North Macedonia - Dionysus Trail
The Dionysus Trail is named after the ancient Greek god of wine and during the week you journey from winery to winery, visiting seven high quality North Macedonian wineries. This ride is run by the same team that operate the Miyak Tribe Trail and it has two seasons:
The first is in November/early December which is a great time to explore the route due to mild weather and beautiful autumn colours. During this time the riding days are slightly shorter due to the winter nights and so you cover approximately 130 km over the six days riding.
The second season is from February through to May by when the wild flowers should be at their best. The slightly longer days allow more riding and you cover approximately 160 km over the six riding days.
You ride on average for between five & six hours each day covering a distance of between 15 to 36 km each day.
You must be riding and physically fit; confident and in control of your horse at walk, trot and canter in the open. The pace is dictated by the terrain and you may be required to dismount and lead your horse on foot at times.
The horses are mainly Balkan mountain horses, with some purebred Arabs and Arab crosses. They are ridden in Western tack, but the riding style is English with a loose rein. The horses are trained to have a very forward going walk and rarely trot.
Your horse is prepared and untacked for you by the support team.
Hard hats are mandatory. There are a couple of body protectors available to borrow.
The accommodation varies from simple guest houses to very comfortable hotels - each with a winery. The food is a highlight of the Dionysus Trail with especially selected dishes to complement the wines of the region.
You also visit a bee farm to learn about the production of honey and have the opportunity to participate in a workshop to learn how to make local delicacies such as ajvar.
| Holiday | Experience LevelExp Lvl | Arrive - DepartArr - Dep | Price | Itinerary | Availability | |
|---|---|---|---|---|---|---|
| Dionysus Trail | 8 Feb 2026 - 15 Feb 2026 | 7 nights 7 ngts | £1,753.33 |
|
Full | |
| Dionysus Trail | 22 Feb 2026 - 1 Mar 2026 | 7 nights 7 ngts | £1,753.33 |
|
Full | |
| Dionysus Trail | 8 Mar 2026 - 15 Mar 2026 | 7 nights 7 ngts | £1,753.33 |
|
Book | |
| Dionysus Trail | 22 Mar 2026 - 29 Mar 2026 | 7 nights 7 ngts | £1,753.33 |
|
Book | |
| Dionysus Trail | 29 Mar 2026 - 5 Apr 2026 | 7 nights 7 ngts | £1,753.33 |
|
Book | |
| Dionysus Trail | 12 Apr 2026 - 19 Apr 2026 | 7 nights 7 ngts | £1,753.33 |
|
Book | |
| Dionysus Trail | 19 Apr 2026 - 26 Apr 2026 | 7 nights 7 ngts | £1,753.33 |
|
Book | |
| Dionysus Trail | 3 May 2026 - 10 May 2026 | 7 nights 7 ngts | £1,753.33 |
|
Full | |
| Dionysus Trail | 10 May 2026 - 17 May 2026 | 7 nights 7 ngts | £1,753.33 |
|
Full |
INCLUDES Riding and English-speaking guide; accommodation; all meals; other activities such as wine tasting; drinks at the ranch and at meal times; all transfers.
SINGLE SUPPLEMENT Single rooms in the hotels are possible on most nights but it may not be possible to guarantee single accommodation throughout. Single rooms should be requested in advance and where available in the hotels are an extra €20 per night, payable locally. If you are willing to share, then no supplement is charged.
PAYABLE LOCALLY Alcoholic beverages and all soft drinks at the hotels and guesthouse; tips (optional).
NEAREST AIRPORT Skopje
TRANSFERS are included from Skopje airport.
Return transfers are included from Skopje airport or from a hotel in Skopje (City Park Hotel recommended).
Guests arriving in the mid-morning, or who are already in Skopje, will be taken for lunch and then a short sightseeing tour of Skopje. In the late afternoon you transfer to your accommodation (about 45 minutes' drive).
If you arrive in the afternoon/evening you will be transferred directly to the hotel.
The last night is at a hotel near to Skopje airport and so your flight can depart at any time.
The Miyak Tribe Trail and Dionysus Trail in North Macedonia are some of our most popular riding holidays in Europe.
If you’ve already ridden in North Macedonia and wish to return to ride with Vasko on either itinerary there is a super 10% discount off your return visit in 2026.
The trail takes place in the most important region of North Macedonia for wine production in the central south of the country, centred around Kavadarci. North Macedonia is a southeast European country on the Balkan peninsula. It is landlocked by Bulgaria, Serbia, Kosovo, Albania and Greece.
North Macedonia's climate features hot summers and cold winters.
In The Saddle - Personally Inspected Riding Holidays Worldwide says