Bulgaria Itinerary feedback

I can't answer all your questions, but I was in Bulgaria in March, so here are some things I can share:

I think your itinerary is fine. If you can figure out how to book Boyana Church in advance, do it. I got all the way there from our hotel in central Sofia only to find that we'd have to wait two hours for the next opening. We couldn't wait because we had somewhere to be. It's not a simple matter to book in advance. Be sure to read through the information at https://boyanachurch.info/en/visitors-information-en/. If you don't want to make a reservation, be prepared to wait after you arrive and buy your ticket.

I don't know about day trips to Kazanlak's Thracian tomb, but from VT, if you go anywhere, I'd recommend Arbanasi to visit the Church of the Nativity. That's not a very far drive; you could probably hire a taxi.

We did elements of your planned trip this past April. We used only trains to get around and were happy with them so I have no information on the bus companies which you mentioned. We flew into Sofia and had photograph and fingerprints taken for EES there. It took just over an hour as it was the last flight of the day and there were a number of babies and small children on the flights. The flashing lights and whirring noises of the cameras made a lot of the babies and toddlers cry.

We had planned on visiting Veliko Tarnivo, but like the Hotel California we could check in, but could never leave as could not get any form of transportation out of town. This is despite trying two different dates for the visit. Instead, we substituted Stara Zagora which had an excellent regional museum, and some Roman ruins. After that we visited Burgas and did a day trip by local bus to Nessebar. From Burgas we took the train to Plovdiv and stayed at the Hotel Odrys. I recommend the hotel. Simple room, good beds, lots of hot water and a restaurant with a luscious display of cakes. It was several blocks from the hotel to the Old Town area. Wear very supportive sturdy shoes for Old Town as walking on all the "rocky pavement" is a challenge.

We returned to Sofia for 4 days before taking a Flixbus to Thessaloniki. Per AI, so perhaps a grain of salt here, Bulgarian bus drivers quite often keep the onboard WCs locked and can go 4-5 hours before a bathroom stop. From past experience with Flixbus I knew their bathroom would be accessible.

We took a free walking tour, abut 2 1/4 hrs. long in Sofia and enjoyed it. We also took a day tour to Rila Monastery through Traventuria. This included a short visit to Boyana church, extra charge for visiting the church for 10 minutes. The tour continued to Rila Monastary, some beautiful scenery on the way. At the monastery the tour guide told us the history of the monastery and what it meant to Bulgarians. Guides are not permitted to lead tours in the church. After he finished his talk, perhaps 15 minutes, we were on our own for the next 2 hours and could have lunch at our option. Some excitement on the way back to Sofia when the driver swerved on the road and honked as five pigs had made a break for freedom and were trotting down the road.
As regards the Cyrillic alphabet some streets had their names in both alphabets, and some did not. Not everyone in Bulgaria spoke English, but generally people in the tourist or hospitality business spoke as least some limited English. My husband used CoMaps offline in both Bulgaria and Greece on his phone for directions and maps. We did no driving in Bulgaria ourselves, so I have no information on highway signs.
In Thessaloniki we stayed at the Orestias Kastorias Hotel, which I recommend. The staff were all very helpful and coffee and tea were available all day for free in the breakfast room. We found three good restaurants on Olimpou street somewhat close to the hotel based on the staff's recommendations. We also took a day tour to Meteora from a tour agency based on their recommendations.
Hope this helps and that you will have a wonderful trip to Bulgaria and Greece this September.

Thank you for the information on Boyana church, @Lane. How did you travel to Arbanasi from Veliko Tarnovo? Did you have a car or take a taxi?

Thanks for all the information, @Jerry. Very helpful and I appreciate the details.

Did the Flixbus from Sofia to Thessaloniki stop enroute for rest/snack stops? If so, how many times?

I am confused by you not being able to go to Veliko Tarnovo. Are you saying, you couldn't find any transportation from Sofia to Veliko Tarnovo and had to go to Stara Zagora instead? There appear to be multiple buses/trains to VT from Sofia. What am I missing here?

The travel time from Plovdiv to Thessaloniki seems to be 7.5 hours by bus, which is far too long for my liking. So I am now trying to see if I can breakup the journey enroute and stay an extra night. Sofia is an obvious choice as the total travel time is the same. Something to look into.

Arrive in Sofia Airport. Stay in Sofia for 4 nights and 3 full days.
Explore the city 1 day, day trips to Rila Monastery and Mt. Vitosha
for hiking and Boyana Church on the other 2 days. Bus to Veliko
Tarnovo. Stay 2 nights and 1.5 full days to see the town. Bus from
Veliko Tarnovo to Plovdiv Stay 3 nights and 2 full days in Plovdiv.
Bus from Plovdiv to Thessaloniki

Its a plan and I am certain you will enjoy it. I can only list a few places that I enjoyed and would enjoy going back to but I am not as adverterous as you so I hire transportation in Bulgaria. The last trip was a drive from Sofia to Istanbul. A trip of a lifetime.

Devils Throat Cave: We saw the sign on the road without any indication of distance, but we turned anyway. After 90 minutes on what looked like one of those Death Road Trucker movies we ended up at this pretty amazing place: https://youtu.be/-QTC6uaER5g?si=SA-APzDOiworMTix

Nessebar: Tied with Plodiv as my two favorite stops in Bulgaria https://youtu.be/MJFx7R4IgLY?si=bzeet2IYUngNhDbG

Asen's Fortress Church: All I can say is every once in a while a place speaks. https://youtu.be/oABMTrApf-M?si=aSuZ6ZaKr4OZnLVo Maybe one of the top 5 travel memories in my life.

I can't answer your public transport queries as we rented a car while in Bulgaria (which was very easy, incidentally) but as to your Cyrillic question, yes, most signs etc were only in Cyrillic (at least in 2017). In some places they also have English, like on the metro in Sofia. When we were driving most of the signs telling you where to turn off etc were in Cyrillic. I don't speak any languages that use Cyrillic but I know the alphabet well enough that we were able to navigate that way (plus Google maps of course!). It might be worth having a look before you go- once you learn a few things it's not that hard to figure out proper nouns on signs.

How did you travel to Arbanasi from Veliko Tarnovo? Did you have a car or take a taxi?

Pam, I was on a tour with OAT, so we went in the tour bus. If you don't have a car, I am sure you could hire a driver or a taxi and they could wait for you in Arbanasi to take you back to VT.

Here's some info: https://velikoturnovo.info/en/places/church-of-the-nativity-in-arbanasi/. It also mentions a few other stone churches in Arbanasi, but we didn't visit those.

@Mr. E., thank you for all the wonderful suggestions. I will add them to the list to visit one time or the other. Those videos are lovely and you are a really good representative for Bulgarian Tourism Board :) Thank you for sharing them.

@Cat VH, thanks for all the information on driving. Which company did you use for car rental? Yes, I think I will have to get some practice in Cyrillic before I feel comfortable driving and navigating those signs.

@Lane, thanks for the link on Arbanasi.

I can't remember which company we used to hire the car, but normally we use either Sixt or Europcar, so it is very likely one of those! Having a car makes it easy to keep to your own schedule. We drove from Sofia to the Rila Mountains area for a few days and then back. We had a great time- we especially loved Mount Vitosha and Boyana Church (plus of course Rila Monastery). Good luck with your planning!

pam, I didnt think it would be much help to you but I thought I would throw it out just the same. You never know.

You are off to a place that in my 3 visits over the years left me with a warm and welcoming feeling. I regret not getting back more recently.

I just remembered another stop. The Bachkovo Monastery. The monastery itself is interesting but more important to me is that it is the resting place of Metropolitan Kirill of Plovdiv and Metropolitan Stefan. Two worth visiting and paying respects. https://www.bbc.com/reel/video/p0jnv2c1/watch AND https://youtube.com/shorts/ShcK9K-ZPhI?si=Vr4pM6t71HncZCfy

G-d bless and safe travels.

As I remember the Flixbus to Thessaloniki from Sofia was around 5.5 hours. It left at 7:30 am. Check me with Flixbus as I have deleted the booking paper now that am home. It stopped 1 time for 1/2 hour just inside the Greek border as the driver had to take papers to someone official. It was by a cafeteria with a small gift shop. However, there was a usable, but small, bathroom on the bus.
We could get to VT with no problems. However, each of the two days I tried to leave showed nothing available for the day before, the day of departure and the day after. I tried repeatedly over a number of days and the showing of nothing available never changed. After that I switched to Stara Zagora as a replacement town.

Thank you for all the information again, @Cat VH, @Mr. E, and @Jerry. Yes I was think of Bachkovo Monastery as a side trip from Plovdiv in combination with the magnificent Asen Fortress.

I will have to postpone Bulgaria to another time as I realized I have more to see/do in Greece this visit and cannot spare 10+ days to Bulgaria. I think Bulgaria combines well with Romania and I can take a train between Bucharest and Veliko Tarnovo (unlike Greece which appears to be an island for international trains). I have added all your suggestions to my list of places to visit.