How to Choose the Best Vacation for your Enneagram Type


What’s your Travel Personality based on the Enneagream?

Raise your hand if you can’t get enough of personality quizzes! I have a pathological need to know which Disney Princess, Spice Girl or Parks and Recreation character I am. (Tiana, Ginger, Leslie Knope. You?)

In case we haven’t formally met, I am a world-traveling, self-professed queen of personality tests (which probably says a lot about me), adding letters behind my name like degrees. I’m Angie – HSP, INFJ, C/ID, Obliger, 3w2, Slytherin. If that already means something to you, you and I should have a chat. (I would love more friends who get my exact brand of internal tumult.) And if it all sounds a bit more self-awareness than one person needs, you’re probably a laissez-faire Nine like my husband.

Can the Enneagram change your life?

Some personality tests are designed just for fun (or to mine your personal data on Facebook – zinggg), and those have their place. The real thing though? A real scientific assessment can change your life. Or at least, change the way you think about life. Think this is just my HSP-ness showing? Listen up – this is for real.

Humans lie – it’s just a fact of life. Most of us are even skilled at lying to ourselves, which means we don’t always know why we act the way we do. Personality assessments help us get to the bottom of some of our more perplexing issues. More self awareness is rarely a bad thing and personal growth can be really delicious, if a bit discomforting when you’re walking through it. Working with others is a lot easier if you can figure out what makes you tick as a person. If you’re feeling stuck in relationships, at work or just with life in general, it helps to look inward to figure out if we might just have something to do with the stuck-ness.


Where to start? I love Myers-Briggs (so many letters!) and the Enneagram for digging deep into motivations, desires and fears. Real talk, I’ve been to therapy, and it took many hours and many dollars to get to the crux of what some of these assessments can do in 20 minutes.

I’d taken free online Enneagram assessments in the past and always landed somewhere around One or Three. Because I’m adaptable, most personality tests have left me feeling in the middle, without a definitive type. When reading through the nine types in the Enneagram, I found I could relate to most of them in one way or another. It wasn’t until I took Ian Morgan Cron’s in-depth Enneagram assessment that I was able to dig in and determine that I’m a Three, all the way, with all the good and bad that comes with it.


Ian is a therapist, speaker, podcaster and author of The Road Back to You, and he developed the latest version of the iEQ9 to reveal not just your type, but your unique patterns of thinking, feeling and acting. It’s been a couple of weeks since I took the test and (Like, should I change careers? Move to Costa Rica? Seriously!) I consider myself on the high end of self awareness, but my 40+ page assessment pointed out some glaring blind spots and areas that could use prayer and intentionality. What was once a general inkling of my Enneagram type now is a solid tool with my type, subtype and wings. Just being able to put a name (or number!) to my various natural fears, gifts and challenges has blown my mind in a way I wasn’t expecting.

Let’s be real though. The less shiny parts of my personality aren’t so fun to confront. For example, I get really frustrated when colleagues don’t care about their work and do excellent work and want to work all the time, because work is so important to me. (Meanwhile, if you’ve read my last dozen ranty pieces on influencer marketing, you’re all saying, DUH, ANGE.)

So yes, it can be painful and sticky to confront one’s flaws, but radical transformation only comes when we’re willing to look at things in a new way. (And as a Three, you know I love a good project, even if the project is me!) Now that I’ve been digging in to the Enneagram more, I see so why I’ve made a lot of the decisions I’ve made in my life.

It’s a little bit freaky how a multiple choice test that takes less than 20 minutes can pinpoint your soul.

Even still, there’s something oddly comforting about knowing that there are 9 main personality types and proven strategies for relating to, working with and being married to all of them. Maybe relationships don’t have to be as complicated as we make them.

Take the iEQ9 Enneagram assessment

Does the Enneagram translate to travel? Of course it does! It goes without saying that you’re going to love a vacation so much more if it fits your type. This is why Sevens thrive at a place like Universal Orlando but might be bored at a yoga retreat. I put on my thinking cap (and 60+ countries worth of experience) and searched my archives and my soul for excellent vacations, tours and hotels for each Enneagram type. Dig in, click around and then tell me if the best vacation you’ve been on aligns with your Enneagram type. I’m so curious!



Ones are rational, idealistic, principled and self-controlled. An ideal trip for a One would feature a destination where transportation is efficient and citizens are polite and orderly. Ones also do well when their vacation has a purpose, like learning a new skill or a theme, like wine or castles.

Trips for Ones:

  1. Writing on the Wall: Singapore’s Culture Through Street Art 

  2. Napa Valley Wine Tasting & Food Pairing by Helicopter Tour 

  3. Panda Rescue Center Volunteer for the Day 


Twos are caring, demonstrative, generous, people-pleasing and possessive. They’re probably the easiest to peg, too, as far as trips. There’s even a portmanteau just for them: voluntourism!

Twos are wired to care for others, so they feel best when their vacations can make a positive impact on the world around them. You’ll find the happiest Twos planting trees, playing soccer with local kiddos and building something with their hands. I am a 3w2, so it should come as no surprise that mission/volunteer travel has been such a big part of my journey. BUT PLEASE NOTE! When it comes to volunteer travel, you absolutely have to make sure the organization you’re working with is legit and making the right kind of difference.

Trips for Twos:

  1. Mission trip with local church

  2. WWOOF in New Zealand 


Threes are success-oriented, pragmatic, adaptable, personable and driven. Sound like anyone you know?

I have a deep and abiding insight into the travel life of an Enneagram Three, because friends, I am one. I took my passion for travel and turned it into work. You wanna know what I say every day of my life?

“I really need a vacation.”

And you know what everyone says in response, “Aren’t you always on vacation?”

I wish. I really wish.

We Threes have a knack for finding the project in every fun activity. You give me a weekend and I’ll give you a minute-by-minute guide on how to maximize every moment for efficiency.

So I have a crazy suggestion for my fellow Threes. If left in charge, we turn every vacation into a project. To experience a real vacation that actually does what a vacation is supposed to do, we A) need to leave the planning to someone else and B) need to go somewhere work can’t reach us.

This means going on a trip that has deliverables is NOT a vacation and expectations should probably reflect that. A remote island with limited internet access is a good start. They have digital detox retreats just for Threes like me, and while it gives me actual high blood pressure to think about unplugging, ultimately it’s what we need.

Trips for Threes:

  1. Overwater Bungalow at Four Seasons Maldives

  2. Ultimate 10-Day Namibia Wilderness

  3. Windstar Cruise

  4. Intrepid Digital Detox Trips


Fours are sensitive, withdrawn, expressive, creative, romantic and dramatic. They can be self-absorbed and temperamental. They want to experience the fulfillment of beauty, art and creativity on vacation. Fours love individualized experiences, luxury and certainty. Lots of Fours are accomplished solo travelers because they want to do what they want to do when they want to do it.

Trips for Fours:

  1. Chicago Architectural River Cruise

  2. Tour Around Morocco 

  3. The Fish Hotel in The Cotswolds


Fives are intense, perceptive, innovative, secretive and isolated. As deep thinkers, Fives relish digging to the bottom of historic mysteries. Traveling with a Five is like living in a documentary. They ask lots of questions and come to interesting conclusions. Fact-finding is their favorite, so spending hours in museums or at archeological digs is ideal.

Trips for Fives:

  1. Explore Machu Picchu

  2. Ultimate Egypt Archaeology Tour

  3. Solstices at Stonehenge

  4. Exploring Israel / Palestine


Sixes are committed, security-oriented, engaging and responsible. Sixes can be cautious at best and suspicious and anxious at worst, so their most fulfilling vacation is one where they feel secure and can still have a good time. A group tour with a trusted company like Intrepid is a great option, and travel insurance is a must for hesitant Sixes!

Trips for Sixes:

  1. Guided Tour of the Balkans

  2. Classic Peru Tour

  3. Restful Week in Nevis


Sevens are busy, fun, spontaneous, versatile, distractible and scattered. They want to do everything, everywhere, all the time. They love to have fun and be on the go. They’re literally and figuratively all over the place. Sevens would do well on mega-cruise ships with a million things to do, foods to try and shows to see. You can find a happy vacationing seven dancing in the Conga line, rock climbing on deck and taking a towel animal class.

Trips for Sevens:

  1. Royal Caribbean Cruise on an Oasis class ship

  2. Weeklong Extravaganza at Universal Orlando

  3. Action-packed Weekend at Atlantis in The Bahamas


Eights are self-confident, decisive, willful and confrontational. They’re boisterous and bold and not afraid of a challenge. Eights do well traveling alone because they’re confident and feel capable of handling whatever life throws their way. They also do well in countries with similarly confident citizens.

Trips for Eights:

  1. 24 Hours in Havana, Cuba

  2. Adrenaline & Survival Skills in Australia

  3. Gladiator Class in Rome


Nines are easygoing, self-effacing, receptive, reassuring, agreeable and complacent. I suspect my husband is a Nine, though he has never taken a personality test in his life. They’re quite happy to go along with whatever their companions want to do. They find taking it easy to be pretty easy and fit right in with whomever shows up.

Trips for Nines:

  1. Luxury Resort in St. Lucia

  2. Yoga & Spa Adventures in Bali

  3. Panama & Costa Rica Discovery Tour

Have you taken the Enneagram assessment? What’s your type? And does ideal vacation match up?

FTC disclosure: I was given a code to take the #iEQ9 Enneagram assessment, but as always, that doesn’t affect my opinions or content. This post may contain affiliate links which, if you use them, will result in a small commission for me at no extra cost to you. Win-win!


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