Hi R M
Hopefully we can help you narrow the options down.
Some basic info:
http://www.langheroero.it are the excellent tourist office in Alba - atypically efficient and energetic, and an exceptional resource including extensive winery listings and they even introduced a winery booking service a few years ago.
Barolo and Barbaresco aren’t far apart, so certainly feasible to fit both in during your stay. Either base in Alba and drive each day, or why not base in one of the regions and plan at least one day where there is no designated driver, but you walk to and between the wineries - perhaps even walking through the very widely accessible vineyards to get there. A picnic amongst the vines might be a nice variant on eating out.
Alba has some very good food shops, so (depending on customs restrictions) can be worth pencilling in at least a couple of hours for picking up so nice stuff to take home (or for picnics / self-catering)
Airport options are Milano (probably Malpensa) or Torino. We’d always favour the latter, but not much in it distance-wise. The driving from Torino is fairly straightforward, but can be quite busy at peak times until you pass Torino. The only other potentially stressful junction comes near Alba.
Be aware that Barbaresco and especially Barolo (the eponymous villages) are every year becoming more of a target for coach tours. Both still have plenty of merit, but Barolo these days is a place we go to for a specific purpose only, before heading back out. It’s nowhere near the level of the more cynical tourist traps that have developed over the years in famous places in Italy, but it seems to get a little closer every year. Don’t let me put you off them though - we notice the change from previous visits, but you’ll approach with a fresh perspective. Personally I very much preferred Treiso, Monforte, Serralunga, Castiglione Falletto, La Morra and Verduno (and look forward to visiting Neive and some of the more outlying Barolo villages)
Winery ‘opening times’ aren’t rigidly set out, but the Langhe / Roero site above does list the times they’ve been advised by the wineries - as well as days of the week they’ll take visitors, with some only doing weekdays and I suspect some also still respect the traditional Italian later start on a Monday. Appointments almost universally required, though oddly we had a wonderful drop in chat at a small old-time producer in Serralunga d’Alba (where his ‘cellar door’ was his front room).
Now the questions:
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Time of year. Recommendations may be different if you are going in winter or summer, or inbetween.
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Hotel or self-catering apartments? We always favour the latter for the extra space, freedom of timings and flexibility to eat out or stay in and crack a few wines picked up at the wineries. Indeed this latter option can be very useful if you have limited room on the flight to take wine back, thus allowing you to buy at least a bottle at each tasting, without ending up with too many to take back. We’ve stayed self-catering in Treiso, Monforte, Serralunga and Santa Vittoria d’Alba, plus a B&B in Corneliano d’Alba, so can give feedback on those if thinking about staying in any of those villages. Ditto restaurant recommendations once you’ve settled your plans.
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Any favourite or “I’d love to go there” wineries? Some of the really grand names are difficult to get an appointment at, but the vast majority are willing and genuinely hospitable. Indeed I can only think of a single genuinely disappointing visit, though in truth I’d expected it from a grand old name resting on their historic name.
Once you’ve started to develop a few names (perhaps start by getting each member of the trip to start by naming a single winery), try to pick other wineries in the same area. Not only is it interesting to compare wines often made from a similar vineyard selection, it’s also practical. Indeed if you put your mind to it, you can schedule visits so there is no driving between arrival and departure of the village, giving the driver the chance to taste freely and maybe even have a small glass of wine with lunch. I tend to make use of google maps to ‘zoom out’ from a winery to see what is nearby. As discussed on other such threads, it can be very rewarding to slot in a lesser known winery to compare/contrast with a bigger or better known winery.
I hope this helps, but happy to cover specifics as you start to close in on your preferred location(s)
regards
Ian