What You Need to Know to Plan your Dream Trip

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Part 1, Plan Your Dream Trip: Flights

Together we have traveled to over 50 countries. We have worked in quite a few, spent what would cumulatively amount to years traveling and somewhere along the way learned a few things that will probably be helpful to help you plan your dream trip.

This is the first in a series designed to help you plan your own dream trip to wherever that may be. It also is the official public announcement of the addition of Trip Planning Resources on Compass & Fork. As we travel and plan a trip we have a handful of sites we have used over and over again and have come to trust. We have put those all in one place for you to find and use as well directly from our site. It is the same functionality as going to the main site, but at Compass & Fork, we share our tips and tricks for using the site to find the best deals.

This What you Need to Know to Plan your Dream Trip series will focus on the practical aspects of planning your trip:

And future posts on cash vs. credit, and what to do once you are there. We don’t know everything but hopefully sharing what we have learned and some of our favorite planning resources will help you plan your dream trip. Organizing a trip yourself can be very rewarding and save some money as well.

What you need to Know to Plan your Dream TripP Flights Weaving Lake Titicaca Peru


1st Step: Book your Flights

So let’s start with flights. This is where I do recommend you start as well. Don’t book accommodation until you have a flight booked.

Some general tips and examples:

  • The more flexible you are about when and what day you can travel the better chance you have of being able to find a cheap flight.

Example: If you search for the entire week, some low cost carriers may only offer service one or two days a week or direct service only on certain days. If you put in a date and just search you miss these options.

  • What you Need to Know to Plan your Dream Trip Eiffel TowerFlights are cheapest booking well in advance or taking advantage of a sale. Early-bird flights are often available and are the cheapest flights of the year, but you need to book 9 months (or more) in advance. So start to plan your dram trip early.

Example: Sales for Early-bird flights for Europe’s summer season usually go on sale in August or September for the following year.

  • Traveling during shoulder or low season can be much cheaper not only for flights but everything else as well. You just need to do a bit of research about your destination and find out what time of year this is. To avoid disappointment check if attractions and activities are open or available during off season. Many things close.

Example: Lots of things in Europe are closed for the winter, and closed in August. Opera season is only certain times of the year. If your dream is to go to see an opera in the famous Teatro Colon Opera House in Buenos Aires, you need to go during the opera season.

  • If you have airline points check and see if you can use them, but also check if it is a good use of points.

Example: Often I find I am better off to just buy a cheap fare than use points. I can save my points to use to go business class (especially on a long flight) or for when a fare is what I deem to be “outrageously expensive. Since points are often based on zones or distance it can be great value to use points to go from North to South America, where the airfares are often expensive.

  • Check the discount carriers. There are a lot of them now and they can be much cheaper (even after you pay for luggage) than the large international carrier. Especially for travel within a country or continent.

Example: Turkey, Europe, the USA, Asia all have very cheap regional carriers. If you want to travel within the countries it can be A LOT cheaper to book travel on these carriers. (To learn more about cheap internal travel, see Money Saving Tips for Traveling Around Turkey.

  • Consider multi-destination, Round the World (RTW) or two one-way tickets as alternatives to round trip. Sometimes it can be cheaper or more convenient.

Example: We used a less used route requiring us to overnight in Bolivia when traveling from North to South America. Because we took this route we flew business class for the same price as economy. And we spent a night in Santa Cruz Bolivia in a great B&B. So we were very happy!

On another occasion I booked USA-London-Buenos Aires as a multi-trip for less than the USA-London fare!


Finding a flight

My search engine of choice for flights and where I usually start researching is Kayak.com. Kayak is a search aggregator, it goes out and searches airline sites and other travel booking sites and brings you back the results. It usually redirects you to the airline site or other travel site to book.

Why I like it:

  • It is comprehensive- it will search most airlines and return results even for the budget carriers. One exception is Southwest Airlines in the USA. It will show you Southwest services a route but because Southwest does not provide their fare information, you have to go to Southwest to check the fares. That’s the only exception I have found.
  • You can search +/- three days. Using this criteria let’s you see an entire week of fares so you can find which days are the cheapest for travel.
  • It is accurate. On a lot of sites they show you a fare but when you go to book it, the fare is “no longer available” instead showing you a higher fare.
  • It does one-way, round trip and multi-city bookings.
  • You can set fare alerts and it will send you regular updates to let you know if a fare has gone on sale.
  • It also for some routes will “predict” if you should buy now or wait to get a lower fare.

What you need to Know to Plan your Dream Trip Flights Kayak

If I am happy with what Kayak returns then I am done. I can go to the airline site and book it. I have used the site enough to trust the results.

If I am not happy with the results, it is usually for one of three reasons:

  • I think it costs too much
  • The flight takes too long
  • I don’t like the routing

Then I go to ITA Software. This is the company that makes the software used by most flight search engines. You can’t book a flight here, but it can tell you EVERYTHING you ever wanted to know. (This is where I found the business class fares between North and South America for the cost of economy.)

What you Need to Know to Plan your Dream Trip Flights ITM Software www.compassandfork.comWhy I like it:

  • It searches everything.
  • You can set it to show you unavailable fares. That’s right you can find out what the cheapest fare available between two points. It may not be available but if you are looking well in advance, this can indicate this is the sale fare when it does come on sale.
  • You can find more obscure routes.
  • You can find every carrier for a route.
  • You can search nearby airports.
  • You can check if the fare is different if you book it elsewhere. (For example booking a South American flight outside of South America is often more expensive than booking it inside South America.)
  • You can set number of stops.
  • You can see an entire month of fares displayed on a calendar.

You can send the itinerary to yourself via email or get the unavailable fare codes and then work out how to book it, either on the airline site, another travel site, or working with a travel agent.

Plan your Dream Trip: Booking a Flight

For booking a flight, I usually book directly on the airline website. This gives you the ability to check-in, manage your booking, and makes changes if you need to without either working through a third party or incurring additional change fees from the third party.

If you need to travel on two different airlines, but need it on the same itinerary, I recommend using a travel agent rather than an online booking site, but if you are comfortable using an online booking site. I would start with Kayak and see what it recommends for the itinerary. If your not happy contact a travel agent for help to plan your dream trip and get your flights sorted.

What you need to Know to Plan your Dream Trip Sunset Key West www.compassandfork.comThe reason you want two different carriers on the same itinerary can vary but it usually has to do with travel insurance, luggage limits and insurance coverage. An example to illustrate. If you book a ticket on Carrier A NYC to London, then a second ticket on Carrier B from London to Frankfurt same day, these two tickets are not connected.

  • Luggage: Your luggage allowance may be different, i.e. you will go from an international allowance (sometimes more generous) to a domestic allowance (which is sometimes nothing). Also you may not be able to check your luggage to your final destination. This means having to recheck your luggage at the first destination, in my example, London. This can be very time consuming as can mean exiting the secure area, waiting in line and re checking luggage.
  • Connections: If your first flight is delayed or canceled, these tickets are not connected the second carrier is under no obligation to re-book you on another flight. If it is the same itinerary, they need to put you on another flight to your final destination.
  • If for some reason luggage is delayed, lost, or the second flight is delayed or canceled you may have issues as you are not “in-transit” by many definitions. If it is on the same itinerary this usually covers this issue. This can affect insurance claims, getting luggage delivered and re-booking of flights without fees.

If you want to book two unrelated carriers to your destination my advice is to get it on the same itinerary. Do what you can to plan your dream trip so it runs smoothly.

Also at the time of booking it is helpful to think about what method you use to pay for your flight. Buying with a credit card usually offers more consumer protection. If the flight is canceled or the airline goes out of business before you fly, the credit card will refund your charges, debit cards do not usually offer the same protection. Also your credit card may offer travel insurance which offers another layer of protection. Each card and insurance policy differs, you need to check with the card issuer to understand their terms and conditions and decide if it is right for you. We have a couple of cards where if the flight is purchased on the credit card travel insurance is included. We usually use one of these cards to purchase airfares.

If you enjoyed this post, please use the form below to subscribe to our newsletter and receive all the future posts in the How to Plan your Dream Trip Series. Future post topics include transportation, cash vs. credit, and what to do once you are there. You might also enjoy our Healthy Travels Series: What you Need to Know, which covers what you can do to stay healthy before, during and after your trip

For more destination specific planning tips to help you plan your dream trip check these previous posts:

Travel Tips & Resources for Planning Your Trip

Traveling in Italy: What you Need to Know

Money Saving Tips for Traveling Around Turkey

Patagonia Travel Tips and Planning Your Trip

How to Save Money on Your Trip To Vietnam

How to Make the Most of 2-3 Weeks in Peru

What You Need to Know About Traveling in the Greek Islands

You can find all our travel planning tips here.

And lastly, you can find resources we use and recommend to help you plan your dream trip in the Planning Your Trip section here on Compass & Fork.

Do you have any other tips or tricks to find cheap flights? If so please let us know in the comments. And if you have any questions please leave a comment below. We do answer.




What you need to Know to Plan your Dream Trip Series www.compassandfork.com


22 Responses

  1. I don’t think I’ve ever used Kayak before, but I’ll definitely try it next time I’m booking flights. I wonder if it’s true that Wednesday at midnight is the best time to book? Planning is definitely not my strong point so I appreciated this, thanks.

    • Editor

      I see a lot of articles that talk about the best time to buy, I am not sure I believe any of them! Mid week seems to be a bit cheaper but in my experience it is how early you buy your ticket that has a bigger impact than the day of the week.

  2. Gemma
    | Reply

    This is extremely useful, thank you for sharing. I need to try out ITA, I’m familiar with Kayak but always seem to opt for Skyscanner. Time for change! We also need to be more flexible on when we leave, we saved lots by flying JFK to ‘anywhere’ in Europe, that worked in our favour.

    • Editor

      Gemma, we have had the same experience flying out of JFK. We often fly to NYC, stay a few days and then fly out of JFK. Thanks for your comments.

  3. Bethaney - Flashpacker Family
    | Reply

    Planning is such an important part of travel. It’s also great to be flexible and leave some things open so you can go with the flow!

    • Editor

      Yes going with the flow versus pre-planning is a fine balance. We often do a bit of both, pre-planning our flights but going with the flow for accommodation or internal travels. It also depends on whether it is a peak time in the country you are visiting. Thanks for your comment Bethany.

  4. Mar
    | Reply

    What a comprehensive post! I find that, if you are booking during holiday period or if you are going for a shorter trip, I have to toggle back and forth between the fights and the hotels because maybe the flights are cheapest at certain dates but the place I want to stay at is not. I have also discovered Google Flights, pretty neat and full of info on flight timeliness, width of seat, plug availability, wifi…

    • Editor

      Thanks for the heads up on Google Flights, we will check that out. There is always a bit of give and take between accommodation and flights that’s for sure.

  5. Joe Ankenbauer
    | Reply

    I use ITA all the time! Especially when planning out trips way in advance. You have a great list here, thanks for all the tips!

    • Editor

      Joe, it sure does pay to do some planning. Thanks for your comment.

  6. There are really great tips here. It’s really handy especially to newbie travelers who are still in doubt of traveling to heir dream destination.Thanks for the share!

    • Editor

      Thanks Karla. Anything to encourage people to get out there. So many great things to see!

  7. arvin
    | Reply

    I travel 2 to 4 times a year and these are some of the best flight suggestions, I also use kayak, google flights (google owns ITA Software) and lately starting buying from the airline website!

    • Editor

      Thanks for your comment. It really pays to do your research to the bottom line of how much your travels cost you. A good investment in time.

  8. Jessica
    | Reply

    Another site to be bookmarked. I am crazy on searching the cheapest flights for my next trip so Kayak would not be a bad idea to try. thanks for this. 🙂

    • Editor

      My pleasure Jessica. Investing some time up front can dramatically cut the cost of your travel. Thanks for your comment.

  9. Kimberly Erin @ Walkaboot.ca
    | Reply

    Very informational post…I have yet to yuse Kayak as well…but I know lots who do…Maybe ill give it a shot and see if it comes up with anything great,

    • Editor

      Kimberly, you certainly have nothing to lose. See how it goes. Thanks for your comment.

  10. Chris
    | Reply

    I’m a fan of the ITA Software as well, although for a time the page stopped working for me until they released 3.0 (perviously it had been fine).

    We also often use Google Flights for alternative destinations (often it may be cheaper to fly nearby and catch a bus the rest of the way) and Momondo.

    Nice point about the insurance cover from some credit card purchases, however I’d recommend nobody travel without adequate Travel insurance full stop! 😉

    • Editor

      Chris, there are some good tips as well. Good point about Google flights. Insurance is worth it, we have learnt that. Thanks for your informative comment.

  11. Doreen Pendgracs
    | Reply

    Thx for this post. I’ve not yet used Kayak to book a trip, but will definitely check it out next time I am researching flights and a destination.

    • Editor

      Doreen, give it a try and see how it works out for you. Thanks for your comment

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