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Do It This Year: How to Plan a Destination Trip Conquer cheap flights and travel checklists to start living your best life

[Feature image by Gianella Castro]

You’re feeling that “new year, new you” vibe. 

For the last few years, you’ve been dying to take off from work to binge on new tastes and flavors, consume exotic liquors, and snap s0me completely foreign views. It’s okay to admit it. 

Why haven’t you used that PTO? Is it because you haven’t settled on costs or attractions or travel companions?

Is it because the thought of venturing to a completely new locale is, a little daunting? 

Look no further. We’ve done the research and created the ultimate guide on how to plan a destination trip as cheaply and resourcefully as possible.

Table of Contents

Here’s how to plan a destination trip:

plan a destination trip singapore
Larry Teo

How Far You Should Plan in Advance

Generally, the earlier in advance you plan your destination trip, the cheaper it will be.

But there is a sweet spot for exactly how soon in advance you should plan everything.

When it comes to buying airfare, the recommendation is to buy 20-120 days before you’re expecting to fly (read section on “how to buy cheap airfare” below).

When it comes to booking hotels and rooms, one month prior to your stay is the suggested timeframe to lock in your rental at the optimal price, according to Trivago.

destination trip plan booking hotels

And if you’re traveling Europe, this infographic below breaks down how many weeks in advance is optimal for hotel book, no matter what month in the year it is.

plan a destination trip europe hotel booking

How to Save Money For Your Trip 

Saving money to book your destination trip can be done in a few different ways:

Do some simple math. Budget yourself, and be strict about it.

Compare your income vs. your bills, then approximate how much you’re willing to spend on a destination trip.

Once you know how much you need to save in total, you can set aside a specific amount per paycheck until the date of your trip. 

Increase your income somehow.

Bad at limiting and analyzing your spending? Pick up a side gig or a part-time job.

Sell stuff on Etsy. Go on Upwork or Fiverr and get paid for doing some freelance tasks. 

Figure out how much money you need to save each week or month, and make a plan for how to reach that, whether it’s spending less or making more. 

plan a destination trip budget
Christine Roy

How to Buy Cheap Airfare 

Take advantage of online resources

Mobile apps like Hopper help you gauge when airfare prices are expected to go up and down.

Find and book cheap flights on websites like JustFly and Google Flights (two of my favorites).  

Clip coupons and coupon codes for airline discounts and vouchers on sites like RetailMeNot.

Join an airline’s email list

Stay up to date on upcoming deals and sales notifications. Sometimes airlines will host random limited time offers like $95 round trip airfare from specific cities and airports.

This will help if your destination trip involves a typically pricy stop in main hubs like NYC, Miami, or LA.

A lot of these platforms also provide a “track pricing” feature so you’ll be notified via email or app notification when a flight you have your eyes on is expected to drop in price.

From practice, I’ve personally found that airfare is cheapest on Tuesdays and Wednesdays.

This handy infographic outlines the best times to buy plane tickets, including how far in advance to book your flight.

plan a destination trip cheap airfare

How to Know the Travel Requirements

Traveling abroad to new lands? It’s important to know what documentation you’ll need to enter and exit a foreign country.

You will also need to receive the necessary vaccines and meet specific medical requirements before you go, especially for places with a high risk for contracting infectious diseases.

plan a destination trip documents
Agus Dietrich is a great resource to bookmark for future reference. It outlines everything you need for international trips, including travel checklists and a list of the visas and vaccines you need.

No matter where you go, it’s always smart to rearch local laws so that you can stay safe, be responsible, and avoid being stuck in jail somewhere far from home.

Don’t forget to google local customs and cultures, too. Every place is different, which means people will act differently than how you act in your hometown.

It’s not that you should go into a new place with biases, but it’s nice to act respectfully in accordance with local custom and to prepare yourself for what to expect. 

Check out National Geographic’s list on Where to Travel in 2019.

How to Book Cheap & Safe Hotels, Hostels, and Airbnbs

Booking cheap and booking safe are not synonymous, but they can be. Thoroughly research the places you’re looking at booking. 

plan a destination trip lodgings

Always read past guest reviews posted on websites like Google Reviews, Trip Advisor, or the individual hotel booking apps themselves. Check out your lodgings with Google Street View

Staying in an Airbnb? Do your due diligence and check your potential host’s profile. Pro Tip: Don’t be afraid to try to scope them out on social media, if possible.

We’re not saying you have to stay in the Ritz Carlton here, but where you sleep every night will impact your overall experience.

If your dream is to hike abroad, and you don’t care about cleanliness or having amenities for a few days, hostels are a free (or extremely cheap) shelter option for travelers.

You can also look into Couchsurfing or use traveler social apps like Global Freeloaders to stay with friendly hosts.

You can never be too safe, especially while traveling. Get a bad feeling about someplace, something, or someone? Trust your gut. Remember that it’s better to be safe than sorry.

How To Plan Activities

plan a destination trip sites
Ryogi Iwata

Figuring out what you’re going to do is the best part of the trip planning experience! No matter where you go, there are so many ways to have fun on your destination trip:

  • Explore on your own, or use apps to meet other tourists while doing your own thing.
  • Join a group tour with Contiki or Intrepid Travel. It’s awesome to meet new friends and do cool things with them, but beware that you’re locked into a very rigid, set schedule of activities with people you can’t escape from. And from past experience, Contiki tends to attract a younger, rowdier, college-esque crowd. 
  • Browse travel hashtags and location tags on Instagram to see what people do and where they go in the spot you’re traveling to.
  • Search for Groupon deals or use a Groupon Getaways package.
  • Find the best restaurants and tourist spots to visit.

Pro Tip: From experience, Pinterest is a huge help in for planning travels.

Simply search “what to do in [town/city]” and thousands of beautifully crafted listicles and activity suggestions will pop up.

This is how I found places to eat, things to do, and sights to see for a road trip. 

Any tips and experiences to share of your own? Let us know it the comments.

Whatever you decide to do, and however you wish to go about it, we hope you have the time of your life on your dream destination trip. 

Read next – What to Wear While Traveling

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