Advanced planning reservations

I think you can book airlines 330 days out which is ten months. I have booked many Rick Steves recommended hotels less than four weeks out and even a couple just the week before when plans have changed. A lot depends on the time of year for travel. Have no experience with traveling in late June, July, August, or early September. But we have never encourage a problem with getting reservations when we need them. We do our initial planning about six months out. Generally pin down airline tickets especially when using FF, and then fill in the blanks as we go. Also think it is personal preference as to what you are comfortable with concerning pre-planning. There are some on this site who cannot move an inch unless it has been recorded on their face book page and in their computer for months in advance. Others are more flexible. We tend to lock in the first couple of days/nights and the last couple of days/nights and the in between is hit and miss depending on when and where we are going. Have yet to spend a night sleeping in the train station but we were close a couple of times.

It depends on what kind of a trip it is. I find that in recent years, my trips have become increasingly "tightly scripted" - going to places that are fairly popular, for a relatively short trip (2-3 weeks), where I am trying to cover a lot of ground (sound familiar to anyone?). For those trips that fit that profile, I have found that the more planning I do up front - and the more exactly I have committed to each item - the more it makes me feel like I have the freedom to enjoy the trip. Yes, I recognize there's a contradiction in there: committing to the details months in advance certainly locks you in, in terms of the big picture (we will be in City X on Day 3-4, then we will be in City Y on Days 5-7...). You can't switch to City Z in between if you decide at the last minute. But what you gain is the ability to travel trouble-free and to make the best use of your limited time, without having to waste time chasing a room to sleep in or figuring out how to get from point A to B. My last trip was tightly scheduled and booked in great detail months in advance, it went smooth as silk and was great - but I know that's not for everyone. BTW, your premise is incorrect: you certainly can book airline flights much further out than 3 months. For most airlines, it's actually almost a year (330 days for most). Of course, if you book a flight many months ahead you can expect a schedule change at some point; that's often (but not always) a minor change, shifting flight times by a few minutes (typical profile of major airlines), but occasionally a flight may be shifted significantly or (very rarely) canceled entirely. In any case, if you have a ticket the airline needs to accommodate you (as long as they haven't gone out of business). I routinely book flights 10-11 months ahead, and rooms 4-6 months in advance.

To follow-up on David's observation about scheduling plane itineraries way in advance and flight changes, I have to say that more recently I have noted a great frequency in flight changes, even on tickets I only booked a couple of months in advance. It seems the airlines are trying to ensure that each flight is full as possible, so if they have to cancel one flight and distribute the passengers to others, they will. I have had changes by just a few minutes, changes that involved longer stopovers, and changes that involved them adding another stopover to an already-2-stopover trip. I have had the same itinerary changed approximately every two weeks by a particular airline over a two month period; it got to the point that I started anticipating the next email from them announcing changes. It really is getting a bit out of control. So, David's point is very important, and prepare yourself mentally for the possibility that that perfect flight itinerary you found might end up differently.

For people who plan everything down to the less minute they always justifies their approach by saying, "without having to waste time chasing a room to sleep in or figuring out how to get from point A to B." As if the person who isn't planning to last minutes wastes a lot of time. That is not our experience. At the most we waste 10 to 15 every day or so calling ahead for a reservation or spending a few minutes on the phone after we arrive in the city. And the fall back is to hit the TI in the station for recommended rooms - often they will make the call for you. So just because you have planned to the last minute, doesn't you cannot have a smooth trip. But you do loose some of the discounts available for early train books. For us, it is the price we pay for flexibility and not having to met or keep a rigid schedule every day.

This is probably one of the most discussed issues on Helpline. At the end of the day, I personally think that even if you can find some accommodation at the last moment, it is very unlikely it would be the best I could find for that price on that date OR the cheapest for that quality than if I had booked in advance. And I've never booked hotels in recent (last 4 or 5) years by any means except online. I will never trust a TI office to book me a room more than my ability to check TripAdvisor or Booking or what else.

I book my hotel rooms online between 4-6 months out and have never had a problem getting in the places I want. This is for travel in May or September, my two preferred months. I usually get the airline tickets 3-4 months out, so I might have rooms reserved before I have a flight reserved. Every hotel I have ever reserved had a cancellation policy where if I cancelled a week or two ahead of the scheduled arrival there was no charge, so it hasn't been a problem.

I usually have ceased adding to this discussion, believing that personal preference is what it is. Mine is to book a few rooms here and there in more popular and larger cities, leaving some flex in between for changes (intended or un-intended) as we go. My experience with getting rooms on the road is that it takes me no longer to get to my room, many times less, than if I had booked ahead, and the quality and price is the same as if I would have booked ahead. The exception to price is using a discount booking site on-line, but I have done that the day before as well. If you prefer to have all arrangements made well ahead, then great. I do however have issue with those that book well ahead, or multiple places, with the full intent of cancelling rooms as plans firm up. Only my opinion, but I think it rude and inconsiderate, especially to smaller hotels and travellers that may be missing out because all rooms are "booked". I don't know what RS hotels are booked full 8 months out, but from observing patterns on the board, it would seem that a number of those reservations are phantom ones destined to cancel as the date approaches.

The old Frommer's advice to look for a hotel near the train station often works. I think the best places to do this would be Nice (I've crossed the street there and found a decent hotel twice), some stations in London, Gare du Nord in Paris, La Spezia south of the CT (I've done this a few times). The area near Termini station in Rome is full of budget hotels (I found hotels here last-minute in under half an hour) I prefer to have a little "wiggle-room" in my travel schedule, so sometimes I go looking after arriving in a new town.