Choose this option for a more elevated take on your Dolomites cycling holiday, with stays in carefully selected 4-star hotels that bring extra comfort to each day.
This self-guided Dolomites cycling holiday is all about smooth valley riding, iconic routes like the Drava cycle path and the Cortina railway trail, and the freedom to shape each day to your own pace. You’ll roll through alpine villages, past shimmering lakes, and beneath dramatic peaks that never quite leave the horizon, all on well-maintained paths with no major climbs. With routes, transfers, and logistics taken care of, it’s a seamless, stress-free way to experience the Dolomites on two wheels, where the riding feels easy but the scenery never does.
You arrive in Toblach/Dobbiaco and settle into your 4-star hotel, your base for the entire week. Take some time to explore the village, spin the legs if you feel like it, or simply ease into the alpine atmosphere because your rides start tomorrow.
Accommodation: 4-star hotel in Toblach/Dobbiaco
Meals: Dinner
You follow the gentle flow of the Rienz River along well-maintained cycle paths through villages and open valley landscapes toward Bruneck. Stop to explore Bruneck Castle or the open-air museum in Dietenheim, or extend the ride into the Tauferer Ahrntal valley for a longer day. In the afternoon, a transfer brings you back to your hotel.
Meals: Breakfast, dinner
Cycling: 25–30 km (15–19 mi), or 55–60 km (34–37 mi) with extension
Accommodation: 4-star hotel in Toblach/Dobbiaco
Today you ride into the Sexten Valley, framed by dramatic Dolomite peaks. The route leads into the Fischleintal valley before looping back toward San Candido, known for its Romanesque collegiate church. After a break at the source of the Drava River, you return to your hotel.
Meals: Breakfast, dinner
Cycling: approx. 40 km (25 mi)
Accommodation: 4-star hotel in Toblach/Dobbiaco
You set off toward San Candido and cross into Austria shortly after Prato alla Drava, joining the classic Drava cycle path. The route gently descends all the way to Lienz, making for a relaxed and scenic ride. Take time to explore the historic center or visit Schloss Bruck before your transfer back.
Meals: Breakfast, dinner
Cycling: 50–55 km (31–34 mi)
Accommodation: 4-star hotel in Toblach/Dobbiaco
A transfer brings you to Cortina d’Ampezzo, where you begin one of the highlights of the trip: cycling along a former railway line through tunnels and high alpine terrain. You climb gradually to Cimabanche, then continue past Lake Dürrensee with views of the Cristallo massif and the iconic Three Peaks. The route leads you back to your hotel via Lake Toblach.
Meals: Breakfast, dinner
Cycling: 30–35 km (19–22 mi), or 60–70 km (37–43 mi) without transfer
Accommodation: 4-star hotel in Toblach/Dobbiaco
Today’s ride takes you into the peaceful Gsiesertal Valley, known for its traditional farms and quiet atmosphere. You can visit Welsberg (Monguelfo) and its castle or take a relaxing break back in Villabassa, perhaps at the local Kneipp facility. It’s a calm, scenic day to round out the week.
Meals: Breakfast, dinner
Cycling: 55 km (34 mi)
Accommodation: 4-star hotel in Toblach/Dobbiaco
After breakfast, your cycling holiday comes to an end. Depart from Toblach/Dobbiaco at your leisure.
Meals: Breakfast
Included:
Add-ons (pricing shown at checkout):
Not included:
This Dolomites cycling holiday is suitable for riders with a basic to good level of fitness. The routes follow well-maintained valley cycle paths with no steep inclines, making the riding comfortable and accessible for most cyclists.
Daily distances are flexible, ranging from 25 km (15 mi) up to 70 km (43 mi) depending on the route you choose and whether you use transfers. Some sections, like the Drava cycle path, are even slightly downhill, making for relaxed and easy riding.
You can adapt each day to your energy levels, shorten routes with transfers, extend them if you feel like it, or take a rest day. As long as you are comfortable cycling for a few hours at a relaxed pace, you will be able to fully enjoy this trip.
Here’s a list of the equipment you need to bring:
Dress comfortably and for the weather in clothes you can move in. We suggest bringing clothing appropriate for the season. Layers are best and don’t wear jeans.
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Self-guided tours are perfect for those who enjoy exploring on their own terms—at their own pace, and with the company they choose. By joining this self-guided Dolomites cycling holiday, we take care of the lodging, breakfasts and dinners, routes, maps, navigation, and more.
Rather than joining a guided group, you’ll navigate the tour yourself, using resources provided by the tour operator. For a hassle-free journey with everything arranged for you in advance, there’s no better option!
As a self-guided tour is built around your preferred travel dates, your guide will take care of arranging accommodations and details after you book. Note that exact accommodations and dates might shift slightly, so don’t make any travel arrangements until the details of your adventure are confirmed.
Group sizes and pricing
A self-guided Dolomites cycling holiday can be arranged for larger groups. Contact us to make arrangements.
Min. age requirements
If your group has participants under the age of 18, contact us prior to booking to make arrangements.
The price for this self-guided Dolomites cycling holiday] is based on twin-share rooms, but a single occupancy room can be arranged at an additional fee. You can add it to your booking at checkout.
The starting point of your self-guided Dolomites cycling holiday is Toblach/Dobbiaco, located in the Hochpustertal valley. Hochpustertal is located in South Tyrol, a bilingual region of northern Italy, so you’ll often see place names listed in both German and Italian (e.g. Toblach/Dobbiaco).
To get there, most people fly into Venice Marco Polo Airport (VCE). From there, you can rent a car, arrange a shuttle, or use public transport via Venice and regional train connections to reach Toblach/Dobbiaco, which usually takes around 3.5 to 5 hours.
We highly recommend that you cover all your bases with insurance. To make your booking and traveling experience as carefree as possible, you’ll be offered to simply insure your trip with Redpoint at checkout.
Redpoint—the official 57hours insurance partner—tailors protection packages for adventure travel, offering a comprehensive travel program, even in remote locations! Trip cancellation, natural disasters, pandemic coverage, medical evacuation, primary medical expenses—regardless of the travel interruption that may happen, Redpoint will have you covered.