Planning Horizon

You're doing fine, I'd say - and way ahead of a lot of folks. I book in the exact order you have mentioned. No planning calendar, I guess, except in my head.

I follow mostly the same pattern, overseas flights first. I should check ransportation connections before booking hotels, but I usually book the hotels (always with free cancellation option), and then figure out how to get from place to place. Then train reservations if needed, then tickets for sights that require/recommend reserved entry. I try to schedule those sights for the day after arrival in a city, or even later, in case of a transportation delay or a strike.

I am almost obsessive about planning - except for daily sightseeing schedule. I haven't counted days to go, but it sounds like I'm leaving just days after you (Sept 8). You look to be right on schedule and ahead of me.

The only thing you haven't mentioned is packing. I don't start packing nearly as early as I used to, but I have a packing list well in advance. I'll start packing about 2 weeks ahead so if there are things I need to prepare or buy, I'm not under any pressure.

BTW do you have an international driving permit (for each driver) for your rental car, GPS and do you know if where the ZTL's are?

Both drivers have IDP's set up.
We have never rented a car in Europe before but wanted to explore the Langhe, Monferrato, and Roero wine regions, as well as Valle D'Aosta, none of which is well served by public transit and selected bits are serviced by guides at exorbitant prices.

Ive read up on ZTL's as it seems a particular point of concern on the Italy board and on the TripAdvisor board. We pick up in Turin outside the ZTL and go to an agriturismo for five days where the largest towns we'll hit will be Alba, Asti and Cuneo. They have small ZTLs. I'll research towns as I figure it out.

In planning, I have a stage of excitement, a stage of anxiety, a stage of boredom or disgust, and then we take the trip.

I plan far in advance.

We like to do a cruise in conjunction with a lengthy land trip. We are retired and can take all the time we want.

First, we decide on a cruise. We have done most of the cruises (15 on NCL and Celebrity) that were on our bucket list, as well as land tours combined with river cruises (4, three on Vantage and one on AMA).

Second, booking the cruise a year and a half out, we get to pick our cabin. Nest, I plan the land trip. The hardest part is picking where to go, since options are many. We have been to 70 countries, and lived overseas for several years, but there are still places on our bucket list.

Third, once we pick the places we plan to visit. after having done some research on things to do there, picking a hotel or B2B is next. Usually do this several months out, but not a year out. After picking a hotel, if there are tours to book that is usually done 4-6 months out. Also, if a car rental is involved, that is booked.

Fourth, air is usually booked 9-11 months out. If using miles, i have found that it is better to book with miles early.

Restaurants, we rarely book in advance.

If you are 38 days from departure, you are a late planning from my perspective, however, your plans are rather limited in scope. When planning such a trip, you must choose rail or car rental.
In Italy, I prefer rail to car rental, but not sure how well your rail connections will work. If rail is your choice, I suggest research your trip and book inadvance, unless you plan to take local short haul trains. If car rental, plan your route and try to plan were you will park, sleep, tour, etc.

You're fine. In fact, you'd be fine if you had your airline ticket, passport and a credit card. You can generally find somewhere to stay, book at tour and get a seat on a train (but you won't get a discounted ticket) at the last minute.

I start building a plan maybe four to six months out and start searching for options right away. Generally I'll have developed a pretty solid idea of the itinerary (where, what, when) before I book the first thing.

The first domino to fall is the airline ticket, usually six to eight weeks before the trip (sometimes more if I see a great price). Up to that point, everything is geared toward research. I'll spend time looking for cars, trains, lodging, sights (hours/closures), festivals, etc. without booking anything. I'll keep exploring different days, hours, take off and landing airports right up until I book the flights.

Once I've booked the flights, I book lodging for my first and last stop. The flight locks in the ends of my trip, so there's no use worrying about being flexible. If you have a prebooked train trip, same thing, both ends are locked in so it makes sense to book lodging now. Some trips I'll stay very flexible, some trips I'll lock in quite a bit ahead of time - it depends on the trip.

I try to arrange my trip to limit the use of a rental car. I'll start by spending days in a city without one, train to the next place, then rent a car. I do the reverse at the end of my trip, drop the car at the stop before my last city, train in to the city then fly out.

As for packing. I don't pack more than a few days in advance but I've developed and refined my pack list over the years - so it goes pretty quickly. I let the packed bags sit for a couple days, in case I think of anything to change or add.

Right on so far. Once I have air, transfers, lodging set, I do spend some time checking days and hours of sights and tours so I can fit them into the puzzle of the days. I like to know late hours, for example, on popular museums so I can plan for us to go in the evening. So my plan for a particular city or town is fairly detailed although it often shifts on implementation based on weather, energy, what else strikes our fancy.

I also do some homework on local transportation, i.e., if we are doing a day trip, I identify possible trains and buses before we leave the U.S. so I have an idea of what we need to do and I like to have a list of restaurants that might interest us, especially when we are returning to a place we know well but want to try new venues.

I think I'm good on transfers... here's the plan.
Arrive in Venice, boat ride to about 5 minute walk to B&B is booked.
We may do a day trip to Ferrara, which is done in 1:27 via a Regionale Velocce train, which apparently won't sell out, happens most hours, and is flat priced
We do a rolling day trip through Padua, which is a quick trip on a Regionale, that happens all the time, won't sell out, and flat priced. We'll check bags at the station, do Padua until our single Freccia train to Turin, which is already reserved (for several weeks).
We depart Turin via rental car (reserved and paid for), to the AT, then to Cogne, then to Milan, where we turn it in.
We will check bags at Milano Centrale, and get the train out to Malpensa later in the day (Car due by 12, flight at 22+).

I think what's wigging me a bit is having 5 days in the Langhe area, with not much in terms of specific plans yet.

I have a tour of San Marco after Darko (what I'd call it), and now have booked most of what we want to do on Mont Blanc.

Thanks for the support. I think I'm over the anxiety and getting excited again... now just have to get through 37 days.

More or less I have a plan and calendar for making réservations. If I am going to be in Berlin by June, the latest I reserve at the Pension by making a personal phone call is mid-March. Usually I do this in Jan or Feb, same as in Vienna. I don't reserve restaurants. Those train routes where I am using a 92 day out discount on-line ticket, I get by the 91st day or so. Likewise with Eurostar, book immediately once the plan starts to take shape. No rental car or apt rental...those are not options.

With 38 days prior to dep, I would have 98% everything reserved that need to be done already...small hôtels, Pensionen, rail discount tickets, etc

I feel like I am more likely to be boxed in by flight commitments than anything else, so I tend to hold off on buying air until my itinerary is pretty firm.

I don't just mean "I want to see Italy, so I'll fly into Rome and not Olso" type plans, but "The stuff I want to see in Lyon is closed on Mondays, which means if I want to spend 5 nights in Paris first I do not want to arrive in Paris on Tuesday or Wednesday" sort of thing.

It is a kind of chicken-egg problem sometimes, but having a tentative plan helps to avoid some unexpected consequences.

If you have special restaurants that you want to eat at, particularly over a weekend and/or a Sunday afternoon, you may want to make those reservations several weeks out. (You can ask the owner of your hotel / B&B to make them for you.)

For the Barolo part of your visit, you can continue to leave your schedule open, but you could also have a list of places you could visit, or towns that look especially scenic.

Thanks, Lexa.

That's about what I'm down to. I think I'm trading a Langhe/Roero/Monferrato day into another Turin day, as wife has found much of interest there. So, four nights to figure out.

I'm excited to read that somebody is going to Turin/Torino. We really enjoyed our brief time there in 2015.

Since you want to explore wine regions, you should make sure that you are clear about driving and drinking. In parts of Europe, the levels of blood alcohol are lower than in the US. I have no idea what it is like in Italy, but you need to know.

Another thing I do about this time before a trip is to prepare a "before-I-leave" to-do checklist. It helps to reduce stress before departure - and also possible en route stress "did I remember to . . . " or "oops, I forgot to . . ."

Paul: I am a sip and spit taster. Italy has a fairly tight BAC limit and apparently enforces it pretty tightly.