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Planning A Momcation? Here Are The Best Locales, Based On Enneagram Type

This Number 5 (aka The Investigator) is Nantucket bound.

Friends vacationing together
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Moms' trips away from the kids are absolutely needed — but that's easier said than planned, right? Sometimes when you plan a trip with your girlfriends, everyone wants something different, making at least one person in the group less than excited about the plans. Or maybe you all love a good trip to Cabo, but after a while, it gets stale. Been there, done that. So, what if you planned a trip explicitly based on your personality type? It would, quite literally, be a "me-time" trip.

While there are a ton of personality tests out there, I'm focusing on the Enneagram test, which identifies nine personality types. Simply put, the Enneagram focuses on "three centers of human intelligence, thinking, feeling, and instinct." It helps us correlate how we function in the world based on we choose to interact with our head, heart, and gut.

Curious to know what moms’ trip might align best with your type? Keep reading for suggestions. And just think: Alternative trip locales based on each mom’s type gives you even more incentive to make room on your calendar.

(1) The Reformer

New York City, New York

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  • New York City, New York
  • Chicago, Illinois
  • Boston, Massachusetts
  • Louisville, Kentucky
  • Seattle, Washington

This personality type is rational and idealistic. You are considered very principled, make purposeful decisions, and can be self-restraining and a perfectionist. It's likely you won't be able to relax with too much downtime, so your best mom trips would include a robust itinerary. To fill up your day, you'll need a destination that will give you a lot to do, so I suggest a weekend in the city. Whether it's NYC or Chicago, these locations will keep you busy and with a wide variety.

The Big Apple is the city that never sleeps, which is perfect for doing all the things in a very short time frame. Chicago's food scene is unreal, and Louisville has bourbon tours — need I say more? If you're also looking for variation in scenery, Seattle is close proximity to mountains, oceans, a rainforest, desert, farmland, and even islands!

(2) The Helper

Grand Cayman, Cayman Islands

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  • Grand Cayman, Cayman Islands
  • Montego Bay, Jamaica
  • Cancun, Mexico
  • Miami, Florida
  • Las Vegas, Nevada

Number two's are caring, generous, a little too nice, and way too accommodating. For you, it's not about where you are or what you do; it's who you're with. Since this personality type leans more on the people-pleasing side, destinations that all your girlfriends will like would appeal most to you. Your joy is in making sure everyone involved is having a good time; other than that, you don't need much to feel content on your vacations.

"Wow" your group with kayaking in Bioluminescent Bay in the Grand Cayman or with panoramic views at the Montego Bay Yacht Club. If you're looking for less athletic activities, you can visit a real shaman in an authentic Temazcal (shaman hut) and take part in a traditional shamanic ceremony. On days when the group wants to lounge, hit the beach in Miami or the impressive pool area at Caesar's Palace in Sin City.

(3) The Achiever

Waterfront park in Charleston, South Carolina

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  • Martha’s Vineyard, Massachusetts
  • Charleston, South Carolina
  • St. Augustine, Florida
  • Laguna Beach, California
  • Asheville, North Carolina

Odds are that you don’t love surprises and prefer to plan ahead of time for what you’re in for. You feel good picking destinations that feel familiar or are considered popular travel destinations; hidden gems aren’t that appetizing to an Achiever. For you, it’s no frill, but all the chill.

And what better way to get away from the stresses of a demanding career than the relaxing beaches of Florida or the laidback town of Laguna Beach? The vineyard is perfect for a cozier getaway that guarantees you some of the best fresh seafood. Charleston promises charming shops and restaurants that won’t disappoint your sophisticated palate.

(4) The Individualist

Bisbee, Arizona

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  • Philadelphia, Pennsylvania
  • Cincinnati, Ohio
  • Bisbee, Arizona
  • Portland, Oregon
  • Washington, D.C.

Known to be expressive and a bit of a drama queen, it is with no surprise that I recommend trips that are centered around the arts and culture scene. For a number four, a good trip is only as good as the inspiration surrounding them. You want to feel totally alive during your time off because that’s what revitalizes you — not just drinks on the beach.

Walk the extensive museum grounds in Philadelphia or the original cobblestones of the “oldest street in America” on Elfreth Alley in Old Town. The Contemporary Arts Center in Cincinnati is one of the first institutions in the United States to display contemporary art, and Washington D.C. is home to the one and only Newseum, which documents the importance of the free press throughout history. If you’re more energized by the “living art” in the streets, don’t worry — Portland hosts monthly art walks outside that showcase local artists. And Bisbee is a desert mountain town built on creativity and individualism. Bonus: It’s less than a half-hour drive to the historic western town of Tombstone.

(5) The Investigator

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  • Burlington, Vermont
  • Anchorage, Alaska
  • Boise, Idaho
  • Nantucket, Massachusetts
  • The Florida Keys

Number five’s are intense, they are inherently cerebral, and prefer isolation. Since these intellectual homebodies get their peace in private, consider a vacation that removes you from the hustle and into nature. The Investigator enjoys time off in more unlikely places.

Enjoy dinner on the shores of Lake Champlain, where you can catch the sunset just over the mountains with the water touching your feet at Splash at the Boathouse, or take a day cruise in Anchorage, Alaska, to see the local glaciers. I love Boise for this personality type because it’s known for a single-person sport: cycling. Idaho’s “Greenbelt” is the perfect trail to get lost on!

As a number 5 myself, I love an empty beach, which is not common these days. Nantucket’s entire island is a public beach, which means you can find your perfect spot without having to pay the private beach price. If you’re someone who likes to escape in books and fantasy, The Florida Keys snorkel experience is next level with The National Marine Sanctuary. Did I mention Key Lime Pie?

(6) The Loyalist



  • Orlando, Florida
  • Aspen, Colorado
  • Honolulu, Hawaii
  • Palm Springs, California
  • Walla Walla, Washington

As you might’ve guessed it, Number 6’s are totally driven by security. It’s all about carefully planned, responsible, and safe fun. The Loyalist does well with trips that are rated PG, and the itinerary is set in stone. You are likely the “mom” of your friend group (figuratively and literally) and are the one to put out fires and save the day. This means an ideal trip for you is one where you’re not on duty, and you’re free to relax. Well, as much as you can, anyway.

Is there anything safer than a vacation at the world’s most magical Disney park? Orlando is an easy “yes” for The Enthusiast. The Après Ski scene in Aspen is world-class but small and cozy enough not to feel overwhelmed. The Island of Honolulu is literally rated one of the safest places in America to visit, and Walla Walla has earned its slogan, “so nice it's named twice.”

(7) The Enthusiast



  • Nashville, Tennessee
  • Jackson Hole, Wyoming
  • Lake Tahoe (California or Nevada)
  • New Orleans, Louisiana
  • Atlanta, Georgia

Let’s cut to the chase — you are the fun mom. You’re spontaneous and upbeat and always ready for the next adventure. You can make friends wherever you go and can adjust easily to different environments, but you’re also easily distracted and can be impulsive. A great trip for you is one where you can do a lot at the last minute, and it’s a guaranteed good time.

The live music scene in Nashville is perfect for a spur-of-the-moment activity because you can find it anywhere, anytime. Jackson Hole is a popular ski destination, which means lots of new people to befriend and make memories with. While the crystal blue waters alone make Lake Tahoe appetizing, its Maritime Heritage Underwater Trail provides a unique opportunity for adventure.

The home of “mardi gras” is known for its seemingly continuous street festivities, and when you need to sober up, their famous beignets will do the trick. If you visit Atlanta, you can take a bike ride on the Atlanta Beltline and stop at one of the largest food dining halls, Ponce Market.

(8) The Challenger



  • Los Angeles, California
  • San Francisco, California
  • Portland, Maine
  • San Antonio, Texas
  • San Juan, Puerto Rico

You’re the “do it all” mom. Number eights are the queens of getting it done and making it look easy. This personality type is self-confident, decisive, and straight to the point. On the downside, this number can also come off as aggressive and dominating. You’d benefit from a getaway that takes you away from saving the world but also puts you in an environment that embraces your assertive way of being.

L.A. has an amazing live comedy scene; enjoy a stand-up comedy show among people who can handle a good joke. If you want to limit the site seeing, San Francisco can be explored entirely in just one day. Portland, Maine, has all the foodie fun you could hope for in a scenic city setting — but you can also tackle some of the country’s most breathtaking outdoor treks.

(9) The Peacemaker



  • Sedona, Arizona
  • St. Petersburg, Florida
  • Joshua Tree, California
  • Savannah, Georgia
  • Newport, Rhode Island

Number 9’s are low-key. They are modest and easygoing and like to remain even-keeled most of the time. This personality type never asks for too much and can be seen as agreeable and complacent. A solid mom trip for you is your quintessential relaxing getaway — no need for a detailed itinerary, just good vibes, and decent food.

Sedona is the mecca of positive energy, with its reported “energy vortexes.” If a good sunset is all you need to fill your cup, Joshua Tree has unreal sunrises and sunsets. For some moms, it’s the little conveniences that make our hearts sing. In Savannah, they have an “open container” law, which means you can stroll the streets with your cocktail with no problem. Sometimes it's fun to live vicariously through others, and touring the infamous Newport Mansions will definitely give you a taste of another life.

Regardless of what kind of trip you choose, what’s important is that you take the trip.