Travel Advisor

Jillian McComiskey
Expertise
- Luxury,
- Family Travel,
- Italy,
- Arizona,
- Caribbean,
- New England
Based in
Connecticut
Languages spoken
English
Profile details
About
I specialize in luxury family travel. I've traveled to over 25 countries and 65+ luxury hotels — and I love helping families plan unforgettable trips with kids.
Travel style
As a former history teacher, I turned my lesson-planning skills into a passion for itinerary planning instead. I've traveled all over the world with my kids, and my aim is to help families learn about the best 4 and 5-star hotels and destinations for families. Travel with kids can feel very daunting — but I'm able to help my clients zero in on the exact properties where mom and dad will also get to relax and enjoy their holiday as much as the little ones.
Favorite hotels
Jillian's reviews
Jillian was a dream to work with! She made booking this vacation a breeze. Her communication was so timely and clear. She even took the time to share her personal recommendations with us. This was also the first trip we've ever received a complimentary room upgrade, all thanks for Jillian! I look forward to booking our next vacation with her!
- Claire B.
Booked travel to Bahamas
- April 2025
Jillian was diligent with follow up and made herself available via phone when we arrived and had some quick questions. She was also able to add additional perks we were so grateful for - especially our breakfasts!!
- Monica R.
Booked travel to Mexico
- March 2025
Jillian was outstanding and provided us with customized options for our family’s preferences and helped to “run interference” when questions came up along the way. She also had great ideas, recommendations and guidance throughout. We will definitely work with her for future vacations even as someone who is very “hands on” in planning travel it is so helpful to have a Trusted Advisor!
- David L.
Booked travel to Bahamas
- March 2025
Jillian was responsive, friendly, and provided helpful tips- everything you need for a great booking experience! She ensured the room was perfect for us and our kids’ ages and reminded the hotel team about our 5YO’s severe nut allergy. Thank you for such a great recommendation and to help book!!
- Sara R.
Booked travel to Playa del Carmen
- March 2025

Get in touch with Jillian
Reach out to customize and book your own experience. Or, just to chat about travel in general.
You can normally expect a response from Jillian within a business day or so. You’ll also be subscribed to our travel newsletter (you can unsubscribe at any time).
