Experience the Splendor

Italian Dolomites Cycling Tour


The Dolomites

Our HighRoad Dolomites cycling tour is our first foray into this legendary mountain area of northeastern Italy. Come with us and climb Giro d’Italia giants like the Gavia, Motirolo, Tre Cime di Lavardo, Giau and, of course, the Stelvio.

like the Alps and Pyrenees in France, the Dolomites are filled with epic climbs and outstanding scenery. Our HighRoad Dolomites tour will spend a few days in the Dolomites themselves before riding west to climb the 48 switchbacks of the epic Passo dello Stelvio, the most famous of all Giro d’Italia ascents.

In between all your daily efforts we will make sure you are well rested and fueled, with our excellent hotel partners and local restaurants.

HighRoad Dolomites is one of our ‘Hors Catégorie’ bike tours, which are reserved for strong riders who can handle multiple days of long distances and sustained, steep gradients.

*Qualifies as a stage of Project Trans-Alps

Tour Distance:  approx. 500 km     

Climbing: approx. 12.500 m


Tour Price

  • Double occupancy: €4180
  • Single Supplement: €750
  • Deposit: €500 per person

Accommodation and Dining

  • 7 nights accommodation
  • All breakfasts, lunches and 6 dinners (including wine)
  • Energy bars, gels, snacks and water on your rides


  • Pick-up at Venice Airport (VCE) and drop-off at Milan Airport (MXP)
  • All ground transport and baggage transfers
  • Owner-operator guides to see to your needs
  • Maps and elevation profiles of each day’s route
  • Support van that will be on the road with you, offering assistance, encouragement, and nutrition
  • 44|5 Cycling Tours jersey and water bottle


  • Transportation to Italy
  • Alcohol outside meals
  • Hotels before and after your tour
  • Personal expenses, such as mini-bars, telephone or souvenir purchases
  • Bikes (we can arrange for rentals)

Day to Day

Your typical day on our Dolomites bike tour will begin with a hearty buffet breakfast, followed by a ride in this most legendary of mountains. Most rides will end back at your hotel (or the next one along the route) for a post-effort lunch. However, on longer days in the saddle (Day 6 and 7 for example) it will be a quick – and light – lunch on the road. You will always have a few hours in the afternoon to relax and explore your surroundings before we meet for a dinner of delicious local fare.

Transfer to the mountains and shake-out ride

Your HighRoad Dolomites cycling tour begins at Venice airport (VCE), where we’ll pick you up and transport you to the heart of the mountains and our first hotel in the fashionable ski town of Cortina. After setting up your bikes we’ll take a “shake-out” spin through the valley hamlets. In the evening we’ll have our traditional ‘welcome dinner’ and talk about the amazing rides to come.

Ride: Tre Cime Loop. Approximately 52 km and 1400 m of ascent

Today’s short loop with keep you busy with plenty of climbing, with the highlight being the ascent into the middle of one of the most famous landmarks in the Alps – Tre Cime di Lavaredo. The climb is steep and spectacular with 360 degree views from the top. We will be back in Cortina for a late lunch, giving you the rest of the afternoon to walk around the town and rest the legs for tomorrow.

Dinner will be at a local restaurant near your hotel.

Ride: To Corvara via Passo Giau, Santa Lucia, Falzarego and Valparola. Approximately 67 km and 2300 m of ascent

Today we dive deep into Italian cycling lore with climbs of the Giau and Falzarego, both fixtures of the legendary amateur cycling event, Maratona dles Dolomites. We are now in the heart of the Dolomites, which the views from the Giau will confirm. We are now riding west, with our destination being Corvara, the center of the cycling universe in the Dolomites.

Ride: Sella Ronda. Approximately 52 km and 1700 m of ascent

As one cycling journalist put it, ’If I had one last ride to ride, I would ride here.’ The Sella Ronda is a loop that everyone wants to ride when they think about the Italian Dolomites, and you will ride it, of course! The loop is not long or overly difficult, but does include 4 mountain passes and has some stunning views. We will be back in Corvara for a late lunch and time to rest up for tomorrow’s longer stage.

We’ll dine in Corvara tonight.

Sella Ronda on a Dolomites bike tour

Ride: Corvara to Merano. Approximately 100 km and 1200 m of ascent

Today we transition from the Dolomites proper to the historical spa town of Merano. After climbing the Gardena one more time we head to lush, green rolling hills that contrast dramatically with the craggy Dolomites we area leaving behind. Don’t worry, though, you still have some climbing to do! The last half of the ride is on a bike path along the Adige River, which leads us to our luxury castle accommodation for the night.

Village church in the Dolomites

Merano to Bormio via the Passo dello Stelvio

This is the day many of you will have been waiting for – the mighty Stelvio! We will climb via the most famous northern side, with its 48 (yes, 48!) numbered switchbacks, after a long, flat run-in across the Adige Valley. The Stelvio has a long and storied cycling history with many appearances in the Giro d’Italia. It remains the highest finish of any Grand Tour.

Dinner will be at our hotel in the heart of Bormio.

Happy cyclists on top of Stelvio Pass on a Dolomites bike tour

Ride: Mortirolo, Gavia Loop. Approximately 110 km and 3050 m of ascent

It’s hard to believe, but the Passo del Mortirolo has only been used in the Giro d’Italia since 1990. It was an instant hit back then, though, and has been the scene of many a suffering peloton since then. It is one of the hardest climbs in professional cycling, but this is the last day of your tour – and think of the bragging rights!

Often given the label of ‘Cima Coppi’ (the highest pass in a given year’s Giro), The Passo di Gavia is the 2nd tallest on our tour (behind Stelvio). The pass is famous for being the staging ground of one of pro racing’s most epic days – when Andy Hampsten took the lead of the Giro in 1988 over the Gavia in a freezing blizzard.


After breakfast we will transfer you to Milan Airport (MXP)


44|5 has chosen your Dolomites accommodation for the best mix of comfort, cycling services and location. You’re always within walking distance of village centers, restaurants, bike shops and other necessities.

Hotel Bellevue Suites and Spa****

We start our Dolomites cycling tour at the Bellevue Suites and Spa. Built in the 1800s, this spa hotel has seen such illustrious guests as Ernest Hemingway and Frank Sinatra come through its doors. Today the hotel welcomes the ski set in winter and, of course, mountain-loving cyclists in summer!

Sporthotel Panorama****

This friendly hotel on the slopes overlooking Corvara is your home for 2 nights. Yes, you need to climb to get to your hotel, but we assure you that the views are worth the effort!

Sporthotel Panorama in the Dolomites

Castel Rundegg****

Originally built in the 12th century, lovely Castel Rundegg sits on quiet grounds just minutes to the center of the pretty town of Merano.

Baita dei Pini****

Our large chalet-style hotel in Bormio is the perfect base to come back to after climbing such legends as the Stelvio, Gavia and Mortirolo.

Dates & Prices

Tour Dates – 2024 custom dates only

Tour Availability – Contact us

Price Per Person – €4180

Single Supplement – €750

If you have a group of 6 or more riders we can make a custom and private tour in the Dolomites for your group. Contact us to start the conversation.


Travel Details

Arrival Airport – Venice (VCE)
Pick-up Point – Airport: Noon
Departure Airport – Milan (MXP)
Flight Time – Book a flight out for early afternoon or later

Either Venice or Milan would be excellent cities to spend a few days before or after your tour. Another great idea, if you’d like to relax your legs in a beautiful setting, would be to stay on Lake Como, or one of the other lovely lakes north of Milan.


What people have to say about our HighRoad Tours

More than just guides

Both John and Gerry were very knowledgeable and helpful with the entire process and planning of our trip. A group that start out as 3 and grew to 7, they created a custom trip, fully supported, guided and included outstanding food! They shared their knowledge and history of the areas visited ( Mount Ventoux and… Read more “More than just guides”

Ed - USA

Excellent Trip

We had a group of 15 – 11 riders and 4 non-riders for a 10 day custom trip, climbing big hills, eating and enjoying the French ambiance of the area. We’re a “diverse” group, requiring significant adaptation, both before and during the trip. John and Gerry are patient and accommodating throughout, As a result, we… Read more “Excellent Trip”

Ken - USA

Incredible Trip

I want to personally thank you both for an unbelievable, unforgettable, incredible trip. The roads were beyond belief, by far the most entertaining, best riding roads I’ve even done on a bike trip. And the food, the food…. every meal a delight. Even the simple and wonderful pizza al fresco or bistro lunch. Roadside picnics… Read more “Incredible Trip”

Rich - California