Chisinau City Tour The capital city of Chisinau is a great spot to start, especially as the city is very compact and walkable, so it's easy to navigate. I spent the entire day walking, although a city tour could be done in 3-4 hours. The highlights I would recommend are The Triumphal Arch, and The Parliament Building, walking the local parks, and checking out the many monuments. For something random, visit The 1 Ban Monument, which is to commemorate Moldova having their own currency.
Just a one hour drive east from the capital and you'll reach the city of Bender, which is home to Bender Fortress. The Ottoman Fortress was built in the 16th century and saw consistent fighting between Turkish and Russian forces. You can go inside, and also head up top where you'll get a great view of the Dniestr River. For the history buffs, there's also a museum inside. Within the complex, there's also the restored Alexander Nevsky Church, with it's golden domes that will instantly catch your attention.
A 30 minute drive North of Chisinau and you'll reach Cricova Winery, which is the second largest winery in the country. They operate regular tours of the premises, which also includes wine tasting, and a tour of their tunnels, which span 120km. Even if you're massively into wine, Cricova is a historical landmark of the country and the tour is enjoyable. The Russian President Vladimir Putin actually chose this venue to celebrate his 50th birthday. Another interesting fact is that the largest importer of Cricova wine is actually Kazakhstan.
There's a breakaway state by the name of Transnistria, which is only a one hour drive from Chisinau. It's only a narrow piece of land sandwiched between the Dniestr River and the Ukrainian border, but even has a capital city called Tiraspol. If you're a fan of monuments, Transnistria is full of them. I'd recommend checking out The Suvorov Monument, The Tank Monument, Moldova National Opera Ballet, and the Moldova War Memorial.
When you're standing in the centre of Transnistria, you'll literally feel like you've entered a Soviet time warp.
Eternity Memorial Complex
There's a large war memorial in Chisinau called "Eternity Memorial Complex" which is dedicated to the Soviet soldiers who died in The Second World War. In the centre of the memorial complex there's a large pyramid style structure consisting of five 25 meter tall stone rifles, which hold an eternal flame inside. There's also many monuments around the complex as well as whole section dedicated to gravestones of fallen soldiers.
There's a large Moldovan Orthodox monastery in Chisinau which is dedicated to Saint Theodore of Amasea. It's located in the centre of the city and is beautiful both inside and out. Most of the external building is blue with gold domed roofs, whereas the inside is similar with blue painted walls and a gold alter. In 1962, many of the churches in Moldova were either closed or had their purpose changed, but this is one of the sole survivors. Worth noting that the monastery is active, so you may not be allowed inside during a service.
As a former member of the Soviet Union, there's an abundance of Soviet style architecture throughout the city of Chisinau. Yes, some of the buildings have that cold grey concrete design, but I feel they bring character to the city and is a reminder of a dark past with a brighter future. The former National Hotel, now abandoned, is an iconic landmark of the city.
For a nice standard of accommodation in the centre of Chisinau at a low entry cost, look no further than Thomas Albert Hotel. This is a small hotel with 20 rooms, as well as offering a restaurant relaxation area. If you're travelling in the winter, I can confirm there's no issues with the hot water. This is also a great central point to use as a base, with many sites within easy walking distance.
My recommendation will be Kymahek Restaurant, which is located in Tiraspol, the capital of Transnistria. This is a traditional local restaurant wooden floor, wooden ceiling, and wooden tables. You'll feel like you're in a large log cabin. The menu is extensive, although mainly focusses on Moldovan dishes. The cold meat platter was a worthy appetizer, followed by a local horse stew.