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Cycling the Wine Trails of Umbria

Cycling the Wine Trails of Umbria

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  • Holiday typeSelf-guided cycling
  • Duration8 nights
  • Accommodationhotel-to-hotel
  • Activity level
  • From $2215per person, tour only
  • Departures
    Every two days from 13 Apr '19 to 22 Oct '19
  • What your holiday price includes
  • 8 nights hotel-to-hotel accommodation in a mix of and hotels
  • All breakfasts and 6 evening meals
  • Services of your local Headwater Representative
  • Headwater Wine Collection Service
  • GPS route directions and maps
  • RideWithGPS navigation app
  • High quality hybrid bikes
  • Luggage transfers between hotels
  • Optional Upgrades
  • Electric bikes available
  • Room upgrades and extra nights at selected hotels
  • City break add-ons in Perugia and Rome
  • Excellent choice for
  • Food lovers, wine lovers, flora & fauna, art & history, swimming opportunities, solo travellers, couples
      from 48 reviews

Mrs Johnson says...
Cycling the Wine Trails of Umbria was a great holiday for us. The mix of easy cycling on the flat plain and a few challenging climbs was just right, in ...
Read reviews »


Cycling the Wine Trails of Umbria

  • Unspoilt cycling: olives, sunflowers, vineyards and apricot orchards
  • Gorgeous summer climate, soft terracotta colours, sun-drenched landscapes, panoramic views
  • All hotels serve superb cuisine and amazing-value wines, most with a swimming pool
  • Beautiful hilltop villages and hamlets
  • Assisi, the jewel in the Umbrian crown; gorgeous Spello, Etruscan Perugia, mediaeval Montefalco

Few places can stir emotions quite as intensely as Umbria. To visit here is to embark on a journey into a timeless world of sun-drenched landscapes, ancient hill villages and some of the friendliest people we've ever met.

This 8-night self-guided cycling holiday combines scenic pedalling through olive groves, sunflower fields, vineyards and apricot orchards with the chance to explore some of the most fascinating towns and historic villages in the country. You'll freewheel along the stately Roman Via degli Ulivi and follow in the footsteps of emperors at the sacred springs of Campello sul Clitunno.

Highlights include the lovely hilltop wine village of Montefalco, 'the balcony of Umbria', and the fascinating historic city of Spoleto crammed with exciting Roman remains including Emperor Vespasian's mother's house, baths and mosaics. Of course, no trip here would be complete without spending time in magical Assisi. Be sure to visit St Francis' Basilica with its beautifully ornate frescoes, and his peaceful forest retreat on Monte Subasio where he'd stroll and preach to the birds.

The hotels we've selected for this holiday are pretty special too, ranging from a stunningly restored ancient hamlet, set in its own manicured gardens, to a panoramic 4-star hotel in Spello with its own spa and one of the most prestigious wine cellars we've ever stumbled upon!

We're here to help

If you have any questions about this holiday call our sales team on 1-800-267-3347, use our live webchat or email usa@exodustravels.com

Day-by-day itinerary

We're here to help

If you've any questions about this holiday call our sales team on 1-800-267-3347 , or email usa@exodustravels.com

Day 1 Arrive at Spello

Arrive in picturesque Spello in time for dinner in your hotel's atmospheric restaurant. (Staying at La Bastiglia Hotel, Half Board)

Day 2 Spello to Spoleto 50km/31.5mi

Today is level cycling most of the way along the Teverone Valley with some of the best views of the week. We strongly recommend the short uphill detour to Trevi, a beautiful hilltop village dating back to Roman times and capital of the Umbrian olive oil industry. Finally, travel Into Spoleto where our hotel is situated in the centre of town. (Staying at Hotel Charleston. Breakfast only)

Day 3 At Spoleto

The fascinating historic city of Spoleto, apart from being a great art city, Spoleto has buildings seemingly reflecting every major architectural style in history, including a Roman arch, a C10 church, a C12 Duomo and an 80m high, C14 aqueduct. The castle here is a former prison and now houses an impressive art museum. For lunch, you'll find lots of lovely cobbled squares filled with traditional trattorie. (Staying at Hotel Charleston. Breakfast only)

Day 4 Spoleto to Marcellano 44km/27.5mi

The wines of Montefalco are known throughout the world, in particular the fine red, Sagrantino. There is a climb up to the old village itself, 'the Balcony of Umbria', but you are well rewarded with wine-tasting, magnificent views and beautiful mediaeval streets. Continue from here past lush green fields, poppies and buttercups before your last climb up to the mediaeval village of Marcellano. Your 4-star hotel is set within its own lovely gardens, in a hilltop location, with fabulous panoramic views across the entire valley. (Staying at Grand Relais Laurenti, Half Board)

Day 5 At Marcellano

It's tempting to spend the day relaxing by the pool in the hotel's tranquil grounds, but it would be a shame to miss the Roman walled town of Bevagna (10 mins by taxi; or you can cycle) - Umbria's hidden gem. Visit the C13 Gothic Palazzo dei Consoli, the golden mediaeval theatre, or the C2 Roman temple and baths that include a spectacular lobster mosaic. Alternatively, you can opt for a circular cycle to Ceralto Castle. (Staying at Grand Relais Laurenti, Half Board)

Day 6 Marcellano to Torgiano 42km/26.5mi

It's picture-perfect views all the way this morning as you arrive at the impossibly photogenic, mediaeval village of Gualdo Cattaneo with its imposing C15 castle and C13 crypt. There's a downhill whizz before gentle, flat cycling across the plain and a final short ascent into the old wine town of Torgiano, famous for its Lungarotti cellars. (Staying at Hotel Al Grappolo d'Oro. Breakfast at hotel, evening meal at a local restaurant)

Day 7 At Torgiano

There is a dedicated wine and olive oil museum - with tastings - in Torgiano's pretty centro storico. Alternatively it's a short bus or taxi ride (approx 15 mins) to the university town of Perugia, famous for one of Italy's finest art collections and home to the renowned Baci chocolates. For the more energetic we provide route notes for an optional cycle ride to the local capital of painted ceramics, Deruta. (Staying at Hotel Al Grappolo d'Oro. Breakfast at hotel, evening meal at a local restaurant)

Day 8 Torgiano to Spello 43km/27mi

Your last day's cycling takes you along the 'Wine and Art Road' to Brufa (with lovely views of Perugia and Assisi) and on through the Chiascio Valley, along country lanes passing sunflower fields, ochre-coloured farmhouses and redolent meadows of wild apricots and figs. There's time to visit spectacular Assisi - the beautiful Piazza del Comune, the C13 Giotto frescoes and of course, the UNESCO-recognised St Francis' Basilica - before cycling on along the lovely traffic-free Via degli Ulivi and through olive groves back to Spello. (Staying at La Bastiglia Hotel, Half Board)

Day 9 Leave Spello

Where you stay

During your holiday you stay at the following hotels. If you'd like to extend your time at any of these or, if you'd like to enhance your stay with an upgraded room, just let us know at the time of booking. If you'd like to keep your bikes with you for any extra nights we can arrange this for you for just £25 per adult per day and £18 per child per day.

To find out more call our sales team on 1-800-267-3347, use our live webchat or email usa@exodustravels.com

Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Albergo La Bastiglia Hotel, Spello

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The La Bastiglia Hotel boasts a beautiful setting at the foot of Mount Subasio, the enchanted mountain of Saint Francis. Originally an ancient mill the hotel has been lovingly restored and transformed into an unforgettable place to stay. There are 33 rooms divided into three categories, many overlooking the typical Umbrian landscape of cypress trees and olive groves. The restaurant serves a mix of ancient recipes and modern creations using the freshest ingredients. On display inside the hotel there is a collection of ceramics, antique furniture and important paintings from the private collection of Schifano and Norberto.

Room upgrades: Superior Room, Deluxe Room, Junior Suite or Junior Suite Deluxe.
Superior rooms are larger, and have a small balcony and bathroom with shower. Deluxe rooms are larger with a balcony and bathroom with a bath. The Junior Suite includes a Jacuzzi in the bedroom and a panoramic terrace with solarium. The Deluxe Junior Suite can accommodate up to five people and has a private panoramic terrace with table, chairs and sun loungers and a Jacuzzi for 2 people.

Extra nights: Please contact us for details.

Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Hotel Charleston, Spoleto

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Completely renovated in 2011, Hotel Charleston is set in a 17th-century building in Spoleto's historical centre, next to the Modern and Contemporary Arts Museum. Its elegant, individually-decorated rooms feature a modern design. Wi-Fi is free in all public areas. Rooms are individually decorated, and come with exposed wooden beams on the ceilings. Each is equipped with a minibar, and a flat-screen TV with satellite channels. A buffet breakfast is available each morning, and is served out on the terrace in warm weather.

Room upgrades: Junior Suite.
Junior suites are spacious and elegant with seating area, parquet floors and exposed wood beams.

Extra nights: Please contact us for details.

Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Grand Relais Laurenti, Marcellano

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Just outside the walls of the pretty hilltop village of Marcellano lies the supremely welcoming Grand Relais Laurenti, where nothing seems to be too much trouble. A recently restored former convent (formerly known as the Palazzo Gradoli), parts of the hotel date to as far back as 1516. Opened in 2006, the owner Laurenti Torrello spent thirteen years restoring the premises in order to ensure that all work was done to a suitably high standard. The well put together rooms have a distinctly cosy feel to them and retain original features such as the wooden beams on the ceilings.

In addition to the hotel, the Grand Relais Laurenti owns 90 hectares of the surrounding land which is used by their own farm to raise livestock such as cattle and lamb to supply the restaurant with meat. They also produce their own olive oil from their own olive groves and pride themselves on their ability to source only the finest ingredients (such as truffles and porcini mushrooms) from the surrounding area. The restaurant itself has two chefs who provide a mixture of traditional regional food and more elaborate international fare.

Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Hotel Al Grappolo d'Oro, Torgiano

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Situated in the centre of the mediaeval town of Torgiano is Al Grappolo d'Oro (The Golden Bunch of grapes), a recently restored 19C residence. The hotel has 15 rooms, each individually decorated in a modern style with warm colours and furnished to a high standard, offering a cosy, welcoming stay. The art filled reception/lounge area gives the hotel character from the start but features such as the pool in the garden to the rear and the downstairs bar (along with the well-stocked breakfast buffet) mean that despite the B&B nature of the hotel, there is still the possibility to spend time relaxing here during the day.

The owner Antonello Rossi also owns the wonderfully traditional Italian restaurant 'Siro', which lies around 300 metres away from the hotel and where evening meals will be taken.

Room upgrades: Junior Suite.
Junior Suites are more spacious with ample and bright, classic furniture and wooden floors.

Extending your stay

If you'd like to extend your trip with extra nights at the start or end, or if you'd like to arrange a stop off point en-route, then we recommend the following hotels.

Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Hotel Fortuna, Perugia

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The traditional 3-star Hotel Fortuna is set right in the heart of the historic city. The building itself dates to the 14th century and was tastefully renovated in the early 1990's. There are still some original features - look out for the arched windows downstairs. All rooms are en suite with satellite TV, telephone, minibar and radio. There is a roof garden terrace - great views over the city and a bar/ lounge area. The hotel has also recently added a gym

Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Hotel Astoria Garden, Rome

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The 3-star Hotel Astoria Garden has a most unusual feature: an internal garden complete with banana and orange trees! Centrally located near the main railway station, but in a quiet residential street, this is a really good base from which to explore. There are 34 rooms, all air-conditioned and recently refurbished. They have telephone, television, and ensuite bathrooms.


Transfers included from Foligno train station at 17:15, and back to Foligno train station at 10:15.

Please call our sales team on 1-800-267-3347 or email usa@exodustravels.com to arrange connecting flights.


Everyone who goes on a Headwater holiday will be emailed a link to our post-holiday questionnaire where they can give us an honest assessment of all aspects of their holiday - everything from how quickly we answer the phone to how clean the hotels were - plus an overall rating and comments about their holiday.

Any feedback collected is posted to our website, so that people can make an informed decision based on past experiences before heading off on holiday. We don’t edit the reviews, the only thing we do is proofread them and alter any typos, where necessary, to ensure they are easy to read for everyone. All reviews will be published (except in certain extreme circumstances), and a member of the Headwater team will respond to any constructive criticisms/comments under the reviews, at their discretion. So, for the real tales, twists and turns of our holidays, look no further than the reviews from our previous travellers.

Mrs Johnson, 08/10/2018

Cycling the Wine Trails of Umbria was a great holiday for us. The mix of easy cycling on the flat plain and a few challenging climbs was just right, in particular the ride up to Assisi was worth every hard fought breath. We travelled in late September/early October when the weather was cooler , but I may have found the climbs more uncomfortable in the heat of summer. On the 'rest' days we adapted the suggested routes as they often involved big climbs; in particular our excellent local reps, Luke and Eleanor (one of the main reasons we use Headwater) suggested we visit Bavagna en-route to Spoleto instead of on the later day cycle ride, this proved to be really good advice. The evenings were quite cool and we didn't have the opportunity to eat outside, except for one breakfast in Marcellano. We also made little use of the outdoor pools owing to the cooler weather( the one in Spello couldn't be used as it wasn't clean). The welcome in Marcellano was fantastic and as we were more or less the only guests for the weekend it felt quite special.

Mr Dewey, 20/07/2018

Overall an enjoyable experience. Underpinning the whole holiday was the comfort of knowing the good quality of each hotel. In particular the food and dining experience at Albergo La Bastiglia was outstanding, definitely the best food we had! All the hotels offered a different experience; a town centre -Hotel Charleston; a warm welcome at Grande Relais Laurenti (shame about the area it is in - nothing much there and slightly shabby on the approach); the lovely room and pool area at Al Grappolo d'Oro and the nice food at their restaurant down the road although there was some confusion over what we were allowed to eat; and it was great to return to Albergo La Bastiglia with its wonderful food and setting in the lovely town of Spelo.

The bikes are robust but quite heavy but do the job. RideGPS guided us well but would benefit from some refinement such as the ability to listen to a repeat of instruction as in traffic (especially in towns) it was often difficult to hear and sometimes information was missed.

Circumstances meant that we had a rep with little experience or knowledge of the area as she had been drafted in from Tuscany at late notice. This meant that we had no hints or tips about places to see/eat along the routes, or any guidance about the routes. We did the optional ride from Marcellano to Bevagne and it pushed my wife to her limits (and she is fit ) as the route was extremely steep. We felt that 'insider' knowledge may have prepared us for this. At each of the destinations she was there to meet us with our luggage which was good. She also quickly replaced a broken phone holder.

On the whole we enjoyed the routes we went on. most being on quiet country roads and cycling paths although some of the latter were difficult to ride on if they were stoney and downhill such as part of the route down from Trevi and one down from Eggi. The highlight was reaching Assisi which we really enjoyed despite a strenuous climb up coming at the end of a 33km ride.

A great experience all round.

Mrs Williamson, 22/06/2018

Umbria offered great routes and food options, accommodation could have been stronger.

Mr Cadman, 20/06/2018

Fantastically well organised and great hotels. Interesting and sometime a little challenging cycle routes with some of the best view you will see. Routes pass many land marks with detour options as well. Will be using headwater again .

Mrs Holt, 20/06/2018

Good route - beautiful landscapes, pleasant cycling through a mix of agricultural scenery and hilltop villages. A few tough climbs, - timing them around lunchtime means you are rewarded with an opportunity to explore and eat in a great spot! Usual mix of individual hotels, although one fell far short of expectation and was substandard. Bikes brand new and easy to use.

Mr Smith, 17/06/2018

A good introduction to cycling holiday easy going but with a few challenging climbs. Good hotels,food and wine

Mrs Roundtree, 05/06/2018

We had an excellent cycling holiday in Umbria. The cycling was a bit tougher than we had expected but this is probably a factor or our age and the general geography of Umbria where destinations are generally on top of hills. The hotels were generally good and well located and our on the ground representative was very helpful.

Mr Mcgeoch, 29/05/2018

To get away from the crowds (especially those that like to sit on a coach for hours on end) and to enjoy the natural countryside and historic villages. The exercise in cycling helps to justify our enjoyment of the amazing food on offer in the evening.

Mr Bridge, 31/10/2017

Interesting area to visit; good Italian food

Mrs Lee, 16/10/2017

Sometimes challenging, but great fun,lovely wine and food.

Mr Bastone, 03/10/2017

Great combination of healthy exercise, excellent hotels and high quality food and wine!!

Mr Sherry, 19/09/2017

This was a really lovely holiday experience. Beautiful countryside and wonderful views throughout our trip. This was our second Headwater holiday which lived up to our expectations.

Mr Fisher, 13/09/2017

Excellent holiday, great hotels, efficient transfers and electric bikes were brilliant. Please extend use of electric bikes to other holidays as this will be a priority for us in the future.

Mr Goddard, 06/09/2017

Organisation and customer care was excellent. Our rep--Jen Toy--was brilliant and extremely helpful

Mr Isherwood, 05/09/2017

Headwater picked a fine selection of independently run hotels that were a joy to stay in. The cycle routes were well selected on safe quiet roads and the GPS made them easy to follow. We had a great time

Mrs Pattison, 18/06/2017

Less hilly overall than expected with long very flat rides in between long climbs and some big steep hills. Challenging in the heat. Stunning scenery all the way with beautiful picturesque hill top towns. Wonderful region to visit with friendly locals, great food and wines.

Mr Catchpole, 04/06/2017

Umbria is a beautiful part of Italy and it is well worth visiting all of the hilltop towns as they each have their own unique atmosphere - but be aware that there is a lot of climbing! The hotels, especially the Grand Relais Laurenti, are very welcoming and the standard of accommodation in all of them is excellent.

Mr BeaumontThomas, 20/10/2016

Our first Headwater holiday and we can really recommend Umbria as a destination. We worried about whether the bikes would be up to scratch and the potential restrictions of half-board, but on both counts we were pleasantly surprised. The week's route circling the valley meant that the long views often included hill towns we'd visited or would be visiting. This created a real sense of achievement! And most of all, the fantastic cycling meant we could indulge in all that amazing food and wine and still come home only a couple of pounds heavier!

Mr Aung, 26/09/2016

Cycling in Umbria- need to review road going down from Gualdo Cattaneo down the hill to Torre del colle. Steep 15% average with turns .High risk even for reasonably experienced cyclist.Could an alternative route be looked at even if the roads are busier?

Mr Tennant, 19/09/2016

Great experience but slightly inconsistent and ambiguous route instructions which are very difficult to relate to the overall large maps

Mrs McKay, 02/09/2016

Beautiful scenery. Cycling hard at times - some demanding hills. Hotels very good with individual attractions. Pools a great asset at end of a hard day cycling or on day off. Lots of good (and cheap) cafes on route. Interesting places to visit including Montefalco. Assisi very busy and expensive.

Overall a great holiday.

Ms Kidney, 08/08/2016

A wonderfully well planned holiday in the most beautiful surroundings with quality accommodation.

Dr Sheldon, 18/07/2016

Nice balance of luxury, activity and historical interest. We like the alternate days of rest/ cycling, and the independence of travelling on our own.

Mis Barrie, 14/06/2016

Many unspoilt cycle routes with stunning views

Hotel pools all very welcome after a hard day's cycling

Mr Loughlin, 30/05/2016

We expected 4 star hotels but got small 2 star rooms . Food was mostly not impressive and service poor . Staff were friendly and cycle agents excellent . Umbria lovely but route would have been very demanding without the power assist cycles which were excellent for ladies but ran out of steam for gents towards the end of each day

Mr Witts, 18/10/2015

Interesting cycle tour with plenty to visit.

Mrs Dietz, 26/09/2015

A delightful area for cycling, mostly great locations for hotels, overall an excellent holiday. Our only reservation is Torgiano, where the hotel was anonymous and the little town uninteresting and the Tourist Office useless in our queries about buses.

Mr Thomas, 03/08/2015

We were a family group of four. Mum ,Dad and two grown up children, son aged 27 and daughter aged 30. We had a really enjoyable trip, exploring all the towns and villages along the route. We really enjoyed a totally relaxing and stay put day at the Grand Relais Laurenti. We had the place to ourselves! Wonderful setting, fantastic views. The 'city centre' Hotel Al Grappolo was our least favourite and it was not the sort of place that you would want to spend the entire day (like Grand Relais Laurenti). The food was excellent especially for vegetarians. Four courses was to much! And the wine was very good and very reasonably priced.

Dr Dewar, 21/07/2015

Great holiday - cycling was wonderful through a picture perfect valley; a few climbs to hill-top towns but views compensate enormously. Well chosen hotels. Only minor gripe was that two hotels had a full menu (one with minor 2 euro mark-up for some dishes), while two have a very fixed menu with 2 and 3 choices respectively. On return to Bastiglia we had the same menu which had rabbit which we don't eat (just a promise we made as we keep rabbits !). This would have been just OK but we stayed two more nights and had the same menu given to us. To be fair we negotiated a slight change although our starter was still based on parma ham each night. The hotel was lovely but it did make us feel like we were second class diners who couldn't afford the full menu, which I am sure is unintentional but the created effect. We nearly dined elsewhere on the last night to get some variety of choice but this is probably our fault for staying 4 nights here - wonderful hotel but wouldn't half board in future if stay extra nights.

Mrs Gee, 12/07/2015

A great way to see and experience the parts of a country that other travel companies often don't reach.

Mrs Duncan, 02/07/2015

Welcome at La Macchia by the older couple felt off hand. Staff, however, were helpful and appeared over worked in the dining room. Food was good at Grapolo d pro but service was slow and we left before being offered a last course. Cycle routes good and notes clear Only got lost once.

Dr Bungay, 12/06/2015

Wonderful countryside, good cycling, plenty to see and stop at, so the routes filled the days with lots of interest. It was 30oC in the first week of May, and would be best when temperature was 25ish, which is what we had hoped by booking an early holiday. I don't know how it could be enjoyable in August.

Mr Yellen, 03/06/2015

trouble free and relaxing

Mrs Blay, 31/05/2015

Very enjoyable. You don't feel that you are part of a crowd but have the reassurance of the back up provided by a local representative, if required.

The routes were well put together but you need to be reasonably fit before you go.

Although you are travelling to a warmer country you need to be prepared. We had one very wet day and would have been lost without decent waterproof tops and trousers..

Mis Devlin, 13/10/2014

It wasn't the relaxing biking holiday I was hoping for. Some parts were, but the published route involved too many busy main roads. There were a lot of mistakes in the notes, which added stress. I do wonder if anyone had actually rode it from Headwater? It could have been a lot better - for instance leaving La Macchia, instead of going down the busy main road, we went into town on the back roads, over the railway, then along a parallel road, then onto a cycle track - easy to do and much less traffic.

The hotels were not brilliant. We didn't eat the four courses offered at meal times, as it was just too much. I would have rather paid a bit less and just had two courses.

I may sound churlish, about the birthday cake, but the reason we went on this week was because we had a family tragedy the year before on my birthday, and I specifically wanted a totally un-birthday normal day. It worked fine, and I had genuinely forgotten about it, so was very angry and embarrassed about what happened. They should not have been looking at my passport - the only reason they had it was for legal reasons.

Mr Hall, 19/09/2014

Excellent hotels and food in lovely locations. Italian roads lack signage and the camber on some roads is bad especially when trying to ride and navigate in heavy thunder storms. The maps issued are of too small a scale and our trip involved two maps. It would be preferable to order special maps based on a 30 mile radius of Spello with a bigger scale. From the Headwater book in each hotel, it is clear that most people get lost. We did on each of our transits but perhaps that is the fun of it.

Mr O'Driscoll, 03/09/2014

A great holiday for cycling enthusiasts who like good food and wine, a few historical and cultural sites to visit, and time to relax after getting off your bike.

Mrs Mendham, 26/08/2014

We enjoyed the holiday but the directions were probably the worst we have ever had. They are not clear and some directions referred to signs/cafes etc that no longer seemed to be there. In Gualdo Catanneo the instructions sent us all round the village back to where we started but the road had collapsed and we had to go back. In fact we could have pushed the bikes 50m down the hill back to where we started! Often directions are given in distances but when you have no means of judging distance it is hard to know if you are in the correct place. There should be more information on how to get to places on the off days. We went to Perugia but found out how to get there on our own. It was simple and this information could be made available on your website. The bikes are very heavy and poorly maintained. I could only use 18 of the 21 gears until my husband fixed it after 3 days - not great on the Umbrian hills.

Mr Hill, 10/08/2014

We had a wonderful holiday (our second with Headwater) and consistently hot weather in July; although it was too hot really and quite debilitating at the end of each travel day when having to cycle up hill to reach the next hotel. Each hotel was of a high standard with a pleasant welcome and the food was amazing. We look forward to trying another Headwater cycling holiday but will take more consideration of the cycle rating and likely weather conditions next time.

Mr Somers, 31/07/2014

Cycling was fabulous along mainly quiet beatiful roads with some climbs which were all rewarding and enhanced the riding. Hotels were great, all small family run and so friendly. Food and wine was fantastic. Our 2 teenage girls (ages 16 and 15) hardly complained at all for the duration! Great family holiday!

Mrs Gregson, 19/06/2014

The holiday was a fantastic way to enjoy this beautiful area. An Italian feast!

Mr Duncan, 31/05/2014

There was 5 in our family party. 2 x over 65 1 x over 40 & 2 x 36 to 39

All enjoyed the trip very much. However I have sent an e mail to Lisa regarding the representative.

The hotels , staff & food were excellent & we were made most welcome.

Mr Ray-Johnson, 30/05/2014

Stimulating and sufficiently challenging to arrive home with a sense of achievement as well as enjoying the local culture, history and scenery. Whilst we are still fit, we will consider taking another Headwater Cycling trip again.

Mrs Bruce, 31/01/2014

We cycled every day and enjoyed being in the area; our trip had some changeable weather, including warm sun, heavy rain and strong winds. If you had another cycle route in the area, we'd certainly like to consider returning!

Mrs Kinmonth, 04/10/2013

Harder cycling than expected, mainly due to wind.

Mrs McLynn, 20/09/2013

Javier, the rep, was excellent! He had so much local knowledge, he knew and updated the routes, and he gave much useful advice on safe cycling and

cycle maintenance. He also made it clear that if we had any problem he was only a phone call away! Well done!

Mr Kerr, 18/09/2013

A great way to explore Umbria, including the interesting towns of Spello, Spoletto, Motefalco, Bevagna and Assisi. The cycling is challenging enough and the well chosen hotels provide welcome refuge and refreshment at the end of the day. On the stay-put days it's good to have the opportunity to sight-see or relax, depending on your mood. We enjoyed the regional food and wine and our dinner at the Trattoria di Oscar in Bavagna was a particular highlight.

Mr Rutter, 08/08/2013

We really enjoyed our cycling holiday. The route instructions were excellent and easy to follow. The Rep Javier was great, welcoming friendly and extremely helpful. He knew all the routes really well and checked them daily with some revisions where roads were closed or signs changed.At the start of the holiday he would turn up on a route ,unexpectedly, to check if we were alright so this was very reassuring when we were getting into the swing of things. The routes were on quiet roads or cycle paths and we felt we saw the real Italy with picturesque medieval towns and villages. We liked all the hotels, each with a different character and with lovely local food. The towns were full of Italian culture and we enjoyed exploring the narrow streets and tasting local food and wine. Well done Headwater, we can't wait for our next holiday.

Dates and prices

You can be confident that our pricing includes all the standard requirements of your holiday and many additional extras. Always ensure that you are comparing like for like when booking your holiday. Find out about The Headwater Price Promise to ensure you're getting the very best value for money.

For further details, or to check availability, speak to our sales team on 1-800-267-3347 or complete our holiday enquiry form (we'll contact you at a time that's most convenient for you).

To enquire about this holiday, or for further information, call our sales team on 1-800-267-3347 or complete our holiday enquiry form.

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23rd May US$2215 Check availability
25th May US$2215 Check availability
27th May US$2215 Check availability
29th May US$2215 Check availability
31st May US$2215 Check availability
Jun 2019 Tour only Availability
2nd Jun US$2215 Check availability
4th Jun US$2215 Check availability
6th Jun US$2215 Check availability
8th Jun US$2215 Check availability
10th Jun US$2215 Check availability
12th Jun US$2215 Check availability
14th Jun US$2215 Check availability
16th Jun US$2215 Check availability
18th Jun US$2215 Check availability
20th Jun US$2215 Check availability
22nd Jun US$2215 Check availability
24th Jun US$2215 Check availability
26th Jun US$2215 Check availability
28th Jun US$2215 Check availability
30th Jun US$2215 Check availability
Jul 2019 Tour only Availability
2nd Jul US$2325 Check availability
4th Jul US$2325 Check availability
6th Jul US$2325 Check availability
8th Jul US$2325 Check availability
10th Jul US$2325 Check availability
12th Jul US$2325 Check availability
14th Jul US$2325 Check availability
16th Jul US$2325 Check availability
18th Jul US$2325 Check availability
20th Jul US$2325 Check availability
22nd Jul US$2325 Check availability
24th Jul US$2325 Check availability
26th Jul US$2325 Check availability
28th Jul US$2325 Check availability
30th Jul US$2325 Check availability
Aug 2019 Tour only Availability
1st Aug US$2325 Check availability
3rd Aug US$2325 Check availability
5th Aug US$2325 Check availability
7th Aug US$2325 Check availability
9th Aug US$2325 Check availability
11th Aug US$2325 Check availability
13th Aug US$2325 Check availability
15th Aug US$2325 Check availability
17th Aug US$2325 Check availability
19th Aug US$2325 Check availability
21st Aug US$2325 Check availability
23rd Aug US$2325 Check availability
25th Aug US$2325 Check availability
27th Aug US$2325 Check availability
29th Aug US$2325 Check availability
31st Aug US$2325 Check availability
Sep 2019 Tour only Availability
2nd Sep US$2325 Check availability
4th Sep US$2325 Check availability
6th Sep US$2325 Check availability
8th Sep US$2325 Check availability
10th Sep US$2305 Check availability
12th Sep US$2305 Check availability
14th Sep US$2305 Check availability
16th Sep US$2305 Check availability
18th Sep US$2305 Check availability
20th Sep US$2305 Check availability
22nd Sep US$2305 Check availability
24th Sep US$2305 Check availability
26th Sep US$2305 Check availability
28th Sep US$2305 Check availability
30th Sep US$2305 Check availability
Oct 2019 Tour only Availability
2nd Oct US$2305 Check availability
4th Oct US$2305 Check availability
6th Oct US$2305 Check availability
8th Oct US$2305 Check availability
10th Oct US$2305 Check availability
12th Oct US$2305 Check availability
14th Oct US$2305 Check availability
16th Oct US$2305 Check availability
18th Oct US$2305 Check availability
22nd Oct US$2305 Check availability

The prices quoted for each individual departure supercede those published in our current brochures. Air prices are subject to change and we advise early booking to obtain the best prices. Please see our Planning your holiday and What's included in the price? pages for additional information.

Holiday details

Please contact us for child prices.

Holiday type
Self-guided cycling Managed locally by Headwater appointed rep.

Every two days from 13th Apr 2019 to 22nd Oct 2019, for 8 nights.

All breakfasts and 6 evening meals

Electric bikes
It is possible to hire electric bikes for this holiday at a supplement of £100 per person. As these are available on a first come first served basis, we recommend early booking to avoid disappointment. Please call us for further details.

Tailor-made travel

Tour only
Transfers included from Foligno train station at 17:15, and back to Foligno train station at 10:15.

How to book

For further details, or to check availability, speak to our sales team on 1-800-267-3347 or complete our holiday enquiry form (we'll contact you at a time that's most convenient for you).

To enquire about this holiday, or for further information, call our sales team on 1-800-267-3347 or complete our holiday enquiry form.

We are ATOL registered We are an ABTA member
Independent customer reviews and ratings

Due to the tailor-made nature of our holidays, we need a little more information in order for us to check availability for Cycling the Wine Trails of Umbria. Simply complete the form below and a member of our sales team will contact you (when it's most convenient for you) to provide availability information, travel options and an accurate price. Of course there's no obligation, but if you do wish to proceed with a booking they will be on-hand to assist you throughout the process.

Alternatively, you can call our sales team on 1-800-267-3347 to discuss your requirements in more detail.

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We've been creating high-quality relaxed activity holidays since 1985 and our wealth of experience means we're able to build the perfect tailor-made tour for you. Our 'Gold Trusted' rating on Feefo, the independent review site, underlines our exceptional levels of customer service, and our ATOL bonding and ABTA membership guarantees your holiday is safe with us.

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