"Old Boy" bar and the whole Likerka.loft is a nice place for Friday hanging out. Another new and fancy spot is "Tipographya", where you can find street food, bar, yoga lessons, cinema, concerts and parties.
Good-quality restaurants are "Stechkin" (better visit in summer when outdoor area is working), "Public", "Pryanosti&Radosti" and "Petr Petrovich", where they brew its own beer. Good coffee spot is "Kult".
Swimming pool in Fedorovka village
Abandoned swimming pool with stained glass ceiling is located in Fedorovka village, Uzlovsky area (check with the map to make sure you're going in the right direction). In this village there is only one street (called Shkolnaya) and you can see the dome from the road.
The dome is made of different colored glasses and it's a miracle that this mosaic has survived since USSR dissolution being unguarded. However, there is at least one broken window at the bottom of the building allowing to get inside. Besides its colors, the pool also has incredible acoustics – at least two music videos were filmed there.
Romantsevsky mountains are located near Konduki village, you will see hills from a distance. From 1960s to 1990s coal mining was conducted there, after the quarry was naturally filled with groundwater. Nowadays it looks quite alien especially for Russian central part (that is mostly flat). Highest point here is 200m which offers breathtaking views of the hills and blue clear water.
Best time to enjoy is obviously sunset. Here you also go swimming, have a picnic or spend a night in a tent (no organized camping but amazing night sky watching). Note: better drive there in dry weather cause the road is not paved final 500 meters.
Geographically logical final of this route is a stay at Bolotov.Dacha – cosy and eco hotel on the boarder of Tula and Moscow regions. It is a house in in the style of Russian manor with relevant entertainments – oared boats, bicycles, horse riding, local eco farm, delicious home-made food (for "donation" of pay-what-you-want). In evenings films are shown on a large screen in the spacious living room.