How to Plan an Affordable Weekend Trip in 5 Easy Steps

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How do you travel so much? How do you afford to explore as much of the world as you do? Why can I never find cheap flight deals or understand how to take a weekend road trip? We have lost count the number of time we are asked these questions regarding how we are able to travel the world and so we felt it was time to start sharing some of our secrets and hopefully help you figure out the “how to” when it comes to planning a weekend getaway. If you want to plan a weekend trip, you need to be prepared and plan accordingly. Let’s take a look at a few ways in which we are able to accomplish so much and yet still maintain our regular 8-5 jobs.

plan a weekend trip

Whether you are an avid traveler or simply looking to find some time to take your next weekend vacation, travel planning is critical in order to create an experience that you will not only enjoy but will also be affordable. When you achieve both of these components, that will have a knock-on effect that allows you to plan more trips in the future…it’s a bit like the old domino effect that we always hear about. But it’s so true and we can 100% attest to this philosophy after 10+ years of experience traveling the world.

Planning a Weekend Trip

We have decided to share our 5 easy steps to planning (and subsequently booking) the perfect, affordable (yes, that’s critical!) weekend getaway. Follow these 5 core principles and you can start planning the moment you finish reading this article! Let’s take a look at our insider tips to creating the perfect weekend getaway itinerary.

  • Location, Location, Location
  • Planes, Trains and Automobiles
  • From Hostels to 5-Star Luxury
  • 24 Hour Challenge
  • Spontaneity Always Wins

Don’t worry, we are going to break each of the above categories down so you get a better idea of what we are referencing with each of these. But we are really confident that if you follow these strategies, you will ready and raring to book a trip in the near future.

airport departures board

Remember, our focus here is to create an AFFORDABLE experience and so this is always going to be subjective as every budget is different. We are basing our recommendations on an average lifestyle, one that we consider ourselves to be part of as we very rarely stay in 5-star luxury resorts or fly first-class.

Location, Location, Location

It may be rather cliché but let’s be honest folks, the number one component of planning any trip, regardless of the length of time, is the desirability of the location. You could argue that this is less important when planning a weekend getaway given that the length of time is shorter and if you hate the destination, well you will be back home sooner rather than later. But actually, we would argue the exact opposite. If you choose the perfect destination, you will be inspired to either go back again or in the very least, have a strong desire to keep exploring! And that’s what traveling the world one weekend at a time is all about…the desire to keep going!

find the perfect location

So how you find the perfect destination? Well, there are a myriad of tactics here and ultimately it’s going to be down to personal preference. Let’s start by thinking about locations that are convenient to your home town. What do we mean by convenient? Realistically, if you are planning a road trip (don’t worry, we will come back to this a little later), you are not going to want to drive more than 4-6 hours for a weekend getaway. For the experienced (or should I say “daring and adventurous”) travelers out there, you could probably push this to 8 hours but for the beginners, let’s start with a gentle road trip destination.

weekend road trip

Dependent on where you live is going to determine the feasibility of finding a reasonable location within this vicinity. Once you have a list, consider adding a few “dream” destinations to this but again staying within the realms of reality by focusing on your home country (if you live in Europe, you can extend this to neighboring countries for sure!). By now, the excitement and adrenalin should be pumping through your veins because you will soon be ready to start hitting up your favorite travel blogs (hint, hint), drooling over your favorite Instagram and Pinterest images and searching Google to your hearts content.

weekend trip pinterest planning

For your first trip, let’s go with three road trip destinations and three “potentially realistic” dream destinations. Now it’s time to take these locations and head to phase two of this preparation – aptly named…Planes, Trains and Automobiles!

Planes, Trains and Automobiles

After deciding upon a possible destination for your weekend getaway, it’s time to start look at numbers and considering just how realistic this trip is going to be. Again, the reality of this decision is going to be very much dependent on your personal budget and how much you determine to be “realistic” to spend on a weekend getaway. If we start by looking at flights, if you are leaving on a Friday and returning Sunday evening, you are probably not going to want to spend more than $200 per person – that immediately is going to restrict the number of available destinations (for the Europeans reading this, you have quite a few more options due to the plethora of low-cost airlines) but it’s still possible.

barcelona getaway park guell

Our #1 tip is to utilize Google Flights. Similar to other travel metasearch engines such as Skyscanner, we think that Google Flights is the best one out there, notably because of the really cool map feature where you can enter your home city, enter your chosen dates and then browse around other destinations and their updated prices. A word of caution here, some airlines do not participate on here such as Southwest Airlines so if you know your airport is a hub for a certain airline and you don’t see it on the results, consider visiting their direct website before proceeding further.

weekend getaway flights

Flights are not the only way to take a weekend getaway. Of course, those dream destinations are probably only realistic via plane travel but you may be fortunate to be able to consider hopping on the train if you find a cheaper alternative route or perhaps simply because you have always wanted to travel this way – the biggest issue of course with this is you are going to be extremely limited on destinations and the travel time is likely to be slightly longer. It is worth considering though.

eurail train pass

Finally, the infamous road trip option. As you consider thinking about three chosen destinations that are nearby your hometown within that 4-6 hour radius, start plotting out some routes – again Google’s Maps tool is a great option but there are plenty of available websites and softwares that you can use for this. Do you want to get there as quickly as possible? If so, the interstate route is likely to be the optimal route. Do you want to stop along the way and admire the scenery? These are questions to consider when planning the trip!

weekend road trip

From Hostels to 5-Star Luxury

Ok, so you have your heart set on a destination and you either have your road trip planned out or your flights booked. For a weekend trip, the likelihood is that you will need somewhere to stay for two nights. For those of you that are really trying to stick to a tight budget, accommodation options such as hostels or low-profile hotel chains may be your preferred option but also given that you are only having to book two nights, you may be able to indulge in a slightly higher priced property than perhaps you would if you were looking at a longer stay.

singapore westin

One of the best ways to search for great hotel deals, particularly if you don’t really have a preference on “brand name” is to utilize a resource such as Priceline. Whether you opt for an “express deal” where you won’t know the exact hotel until after you book, or simply opt for one of the “Guest Favorites” or “Pricebreaker Deals”, there are plenty of affordable options available to suit every budget. This is also a great resource because you can search for specific neighborhoods which may offer ideas on the best places to stay – if you are unsure, perhaps switching this step with the next one (planning things to do in the destination) may be more appropriate.

hollywood hotel los angeles

If you are passionate about starting to travel more frequently, whether it’s just on the weekends or perhaps with some longer vacations thrown in there, you may want to consider opting for a hotel chain where you can start earning loyalty points. We are avid, loyal Diamond members of Hilton Honors and always try to stay at one of their properties wherever we travel around the world.

hilton orlando

It’s not always the most cost effective but the long term benefits give you free breakfast, free nights etc. It’s one of those that you may not see the immediate benefits but you have to trust the process…we can 100% attest it’s worth it!

24 Hour Challenge

You may be wondering what a 24 hour challenge has to do with a weekend getaway…well, in our opinion, the biggest problem people face is trying to experience too much in a short timeframe. The temptation when spending a weekend away at a new destination is to try and cram as much as possible into exploring the destination. This is actually one of the worse things you can do because you will get easily burnt out and possibly return home regretting even taking the trip.

elk horn iowa

Now I will add the caveat that much of our travels are the exact opposite of what we are recommending here but after many years of traveling like this, you certainly become seasoned professionals. However, when you first start out with planning weekend getaways, try the tactic of planning an itinerary for a single day trip.

wild atlantic way ireland

Even though you may have up to 36-48 hours to explore the destination, having enough things to do in 24 hours will then allow you to spread these over the multiple days. What does this then allow? Step 5 of our strategy to planning the perfect weekend…spontaneity! More on that later.

brooklyn bridge new york city

Every destination is different – a weekend trip to New York City is going to require careful planning because there are so many attractions worth visiting. However, a trip to a lesser known destination such as Oklahoma City may not have quite the number of iconic attractions, yet you will still benefit from taking the time to identify spots you cannot afford to miss. If you love sampling local restaurants or coffee shops, go ahead and put them down on a list because the moment you arrive in the destination, you want to be ready to visit every spot without having to try and figure out opening times, location etc.

oklahoma city street art

Spontaneity Always Wins

Regardless of how much planning and organizing you do before heading on your weekend getaway, there will ALWAYS be something that you don’t plan for. It is critical that you allow some time in your itinerary to be spontaneous and experience something that you hadn’t already scheduled.

weekend trip to nashville

If you allow spontaneity to take over (albeit still trying to stick to an itinerary), your experience will be enhanced to a level you could never have imagined. The main benefits of this, aside from the fact you will likely have an amazing experience, is that you will be raring to book your next trip because you realize just how many hidden gems are out there waiting to be discovered.

hillsboro village nashville

Spontaneous travel allows you to have the flexibility to enjoy the adventure of a lifetime. This is another potentially cliché statement to make but it should go without saying that having a “laissez-faire” attitude when exploring a destination will likely spark some amazing experiences. It’s sometimes a Catch-22 situation trying to establish the fine line between having an organized itinerary and allowing that carefree approach to life to enhance your getaway. But that is exactly why following step 4 is critical to achieving the perfect weekend getaway because it allows you to build in some time for these spontaneous events to occur.

pisa italy

Summary

You did it! You have followed our 5 simple steps to booking the perfect weekend getaway. All that you need to do now is actually book your trip and whisk yourselves away to enjoy an amazing short vacation. While many of you reading this may think these steps are obvious, we feel that this is something everyone should take a step back and think about because it’s all about creating a sustainable system that will enable you to travel more frequently. That is exactly what we are focused on trying to inspire – more travel!

hobbiton day trip new zealand

We hope that you are able to travel the world as frequently as we do but if not, and you are only able to take an occasional weekend getaway, go ahead and follow these 5 steps and we assure you that your trip will be amazing! Let us know how you plan your weekend getaways…what are your keys to success? How do you achieve the dream getaway? Are you most concerned about the location or budget or something else? We want to hear your stories, so feel free to share them in the comments below! Happy travels folks!

4 COMMENTS

  1. Well done, guys! We agree: Spontaneity is sort of like the best “upgrade” for a trip. We typically have must-see points in our itinerary, and then points of interest that we are flexible on. That way, when spontaneity hands us a plate full of fun, we don’t miss out on whatever brought us there in the first place. Now we’re itching to plan a getaway! 🙂

  2. Thanks for the simple to follow article! I definitely feel when I try plan a weekend away I probably focus most on basic research of the budget and then whilst there the spontaneity kicks in and then we end up adding some extras in. Great advice. Thanks again!

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