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Greetings Internet Stranger! If you’re traveling around the Balkans, you’ll probably want to hit up every country in the most efficient way possible. Gotta check ’em all off your bucket list after all. So I suggest heading from North Macedonia to Bulgaria by following this stunning Skopje to Sofia day trip itinerary. If you drive, like I don’t, you can take this trip entirely on your lonesome.

But even if you can’t drive, this trip is still highly possible. (And I should know, as I know no more about driving than a newborn baby dragon does.) Instead, hire this wonderful company called My Day Trip. This way you’ll have an affordable yet private driver take you on your Skopje to Sofia day trip. You can choose different stops along the way if you wish. Just be sure to stop at Rila Monastery because it really is spectacular. Feel free to create the itinerary that works best for you!

skopje to sofia day trip

Skopje to Sofia Day Trip

Where to Stay?

Sofia is a charming and very walkable city, so you’re going to want a location right in the center of town. I strongly recommend the Rosslyn Thracia Hotel. The staff is super friendly, the room is comfy, there’s a yummy breakfast spread every morning, and it’s within walking distance of lots of cute coffee places and shops.

If you’d like a great deal on this hotel, just click here. And if you’d rather explore hundreds of other excellent hotels in Sofia, click here!

Skopje to Sofia Day Trip

What to Pack?

skopje to sofia day trip

You’ll need comfy shoes for all the walking we’re going to do today. If it’s summertime, I love my special pink Birkenstocks. These aren’t your grandpappy’s Birkenstocks anymore. They come in every shade, and I always get compliments on my electric magenta shoes.

Kosovo is hot in the summer, so don’t forget the sunscreen. My favorite is the Neutrogena spray bottle because it’s so easy to apply. And as a solo traveler, I can actually use it myself on my own back. I just put it in my purse and re-apply throughout the day.

skopje to sofia day trip

Finally, if you’re American, you need a universal adapter if you’re going to plug in electronics. European electrical outlets don’t work with American plugs. I suggest the NEWVANGA travel adapter. It’s usable with any electrical outlet in the world, so you won’t need to keep buying new adapters. I always carry two with me, just in case something happens to one.

skopje to sofia

Skopje to Sofia Day Trip

Morning: Rila Monastery

Rila Monastery is absolutely one of the most beautiful places in Bulgaria. It’s so important that they actually put the image of this monastery on the back of some Bulgarian currency. I’m so glad I got a chance to see it on my Skopje to Sofia day trip, and I’m positive you’ll love it too, especially if you love terrifying murder angels and being yelled at in Bulgarian. But where to start our tour of Rila Monastery? Why with…

Three Fun Facts: Rila Monastery

skopje to sofia day trip
1) Who Founded This Monastery?

There’s a clue in the monastery’s official name: the Monastery of Saint Ivan of Rila. Yes, twas Saint Ivan who is responsible for this majestic creation. For some reason, some of the English signs at the monastery refer to him as Saint John. (Ivan in Bulgarian = John in English.) I’m not fluent in Bulgarian or anything, but I think most English speakers can handle the name Ivan. It’s not like he was Saint Zhelyazko.

If we want to be strictly honest, and we do because we’re in a monastery and God might smite us for lying, Saint Ivan probably didn’t actually found the monastery himself. He was a saintly hermit who lived in a cave nearby and attracted many students who wanted to learn from his wise, silent, hermitty ways. So it’s really his students who founded the monastery. But The Monastery of Saint Ivan of Rila’s Students doesn’t sound quite as prestigious.

skopje to sofia
2) What’s the Best Thing to See?

In this humble blogger’s opinion, it’s definitely the stunning paintings that cover both the interior and exterior of the monastery. You can’t take photos inside the monastery, but you can take as many as you want outside. Be sure to find this elaborate portrayal of the Archangel Michael getting all stabby. What is up with his shoulders? Where did those faces come from? Did he cut them off some demons and stick them on like epaulets?

skopje to sofia day trip

I guess he didn’t take the faces off of these demons though. They still look pretty cheerful. I feel grateful that this images were made in a time when most people couldn’t read. That’s why they are still comprehensible even if you don’t know how to say “demon” in Bulgarian.

skopje to sofia day trip
3) Anything Else To Do?

Sure! Are you interested in Bulgarian Orthodox icons? Then you can pay a tiny fee and see them in a separate gallery. Just don’t try to take photos inside because there’s a mean old man who sits in front of the icons yelling at people who try to snap them. So my photos of the exterior of the monastery will have to serve as an adequate substitute.

skopje to sofia day trip

There is also a museum in the monastery that charges admission, but I didn’t think there was enough time to visit. You can also grab a snack from one of the snack shops outside the monastery since we won’t have a proper lunch break on this itinerary. None of these places took credit cards when I was there. If you don’t have Bulgarian cash, there are ATMs outside the monastery. My driver said this was sacrilegious, but I say monks gotta eat too.

skopje to sofia day trip

Skopje to Sofia Day Trip

Afternoon: Explore the Great Bulgarian Outdoors

So we spent the morning of our Skopje to Sofia day trip exploring one massive destination. But for the afternoon, we’re going to make a couple of little stops. We’ll see the finest, nay only Bulgarian waterfall I have ever visited. Then we’ll check out some highly controversial ruins. As always, I will keep you informed with…

Three Fun Facts: Skopje to Sofia Day Trip

goritsa waterfall
1) What’s the Prettiest Stop?

That would definitely be the Goritsa Waterfall, pictured above. Keep in mind that it’s a bit of a hike to get here from the parking lot, so don’t make this stop if you hate walking uphill. The waterfall gets its name from a legend about a girl named Goritsa. Apparently she was running away from a Bad Man and flung herself in the river to escape a Cruel Fate. Oh Bad Men, when will you learn to be good?

Since this Skopje to Sofia day trip involves spending a lot of time in the car, you’ll thoroughly enjoy the chance to stretch your legs and breath in the outdoors here. Probably you’ll find quite a few other Bulgarians/American/French people here, but not so many that it will be crowded or unpleasant. People were quite polite about giving everyone a turn to reach the best spot from which to take photos.

skopje to sofia day trip
2) What’s the Most Interesting Stop?

In my opinion, it was Krakra Fortress, which is the ruins of a genuine medieval fortress from the days of the First Bulgarian Empire. It was destroyed back in 1063 in an earthquake, and then it had to be rebuilt. There used to be 75 buildings in the fortress, including seven churches, but as you can see from my photo, the fortress has since fallen on hard times. Now there aren’t any building, just rows and rows of limestone bricks as far as the eye can see.

skopje to sofia day trip

Supposedly there is sometimes a small admission fee to get into Krakra Fortress, but no one was taking money when I got there. So I got to ramble about the medieval limestone ruins all on my lonesome without paying a penny. As an American, I’m always so impressed to see anything this old. The oldest building in my hometown New York City is actually a XXX movie theater from the 1970s in Times Square.

skopje to sofia day trip
3) What’s the Worst Stop?

Also at the Krakra Fortress, you can see these hideous fake attempts at making walls for the fortress. These were done by the Bulgarian government in recent times to try to attract more visitors. I mean, they might work because people will surely come from miles around to see an example of what bad restoration looks like. And how would poor Krakra feel if he came back from the dead, ready to revive the Bulgarian Empire, and was confronted with this nonsense?

skopje to sofia day trip

The fortress also gives great views of Pernik, the nearby industrial city, to satisfy all your longings for Communist architecture. My driver referred to Pernik as either “the ass of Bulgaria” or “the asshole of Bulgaria”, I can’t remember which. I think that’s very mean! I would love to visit Pernik when I have some more time in the country. I’m sure it has tons of inner beauty.

skopje to sofia day trip

Skopje to Sofia Day Trip

Evening: Dinner at Cava

When you arrive at your hotel in Sofia, you’ll probably be a little tired from driving all day, climbing up waterfalls, and being confused by the Bulgarian government’s idea of conservation. So I suggest having a relaxing dinner at a charming Bulgarian tapas restaurant called Cava. If you visit Sofia in the summer, you’re going to see TOMATOES on all the menus. And there’s nothing better than an in-season tomato on a Mutton Lettuce and Tomato Sandwich, when the mutton is nice and lean.

I suggest starting with some excellent Bulgarian cured meat and tomato bruschetta. (The waitress was very clear that it was not prosciutto.)

skopje to sofia day trip

Then move on to an heirloom tomato salad with fresh local soft cow cheese. If there’s one thing Bulgaria knows, it’s dairy products. But we’ll learn more about that on our next 24 hours in Sofia.

That’s a Perfect Skopje to Sofia Day Trip!

What would you do on a Skopje to Sofia day trip? Is it sacrilegious to have an ATM outside a monastery? And what is the ass of Bulgaria? Please leave your thoughts below!

Note: If you want to know how I put my travel itineraries together, just click here. Keep in mind that while each article is about how to spend 24 hours in a place, that doesn’t mean you should ONLY see Sofia on a Skopje to Sofia day trip.

Stella Jane
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