Stand on Ulitsa Petrovskaya where it meets Spartakovski Street and you are at the main entrance of Gorky Park, with the oldest drama theater in the south of Russia a short walk along the same street. Taganrog is a port city on the north shore of Taganrog Bay in the Sea of Azov, and its centre rewards a slow walker more than a scheduler.
The city suits travellers interested in literature, architecture and the Black Sea region's layered past: it is the native city of Anton Chekhov, it was founded by Peter the Great in 1698, and it holds a compact group of museums and historic houses.
1. Alferaki Palace
Alferaki Palace is one of the eight museums in the city and one of the architectural landmarks of Taganrog. Its rooms and collections make it a natural first stop for understanding the city's merchant and aristocratic past.
Pair it with the other central sights on Ulitsa Petrovskaya, since the palace sits within the same walkable downtown area as the theater and the park.
2. Taganrog Museum of Art
The Taganrog Museum of Art is one of the city's eight museums and holds the fine art collection. It is worth the time if you want a quieter, indoor counterpart to the historic houses.
Combine it with Alferaki Palace in the same outing, as both are listed among the city's museums and lie in the centre.
3. Birth house of Anton Chekhov memorial museum
This memorial museum marks the birth house of Anton Chekhov, the city's most famous native. Chekhov featured Taganrog and its people in many of his works, including Ionych, The House with an Attic, The Man in a Shell, Van'ka, Three Years, Mask and My Life.
Visit it as the first stop on a Chekhov trail, then continue to the Chekhov Gymnasium and The Chekhov Shop, which are also among the city's museums.
4. Chekhov Gymnasium
The Chekhov Gymnasium is one of the eight museums in Taganrog and relates to the writer's school years in the city. It adds context that the birth house alone cannot give.
Do it in the same half-day as the Birth house of Anton Chekhov memorial museum and The Chekhov Shop to avoid doubling back across the centre.
5. The Chekhov Shop
The Chekhov Shop is listed among the city's museums and completes the group of Chekhov-related sites. It is a small stop that fits neatly between the larger ones.
Keep it for the end of your Chekhov sequence, when you are already in the central streets.
6. Taganrog Chekhov Drama Theater
Located at Ulitsa Petrovskaya 90, this is the oldest drama theater in the south of Russia, founded in 1827. An evening performance is one of the best ways to spend time in the city after the museums close.
Check the program in advance and combine the visit with a walk on Ulitsa Petrovskaya, which also leads to the main entrance of Gorky Park.
7. Gorky Park
Gorky Park sits downtown, with its main entrance at the crossing of Petrovskaya and Spartakovski streets. It is open day and night and is free of charge.
Use it as a break between museum visits, or as an evening stroll after the theater.
8. Primorsky Park
Primorsky Park is on Instrumentalnaya Street and is free of charge. It is the city's other main park and a change of scene from the central streets.
Go when you want open air rather than another interior; it works well as a slower half of the day.
9. Taganrog City Architectural Development Museum
This is one of the eight museums in the city and focuses on how Taganrog was built. It is the best single place to make sense of the historic houses you will pass on foot.
Visit it early in your trip so the architecture you see afterwards has context.
10. Ivan Vasilenko Museum
The Ivan Vasilenko Museum is one of the city's museums and is dedicated to the writer associated with Taganrog. The city also appeared in the novels of Ivan Vasilenko and Konstantin Paustovsky.
Add it if you are following the city's literary thread beyond Chekhov.
11. Anatoly Durov Museum
The Anatoly Durov Museum is listed among the eight museums of Taganrog. It is a smaller, more specialised stop than the palace or the art museum.
Fit it into a museum-heavy day rather than making a separate trip.
12. Taganrog Aviation Museum
The Taganrog Aviation Museum is hosted at the Taganrog air base, six kilometres northwest of the city. It is the one sight on this list that sits outside the centre.
Plan it as a separate excursion and allow for the travel time, since it is not within walking distance of the downtown sights.
13. Taganrog military museum
The city also hosts the Taganrog military museum, which covers the military side of Taganrog's history. It complements the aviation collection if that subject interests you.
Pair it with the Taganrog Aviation Museum on the same day to make the trip out worthwhile.
14. The historic houses of the centre
Taganrog holds a dense group of named historic buildings, among them the Bishop's House, also known as Kirsanov's house, the Chapel of Our Lady of Kazan, Taganrog, Shtalberg House, Telegraph House and the House of Subsovich, House of Deminoj-Cachoni, House of Voroshilkin, Stepan Akimov House, House of Sirotinykh, House of Lukin, House of Lobanov, House of Averino, Mansion of Handrin and House of Rabinovich.
Treat these as a walking route through the centre rather than as individual ticketed sights, and let the Taganrog City Architectural Development Museum frame what you are looking at.
15. The House of Teacher
The House of Teacher is a mansion where numerous artists have performed. It is a reminder that the city's cultural life extended well beyond its museums.
Note it as you walk the central streets; it fits naturally into the same route as the historic houses.
If you only have one day
Morning: Start at the Birth house of Anton Chekhov memorial museum, then continue to the Chekhov Gymnasium and The Chekhov Shop while you are in the central streets. Follow with the Taganrog City Architectural Development Museum so the buildings you pass for the rest of the day make sense.
Afternoon: Move on to Alferaki Palace and the Taganrog Museum of Art, then take a break in Gorky Park, entering from the crossing of Petrovskaya and Spartakovski streets.
Evening: Walk Ulitsa Petrovskaya and take in a performance at the Taganrog Chekhov Drama Theater at Ulitsa Petrovskaya 90. If you still have daylight, finish with a stroll in Primorsky Park on Instrumentalnaya Street.
When was Taganrog founded?
Taganrog was founded by Peter the Great on 12 September 1698.
Which writer is Taganrog associated with?
Anton Chekhov was born in Taganrog, and the city and its people appear in many of his works, including Ionych, The House with an Attic, The Man in a Shell, Van'ka, Three Years, Mask and My Life. The city also appeared in the novels of Ivan Vasilenko and Konstantin Paustovsky.
How many museums are there in the city?
There are eight museums in the city: Alferaki Palace, Taganrog Museum of Art, Birth house of Anton Chekhov memorial museum, Taganrog City Architectural Development Museum, Ivan Vasilenko Museum, Chekhov Gymnasium, Anatoly Durov Museum and The Chekhov Shop.
Do the parks cost anything to enter?
No. Both Gorky Park and Primorsky Park are free of charge, and Gorky Park is open day and night.
Start with the Chekhov sites and the palace, then build the rest of your days around the parks and the theater.