Planning a trip is an exciting but sometimes overwhelming task. It’s fun reading travel blogs and getting ideas of fun stuff to do and see on your vacation. I can get lost in travel blogs for hours! But it’s also easy to get bogged down in the logistics and costs. That part is not so fun for most people. So how do you plan a trip and have fun doing it? 

Over the years I have followed many travel influencers for guidance as well as learned myself from trial and error. I think I have a pretty good system now! While my planning process may not be for everyone I want to share with you how I go about planning trips and good resources to use to save some money along the way. So, I’ve created this easy to use guide based on my own experiences of learning how to (and how not to) plan a trip. I hope that you can takeaway some tips on how to plan your next vacation!

Getting Started: How to Plan A Trip

First thing is first when you are planning trip, when and where do you want to go? The where is usually pretty easy but can be affected by the when. For example, if you decide you want to go to Canada then you may want to plan your vacation for the warmer months. Or if you want to go to Thailand you may want to avoid their hottest and rainiest months. I personally try to travel during what is called the “shoulder season” because it’s cheaper. That is the month or two before and after a destination’s busy season, and also when the weather is usually still decent.

If you are dead set on a certain destination then you may need to be flexible with choosing when you go. Or if you are limited on when you can go (it can be really hard to get that time off of work!) then you may have to be a little flexible on your destination. I usually have to be a little flexible in both departments, not only for myself but for whoever I am traveling with at the time. 

 

#1: How to Plan For Flights

Once you choose my when and where then it’s time to look for flights. I always start with this and then fill in the rest of the trip details once I know for sure when and where I am going. The flights can also be the most expensive part of the trip if you aren’t careful so I like to watch out for deals. Booking flights first really helps to budget for the rest of the trip too so doing this first is an important part of how to plan a trip.

Side Note

I have been a long time subscriber of Going (formerly Scott’s Cheap Flights) and have saved thousands of dollars on flights thanks to the deals they find. They have a free version that gives you access to 1 out of every 3 deals they find, or you can pay 39$ per year to get access to all of the deals. If you buy flights just once a year it is worth it to pay for the subscription. I have saved way more on flights than the 39$ it costs to subscribe. I have even paid half price for flights to Europe, and the deals that show up in my email often inspire me to visit a new place, or sometimes that place gets added to the oh-so-long bucket list.

In addition to Going, there are some apps you can use to help you score some cheap flights. Skyscanner is a really good one that I have used and it seems to be gaining popularity with travel enthusiasts. Hopper is also a good one, especially for domestic flights. And don’t forget about Google Flights which makes it really easy to search for the lowest price dates. That’s a great resource to use when you aren’t sure when you want to go and you are looking for the best prices (think shoulder season!). 

Plan Ahead to Save Money

Other ways that I save on flights (and I highly recommend you look into these options) is to pick a few favorite airlines and create free mileage accounts with them. It can be a slow building up those miles, but it really can make those flight costs more bearable. Even if you only have a hundred dollars worth of miles to redeem- hey, that’s 100$ you already saved on your vacation! Most airlines have apps that make it easy to track your miles and see how many points you can redeem on your next flight.

Another way I have saved tons of money on flights, and other travel, is through credit card rewards. After my very first trip overseas I was hooked and knew I wanted to see so much more of the world. In order to do that I had to figure out how to make it affordable. The first thing I did when I returned home was research credit cards with good travel rewards. You can read more about credit cards with good travel rewards here Best Credit Cards For Traveling . I went with the Chase Saphire Preferred card and I have hardly paid for a flight since. However, if credit card debt is something that is hard for you to manage you may not want to go this route. Accumulating more debt is not exactly something that will help you plan future trips.

Next up: Research, research, research!

Now that the flights are booked (which is always exciting because it means it is actually going to happen!), it is time for the really fun part- researching where I am going and deciding on what I want to see and do there. This is my favorite part of planning every trip because I get to learn so much about the place I will be visiting!

Where To Start

A good way to start this is to google a basic question like “best things to do in Greece” and let yourself go down the rabbit hole to read about all the cool stuff you can do in Greece. And because I am a foodie, I like to google “best places to eat in Greece” to find fun restaurants, street fare, and farmers markets to visit. If you are a fellow foodie I definitely recommend looking at this early on in your planning phase because I have made decisions of where to stay based on how many great food scenes I can explore. At some point I have to cut myself off or else I will end up planning a years worth of stuff to do in just a couple of weeks! 

I try to narrow it down to a few key things that I feel are my “must do’s” while I am there. I like to have some days planned and leave some days open to go with the flow and be spontaneous. About half the days of planned activities and half the days of no plans is a good balance for me, you will just have to experiment to find what works best for you. But trust me, the days will fill up faster than you can imagine, there are so many soul filled adventures out there!

Research Tips

I keep in mind their location and proximity to one another. This will be important when I am deciding where to stay and how I will get around. I am a big fan of road trips and public transportation so I have no problem hopping around. But if that’s not your style then you may want to pick one place (city, beach, etc…).  Then you can find all the cool stuff to do in just that one area. 

I don’t recommend booking these yet, or at least make sure they are refundable if you do. I wait until after everything else is done then I revisit this section and book. At this point we are just trying to figure out where we will want to call home while we are there. 

3rd Party Sites To Check Out

But when you are ready there are many different reputable 3rd party booking options for tours, admissions, and experiences. The main ones will probably be the first ones that pop up during your google search. I have pretty much used them all by now and can honestly say that I have had a great experience every single time. Trip Advisor, Viator, Get Your Guide, and my personal favorite, Airbnb Experiences  just to name a few.

Airbnb Experiences is my favorite because it mostly connects you to individuals instead of tour companies. I have had much more personalized, meaningful, and unique experiences this way, and in addition I can directly support locals. It’s also a lot easier to cancel and get a refund without having to make any phone calls if you need to. That may be difficult depending on where you are. The downside is that Airbnb doesn’t vet their experiences in the same way as the others. They also have limited options. But once again, I have used them all and would recommend any one of those sites. Learn more about 3rd Party Booking Sites. You will likely use these every time you plan a trip so get familiar with them!

Side note

Early on in my travel days I never wanted to spend the money on tours and opted for self guided tours of sites. I have since changed my attitude about that because you can learn so much more from a guided tour. They know exactly what information is the best to share. And if you are going to a highly visited site (like Mayan ruins for example), the tour guide(s) will insist you practice responsible tourism which is better for everyone. Want to know Why Is Responsible Tourism Important? . Plus you can ask the tour guide questions! To me that alone is worth the money because they are local and will usually tell you so much more than you paid for. Not to mention they can be safer depending on where you are. Now, like with everything, I try to find a balance and mix it up. I do some guided tours and I fly solo for others. You can read about some of the awesome tours I have done in my other posts. 

How To Plan A Trip: Recap so far

At this point in the process you have decided when and where you are going on this trip. You’ve booked flights so you know that it’s actually happening (congratulations!). And you’ve decided on the main attractions you want to see while you are there. You have your trip half way planned, so let’s move onto the next and very important step. Time to decide and book where you will be staying on this exciting getaway! 

Where Will You Plan on Staying?

Through your research you decided on a few main things you want to do in Greece while you’re there. But it turns out they are in three different parts of the country. You will need to divide your time between the three locations and look for a place to stay in each area. This can be really fun because there are many unique lodging options out there in the world! Hostels are a great option if you are want to plan a trip on a budget. In some countries you can find nice hostels for as little as 9$ per night. 

 

 Plan Ahead To Save Money  

Two things to keep in mind while you are searching is that booking a place with a kitchen or kitchenette can cost a few bucks more up front but save you money on eating out. And that for longer trips you may want to splurge on at least one place that has laundry onsite. Read more about my Money Saving Tips For Travelers. Some destinations may be all about eating out and can be doable on a budget (think Thailand!) so that may not apply to this trip but it can definitely save you money in some destinations. And if you want to pack light (I always do) you will eventually need to do laundry. I like to plan ahead or these things because it makes the trip smoother down the road. 

As you plan your trip you will want to start thinking about transportation too because that may affect where you stay. For example, if I am staying in the city then I may want to find walkable places to stay, or be near public transit stations. If I am renting a car and driving around I will want to find a place with reasonable parking, or if I am traveling by train… you get the point!

How To Book A Place

My go to booking sites for this part of the trip planning are Airbnb, Vrbo, Booking.com, and hotels.com. There are many others out there but these are the ones I have consistently found the best deals on. And I have been able to use these with ease (easy cancellations and refunds, plus great communication). A lot of properties are listed on some or all of these sites so you can search them all and find the best prices. Some have rewards programs which can save you some cash and sometimes gets you better deals. I am all about maximizing those travel rewards every way I can! Read more about How to Travel for Free With Travel Rewards here. 

Other Tips

1) read the listings carefully and make sure you know what additional fees and taxes will be charged. I have accidentally paid way more than I was expecting by not paying attention to this. 2) I like to book refundable properties just in case I end up changing my plans. And 3) some properties offer significant discounts if you book for a certain length of time (usually a week) so make sure you read the listings so you don’t miss out. 

How Will You get Around?

This part of the trip can get expensive if you aren’t careful. There are many different options for transportation depending on where you are going and what you are doing. For example, renting a car in Ireland is 100% the way to go because there is a lot to see. Not to mention the infrastructure there is lacking in that department. However, in France you may want to opt for the high speed trains if you want to get around and see the country. France is big! Some countries offer in country budget flights for really low prices. I once flew from Bangkok to Phuket for 40 USD!

Many cities in Europe have excellent public transit systems, and some developing countries offer private drivers for reasonable prices. Then there is always Uber, Lift, Grab, and several other pop up taxi like companies around the globe. Make sure to check them out on line first to read about their safety guidelines. 

Start By Asking Around

This is when you get to do some research again! I recommend starting with a simple google search like “best ways to get around Greece”. This way you can see what people are saying. You can save yourself a lot of money and headache by learning from other people’s experiences. If you see a lot of people recommending one form of transportation, take their word for it! They likely learned the hard way at some time and are hoping to save other people from making the same mistakes. This will help you plan your trip well so take the time to read some blogs or reviews.

Other things to keep in mind here is that some countries are really difficult to drive in, some lack infrastructure, and as always you have to keep safety in mind. Read my top 15 Tips For Traveling Safely . Learning from others is one of the best ways to optimize your trip planning!

How To Plan A Trip: Wrapping it all up!

Now would be a good time to go back and book your tours and activities. And that is how to plan a trip! First you started with choosing our destination and travel dates. Next you booked flights. Then you researched where you want to stay and booked your lodging. And finally you figured out how you will get around. Next up I will share with you how I prepare for a trip! From travel insurance, to packing, to surviving those long flights, and so much more, I’ve got you covered!