Welcome to the Italian Alps: meet your guides at the train station in Bolzano and transfer to the Tyrolean village of Obergeggen where our bikes are waiting. First things first: we’ll have a coffee and a bike fitting before we start climbing the Alpe di Pampeago—a two-meter-wide slice of tarmac that seems to rise right into the pale, jagged peaks of the Dolomites. As we descend into the valley, it’s common to see local farmers in traditional clothing working the hay with the same scythes their grandparents used. The Val di Fassa bike path brings us to the base of Passo Sella: with 11 kilometers at 7.2%, it’s one of four passes that comprise the Sellaronda loop. Break away from the main road and grind gravel for the next half mile, leading right to our luxurious mountain refuge and home for the next three nights. Tonight we’ll feel like true kings of this mountain range as we dine on the terrace, watching the Dolomites turn orange and pink until the very last ray of sunlight disappears.

Meals: Lunch / Dinner
Destinations: Obereggen, Moena, Canazei
Accomplished: 41 miles / 66 km, elevation gain: 6,420 feet / 1,957 meters
Accommodations: Rifugio Salei

Get dialed in for our biggest day of riding: the Sellaronda loop has become an instant classic thanks to its four passes that feature frequently in the Giro—and they’re tremendously beautiful to boot. First up is Passo Pordoi, an average of 6.1% over a span of 9 kilometers; you know you’ve reached the top when you spot the statue dedicated to Italian legend Fausto Coppi. Take a coffee break in Arabba before some serious rollers that bring us to the foot of Passo Giau, the tougher, bigger neighbor to Passo Falzarego. Keep the momentum going up Falzarego, a road which witnessed some brutal battles between the Italian and Austrian armies during World War I. A cold beer and lunch atop the last climb marks the end of our miles for today, but it’s an ideal afternoon to hit the spa at our hotel or head out and hike the Sella range as a cool down. Our dinner is typically South Tyrolean—hearty and comforting food that’s perfect for recovery.

Meals: Breakfast / Lunch / Dinner
Destinations: Arabba, Pocol, Corvara
Accomplished: 72 miles / 116 km, elevation gain: 11,949 feet / 3,642 meters
Shorter Option: 53 miles / 85 km, elevation gain: 8,083 feet / 2,464 meters
Accommodations: Rifugio Salei

The Marmolada is the nearly 11,000-foot massif that asserts a constant and prominent presence wherever we go—but our preferred way to appreciate this gigantic glacier is to ride right up her flatter side. As it happens, this is also the history-making ascent that earned Italian pro Pantani his first Maglia Rosa during stage 17 of the 1998 Giro d’Italia, paving the way for his series of grand tour triumphs. We begin our approach from Canazei via the Passo Fedaia, pausing to admire Marmolada’s reflection in Lake Fedaia’s clear, glacial waters. Relief comes on our descent into the Pettorina Valley, where our route briefly veers into Italy’s Veneto region before we revisit Passo Pordoi. This time, we hit it from the south side for a technical climb up 33 switchbacks all the way to the top of the Sella Pass. Back at our hotel, wind down the day with an al fresco dinner at our hotel on the Sellaronda circuit.

Meals: Breakfast / Lunch / Dinner
Destinations: Canazei, Malga Ciapela, Arabba
Accomplished: 49 miles / 80 km, elevation gain: 8,245 feet / 2,513 meters
Accommodations: Rifugio Salei

Arguably Italy’s most famous pass, the Passo dello Stelvio is also the country’s highest as it straddles the border with Switzerland. Leave our refugio in the morning and transfer to the start of the climb: a 25-kilometer feat at a respectable 7.4%. Our homemade energy snacks will keep you from bonking until the glorious descent into Bormio, a town nestled into the Valtellina valley. Our ride ends right at a cable car that lifts us back into the mountains once again to our luxury log cabin in Stelvio National Park—and at an altitude of nearly 9,000 feet, it feels like you could reach out and touch the surrounding mountaintops. We’ve certainly earned tonight’s dinner, which is also our first introduction to the Nebbiolo wines grown in the Valtellina valley.

Meals: Breakfast / Lunch / Dinner
Destinations: Prato allo Stelvio, Bormio
Accomplished: 42 miles / 67 km, elevation gain: 8,307 feet / 2,532 meters
Longer Option: 59 miles / 95 km, elevation gain: 11,260 feet / 3,432 meters
Accommodations: Sunny Valley Mountain Lodge

Call us crazy, but breakfast tastes different when it’s taken on a terrace with views of the Italian Alps. Once we’re well-fueled, ease into the day with a spin down the valley to wake up our legs—after that, it’s strictly business. The mighty Mortirolo is mercifully at the lowest altitude of the week, because it’s also our meanest climb at 12 kilometers with an 11% average. Bomb into Monno before we take on the last pass of the week: the Passo di Gavia is a legendary 17 kilometers at an average of 7.9% with some 16% ramps—now that’s an epic finish! On our last evening, raise a glass and toast to winning some serious Strava segments this week.

Meals: Breakfast / Lunch / Dinner
Destinations: Mazzo di Valtellina, Monno, Ponte di Legno
Accomplished: 69 miles / 111 km, elevation gain: 11,033 feet / 3,363 meters
Accommodations: Sunny Valley Mountain Lodge

Enjoy one last coffee at Sunny Valley before transferring with your guides to the train station in Lecco. From here, it’s an easy connection to Lake Como, Milan or Venice airports, or wherever your adventure takes you next.

Meals: Breakfast
Destinations: Lecco