Meet a Mom: Jillian McComiskey of Compass Roam! | Greenwich Moms

Jillian McComiskey is a mom of two who, like many Greenwich Moms, relocated to Greenwich from New York City for a great community with a little more space. Five years ago, Jillian and her husband, Niall, settled into the Milbrook community and welcomed their daughter, Claire (3) and Maverick (1). “To say we love Milbrook would be quite the understatement!  It’s such a tight-knit community and we’re so happy to live here,” says Jillian.

A former teacher, Jillian recently launched Compass Roam, a luxury family travel blog that aims to help families find inspiration for their next vacation, as well as the tools to plan and make it happen! For this week’s Meet a Mom interview, we asked Jillian to share all the details of this exciting new project, her favorite travel destinations for families and more! 

Can you please tell us a bit more about your family?
I’m a former teacher turned travel blogger (which brings me here today).  Niall works in finance, and enjoys playing pranks – he first told me he was a spy when we started dating.  Claire loves all things princesses.  And Maverick is already embodying his Top-Gun namesake by living in the “danger zone” wherever he goes.

So cute! Can you share more about Compass Roam?
I very much understand the struggle of vacation planning with kids, and want to help parents take the hassle out of it – I do so by consolidating my research and reviews into easily-digestible guides and reviews consolidated in one spot. There’s no magic wand I can wave to make travel flow seamlessly.  However, there are plenty of destinations that are family-friendly and will welcome your traveling circus with open arms.  Compass Roam is about seeking out those destinations and providing parents with a “one stop shop” resource. 

Here are some highlights of what parents can find on my website:

  • The Ultimate Guides provide comprehensive overviews of a destination, including popular options of where to sleep, eat, and what to do with kids.  These are helpful if you’re seeking some destination inspiration, or want to learn the lay of the land.  
  • Reviews on luxury family accommodations that have all your family needs covered. These articles cover properties in which I’ve personally stayed, and I can therefore vouch for. 
  • Awesome and off-the-beaten-path experiences that will make you feel like a local (and ones you can do with kids).
  • Insider tips on the most scenic and family friendly outdoor adventures.
  • Fabulous foodie finds that will appeal to adults and kids alike.
  • As an added bonus, there’s also plenty of destination inspiration for kid-free (woo-hoo!) vacations too.

If parents are interested in learning how I’ve specifically mapped out a trip, they can access my free itineraries by subscribing to the newsletter.  These may be particularly helpful for parents feeling a sense of “Where do I begin?” or “What’s do-able in X destination in X days with kids?”  Sometimes it’s handy to have a roadmap! 

You mentioned you were a teacher prior – how did you transition from that career into this one?
I consider myself quite lucky when it comes to my dream job checklist.  I’ve been able to pursue 3 passions.  First and most importantly, I love “mom-ing” – with all its craziness and chaos.  Secondly, for 7 years I taught Global History at the Bronx High School of Science – considering I had my first teacher desk at age 5, this job was really a dream come true!  However, from a young age I also had a thirst for travel, and a slight obsession with journaling it.  

When I was 8 years old, my mom won an essay contest on NPR radio.  The prize was a trip for 4 people to Paris, France!  Little did I know this vacation of a lifetime would kick start my travel passions. I collected memorabilia all along the way and created my very first album  – the precursor to blogging. I even made travel scrapbooking the focus of my senior project in high school. I spent the last month of senior year attending scrapbooking workshops and learning more about the process from the “Pros.” At the time, I had recently returned from Italy and wanted to chronicle my adventure in a creative and thoughtful manner. Fast-forward years later, I went on maternity leave as a teacher; it was then that I decided to pursue travel blogging.  Starting a blog had always been a dream of mine, and I knew I could turn my lesson-planning background into creating awesome itineraries and guides for other parents.  So, Compass Roam was born! 

Love it! How is what you offer different than anything else out there?
This is an excellent question! The truth is, there are thousands of travel bloggers out there, so why connect with me? My niche includes luxury family adventure travel, and while many bloggers cover travel with kids, far less focus on luxury travel.  Even I, a lover-of-travel-research, found it difficult to access all the information I was looking for (5-star hotels, kid-friendly activities, delicious restaurant recommendations) in one spot.  Yes, we can all pour through hundreds of TripAdvisor reviews, but then what?  Historically, luxury travelers have hired travel agents to coordinate their high-end trips… but what if you’d prefer to plan a 5-star trip yourself?  Where do you start?  

You start with Compass Roam! As a former teacher, I have adapted my lesson-planning and organizational skills into creating family vacation guides that make dream journeys come alive. My travel guides will have you covered from the beginning of your planning when you’re simply searching for inspiration, to when you’re ready to start filling in all the details.  

What is your favorite destination with kids? For a girls trip? Couples trip?
Great question!  Here are some of my go-to suggestions. 

  • Are you looking to go somewhere with your kids where you can just chill and relax?  Rosewood Mayakoba is one of my favorite luxury resorts in the world.  This property just knows how to “wow”, and the service is spectacular.  Moms and dads – you will actually get to relax!  I wrote a detailed Rosewood Mayakoba hotel review on what parents can expect to find at this hotel.  


  • Are you looking for a luxury vacation, but also want to stretch your legs and explore?  Sedona is one of my favorite spots.  Enchantment Resort will check all your luxury boxes, and the beautiful red rock canyons are right in your backyard.  There are so many hikes that are family friendly, making it an easy place to experience endless adventures.  Here you can find my detailed guide to Sedona, as well as an Enchantment Hotel review


  • Feel like traveling internationally?  I always recommend visiting Italy for families. Italians are extremely baby friendly, and the laid back culture makes it an easy place to take kids.  Borgo Pignano is a gorgeous 11th-century castle where you can take in the Tuscan countryside, all while swimming in a limestone cut-out pool with the kids.  Check out my Borgo Pignano hotel review.   


  • Interested in leaving the kids with grandma and enjoying a romantic weekend away?  Some of my favorite nearby New England resorts are the Mayflower Inn and Twin Farms.  The Mayflower is a short 90 minutes from Greenwich, and the spa is spectacular.  Twin Farms is located 4 hours away in Vermont – it was recently named the top hotel in the world by Forbes and it did not disappoint.  Check out my Twin Farms hotel review


Why should everyone consider using Compass Roam as a resource?
People should consider using Compass Roam as a travel planning resource, because my detailed guides and itineraries will really help save you hours of planning and headache!  If you’re looking for help planning an upcoming trip, I suggest: 

  • Subscribing to my newsletter, where you’ll receive immediate access to itineraries of destinations I’ve already visited. 
  • Emailing me with any questions.  I love talking about travel, so if you need help planning an upcoming trip, I’d be happy to give you any insight via phone or email.  If it’s a destination I’ve traveled to myself, I’ll be able to point you in the right direction and can help map out your itinerary.  These consults are free, but I do ask that you subscribe to my newsletter in return.  

What are your best tips for traveling on a plane with small kids?
Here are some of my “quick tips” that can help with air travel for babies, toddlers and young kids. 

  • First, take it easy on yourself.  Travel days can be tiring, so don’t worry about sticking to strict nap schedules or such – just keep everyone fed and entertained. 
  • Try to schedule flight times for nap time.  You’ll have a better chance of baby sleeping on the plane if nap time coincides with flight time.
  • Bring EASY TO EAT snacks and have them neatly packed.  Think goldfish, pretzels, raisins, blueberries, tiny mozzarella balls, crackers.  
  • Pre-pack back-up outfits in Ziplock bags.  This is one of my life-saving hacks!  If your child has a bathroom accident or there’s a diaper explosion, it’s far easier to grab a Ziplock bag instead of fishing around for clean clothes.  
  • Use a diaper clutch. I like this Skip-hop one; it can attach to the outside of your carry-on, thus freeing up valuable real estate inside your bag.  It also makes it easier to change a baby’s diaper when needed.
  • Have some toys packed, but don’t go crazy:  For my daughter, I usually bring a coloring book, crayons, and an iPad downloaded with games and movies.  For my infant son, he likes playing with post-its, glow sticks, and plastic cups.   


Where can people learn more/follow you?
Please visit my website Compass Roam and follow me on Instagram @compassroam.  I post a lot of tips and advice on my IG account on a weekly basis.  I would love to connect with more Connecticut moms.  I’ve gotten to explore much of the North East/New England during these COVID years and there’s plenty of trip ideas on the blog for families looking to keep it local.    

We love to support local businesses. Can you please share your favorite places to:

Go to dinner for date night:  The Cottage (now in Greenwich) and Oko (Westport).  My husband and I absolutely love the food creations crafted in Brain Lewis’s kitchen.  When we heard that The Cottage was opening in Greenwich, we were pretty ecstatic.  

Go for “Girls’ lunch”:
Every week I take my daughter out for “Girls’ Lunch.”  We usually head to Greenwich Flavor for their delicious Mediterranean food. 

Grab a baked good: 
Raphael’s has delicious baked French pastries and croissants.  Just go there! 

I work out with a personal trainer, Alexa Ramirez for strength training.  She’s awesome and I highly recommend her especially for prenatal/postnatal clients.  She coached me through both pregnancies.  I’ve also been working out at Core Pilates with Annie.  She’s a pro and is also very talented at working with pre/postnatal clients. 

Get your nails/hair done: 
I see Alan at Salan H for haircuts and blow-outs.   When I’m in a mani/pedi mood, I’ll usually go to Muse Nails.  Their salon feels very clean and bright.   

Go shopping for yourself/for your kids:
For the kids, I like the Piccolina Shop or Jacadi for a special occasion. 
I personally love Vineyard Vines, Gretchen Scott and Lilly Pulitzer on The Ave.  

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