Thessaloniki-Sofia

I've tried this car rental idea before and did not find any available through major rental agents on either side of this particular border (nor the Macedonia border) without about $1,000 in extra fees, which were not to drop off in the other country - only to include cross-border paperwork and insurance.

The train was reinstated in 2014 to run once a day, after three years of being clearly cancelled, but it's not running so far this year. If you start by train, you have to connect by bus between Strimon and Kulata. There is also no cross-border train on the eastern end of Greece (only one from Turkey).

Glad to see those details for pick up in Bulgaria. For pick up in Greece, it's a separate company and they don't make it simple: https://docs.abgcarrental.com/location/avis/GR/GR/en/.

Thank you all for your replies! This is very helpful

They make it very difficult/inconvenient/expensive to do so and depending on the border agent, they may selectively choose to know the exact legal implications.

I recommend using a bus instead.

Personally I think the train would be the way to go on this route. Much less hassle. And much cheaper than a rental car. Here is the link to THE site for Train travel The Man in Seat 61. And the Greek Train timetable for Sofia.

https://www.seat61.com/international-trains/trains-from-Sofia.htm#Sofia_to_Athens

Here is the timetable for the Sofia Train;

Train 360/361
Local time
Train Arrival Departure Station Arrival Departure Train
600Α/360 6:55 Thessaloniki 22:22

8:56 9:50 Strimon 19:25 20:20

10:05 Promachon gr. 19:10

10:10 11:00 Kulata gr. 18:21 19:05

11:10 11:11 Gen.Todorov * 18:10 18:11

11:21 11:22 Sandanski 18:00 18:01

12:18 12:19 Blagoevgrad 17:06 17:07

12:47 12:48 Dupnica 16:38 16:39

13:25 13:26 Radomir 15:56 15:57

13:41 13:42 Pernik 15:40 15:41

14:12 14:13 Zah.fabrika * 15:06 15:07

14:18 Sofia 15:00 361/601Α

• Stops only for domestic passengers

Sale of international tickets in stations: Sofia, Blagoevgrad and Sandanski

*Please note that until further notice, the line section Strimon to Kulata and Kulata to Strimon will be operated by bus.

Fares
Route

Indicative prices in Euros (€)

One way

Return
Thessaloniki – Sofia 16.80 33.60
Thessaloniki – Blagoevgrad 11.60 23.20
Thessaloniki – Sandanski 8.80 17.60

The international one way tickets are valid for 15 days and the return tickets are valid for 1 month.

Reserving a seat is mandatory.

Children aged 4-12 and children aged below 4, for whom a separate seat is requested, are charged half the going adult rate. Children aged below 4 travel free of charge.

Groups consisting of 6 people or more are entitled to a 20% discount (2 children aged 4-12 are considered 1 adult).

Small groups of passengers, consisting of at least 1 adult and 1 child and no more than 5 adults and 1 child (2 children are considered 1 adult) are being charged the special CityStar price, agreed between the two countries. CityStar entails, as well, special prices, addressed to students, ISIC (International Student Identity Card) holders.This bilateral offer is valid on Tuesdays, Wednesdays and Thursdays every week.

Typical CityStar prices on the route Thessaloniki- Sofia- Thessaloniki:

2 people pay 38.40 Euros in total
4 people pay 64 Euros in total
2 students pay 19.10 Euros in total
4 students pay 48.50 Euros in total

A special price of 25 Euros for return tickets is also available on the route Thessaloniki- Sofia, provided the ticket was purchased at least 15 days prior to travel. The offer is available for a limited number of seats.

Dosent sound like a private transfer is a whole lot more expensive for the five of you: http://aroundbulgaria.com/transfers/sofia-airport/thessaloniki/