We will be delaying our 40th anniversary celebratory trip from July to late October, hoping that indeed ‘patience makes the heart grow fonder’. Heading back to Italy after a 7 year break.
Over the years we have enjoyed the big 3 (Rome/Florence/Venice) as well as Lake Como, Verona, Cortona, Siena, Portofino and Elba. I’m drawn to Puglia but can do that another time. I think my wine-loving husband would more enjoy Bologna, Lucca and/or Monforte/The Langhe (would like to only unpack twice over the 8 days). We’ll fly roundtrip to Milan from Newark and may try out La Compagnie (unless anyone wants to share warnings).
Open to and grateful for any and all suggestions, keeping these general areas in mind. We like to settle and enjoy places rather than constantly move. We would probably only spend a few hours in Milan and then head to Bologna on arrival. Thanks!
Milano Malpensa presumably (rather than Linate or Bergamo).
For 8 days, I’d be looking at a maximum of 2 bases, and IMO all three good options. Bologna superb for food, and a city not in thrall to tourism. Lucca a charming walled city that should feel welcoming on return from exploring, or to explore itself. Langhe superb for food, wine and walking, plus you’ll be hitting white truffle season (alba the focal point). Note there are other truffle festivals, including a lovely little one in Pianoro (a large village south of Bologna), where I think we may have been the only non-Italians there.
Maribeth, I didn’t see Barolo mentioned. You can’t beat it for food and wine, the hill towns and countryside are lovely, there are wineries to visit. Seems like an ideal place for at least half your trip.
Monforte and Le Langhe were mentioned 
Well, yeah, but not Barolo 
Anyway, Langhe would be high on my list 
If you’re flying NY to Milan you also have the emirates option from jfk which could be good if you’re considering using points.
Re: at most a couple of hours in Milano. It might be best to make it simply a transport hub, unless there is something really easy and simple (and worthwhile) next to the central train station. It’s never fun with luggage in tow.
Oddly we did this once in Bologna, stopping briefly to hit the wonderful food shops between Piazza Nettuno and le due torri, setting us up for our eventual arrival point (Trento IIRC) with some nice food, plus a little something for the train journey. It also allowed us to pre-book train tickets with some leeway built into schedules (i.e. the transfer via shuttle bus from the airport into the city and boarding the freccia train.
Let’s also talk car. A hire car would be something of an overhead in Bologna itself, but maybe for somewhere like Reggio nell’Emilia could really be useful for visits to Parmesan & balsamic vinegar producers. Driving in and around Bologna itself seemed lairy, even by Italian standards. A car almost obligatory for le Langhe, but also very useful if carrying purchased bottles home (so much easier to drive straight to the airport).
If instead choosing Lucca to pair with Monforte, a car useless for Lucca itself, but does allow you to explore some interesting places nearby.
I try to avoid the un-fun congestion and distance to JFK from our home, but definitely will check this option out. Appreciate learning of it. I’m intrigued by La Compagnie as it is only business class, departs EWR only to Milan, Paris and Nice and I have heard good things from a few who have used it.
I’ve flown it, it’s fine but not emirates business or first.
I’d love to see the Duomo and Terraces, but it’s not a deal breaker on this trip. I found a great service I’ve used in France twice: www.nannybag.com. You drop your bag at a business that contracts with them and has secure storage…and then can be hands-free for bopping around for a few hours before heading to the train or airport. Great concept! Very helpful info re: car situation. Renting a car in Lucca and using it to go to la Langhe, with a drop at Malpensa may be the ticket. Appreciate the info.
I am on it. And would never have known they even flew to Milan. THANKS.
Yea they also fly from Newark to Athens
The past two years I’ve traveled to France the last week of October into first week of November. I hate heat and crowds, so I loved the weather we had. Was thinking of the same time period for this itinerary. Do you think that is good timing or should we move it up a couple of weeks for more dependable weather?
This is when we generally travel as well. Generally cooler, you might get some wet weather but we have always been pretty lucky. Exactly your reasons we travel then. Here is a post from a trip in 2017:
It’s our favourite month to visit Italy. Weather often warm, but rarely hot, allowing for relaxing exploration. It seems to hit less rain than May as well. Typically for that sort of time period, we’ve tended to hit just one day with enough rain to affect plans (e.g. head into the city rather than go walking).
The tail end of the mushroom season, start of truffle season, plus still decent fruit/veg and also stalls in the cities roasting chestnuts.
That said, we did see a sharp shift in temperature once from last week in Oct to 1st week in Nov (ironically traveling from Ferrara down to Puglia), so that’s a possibility to think about. Mid october might be worth considering.