a table where the cheese comes from the valley around you. A lake after everyone else has gone in for dinner. The hush that falls over a railway carriage when a glacier appears outside the window. We have left room for those moments deliberately, for long meals, wandering afternoons, changing weather, and the possibility that somewhere between Italy and Switzerland you may remember how good it feels to travel without always asking what comes next.

Ten days, nine nights, two countries, one mountain pass, and very little rushing in between. This isn't a trip built to change you. It's built for encounter, for the slow work of noticing what's already there, the way a place can hold you if you let it, the stillness that arrives after you finally stop looking for it.

TOUR HIGHLIGHTS

• 9 nights in centrally located hotels in Milan, Como, and Swiss Alpine villages

• Day trip to the walled medieval hill town of Bergamo

• Private boat tour on Lake Como visiting Varenna and the gardens of Villa Carlotta

• Al Fresco dinner overlooking the lake from Tremezzo

• A unique, special tour around Lake Como (surprise)

• Lunch at a grotto in the Valle di Muggio, Switzerland's southernmost valley

• A full free day to hike and wander, no itinerary attached

• Private coach and the Bernina Express, 1st class seats, the glass-roofed train over the Bernina Pass

• Carriage ride into the car-free Val Fex, Swiss Alps

• Time for hiking and exploring

• A few surprises along the way we're not giving away years

Kyle, a seasoned travel guide with over two decades of industry experience, has dedicated her life to creating enriching and inspiring travel experiences for diverse groups. With a repertoire of leading thousands of travelers (yes thousands!), she possesses an intimate understanding of the transformative power of travel. Her journeys span across the picturesque locales of Europe and the US, underlining her vast travel experience and knowledge. Yet, with every tour, Kyle's heart for her guests remains the same: to ensure every individual returns home with a revitalized spirit, a broadened worldview, and cherished memories of newfound friendships.

To view our full terms and conditions, please click here. (You will be asked if you agree, so take a moment and read them). 

DAY ONE Milan | Arrival

Milan keeps its secrets close to the surface. Walk under the Galleria at the hour when the light turns copper and the arcade seems to hold its breath, and the city stops being just marble and traffic. It makes its case in smaller currency, a plate of saffron risotto, a tram bell, the grey-gold hour when the light hits the Duomo. Our journey begins here. Arrive by early afternoon and settle in before we set out together on foot, tracing the streets between the Duomo and the Navigli canals. As evening falls we share our first meal as a group at a milanese trattoria, where its a local only vibe.

• Arrive by 1:00pm at the centrally located hotel

• Central walking tour of Milan

• Welcome drinks and dinner milanese trattoria

EASY WALKING: 1–3 MILES ON LEVEL CITY STREETS. SLEEP IN MILAN

DAY TWO Bergamo | A City Stacked in Two

We leave the city behind for a day trip to Bergamo, a walled hill town built in two layers, the modern city below and the medieval Città Alta above, reached by a funicular that has carried travelers up through the Venetian walls for more than a century. We wander the cobbled lanes of Piazza Vecchia, stop for a long lunch, and taste stracciatella where it was invented, before letting the afternoon move at its own pace and returning to Milan for a free evening.

• Funicular to Bergamo's Città Alta

• Walk the Venetian walls

• Lunch in Bergamo, with a taste of stracciatella

• Free evening in Milan

MODERATE WALKING: 3–5 MILES WITH SOME INCLINES AND STAIRS. TRAIN: 50 MINUTES EACH WAY. SLEEP IN MILAN.

DAY THREE | Lake Como

This morning we say goodbye to Milan and travel north to Lake Como, the first of two lakes on this journey. We settle into the hotel before climbing the funicular to Brunate, a hillside village with a view built for lingering, and toast the evening with drinks as the light turns gold over the water.

• Train to Lake Como

• Funicular to Brunate, sunset drinks overlooking Lake Como

• Dinner together

EASY WALKING: 1–3 MILES WITH ONE FUNICULAR CLIMB. TRAIN: UNDER AN HOUR. SLEEP ON LAKE COMO.

DAY FOUR Lake Como

A private boat takes on a tour around the lake with a first stop to Varenna. Then on to the gardens of Villa Carlotta in Tremezzo, where Canova's sculptures share the grounds with camellias and citrus trees older than the villa itself. We end the day a short walk from the villa for dinner, a family-run restaurant with a terrace built for watching the light change over the water.

• Private boat tour on Lake Como

• Visit Varenna

• Explore Villa Carlotta and its gardens

• Al fresco dinner on the lake

EASY WALKING: 1–3 MILES, MOSTLY FLAT WITH SOME GARDEN STAIRS. BOAT: HALF DAY. SLEEP ON LAKE COMO.

DAY FIVE Lake Como | Free Day

For anyone who'd rather have an unhurried day in Como. You can go for a hike, take the public ferry to another village, enjoy exploring Como or just enjoy a day of no plans. The evening is left open, together or on your own.

• Free day in Como

• Dinner, your choice

FREE DAY. SLEEP ON LAKE COMO.

DAY SIX To Poschiavo | Crossing Into Switzerland

We leave Como behind today and climb into the Valle di Muggio, the southernmost valley in all of Switzerland. Nine villages: Bruzella, Cabbio, Caneggio, Muggio among them, sit scattered across a landscape: dry stone walls holding terraces onto hillsides, cisterns cut into rock, small stone huts called nevère built to keep milk cool. Lunch is at a traditional Ticinese grotto and what arrives at the table isn't decoration: it's inheritance. You’ll sample Zincarlin, a cheese made almost nowhere else, cured meats, polenta ground from corn at a watermill in Bruzella. The food tastes the way it does because the rock and the isolation left people no other choice, and that necessity, carried forward for centuries and now simply called a good lunch, is the whole reason this valley belongs on the route at all. From here we continue on a stunning drive by private coach to Poschiavo. Arriving by evening to settle into your seventeenth-century palazzo on the village square, unmistakably Swiss.

• Drive into the Valle di Muggio

• Ticinese Grotto lunch: Zincarlin, cured meats, watermill-ground polenta

• On to Poschiavo, settle into hotel

• Dinner together

Easy walking. Mostly a driving day, with a long lunch along the way. Sleep in Poschiavo.

DAY SEVEN Poschiavo

After yesterday's driving, today asks nothing of you at all. Walk the Via dei Palazzi, where Poschiavini who made their fortunes abroad came home and built Venetian-style villas to prove it, wander down to Lake Poschiavo, or do nothing in particular and let the village set the pace instead. For anyone who wants a little more, a short train ride up to Alp Grüm delivers glacier views without asking for a single step uphill. Dinner together on the square closes the day.

• Free morning: Via dei Palazzi, Lake Poschiavo, hiking, or nothing at all

• Optional: Alp Grüm by train

• Dinner on your own

FREE DAY, ENTIRELY OPTIONAL PACING. SLEEP IN POSCHIAVO..

DAY EIGHT The Bernina Express

This is the day the whole trip has been building toward. A private coach carries us to Tirano, with time for a stop along the way, before we board the Bernina Express. A train with a glass roof that climbs over the Bernina Pass through some of the most dramatic scenery in the Alps. Glaciers, hairpin viaducts, and high mountain lakes pass close enough to touch. We arrive deep in The Swiss Alps by evening and share our first dinner in the village of Sils Maria.

• Private coach to Tirano

• The Bernina Express over the Bernina Pass, 1st class tickets

• Arrival in the Engadin

• Dinner in the village

MOSTLY SEATED. ONE COACH TRANSFER, ONE TRAIN JOURNEY. SLEEP IN THE ENGADIN.

DAY NINE The Swiss Alps | A Valley With No Cars

Our final full day begins with a carriage ride into Val Fex, a car-free valley reached only by horse-drawn carriage from the village square, where the road simply ends at a glacier. The afternoon is yours to spend as you like, a walk along Lake Sils, a quiet hour at the hotel, or the short drive over the Maloja Pass to look down into Italy one more time. Tonight we gather for a special farewell feast together before the journey comes to a close.

• Carriage ride into Val Fex

• Maloja Pass viewpoint

• Free afternoon

• Farewell dinner

EASY WALKING: 1–3 MILES, WITH OPTION FOR MORE. CARRIAGE RIDE INCLUDED. SLEEP IN THE ENGADIN.

DAY TEN Departure

After breakfast we say our goodbyes. You can travel by train via Chur north through mountains that gives way slowly to the lower hills of central Switzerland.

• Train to Zurich, via Chur

• Train to Milan

• Continue to stay