Magical Macedonia

Starting in Skopje and ending in Ohrid, we’ll be circling around North Macedonia and getting to know this newly renamed country which after 27 years embroiled in a dispute with its southern neighbor, has become a shining example for the region on moving forward. This tour includes just about everything you could imagine:  ancient astronomical and historical sites, hidden monasteries, historical vineyards, Yugoslav monuments, picturesque mountaintop villages, one “country” within the country, and mystical lakeside hamlets. You can also be sure you’ll get well-acquainted with top-notch Macedonian cuisine and its legendary national spirit, žolta.



8 Nights/9 Days

Physical Activity

Physical Activity

Mild to Moderate

Group Size

Group Size

6-8 people



Vegas of the Balkans

Don’t let Skopje’s freshly installed Neoclassical face fool you, North Macedonia’s capital is teeming with culture and amazing stories to be told. Our tour commences in one of Europe’s most unique capitals and we’ll be hitting all of its main sights as well as a day trip out to Canyon Matka.

  • Guided city tour featuring Ploštad Makedonija, Memorial House of Mother Theresa, Čaršija (old Turkish bazaar), Kale Fortress, Sveti Spas Church, statues and more statues
  • Ride the cable cars up to Mt. Vodno and the Millennium Cross
  • Traditional lunch in stunning Matka Canyon


Ancient Astronomical Observatory

Only just discovered in 2001, we’ll explore what NASA has recognized an important megalith monastery that’s been used to observe celestial events for 4, 000 years.

Kriva Palanka

Hidden Monastery

Tucked back in the hills about 10km from the Bulgarian border, we’ll visit this stunning Osogovo Orthodox Monastery and its impressive Church of St. Joachim of Osogovo.


Revered Roman Ruins

Stobi is North Macedonia’s most important archeological site and located near Gradsko about 80 km south of Skopje. We make a stop in this ancient town which has been around since 3 B.C. and flourished as a major hub on a road that was connected to Via Egnatia.

Demir Kapija

Boutique Winery Experience

We’ll head south into Povardarie, North Macedonia’s wine region, and straight to Demir Kapija for an overnight stay at the boutique winery, Popova Kula. Aside from having one of the nicest hotels in the country outside of Skopje, you’ll be blown away by its varietals and spectacular natural scenery.

  • Dinner and wine tasting of some of the region’s best varietals at Popova Kula’s charming second-story restaurant
  • Comfortable overnight stay amongst the tranquil vineyards of Popova Kula
  • Visit to the Museum of Wine which covers some 6,000 years of production and ethnology pertaining to the “Drink of the Gods”


Mecca of Macedonian Wine

Home to Tikveš winery, one of the largest and most awarded wine producers in the Balkans, we will stop in Kavadarci to visit its facilities and enjoy a light wine tasting and lunch.


Tobacco Town

As the epicenter of tobacco production in North Macedonia, Prilep is easily identifiable by its luscious tobacco fields and skyline with striking rock formations that legends are made of. We’ll have a quick stop here before we make our way out into its hills  to visit Treskavec Monastery.


Magical Monastery

Once one of the most inaccessible monasteries in the country, Treskavec is now well-connected to Prilep and we’ll be paying it a visit which hopefully will include a meeting with its main man and Macedonian legend, Father Kalist. For nearly sixteen centuries, religious pilgrims have been making their way to this magical point that overlooks the Pelagonia Plain and once we arrive it will be clear why.


Historical Mountain Hideaway

One of North Macedonia’s most charming mountaintop towns, we’ll be spending one night in Kruševo which played an incredibly important role in the country’s move towards independence and is home to one of the Balkans most peculiar spomeniks: Makedonium/Ilinden.


City of Consuls

As the second largest city in North Macedonia, Bitola has an infectious energy that you won’t fail to notice walking down its famed Sirok Sokak, particularly in the evening hours. We’ll spend 24 hours here getting familiar with all its history and cultural heritage sites including the ancient ruins of Heraclea Lyncestis.


Peaceful Biosphere Reserve

Prespa is a paradise for nature lovers and off the radar for most tourists. We’ll spend a few hours here lunching beside the lake and exploring its surroundings before heading over to its celebrity sister, Lake Ohrid.


Mystical Lakeside Resort

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  • Guided city tour featuring Church of Sveti Jovan at Kaneo, Plaošnik, Sveta Sofija Cathedral, Car Samoil’s Fortress, Robev Family House and more
  • Lunch in the quaint fishing village of Trpejca
  • Guided tour to Bay of Bones Museum and Sveti Naum Monastery
  • Sunset boat cruise on Lake Ohrid