If I were to return to Bulgaria, I would follow the same basic route I took on my recently trip: enter Bulgaria from Turkey near Edirne, then to Plovdiv and Sofia, ending in the southwestern mountains before leaving the country. This path seems to include the most interesting cities in terms of history and provides plenty of great hiking opportunities. Of course the five days we spent along this route was not enough time to experience most of what is offered so here are some notes on what I didn't do but became aware of and would seek to do if I were there again.
First, I would enter Bulgaria after spending time in Edirne, Turkey. Edirne features what Ottoman architect Mimar Sinan considered his finest work, the Selimiye Mosque. http://en.wikipedia.org/wiki/Selimiye_Mosque. There are other Ottoman mosques dating back to before the time when the Ottomans conquered Istanbul which show the progression of architectural styles leading up to the pinnacle of Sinan's work.
On the Bulgarian side of the border, I would head straight for Plovdiv (if I really had a lot of time I would also visit Stara Zagora and get to nearby mountain city of Karlovo from which more hiking is available). Many Bulgarians asked whether or not we had seen Plovdiv so it comes highly recommended. The highlight seems to be the old town, which has a 19th century appearance. There are also Roman remains and a fourth century church called the Church of St. Constantine and Elena. They nearby Bachkovo Monestary in the Rodopi Mountains seems to be thought of after Rila Monastery but Rila has been destroyed more often and rebuilt more recently so I think I would appreciate the Bachkovo Monestary more than Rila. The Bachkovo Monestary was built in 1083 by two Georgian brothers and helped preserve elements of Bulgarian culture during the 500 years of Ottoman rule over Bulgaria--the exemplary tale being that the monks, apparently on the eve of some incursion by the Turks, hid an icon of the Virgin Mary and Child in the moutains allowing its preservation and rediscovered by shephards centuries later. I didn't hear the whole story but I imagine monks hiding the venerated icon before being attacked--perhaps it was the last thing they did before being killed.
I imagine that visiting the Bachkovo Monastery would put me on a mountain with well marked trails and mountain huts such as Rila provided. I love the balance of wilderness exercise and a museum / historic city experience. The tourist interest in the monasteries seems to inspire Bulgarians to provide options of public transportation to the mountains as well as well maintained hiking trails in the area.
After Plavdov and environs, I would return to Sofia. Downtown Sofia is an affordable European capitol and there are many churches and museums I bypassed. I would also return to Mt. Vitosha for additional hiking.
I would certainly return to the Rila Mountains and spend more time there. The trails were incredibly well maintained with colored trails and enough signage to prevent the first time visitor from worrying much. While we hiked in the Rila Mountains, we didn't make it to the featured destinations. A hike starting in the outpost town of Maliovitsa and straight up the path to Mt. Maliovitsa and then to Sedemte Ezera (the Seven Lakes) and ending at Rila Monestary should be given two or three days. To get to Maliovitsa, go the Yug bus station in Sofia at 9 a.m. (only available once a day). This seems the best option as you can start hiking and at least get to the Maliovitsa mountain hut the same day. I got mixed reviews about the mountain huts (hizha) and we didn't make it to one to allow for my own observations so I would take along minimal camping gear so as to not be reliant on them.
We considered this route for our recent stay but we were dragging too much stuff along so we made Blagoevgrad our base. This was effective. Blagoevgrad is a big enough city to have things available and is right on the train and bus routes between Sofia and Thessaloniki. It is a college town and was very quiet due to summer break. It also is easy to get from Blagoevgrad to Rila Village and then Rila Monestary and Mountains. It may be best to get up to Rila Village and spend a night there as the buses from Rila Village to Rila Monestary run at 7:40 a.m.; 12:40 p.m. and 3:50 p.m. (with returns available around 6:00 p.m.). It may be cutting it close to hike from Rila Monestary to a mountain hut after taking the 12:40 p.m. bus so the 7:40 a.m. bus would make the most sense.
The manager of Pirin Apartment in Blagoevgrad told of his spending a week every September hiking in the Pirin Mountains. He prefers the Pirin Mountains to the Rila Mountains and hiking there would be a major draw inspiring my return. I'm not sure if there might be another city more convenient as a base for the Pirin excursion but Blagoevgrad is not too out of the way and if Rila and Pirin Mountains are explored on one trip, Pirin is close enough to Blagoevgrad that backtracking wouldn't be too inconvenient.
Aside from Greece, Bulgaria borders other Balkan countries and taking off from the southwest to places like Kosovo, Serbia and / or Croatia might be more appealing than a return to Greece.
For a reader who is reading this as a temptation to travel to Bulgaria, here are some practical considerations. Even with the weak dollar in 2008, everything was on the affordable side. We spent less than $10 per person per meal for abundant food at mid-range restaurants, which is remarkable compared to the typical no-less than $20 that I've encountered in western European cities. The bus rides and train rides between cities and countries were in the range of $20 to $40 dollars. There was a lot of English but we traveled most of the time with a Bulgarian friend. Spanish came in handy a few times--even in the mountains we encountered shepherds and were able to communicate due to my knowing Spanish and one of them knowing Italian.
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