I am about to book my first big trip and curios what I need to look out for before I do. Any advice/recommendations for how you plan your itinerary once flights/hotels are confirmed?

Thanks!!

Read read read. Guidebooks, wikitravel, travelblogs, flyertalk, tripadvisor, etc etc. talk to others who have gone where you're going before you (provided you're not on the Enterprise). Pick out the parts that interest you and dump the rest. Plan your itinerary then drop 50% and budget 50% more.

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Got it, thanks! For someone that doesn't have too much free time, how can I plan an itinerary relatively quickly? This sounds like a lot of research - do you find your trips take up a lot of time to research?

I never plan too much - I'll usually book say a three week trip and then just wander. For example, I booked a trip DXB-EBB and wandered all over Uganda and Rwanda and spent an afternoon in Goma, DRC. All very unplanned. That has worked best for me.

Know yourself and go from there. Are you the kind of person who will be comfortable wandering on your first big trip? Or do you prefer to have things planned to a t? Maybe meet halfway and pick one or two "must dos" in each city and leave the rest up in the air. If you can plan around your personal comfort zone, you'll have a great trip.

If you don't have time for TONS of reading, pick one or two options. I'd get at least one guidebook to bring with (read on the plane or at night) and pick the highlights that appeal the most to you.

Where are you headed? I've always found the Destinations forum here very helpful!

Depending on destination, check out the tours offered by the big bus tour companies (cosmos, contiki, etc) or private operators. They usually hit the big sights in a reasonably sensible order and can give you some guidance. Just remember they make lots of quick stops that are planned and timed by the hour that you probably can't replicate exactly on your own, not should you want to if you want to really see and experience a place. Most guidebooks (lonely planet, rough guides, frommers, etc) will have a couple rough itineraries laid out as well. It depends on lots of things - rental car vs train vs bus, expensive vs budget, resorts vs hostels, cities vs countryside, food vs museums....

I find the planning almost as enjoyable as the travel itself. I've got enough rough ideas for trips planned to last me 20 years, now to find the time to take them. It will depend on your comfort and experience. I usually read a ton and have lots of options ready but actually plan little and take it as it comes and leave it flexible. You can get a lot of info from your fellow travellers on the ground that have just spent a month in your next stop.

You can also post a few details here or in the appropriate destination forum and get some ideas. Easier to help when your age, interests, destinations, budget, likes, dislikes are made known

Good advice on both counts. Although I really don't like trip advisor, I sometimes look at the forums.. I look at a place I know and like, and use that to try to find a profile like me. Look at timeout, or frommers or Fodors and check for what days key attractions might be closed But the cardinal rule of travel is that no one's experience will be the same. You come with a set of baggage literally and figuratively that is unique so don't worry about what someone else says you must do. I've been planning for 30 years for family, and everyone wants something different. I don't like art museums but never missed a battlefield or cemetery, and made sure Ho Chi Minh mausoleum was open on the day we were in Ha noI. . Read not just guidebooks but literature from the country, watch a film about it, or get music .. learn a few phrases in the native language.. Decide whether you are a vacationer vs traveler. The former is easier to plan, the latter is a commitment to see the world. It does not need to take a long time, you will change your mind once you are there but a little preparation goes a long way.

For places I've never been, I always check out the situation with transport from the airport/train station/cruise terminal as well as look up a few of the major streets to pretend as if I've been there (should taxi drivers/touts question me).

Look for travel sites dedicated to the region you're going to. The two I always consult when applicable are Japan Guide (for Japan, obviously) and Travelfish for Southeast Asia.

Perfect. Myself, I like to land at a place and have very little expectation. The first day I wander far enough from my hotel where I don't get lost and can get a feel for what the streets and people are like. After that it is wander, wander, wander. I used to go on bicycle tours alone and all I needed to do was to see a road that looked "intriguing" and if I thought "I wonder what is there" I went to find out.

My parents on the other hand, want organized tours planned to the millisecond. They want to know where they're going to be, what they are going to be doing and have someone escorting them.

To each his own.

This is all great advice, thanks thus far! I understand travel experiences won't be the same for everyone, but aren't there usually "must-do's" in each country that you shouldn't miss? Personally, I am trying to book Thailand and Cambodia (cities are TBD) and just want a site/guide that tells me what not to miss. Any experts out there have any thoughts and/or suggestions?

curiostraveler, welcome to FlyerTalk! This site has a dedicated forum on Thailand and the Asia forum may help you with Cambodia.

http://www.travelfish.org/trip_plann...ns-and-islands

http://www.travelfish.org/trip_plann...-one-week-trip

I have a good friend that I travel with and once we determine a destination or general area, we create a Google Sheet and start filling it with ideas/things to do that we found on the internet. I also fill out the sheet with a bunch of flight and hotel options using miles/points (I probably do too much, but I get really excited so I like to see what all is available). The Google Sheet is great for sharing with your travel companions and then you have 1 go to place for all the things you found interesting on the internet and all the planning. The flight options that I record are also great since we are using miles and sometimes flights on certain airlines/routes/cabins can be hard to get, so it helps to know all the options and with piecing together the itinerary.

As for what to do once you get there, I prefer a mix of guided tours/activities and wandering on my own. I like to try to do a guided tour/activity early on in the trip because it helps to get an understanding of the area, I can see places that I might want to visit after the tour, and I like to talk with the guide and other participants about the culture, area, and to try and get some local suggestions.