General
You will probably not have learned about Moldovan history at school, unless you're from the region. I found it worthwhile to dive into it a bit via reading two books:
The Moldovans: Romania, Russia, and the Politics of Culture and
Moldova. A History. None of the major history podcasts has ever done a full episode on Moldova or its predecessors, Bessarabia and the MSSR, as far as I am aware.
The
Travel to Moldova Facebook group is interesting to follow for a bit to get ideas, and
this site provides tips for those more into Soviet nostalgia.
Itinerary
My 8-day itinerary of Moldova and its neighbours was:
D1: Afternoon WizzAir flight Eindhoven (NL) to Iasi (ROM)
D2: Day in Iasi, including visit to component of TWHS Princely religious foundations in Wallachia and Moldavia.
D3: Bus to Chisinau (4h). Late afternoon visit National History Museum in Chisinau.
D4: Full Day tour to Orheiul Vechi TWHS, Curchi Monastery, and Cricova Winery TWHS with
MoldovaToVisit&Tours (138 EUR)
D5: Sightseeing in Chisinau.
D6: Visit to Prezdinovie/Transnistria on public transport. Sights of Tiraspol by myself. Tour by car to Chitcani village, Noul Neamt Monastery and Bender Fortress with
PMR Tours (60 EUR).
D7: Visit to Odesa (UKR) on public transport. Guided walk with
Ukraine_by_locals (38 EUR)
D8: Afternoon flight Chisinau - Amsterdam via Warsaw with LOT.
I would have liked to spend 1 or 2 more days, since days 4, 6, and 7 were long travel days. There are a few options:
* If you rent a car, you can additionally spend a couple of hours in the north of Moldova, to track down the Balti Steppe TWHS and a component of the Cucuteni-Trypillia Civilization (the one near Balti is a ditch..), Soroca castle and the Struve component. They all seemed so underwhelming that I did not make an effort.
* You could go south to Gagauzia, another semi-autonomous part of the country, but with little that makes it stand apart.
* And there are some places in Romania not too far away, such as the Neamt Monastery TWHS and of course the Churches of Moldavia.
(T)WHS
If we agree that every country should have at least one WHS, the Struve component honestly does not cover it and does not teach you anything about Moldova. Orheiul Vechi and the Underground Wineries would be the most likely candidates; I'd suggest including both, as they cover medieval and 20th-century history.
Hub
Chisinau has developed into an excellent hub for this region. It has modernized a lot over the past few years, and I found it a very pleasant city. It has an extensive (trolley)bus system, which is easy to use at a flat fee of 7 MDL (0,35 EUR).
Chisinau Airport sees mostly low-cost airlines from all over Europe. Moldova's own carrier, FlyOne, is usually not recommended because of its unreliability. The airport itself is a bewildering crossroads, where you may see orthodox jews mix with Ukrainians who don't like to be spoken to in Russian by the Moldovan staff.
You can also fly into Iasi (Romania): there are direct buses from that airport to Chisinau. Within the city of Iasi, minibuses to Chisinau depart from the parking lot of the large Carrefour supermarket not far from the railway station.
CommunicationEU roaming works in all included territories, except for Prezdinovie/Transnistria (here I just went without service for a few hours; some signal does come through via Moldovan towers).
Useful apps are: translate in Romanian, Ukrainian and Russian (did not use them); Bolt (although Letz is more popular in Moldova), maps.me.
Cost and money
All "countries" involved in this trip (Romania - Moldova - Prezdinovie/Transnistria - Ukraine) have their own currency, so you keep changing money. Fortunately, there are exchange booths everywhere. I mostly only changed 20 EUR and used a CC for the rest of the expenses in Romania and Moldova. Costs are low, public transport and food are good value.