How To CRUSH Travel Goals: A Guide for Millennials

Lindsey Dukes
January 16, 2024

The only way to CRUSH your travel goals is to PLAN!

That may not sound too appealing (yet) but it's the only way you're going to be able to get all the stamps your heart desires.

Plus, we'll show you a technique that enables you to enjoy the process instead of dreading it. And since Millennials are choosing to travel differently than every other generation, we'll give you the tips to maximize your plans.


The Roadmap

As fun as spontaneous travel is, let's be honest - most of us need to plan ahead to make it happen. Especially when traveling abroad.

Did you know only 36% of Americans hold valid passports and only 20% travel overseas?

What's worse, more than half of all paid vacation days go unused. Why? There are several reasons but one answer for sure is – you guessed it – lack of planning.

How many times have you caught yourself saying, "I wish I had the time/money to take an epic trip to <fill in the blank>"?

Well, guess what helps bring those wishes to life? Planning.

Turns out Benjamin Franklin just might have been onto something when he said:

"Failing to plan is planning to fail."

Here is your roadmap to CRUSHING your travel goals. And don't worry, it's designed for enjoyment.

1. Work Backwards


Steve Jobs knew what he was talking about when he said:

You have to start with the customer experience and work backwards to the technology.

Instead of focusing on vacation days, holidays, or logistics, first just simply figure out where you want to go.

Nail down your top three destinations. 

This is important for several reasons. First, after you do your research on where you want to go, you're going to become energized and motivated to make it happen.

But Millennials have proven they want to travel differently (and responsibly). No longer are vacations all about staying at a fancy all-inclusive resort in Cancun and never leaving to explore. Instead, they want to travel like a local and taste the culture. 

Therefore, when doing your research, make sure you're reading reviews from Millennials like yourself and not from 60 year olds on Trip Advisor who have a very different view of the world and travel than you do. Seek to travel with companies that share your same vision and passions who also try to keep the money local to the countries they visit.

Also, it's hard for a travel goal to feel like a potential reality if you're just worried about your work schedule. Instead of getting bogged down by those stressors, start with what motivates you: travel! 

After you nail down your top three destinations, consider completing the following two steps for each of them.

2. Plan the Budget


Usually, budgeting sucks, but this isn't any kind of budget, it's a #travelgoals budget.

You know where you want to go and now you get to do the research on how you can get there.

Learn more about the country you want to visit and figure out the total cost. Think of it like a fun project and imagine yourself being there as you calculate the numbers.

This step can be super easy if you travel with Under30Experiences since they handle accommodations, transportation, most meals, and activities. That way, you know all the costs up front (it's often cheaper than if you traveled on your own) and you don't have to spend time doing pricing research. 

Once you have a total cost, break it down to a monthly (and even weekly) amount to determine how much you'll need to save on a smaller scale. 

It's crazy how much less intimidating saving $167/month or $39/week sounds than $2,000/yr.

Point here is - if you start planning far enough in advance, you CAN save enough to travel

Maybe you'll have to make a few sacrifices but the experience you gain from traveling is absolutely worth it.

A recent study showed that 72% of millennials prefer to spend their money on experiences rather than material you definitely aren't alone in making travel a financial priority.

3. Plan your time off


If you happen to work remotely or have unlimited vacation, then you can skip to the next section.

The reality for many of us, is that time off from work is a limited commodity. So, what's the best way to go about getting time off from work?

First - check your company's vacation policy. In most cases, even if you've used all of your paid vacation you can still ask for additional time off.

The main thing to keep in mind when asking for any additional time off is making sure you have a game plan for your absence before you even approach your boss.

Make sure you have someone to cover your workload while you are gone, and/or offer to work extra hours before and after your planned vacation to complete any necessary tasks. You want to make sure your employer is comfortable knowing that your work will be taken care of even while you are away.

Secondly, ask at a good time. Approach your boss when you think they will be most receptive.

Planning and asking as far in advance as possible usually helps stack the chips in your corner.

Lucky for you, Under30Experiences trips are designed with young professional work schedules in mind. 

Trips start on a Thursday and end on a Monday so that you won't have to take off more than three days of work.

If you start planning next year's travels NOW, you can nail down your dates, request your time off, and relish in the joy of anticipation!

4. Have a backup plan

Having a backup plan is an important part of working backward.

A solid plan is great, but allowing room for error (and proactively mitigating it) is key for keeping stress at bay. 

We want the entire goal crushing process to be enjoyable, unexpected changes included.

If you travel with Under30Experiences and for some reason need to reschedule your trip, you can switch it FOR FREE! Your trip comes with a built-in backup plan. How rad is that?!

Another way you can proactively relieve travel induced stress it to fly with airlines that offer free flight modifications, like Southwest.

Last but not least, travel insurance should always be a part of your backup plan. If all else fails, most travel insurance policies offer trip cancellation coverage that will reimburse any expenses you lose due to not being able to travel.

Having a backup plan sets you up for minimal stress and maximal stoke.

5. Make it happen


This goal crushing guide is full of things most millennials are already aware of but sometimes you just have to be reminded to DO IT!

Now you know that it absolutely IS possible to take the trip of a lifetime next year. 

And remember, the joy of anticipation is a real thing. Once you decide to gift yourself an experience like travel, the months and days leading up to it will be brighter.

Pick a place, make a budget, get prepared, and go have experiences of a lifetime.


Check out some of the trip dates that we already have available for 2018.

Looking to take a spontaneous trip a little sooner? We've still got 2017 dates open too!

Co-authored with Miles Demars-Rote

Lindsey Dukes
Lindsey loves helping people become the best versions of themselves through her work as a fitness coach, and a U30X marketing ninjaette & occasional trip leader. She loves travel, adventure, music, deep chats, people, and all things yoga, fitness, nutrition, and human optimization.


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