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Dolomites cycling holiday

Self-Guided Dolomites Cycling Holiday: One Hotel, Endless Rides

7 days | Easy to Moderate | 5.00
From $1,167 ()
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Unpack once, ride everywhere for 7 days! From a single base in the Dolomites, you roll out onto quiet valley paths where the air smells of pine, sun-warmed grass, and fresh espresso drifting from village cafés. One day follows the turquoise Drava River into Austria, another slips through cool, echoing tunnels on a railway-turned-bike path beneath towering rock walls. The rides are smooth, the terrain forgiving, and everything’s taken care of: routes, transfers, logistics, so you can just pedal and enjoy. By the end of the week, it’s not just the riding that sticks, it’s how easy it all felt.

Adventure Highlights

  • One hotel, zero hassle: One cozy base, a new ride every day: no suitcase shuffling, no logistical headaches, just pure riding
  • Where rails meet peaks: Pedal an old railway through tunnels and high passes while the Three Peaks keep stealing your attention
  • Easy miles, big mountain energy: Cruise gentle valley paths with zero grind and maximum wow: this is the Dolomites without the suffering
Duration
7 days
Season
May through September
Group size
Up to 12 people
Accommodation
Comfort: 3-star or 4-star hotels in the Hochpustertal valley
Difficulty
Easy to Moderate: Good fitness required, cycling 25–70 km (15–43 mi) per day on mostly flat valley paths with no steep inclines
What's included
Lodging, breakfasts and dinners, routes, maps, navigation, and more

The adventure, day by day

Choose this option for a more classic and budget-friendly stay in comfortable 3-star hotels that offer everything you need to recharge.

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.

Day 1: Arrival
Toblach church

You arrive in Toblach/Dobbiaco and settle into your 3-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: 3-star hotel in Toblach/Dobbiaco
Meals: Dinner

Day 2: Riding the Pustertal Valley to Bruneck
Bruneck river

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: 3-star hotel in Toblach/Dobbiaco

Day 3: The Sexten Valley loop
Sexten valley

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: 3-star hotel in Toblach/Dobbiaco

Day 4: Drava cycle path to Lienz
Drau cycle path

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: 3-star hotel in Toblach/Dobbiaco

Day 5: Cortina to Hochpustertal — railway trail ride
woman cycling in Italy

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: 3-star hotel in Toblach/Dobbiaco

Day 6: The Gsiesertal Valley
Cycling on a twisted path in Italy

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: 3-star hotel in Toblach/Dobbiaco

Day 7: Departure
Cortina Italy cloudy

After breakfast, your cycling holiday comes to an end. Depart from Toblach/Dobbiaco at your leisure.

Meals: Breakfast

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.

Day 1: Arrival
Toblach church

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

Day 2: Riding the Pustertal Valley to Bruneck
Bruneck river

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

Day 3: The Sexten Valley loop
Sexten valley

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

Day 4: Drava cycle path to Lienz
Drau cycle path

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

Day 5: Cortina to Hochpustertal — railway trail ride
woman cycling in Italy

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

Day 6: The Gsiesertal Valley
Cycling on a twisted path in Italy

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

Day 7: Departure
Cortina Italy cloudy

After breakfast, your cycling holiday comes to an end. Depart from Toblach/Dobbiaco at your leisure.

Meals: Breakfast

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What others say about this adventure

5.00 (3 reviews)
Y
Yifei Xu

We were tourists from out of town, and the staff here were incredibly kind and helpful. They went above and beyond to assist us in every possible way. If I could, I would give them 10 stars! Truly grateful for their warm hospitality.

m
mike allison

This company was exactly what we needed for our cycling trip. They were very quick with correspondence and the information they gave us was thorough and clear. We didn’t have a lot of pre-trip questions but I got the sense that if we did, they would answer them happily and promptly. We had a little mixup with gear but they had a shop that was a 3-minute walk from our hotel and they took care of it. Highly recommend!

N
Natalie Bravo

They were incredibly kind and helpful to us!

5.00(3 reviews)
Y
Yifei Xu

We were tourists from out of town, and the staff here were incredibly kind and helpful. They went above and beyond to assist us in every possible way. If I could, I would give them 10 stars! Truly grateful for their warm hospitality.

m
mike allison

This company was exactly what we needed for our cycling trip. They were very quick with correspondence and the information they gave us was thorough and clear. We didn’t have a lot of pre-trip questions but I got the sense that if we did, they would answer them happily and promptly. We had a little mixup with gear but they had a shop that was a 3-minute walk from our hotel and they took care of it. Highly recommend!

N
Natalie Bravo

They were incredibly kind and helpful to us!

Things to know

  • Included:

      • 7-day self-guided Dolomites cycling holiday (5 days of riding)
      • Accommodation for 6 nights in 4-star or 3-star hotels (you can choose your preferred lodging)
      • 6 breakfasts (buffet or full board) and 6 dinners (3 courses)
      • All transfers mentioned in the itinerary
      • Videobriefing
      • Detailed documents & well-planned routes (maps, route description, places to visit, important telephone numbers)
      • Navigation app
      • Telephone service hotline for the entire tour

    Add-ons (pricing shown at checkout):

      • Single occupancy room
      • Bike rentals
      • Extra night before the trip — please leave a note at checkout if interested

    Not included:

      • Flights
      • Arrival to the starting point of the tour
      • Departure at the end of the tour
      • Lunches
      • Drinks
      • Tourist tax
      • Personal expenses
      • Anything not mentioned in the “Included” section above
      • Insurance — recommended, available to add at checkout
  • 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:

      • Day pack large enough to carry everything you might need throughout the day (around a 25-40L bag)
      • Water bottle or hydration bladder (2L capacity)
      • Cycling shoes
      • Comfortable cycling clothes
      • Spare clothes for layering
      • Waterproof rain jacket
      • Sunhat
      • Toiletries (sunscreen, hand sanitizer, etc.)
      • Sunglasses
      • Camera — optional (but recommended)

    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.

    Got everything you need? Grab your gear through Active Junky and earn cash back on top outdoor brands — plus a $10 bonus on your first $25+ purchase. Shop now at Active Junky!

  • 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

      • This tour can operate with even just one traveler. The maximum group size is set at 12 participants.

    A self-guided Dolomites cycling holiday can be arranged for larger groups. Contact us to make arrangements.

    Min. age requirements

      • If you are older than 18, you’re good to go.
      • Minors younger than 18 may be permitted to join the self-guided Dolomites cycling holiday on a case-by-case basis, but must be in the presence of a parent or legal guardian.

    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.

  • Deposits

    Secure your spot with a 30% deposit upon booking! The remaining 70% of the trip price must be paid 90 days prior to departure at the latest. If booking within 90 days of departure, the full amount is required at the time of booking.

    Cancellations

    Booking fees are non-refundable after a 48-hour grace period. During checkout, however, you can choose one of 57hours’ flexibility options—Basic, Flexible, or Super Flexible. Depending on which one you choose, a different cancellation policy will apply to your booking.

    Basic

      • If cancelled within 48 hours of booking, a full refund will be issued.
      • If cancelled 60 or more days before departure, a 70% refund of the total trip price will be issued.
      • If cancelled within 59 days of departure, no refund will be issued.

    Flexible

      • If cancelled within 48 hours of booking, a full refund will be issued.
      • If cancelled 60 or more days before departure, a full refund of the total trip price will be issued.
      • If cancelled 30-59 days before departure, a 50% refund of the total trip price will be issued.
      • If cancelled within 29 days of departure, no refund will be issued.

    Super Flexible

      • If cancelled within 48 hours of booking, a full refund will be issued.
      • If cancelled 30 or more days before departure, a full refund of the total trip price will be issued.
      • If cancelled within 29 days of departure, a 50% refund of the total trip price will be issued.
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