Dolomites Journey Bike Tour

Otherworldly Scenery and Undiscovered Terrain in the Italian Alps

7 days / 6 nights Level: 4Price From: $5,095Collection: Challenge

Tour Highlights

  • Ride northern Italy’s greatest, hardest, and most historic climbs, including the legendary Passo dello Stelvio and Passo di Gavia, plus Passo Pordoi, Passo Falzarego, and Passo Giau in the heart of the majestic Dolomites
  • Explore the wild and remote edges of the Eastern Dolomites—truly satisfying for switchback aficionados
  • Escape into Slovenia’s quiet vineyards before plummeting to the edge of the Mediterranean Sea in Trieste
  • Traverse fundamentally distinct cultural enclaves, drastically different climatic conditions, and an array of landscapes—from fragile ecosystems to urban environs
  • Ride like a pro in custom Rapha x DuVine gear: jersey, socks, and cycling cap are complimentary on all Level 4 tours


Casunziei pasta, speck, polenta, goulash, Puzzone di Moena and Caprino di Cavalese cheeses, forest mushrooms, lake trout, and warm apple strudel


Unknown wines grown in these high mountain valleys like spicy Traminer and fruity Teroldego

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Print Itinerary
  • Day 1

    The Mortirolo

    Your guides will pick you up in Tirano for a quick transfer to Aprica where your Cannondales await. Enjoy a cup of coffee before we start climbing the backside of the Mortirolo, a ride that Lance called the hardest climb he ever did. After our descent, rest your legs at the hotel, or take a more epic route and throw in a detour over the Passo di Gavia, a legendary 17 kilometers at an average of 7.9% with some 16% ramps. Tonight, regroup in Bormio where the chef is cooking for us with ingredients fresh from the garden.

    Meals: Lunch / Dinner
    Destinations: Aprica, Tirano
    Accomplished: 41 miles / 66 km, elevation gain: 5,461 feet / 1,665 meters
    Longer Option: 61 miles / 99 km, elevation gain: 9,596 feet / 2,925 meters
    Accommodations: Hotel Funivia Bormio

  • Day 2

    The Stelvio

    Arguably Italy’s most famous climb, the Stelvio is also the country’s highest pass. Leave our country hotel behind as you settle in to tackle this 21-kilometer climb at a respectable 7.1%, powering yourself with our homemade energy snacks along the way. Fly down the 48 switchbacks on our descent into the valley on roads lined with apple orchards. Follow the Adige towards Naturno where we will be staying the night. Our dinner is a country affair as we take the road up to Juval. Enjoy hearty, typical Dolomite cuisine at your guides’ favorite restaurant.

    Meals: Breakfast / Lunch / Dinner
    Destinations: Bormio, Rabla
    Accomplished: 56 miles / 90 km, elevation gain: 5,665 feet / 1,727 meters
    Accommodations: Hotel Botango

  • Day 3

    Undiscovered Roads of Bolzano

    Have oats and eggs for breakfast as we get ready for one of our toughest days. Today we conquer two mountains on tiny roads so unknown that the passes are nameless. But that doesn’t mean they’re forgettable. Your legs will still twitch tonight as they remember the 18% sections. This is the day to win your Strava segments and upset the locals. In between our two nameless mountains, we enter civilization to visit and have lunch in the beautiful town of Bolzano. Our hotel is situated in a stunning Alpine paradise, and tonight a carnivorous feast awaits us at dinner.

    Meals: Breakfast / Lunch / Dinner
    Destinations: Merano, Bolzano
    Accomplished: 60 miles / 96 km, elevation gain: 11,293 feet / 3,443 meters
    Accommodations: Hotel Adler Carezza

  • Day 4

    Costalunga, Passo Pordoi and Passo Falzarego

    Today’s passes are well-known warhorses, frequented in the Giro. First up is the Costalunga; at only 10 kilometers, we’ll call it a “warm-up” climb. Up next is the more famous Passo Pordoi, in the middle of Sella Group with a statue dedicated to Coppi on top. This climb boasts an average of 6.1% over a span of 9 kilometers. Last but not least we cross the Passo Falzarego. The name Falza Rego means false king in Ladin and refers to a king of the Fanes, who was supposedly turned to stone for betraying his people. For those that would like more of a challenge, Passo Giau is Falzarego’s bigger, tougher neighbor. The cold beer awaiting you in Cortina will make it all worthwhile. Tonight is a free night in this ritzy mountain town.

    Meals: Breakfast / Lunch
    Destinations: Canazei, Arabba, Cortina
    Accomplished: 62 miles / 100 km, elevation gain: 8,840 feet / 2,695 meters
    Longer Option: 69 miles / 111 km, elevation gain: 10,699 feet / 3,262 meters (Passo Giau)
    Accommodations: Ambra Cortina

  • Day 5

    Tre Croci, Ciampigotto, and Zoncolan

    Wake up and slip into your favorite kit, freshly laundered by your guides, and get ready to leave the “known” parts of the Dolomites behind for the wilder eastern region. Start your day up the 8.1-kilometer Tre Croci at 7.1% before taking on Sella Ciampigotto. Wash down lunch in the mountain baita with an incredible strudel and descend to our next hotel in Ovaro in the shadow of Mount Zoncolan. At 10 kilometers and 11%, it’s the steepest climb in Italy. Admire it from the windows of your hotel or sprint up to the top to claim the Col sign. Tonight we feast on some typical cuisine.

    Meals: Breakfast / Lunch / Dinner
    Destinations: Auronzo di Cadore, Ovaro
    Accomplished: 55 miles / 89 km, elevation gain: 5,842 feet / 1,781 meters
    Longer Option: 67 miles / 108 km, elevation gain: 9,542 feet / 2,909 meters
    Accommodations: Osteria da Alvise or La Perla

  • Day 6

    Down to Slovenia

    Our route profile looks like a crooked king’s crown today as we lose 400 meters of elevation. It’s one of your “easiest” days, as you pedal where few cyclists have gone before on both flat and steep roads. (Strava segments are up for the taking.) Mountains give way to vineyards and low hills as we cross the border into Slovenia. Enjoy a stunning view from your hotel room tonight and raise a glass of wine to toast to an unforgettable week in the Dolomites.

    Meals: Breakfast / Lunch / Dinner
    Destinations: Tolmezzo, Medana (Slovenia)
    Accomplished: 73 miles / 118 km, elevation gain: 5,632 feet / 1,717 meters
    Longer Option: 86 miles / 138 km, elevation gain: 10,296 feet / 3,139 meters (Zoncolan)
    Accommodations: Castello di Spessa or Gredič Estate

  • Day 7

    Ride to the Sea

    Zigzag your way through the Slovenian countryside and into Italy as we head for the little seaport of Duino. The roads are winding, small, and gently rolling: perfect for cycling. It’s our version of the Champs d’Elysees, as we wrap up an incredible week on the bike. Crest the last ridge and admire the Mediterranean sparkling below. Get ready to spray Prosecco and enjoy a celebratory lunch in Duino. Afterwards, we’ll say goodbye as your guides see you off at the train station.

    Meals: Breakfast / Lunch
    Accomplished: 37 miles / 59 km, elevation gain: 2,312 feet / 705 meters

DuVine itineraries may be subject to slight route changes, hotel substitutions, and other modifications.

Arrival Details

Airport City: Milan or Venice, Italy Pick-Up Location: Hotel Centrale in Tirano Pick-Up Time: 8:00 am
Departure Details

Airport City: Milan or Venice, Italy Drop-Off Location: Monfalcone train station Drop-Off Time: 1:30 pm
Travelers Take Note

Our Journey tours are designed to reach small towns where hotel options are often limited and/or seasonal. Due to availability and routes, groups may sometimes be split between different properties. Note that air conditioning may not be standard in hotels in this area.

Upon booking this tour, you will be asked to complete a short form. We use this information to ensure all Level 4 trip participants are adequately prepared for our most difficult riding and have proximate cycling experience to the rest of the group.

Due to altitude, weather can change quickly. Expect anything from peak summer heat to hail and snow in a single day, and pack accordingly. Helpful hints about dressing for all climates can be found on our blog.

Please note that e-bikes cannot be reserved for this tour.

Any scheduled tour can be made private. Your group, your dates. Go Private

2024Single Supplement From: $500

See our cancellation policy

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  • Thoughtfully selected accommodations that reveal the true character of the region in ideal riding locations
  • Luggage transfers


  • Daily breakfasts, all lunches, and 5 cyclist-friendly dinners at our favorite local restaurants and renowned culinary establishments
  • Nutritious energy snacks, hydration, and shakes to support endurance and recovery
  • Local wines and beer with every meal


  • Wine tastings and activities as outlined in the tour itinerary
  • Entrance fees to historic sites, museums, parks, and all other exclusive events
  • Gratuities for baggage, porters, and hotel service


  • Top-of-the-line Cannondale carbon fiber road bike
  • Exclusive Rapha x DuVine jersey, socks, and cycling cap
  • Complimentary DuVine gear, including a DuVine t-shirt, water bottle, and drawstring bag
  • GPS with pre-programmed route maps


  • Expert bilingual guide with extensive cycling experience and local knowledge
  • Support vehicle that follows the day’s route, distributes refreshments, and offers lifts
  • Pick-up and drop-off before and after your tour from predetermined meeting points
  • Laundry service provided mid-week
  • Daily bike maintenance to ensure optimal performance

See our FAQs page for answers to common questions.

See FAQs

Synapse 2 RLE

Manufacturer: Cannondale

Type: Road

Included in trip price