How To Plan A Vacation

Planning a vacation is supposed to be exciting and relaxing, right? However, once you actually sit down and get down to the gritty details of your trip, the task can seem quite daunting and make you question your choice of destination. However, planning a vacation is an art form that only develops through trial and error. Below I will outline some tips and advice for planning a trip that I have learned through my own mishaps and successes.  Here are the tips for planning your vacation after deciding on your destination: 

1. Research the Weather

how to plan a vacation

You'll want to make sure that you check your location as well as seasons to avoid. Traveling to southeast Asia during late summer? Just make sure you know that this is typhoon season and any outdoor activities could quickly become a problem. What about Moscow in February? Only if you’re a cold weather lover! Along with weather, take a look and see if there are any major holidays happening at during your intended travel time. If you’re okay with crowds then go ahead! If you want to avoid waiting in line and possibly inflated hotel prices, try going in the off season. I once made the mistake of traveling in China during the Chinese New Year. HUGE mistake. Not only was everything twice as expensive, it was also nearly impossible to move around the touristy spots without getting run over by tour groups.

​2. Booking Your Ticket

Now that you know your destination and intended travel season, it is time to get on with booking that flight! My favorite site to use when planning a vacation is This site allows you to play around with a world map to see the cheapest locations for your dates. I also find that this site has some of the cheaper flights flying out of my side of the globe. Another favorite of mine is What I like about this site is that it has a price prediction box for the flights that you search. It will give you advice and trends for your destination on your chosen dates. It will give you advice such as ‘buy now’ or ‘wait 7 days.’ I have found that the advice offered on this site tend to be fairly accurate. On top of all this, Google Flights just came out with a service that will show you if a flight is going to be going up in cost or dropping. It’s a pretty slick service that’s new and one you should try out.

3. Booking Your Hotel

how to plan a vacation

Once your biggest and most concrete purchase, your flight, has been taken care of you can move onto your hotel. First decide your budget and accommodation expectations. One thing that I always remind myself of when planning my trip is that the cheapest accommodation option is not always the most convenient or cheapest in the long run. My rule is that if I need to take a taxi or use the public transportation for more than a small distance, I will pay a little more to book a hotel closer to the center of the city. Besides money, you will also potentially be wasting your valuable time traveling around a city that you're not too familiar with. If you are a super budget traveler like myself and want to get a local feel from your destination you can try out couch surfing. is a networking site for likeminded travelers. People will offer up their couch or a spare bed to travelers. Guests are expected to spend time with hosts and maybe treat them to a meal or bring a gift as a token gesture. Although this is not for everyone, there are plenty of other options for getting a local feel. is a great way to get a feel of the local culture while also remaining a bit more independent. If you are not into a hostel or homestay try out This site is pretty good about having free cancellation on certain hotels as well as lets you accumulate nights in a straightforward system. My number one rule of advice is to read hotel reviews before booking anything!

4. Print Destination Guides​

I always print out the three day destination guide from No matter how long my trip is, I find that a three day guide to a city provides just enough information but at the same time not too much. Trip Advisor is great for this because most major tourist destinations will have three day guides plus guides for outdoor lovers, history lovers, and other topics. Printing out a guide will also save you a good amount of space in your luggage as opposed to packing in a heavy travel guide.  If you don't want to download a three day guide, I would make sure you find one thing you want to do everyday.  It's important to have one planned or scheduled thing to do a day.  If you go over that, you may get overwhelmed by doing too much or too little. I'd recommend just picking one thing a day wherever you're going.  

For me, all of these items are the biggest obstacles to get over when planning a trip. Once you have the major details planned like flights, hotels, and key sites to see, everything else is much smaller and easier to tackle. After you’ve checked these things off your list it will be much easier to get excited about your trip and to spend more time asking around and doing more research on your travel destination.  When you're ready to get going, make sure to find the best backpack for your next trip out there.  You can also find a great carry on backpack if you need a smaller bag too. 

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