Give the two countries distinct halves
Use Bucharest and Brașov for the Romanian opening, then travel to Iași before crossing into Moldova. Keep three final nights in Chișinău, with one booked cellar day and one return trip to Orheiul Vechi. This avoids carrying luggage into the village and protects the departure.
The Brașov to Iași day is long. Read every rail segment and any replacement bus. The Iași to Chișinău crossing can use a coach or dated train, but the train uses Iași-Socola rather than the main station. Leave the arrival evening free for border delay.
Treat the cellar and Orheiul Vechi as separate outings
Confirm the winery language, transport and return. For Orheiul Vechi, name the village and select the last practical return before walking. Do not add Transnistria to fill an open day; current advice is against all travel there.
Use station-friendly rooms in Brașov and Iași because those stays sit between long journeys. In Chișinău, keep one base for all three nights so the cellar and Orheiul Vechi days do not involve luggage. A missed border arrival should shorten the first capital evening, not force the rest of the route later.
With eight days, remove either Brașov or Orheiul Vechi rather than compressing every city. The example total excludes international tickets, cellar packages, private drivers and major Bucharest admissions.