It depends on what I’m doing

If I’m going somewhere out of easy driving distance and hoping maybe some friends will come along, I’ll start floating the idea about a year out, start making more solid plans about 6 months out. Give people time to get passports, save up for plane tickets, etc.

If it’s an overnight to a long weekend with just me and my wife, maybe a couple weeks, we could probably do day-of sometimes but we gotta make sure someone can watch our dog.

I’m terrible at this. My wife is the keeper of the calendar. Idk what the fuck is going on two weeks out and I never do.

My wife and I usually plan big vacations about a year in advance so that we can follow flight prices and whatnot to get a good deal. We also book a few days at a cabin for our anniversary every year, so we just book the next year’s reservation while we’re there, since reservations can fill up even several months in advance.

Only planning a week in advance seems stressful to me - we planned a last-minute (for us) road trip vacation earlier this month for the long 4th of July weekend, and it was tough to find cheap places to stay that weren’t super grungy.

If I’m taking time off work and it’s more than 1 or 2 days in a row, then a minimum of 1 month in advance is required. If I’m buying a plane ticket, then at least 2 months so I can actually afford it.

I’m very last minute in planning most things in my life

My wife and I plan 6-12 month out, and sometimes more. At least for the dates of our vacations. My wife runs a small dog boarding service out of our home, and limits the number of dogs she boards. As a result she has clients that will schedule boarding up to a year in advance. So we need to block out our vacation time early enough to prevent clients from making reservations at those times.

At some point after we block out the time we’ll figure out where we want to go.

If it’s just us, it’s pretty much based on how soon we can get PTO for those days, so 1-3 months.

But coordinating a vacation with others requires you to go WAY far out and basically harass people as you continuously remind them.

Road trip? Usually week or night of.

Airline travel within 4 hours, domestic or international is usually 2 days before hand.

Airline travel across the world is usually planned as a time block a month or two ahead of time. The actual destination and activities being planned as the dates get closer.

Exceptions are scheduled events. If I have an event to attend in a location, I’ll make a hotel reservation and book tickets for the thing. Then checkup options for travel there. Sometimes it’s part of a multileg journey.

Often I don’t know where in the world I will even be the week leading up to the thing. So I tend to either not purchase travel tickets, or buy a few different ones from hubs globally that are cheap and easy to get to.

Who the hell can afford a vacation?

Months before. By the time it comes around, the only thing we’re doing is calling the cab to the posh airport hotel (because fuck yeah) and bugging out.

Last few years we have been booking vacations when we have big race events, to put 1 and 1 together and save money. So 1 year in advance (that’s when ironmans registrations opens up).

Back when we where only traveling, usually from Feb/march for august. Go get best deals and low tickets.

We usually go to a small holiday home my dad owns for a week or two in summer - we need to book that early in the year.

Then we do maybe one or two long shorter train trips to other European cities. More often than not that’s to see a musical theatre production, so we book those when they are announced, maybe half a year in advance. Otherwise it could be just days or weeks out!

So big vacations we typically plan two to three years in advance and book as soon as the booking opens for the parts of that holiday. Usually means flights about 12 months before, accommodation usually a bit before then. Something like Disney or a sailing holiday we can book two years in advance as an entire package, which in the EU means we ATOL protected, far safer that far out than booking separate. I have terrible anxiety when booking lots of individual components like a backpacking holiday in Japan that had us staying in half a dozen hotels/apartments, hiring a couple of cars, getting internal flights, prebooking tickets to Sumo and Ghibli and so on, but its essential to get the best prices.

We are still paying for a family holiday in a cottage or villa as our kids are still starting their careers. This I book a year in advance, but we plan the locations far in advance of that and scope out where we want to stay.

As we work from home we can work from our van a fair bit. Earlier in the year we did a tour of wales over three weeks while working part time, later this year we are doing a three week tour of Cornwall/Devon/Somerset. We also get away a few long weekends around the bank holidays. As we stay at adult only sites that are very popular and will sell out quickly around the dates we want to go, these are booked as soon as booking opens for them, usually October the year before.

Booking early gets us far better pricing and we get to go where we want, stay where we want. Plus the planning and research is a big part of the enjoyment for us, its also essential if you want to make the most of a planning heavy holiday like Japan or Disney and not pay through the nose to use a quality planning service.

Without flights two or three weeks before. For roadtrips we usually only book the first hotel and then decide along the way. For air travel we book 2 or 3 months in advance and then often also do roadtrips using rental cars booking only the first and last hotel in advance.

The only short vacations I really need to plan long time in advance are multiday bike trips where I want to take a bike on a high-speed train (because there are only few places and they are booked out super early). For example for a Bike-Tour from Innsbruck to lake Garda we had to book the train 5 months in advance.

I’ve planned international travel a week before and other trips far longer. A lot of what determines planning time is logistics of all going, if there are events during that time, holiday planning, and travel demand.

It sounds like the family friend is planning a big trip, so knowing before the one year hotel window is probably necessary.