Is it still too bloody hard to plan and book a holiday yourself economically and intelligently? Whether it be choosing where you want to go or Booking flights and hotels, it takes time effort and usually some level of frustration.

The idea of this post is to open your eyes to the range of innovative Travel sites out there that can help you book trips online. It will also outline some opportunities in the online travel space. Since there is alot of information below, click the following links to skip to any of the sections below:

• 9 Cool Travel Sites You Didn’t Know About
• The Cheapest Ways to Find and Book Flights
  
• The Cheapest Way to Find and Book Hotels and Hostels
  
• Deciding Where To Go on Your Holiday And What To Do

Having spent countless hours of online research for my own trips, I’ve been able to cruise through 30 countries with perhaps far more insight than I would have had 20 years ago. I’ve also learned plenty of lessons along the way. But, the key difference between now and 20 years ago is that the onus of effort now mostly fell on me rather than a travel agent.

Thinking over my trips, I have compared booking sites for best prices and quality, scanned different flight maps and routes for the best ways to arrange my trips, asked friends and travel agents for advice, and scanned through and filtered hundreds of user reviews on a range of different sites. Compound this with many of my friends doing almost exactly the same work and you have a generation of Aussie dollar fueled travel agents in the making.

The range of options below vary in terms of effort and payoff. I’ve tried to give my assessment of how useful they by outlining how often I use them when planning and booking trips overseas.

9 Cool Travel Sites You Didn’t Know About

Room 77 – A particularly smart tool I have used to discover hotel rooms in different cities around the world. I prefer the number of choices it gives you in how you filter the results and like that it integrates reviews into the search results. I also like that it lets you see the search results of a hotel search on a map easily. Here is an example of a Room 77 search of hotels in Tallinn Estonia in map view.

Mygola – This tool is like a crowdsourced trip planning service that allows you to request personalised trip planning from their range of trip planners. Usefully, it also allows you to search the range of other people’s completed trip planning requests. From what I have seen, the site seems useful though you have to have confidence in their planners to rely on the site completely. Here is an example – Things to do in Instanbul. I also quite like their payment model (free for some level of service or $30 a trip / $99 a year for quick personal service).

Airbnb / Wimdu / VRBO – These sites are cool. They allow you to avoid hotels and book people’s apartments directly from them in other cities. Have used Airbnb which has the best service and safety in St Petersburg, Medellin, Hong Kong and Stockholm.

Adioso Flight Bookings –  Whilst this site is still in beta, I like what they’re trying to do. They give a range of far more useful flight search options than the standard painful dropdown menu seen on most flight booking engines in the world. Say you know you want to go away this weekend from Sydney but dont know where. Or say you don’t even know when but you know you want to get away soon. A search like this on Adioso could help you outlining a range of the cheapest flights out of  Sydney over the coming months.  It also lets you create flight alerts for places you want to go to be sent to you by email.

Gogobot - This is a social travel guide and planning website. It lets you see how your friends travel, what they recommend and what people you don’t know recommend. I have not used it extensively yet and it could fall prey to the problem of too much information if not done well but it does have some cool features.

Expert Flyer – Probably not on the same level of usefulness for me as those above but this site helps you to ensure you get better seats on the flight bookings that you make by using alerts. Quite useful for very frequent flyers i imagine.

The Cheapest Ways to Find and Book Flights

There are so many flight bookings options out there. Many of them I find add a % to the cheapest airfare you can get at any particular time. As a result, I use a combination of the following to find and then get the best price on flights and often ending up booking directly through the airline or a travel agent after finding the best deals available.

Additionally, don’t buy airline tickets earlier than about 4 months before departure unless it is peak season when you are leaving (in which case do). Airfare prices can rise dramatically within 14 days of departure so if you are going to leave it late, you are likely to pay more. Sign up for general sale alerts on Bestflights below, your favourite airlines and any other good booking sites mentioned here. These can save you alot of money.

Skyscanner – I have used this site for years. Again, whilst it doesn’t cover all routes around the world on all airlines (something I believe these sites need to do), it is very useful in terms of discovering which flight paths are quickest and cheapest to get you where you want to go. In particular, I like their visual flight map where you can see all the flight options out of a city and at what cost they come (say, you’re in Oslo and don’t know where you want to go next). They also let you see a whole month worth of flight options leaving a particular city. E.g. here is a list of flights out of Istanbul in August this year.

Jetabroad - This is my favourite service online for discovering multi-city flight bookings. They are also usually the cheapest or close to it. Can highly recommend this service. When thinking about opportunities in this space, one reason I sometimes still book with the airline or a travel agent after using Jetabroad even thought the prices are similar is the former options allow me to hold a fare before paying.

Bestflights – This company has a very time intensive though useful way of aiding in the flight booking process. They list all the sale fares of each of the different airlines. Choose your region. Choose your range of sales fares (usually >20) and enjoy reading through the deals (e.g. European sale fares). The process is painful though I do tend to use it each time I book flights. I have actually also tried to book through them to reward them but found their booking process tedious because they require you to put down a deposit before getting the full details of the fare when actually booking it. I also didn’t find their sales staff as nice as my regular travel agent. As a result, I use their information and book elsewhere (again something to consider for opportunities in this space).

Kayak - Good for multicity flights but not great. It seems mildly cheaper and more useful when booking hotels and flights in and around Europe.

Hipmunk - Very funky flight booking engine. Like Adioso, tries to give a range of more flexible search options. I still think the process they use is far from solved though as I can often find far cheaper flights either booking direct through the airline or on other sites like jetabroad, bestflights, kayak or my travel agent. As a result, I end up using Hipmunk as a discovery method in some cases (a risk of creating a useful tool in this space).

Adioso Flight Bookings –  Whilst this site is still in beta, I like what they’re trying to do. They give a range of far more useful flight search options than the standard painful dropdown menu seen on most flight booking engines in the world. Say you know you want to go away this weekend from Sydney but dont know where. Or say you don’t even know when but you know you want to get away soon. A search like this on Adioso could help you outlining a range of the cheapest flights out of  Sydney over the coming months.  It also lets you create flight alerts for places you want to go to be sent to you by email.

Matrix.itasoftware.com – A very helpful tool for seeing a range of international flight booking options. Suggested by someone in the comments below.

Flight Fox – A site that lets you create itineraries for users of the site to match with airline fares while competing for a set prize.

Travel agents and Airlines Direct – I still often use a travel agent to finalise my bookings. I usually don’t waste too much of their time and they are quite happy to organise fares for me for particular prices if i go to them with the details after using the methods above. I also always check the price directly on the airline websites.

Finally, if you are after the absolute cheapest fares, you can also use Skyscanner.ru or Trip.ru which always seems to have very cheap fares. You’ll need to speak Russian to be able to book on these sites.

The Cheapest Way to Find and Book Hotels and Hostels

booking.com / orbitz / kayak.com / room 77- These sites are where you’ll discover the hotels you want to stay in and make bookings online. My preference for search is Room 77. My preference for booking is Booking.com and Kayak as they are often the cheapest. Search around and compare to find your best deals. You also usually get good cancellation options booking in advance with these sites and they don’t charge your credit card until you check out of the hotel.

Tripadvisor – I pretty much never book a hotel anymore without checking tripadvisor. It is a little painful sometimes and not always trustworthy but it is a good resource if you can be bothered putting in the time to sift through the reviews. Sometimes I find the place I like on Tripadvisor before even searching the hotel booking sites above. Again, room 77 helps here as it integrates both.

airbnb / wimdu / VRBO – These sites are cool. They allow you to avoid hotels and book people’s apartments directly from them in other cities. Personally, I use Airbnb which has the best service and safety. I’ve used it in St Petersburg, Medellin, Hong Kong and Stockholm.

Priceline / Hotwire / lastminute – Whilst I am sure there is a way to use these sites effectively, I have never really been a fan of not knowing the place i’m staying before I pay. You used to be able to reverse engineer the secret hotels but this seemed harder the last time i tried.

Couchsurfing – Have done this plenty of times over the years and met some great people. I’ve never stayed on someone’s couch overseas but have had plenty of people stay at my place in Sydney. Good for meeting people overseas.

Other options for hotels include those daily deal type sites but I have not used them myself.

Deciding Where To Go on Your Holiday And What To Do

I use a combination of the research above, friends’ tips, tripadvisor, and email alerts to decide where and when to go. Again, I believe there is an opportunity here to help people make these calls more strategically.

In terms of what to do when you are on your holiday, there are a range of social travel startups popping up that can help you organise your time, plan your activities even meet people when you are there.  I also use Tripadvisor and lonely planet forums to find fun things to do in the places I visit. There is also a lot of value in just seeing what happens when you are in a new city so make sure you don’t overplan.

Vayable - A way to directly hire local guides for activities overseas.

Gogobot - This site is a social travel guide and planning website. It lets you see how your friends travel, what they recommend and what others also recommend. I have not used it extensively yet and it could fall prey to the problem of too much information if not done well but it does have some cool features.

Pinterest – I have been storing places I’d like to go on a board on pinterest. It also is a useful way for discovering places to go by searching.

Tripbod - Meant to be original travel experiences from locals overseas. similar to Vayable.

Wannaout – Unlaunched but could be cool.

Wanderfly – Similar to Gogobot and Mygola. Personalized travel recommendations.

Triptrotting - Similar to an idea a friend of mine Alex had a few years back. Meet locals overseas. His site is Meet Travelers though is still growing at this stage.

Evature - meet to be able to allow free-text search for online travel. Would be cool if they can get it working.

Citybot -  A way to get city guides on your iphone / android overseas. Still unlaunched.

Couchsurfing – Good for meeting people overseas.

This is the first of a series of blogs on the topic of travel. If you feel I’ve missed out on some useful options, please let me know or comment below as I’d like to improve this list over time. Please subscribe above if you’d like to hear more tips in the future.