@markr867: just stumbled upon your post...
We travel a lot, always by ourselves (no tours of any kind) and often spend 4 or more weeks in one country. We always book ahead way in advance, in particular flights as we tend to use miles for most of them. The beauty of booking ahead so far in advance is that you can find places to stay that are hidden away or just really special, most of them fully booked if you would travel on short notice.
I also do a lot of research on how to get from A to B, how much it might cost and occassionally I get in touch with local travel agents who sometimes make getting around so much cheaper than the official tourist rate available online or at hotels (in particular in some Asian countries like Cambodia or Myanmar).
Sure, planning is time consuming but it is also fun. It takes away so much stress once you get there, so you can focus on the important things such as mingling with locals and exploring the country in a not so touristy way. We also realized that in many cases prices are negotiable and the more you know about the region in advance the less likely it is that locals take advantage of you.
We started traveling before the availability of the internet, relied on books at that time and did not book ahead more than the flight and the first few nights. During that time we had many very time consuming instances, where we had to find accommodations for the night and ended up in a questionable place. Sometimes you had to be in town latest at 4 pm, the time when the run on accommodations started already. And of course, we missed many beautiful spots along the way, simply because they were not covered by the "Lonely Planets" of the world. Now, traveling got so much easier but unfortunately much more crowded...
Enjoy Portugal, you will love it. Just rent a car once you want to travel outside Lisbon, makes traveling a lot easier and driving around is very easy and uneventful in Portugal. I posted a couple of stories about Portugal you might want to check out, maybe there are some places you like as well. Still not finished with all the postings but holding back as long as Barclays has this issue about crediting miles to our accounts.
It really depends on what kind of deal I can get. I have booked trips a couple of weeks out or a year in advance.
Great question and I enjoyed reading everyone's answers! I have a weird way of planning travel.
First I see if my time share has any cool resorts available on a date that would work for the whole family using either their getaway deals or using my alloted time (that's why I love the Barclay card - I'm hoping I can pay my maintenance fees with it) Once I find one, I'll book it. I only book these resorts in under 1 year though. Once that's done (after having looked at flights) I'll wait to book a flight from 60 - 120 days before take off and keep my eye out on price changes. Seems to be cheaper (60-120 days) than when you get closer to the date, because there's less seats available and the price sometimes goes up as the date gets closer. And by that time I'll have already figured out the best places to see and go.
If I can't find anything through my time share, I'll look on travel sites for deals. If I find a good one that works with our schedule, I'll book it and wait the 60 - 120 days to book airline tickets. I always wait to book hotels (if it didn't come in the package) until AFTER I have my flight booked. No sense in reserving a room if I'm not going to be there that day or week (no flights I can afford).
And for short road trips, those are just a fly by the seat of my pants - I pay whatever or use points, but look for the cheapest options because sometimes it makes more sense to book a less expensive hotel than paying 30,000 points for 1 night when I need 3 nights to total 90,000 points which I didn't have at that time.
I love this travel site! I'm learning so much about new places to explore around the world!
I usually plan my trips 3-4 months before! It gives me plenty of time to get an itinerary going. I have an upcoming trip to Central Asia in a week and I planned that one 2 months before and I thought that was "last minute" for me. LOL. However I got pretty lucky for waiting a little bit since the flight price went down about $400.
So sometimes it does depends on how good the flight deal is :)
I’m a firm believer of booking as far in advance as possible, especially if it is a cruise. That way you get to select the prime location of your stateroom. I continually monitor the price of the cruise and if the price goes down I call the cruise company (in our case we sail on Royal Caribbean) and they always give me the lower price. As for airfare I start looking for airfare deals as soon as the schedule opens for the dates of my travel. I’ve been pretty lucky so far. Some of our fares have gone up considerably and a couple have gone down minutely. The amount they went down was worth it because I got to select our seats with a wide open airplane. Hotels I almost never book with no refundable rates. I’ll make my reservation and monitor the price. If it goes down I’ll rebook for the same nights and cancel the previous reservation. I’ve used this same practice for rental cars as well. I’ve saved quite a bit of $$$$$$ doing this.