NOTE: This was before the horrible invasion and destruction of Crimea.
After an 16 hour train ride in second class from Kiev to Simferopol, and a bus transfer from Simferopol, we finally arrived exhausted, hungry, and dirty as hell in Sudak. Through eye-contact alone, we agree on a taxi and manage to hire the only skinny taxi driver in Ukraine. Not a minute after we had agreed on the fare and set off, did he swoop around the corner and picked up his Mother-in-law to hitch a ride.
The gangly fellow turned out to be a madman behind the wheel. One of his first travesties was almost an old man canning across the intersection. Built on hilly terrain, the streets of Sudak claw their way out of the sea into a maze- thus a traffic jam on the main thoroughfare results in a pertinacious stalemate. Or so we thought. The cabbie proceeded to reverse at 15mph (and gradually increasing speed) up a one way street as if escaping a lava pit. Miraculously, we arrived at the gates of our guesthouse, backwards, Locked gates and a malfunctioning buzzer appeared to be trivial to our proactive Formula One taxi driver. Unsolicited, he scaled the walls and yelled "WOMAN, COME!". Next thing we knew, a short Ukrainian woman was prying open the gates to an sylvan two-story guesthome shaded by cherry trees.
If you go:
Beach & Fresh Market
(Market near the Intersection of Ushakova & Mors'ka St.)
Walk down the road towards the fortress until you almost reach the end of the boardwalk. Along the right, a fresh market sells fruits, cheeses, and vegetables. Take your haul down to the furthest point of the cove to sit on the water's edge and watch Ukrainian women repetitively pose for their boyfriend's camera. After a toe-dip in the cold sea, take the dirt, Mountain Goat-like trail up to the Sudak Fortress (FYI: littered with an impressive amount of glass).
Explore the fortresses' views and various ramparts freely and gaze into the Black Sea's splendor. Tie a piece of fabric on the makeshift statue at the top for good luck. Don't slip down the anthill, the paths are not controlled. Spot the beach cove to the right of the fortress and plan your desultory route to it through side streets.
Isolated Beach Cove
(Near the end of Prymors'ka St.)
Once you emerge from the seemingly private garden path and you'll come to a rocky cove with a restaurant and plenty of chairs to lie on. The water is warmer and the place is rather pleasant (besides the horrible, blasting music which is the norm). I recommend drinking over eating, unless shrimp crumbles mixed with eggs, mayonnaise and tomato sounds appealing.
Transport: Novyi Svit Winery is three miles away, seemingly in walking distance. However, the route is along a winding mountain road. Luckily we took a cab . Even more luckily, we happen to pass a man running after pick-pocket who robbed him as he was walking along the very way.
The winery doesn't sell cold cuvee, you much purchase it around the corner at the store. Drink your cold Ukrainian cuvee on the beach and watch the boats. And, apparently, the jellyfish don't sting.
If you go:
Train + Bus (Don't even try the Black Sea Ferry, it is impossible).
Aivazovs'koho St, 17, Sudak, Crimea, Ukraine, 98000
+380 50 055 6564