Unable to Enjoy Vacation? Make It A “Guilty Pleasures” Trip

Whether you’re traveling halfway across the world or driving just a few hours away, vacations should be stress-free, carefree and fun.

But instead, sometimes they’re exhausting — even stressful.

We can do better!

So if you’re feeling like you’re unable to enjoy vacation, you’re in the right place. This is how to turn your vacation into a guilty pleasure holiday.

Let’s do this!

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What Is “Guilty Pleasure” Vacationing?

A guilty pleasure vacation is where you intentionally indulge in and embrace your favorite pastimes and guilty pleasures.

You don’t worry about what you “should” do or see or experience while on vacation or traveling. Your only goal is personal happiness, relaxation and self indulgence.

It’s a holiday where you’re allowing yourself to do whatever you want and have zero qualms about it.

In my opinion, it’s how vacationing should be — a time to relax and enjoy the things you truly love to do the most.

Benefits of Guilty Pleasure Traveling

• You’re putting yourself first (a form of self care)

• It boost self awareness

• It improves your confidence

• Reduce vacation stress

• Have more fun

• Enjoy vacation again

• Inspire others to embrace their guilty pleasures more and to have fun

• Better embrace your quirks

How to Make Your Vacation A Guilty Pleasures Trip (11 tips)

1. Set the Intention

Fully letting go and allowing yourself to indulge starts with your intention.

Ideally, you’ll have planned your guilty pleasures vacation before you ever go. But even if you’re halfway through your trip, consciously deciding to make it a guilty pleasure trip is helpful.

So here are some quick tips for setting intentions:

• Make your intentions clear, simple and specific

• Make your intentions positive

• Reflect and address any limiting beliefs

• Write it down somewhere

• Practice your intention everyday

• Connect it to your habit(s)

2. Why Are You Not Enjoying Vacation?

It’s hard to fully relax when you have vacation stressors constantly annoying you. So let’s nip those in the bud!

So, what aspects of your vacation (past or present) annoy you?

What reasons are you unable to enjoy your vacation?

Clearly identifying your stressors shines a light on them. From there, you can create solutions and/or avoid them altogether.

For example, if full itineraries cause you stress, then avoiding them and making time for more nothingness or unplanned spontaneity would make more sense.

Other reasons for being unable to enjoy vacation could be the people you travel with, the places you visit or work-related stress you bring with you.

Reasons for not enjoying a vacation are personal, so do some self reflection here to identify exactly what’s causing you stress.

Then think about workarounds or solutions to address them.

3. Indulge In Your Guilty Pleasures

Let this be your permission slip to indulge in your favorite guilty pleasures (and have zero qualms about it).

Whether that means binging on every season of Gilmore Girls (while looking out at a beach), rereading all the Harry Potter books or playing video games to the point that you forget to eat dinner (again), then have at it!

Do the things that make you feel most happy, relaxed and fulfilled. Guilty pleasures are a great way to enjoy vacation again.

So, indulge!

4. Let Go

For me, stress and travel anxiety always come back the more I try to control things.

So let go — or be dragged.

This means having less expectations, detaching from things and learning to go with the flow.

And still yet, guilt may pop up. We can be too hard on ourselves, especially with feeling the need to hustle, stay active and take full advantage of everything.

So occasional resets may be needed.

Learning to let go and not care is a modern skill. But with practice and awareness, it can become a habit — a new default mode for you.

5. Make It A “Me-cation”

Do you and put yourself first. It is called a “me-cation”, after all.

If people-pleasing creates vacation stress, then prioritizing personal fulfillment should reduce it. So this is another permission slip to selfishly and amazingly put yourself first.

Here are some quick tips to make your vacation a proper “me-cation”:

• Set clear and healthy boundaries

• Know your stressors and avoid them

• Start with the intention, first thing in the morning

• Practice self care

• Craft your perfect vacation plans (but don’t feel bad for changing things)

• Do daily self reflection (I like to meditate)

6. Put Your Digital Work Life On Vacation Mode

I’m not anti-tech. I use it everyday for work and all of my brand goals and creative pursuits.

But I do support occasional detoxes — especially if it gets in the way of your vacation (like with remote work).

So here are some quick tips to put your formal digital life on hold:

• Turn off work or annoying notifications

• Avoid checking your email

• Remove work apps (like Slack) from your dock or desktop (out of sight, out of mind)

Explore more:
➤ How I’m Making Social Media Fun Again

7. Don’t Feel Bad About “Wasting Time”

People love to ask how your trip went and what you did.

So don’t feel bad if your response is “Amazing, I did absolutely nothing — I read books, watched YouTube and played video games the whole time.”

The goal of a vacation is to step away, reset and come back to “real life” feeling refreshed and recharged.

And for me, letting go of preconceived ideas of what I “should” be doing on vacation by indulging in my honest guilty pleasures always does the trick.

So don’t feel bad about this (I’m right there with you).

8. Take More Solo Trips

I love solo traveling.

As much as I love the company sometimes, a solid private trip hits just right — especially when it comes to guilty pleasure vacationing!

So carve out more time to travel just for you (i.e., without outside expectations or stress). It’s a great way to enjoy your vacations more.

Also — even if it’s just a couple days away at a hotel — solo vacationing is a great way to practice self care.

Getting comfortable with spending time alone and exploring by yourself is an important part of guilty pleasure vacationing.

So take yourself on a date, explore more alone and take more solo trips. It’s always a good time.

Explore more:
➤ How to Travel More

9. Get Good At Solitude

Guilty pleasures can be fun with close friends, but sometimes they’re better spent alone.

For example, I love exploring deep esoteric topics about the big questions in life, the universe and our role in it all. But some of these topics get pretty out there, confusing and hard to talk about.

So, (for now), I’m more comfortable indulging in these things alone.

I love my solitude and a proper guilty pleasure vacation is perfectly built for introverted alone time.

You don’t need to be hyper social to enjoy vacation.

Explore more:
➤ Solo Travel Tips for Introverts

10. Indulge With Balance

If you’re spending a whole week traveling or on holiday, you don’t need to go all in with your guilty pleasures.

Because even that (indulging everyday, all day) can get old.

As with most things, balance is better. So I like to throw in some exploring, newness or local experiences. I just choose things that I still genuinely enjoy.

Alternatively, you can explore new guilty pleasures — things you’ve always wanted to try but maybe felt embarrassed to do or like they weren’t important enough to spend time on.

Now is the time to indulge away! Just think about how you can balance things too.

11. Learn to Say No

Even if you’re vacationing alone, you may have opportunities or invites to do things you really just don’t want to do.

This never goes away.

So learning to say no is an awesome skill to practice with benefits beyond a guilty pleasure vacation.

Here are some quick tips for learning to say no more often and with more confidence:

• Be clear and confident

• Express gratitude for the invite

• No your boundaries and stick to them

• Address feelings of guilt or FOMO

Later ✌️

Guilty pleasure vacations are your permission slip to do what you truly want to do, without worry of judgment or embarrassment.

And they’re an awesome way to enjoy vacation again.

Simply setting the intention, prioritizing yourself and indulging (guilt-free) are solid first steps. But ultimately, making it a habit (by taking more solo trips, for example) is the goal.

Guilty pleasures boost your self awareness, confidence, happiness and authenticity. So lean into them and embrace them (even if they’re embarrassing).

Naysayers gonna naysay, regardless of what you do.

So just do you.

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