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Kelly Matregrano

Forever the resident group and family trip planner, Kelly has embraced her love for logistics as a luxury travel advisor.

With over fifteen years of experience planning elegant weddings and events, Kelly Matregrano combined her love of travel with her expertise in managing logistics to focus on planning clients’ dream trips. Her approach as a luxury travel advisor is all about empowering her clients to leave the worrying at home, and instead allow them to embody joy while they know all the details of their trip are handled. Whether her travelers are seeking a thrilling stateside adventure, European cultural immersion, or wellness-inspired island escape, Kelly provides a robust approach to trip planning.

As a mom, Kelly is no stranger to the “Where should we go?” brainstorm that inevitably comes with every family vacation — she loves helping her clients plan both the trips they’ve always wanted to take and the ones they didn’t even know existed until she offered up a fresh idea. She partners with her once-wedding clients to extend her services into the runaway of honeymoons and celebration trips with a focus on creating lifetime memories, no matter their stage of life. Personally, Kelly loves traveling to new places to scout the best dining, tours, and hotels, often incorporating a wellness activity like a private yoga session or spa experience. When not traveling, Kelly spends time in Fairfield County, Connecticut with her husband and two daughters.

What has been your most memorable travel experience to date?

One of my most memorable travel experiences was a recent trip to Paris with three friends. We stayed at Madame Rêve, enjoyed the best French food, explored Versailles with a private tour guide, baked croissants, and walked the city streets taking in all the beautiful architecture.

How do you prepare for your trips?

As a planner by nature, I do a ton of research on where I’m going and what area I would enjoy staying in as the basis for the trip. Once I book a luxury hotel, I figure out the best spots for dining and decide what activities would be ideal. I always make an itinerary for myself and share it with whoever I’m traveling with because being organized and planning the details out makes for a smoother travel experience. But don’t forget to leave some room for spontaneity!

Travel Tip

  • Challenge yourself to try new things while traveling—try a local cuisine or a participate in a cooking class or a tour! Be in the moment and take in all the destination has to offer.

Testimonials

Kelly planned our girls' trip to Paris—it was expertly planned and made the experience unforgettable. Our personalized itinerary balanced sightseeing, relaxation, and shopping perfectly, with seamless transportation, charming accommodations Madame Rêve, and pre-booked tickets to major attractions like the Eiffel Tower and the Louvre. The dining recommendations were spot-on. Their availability for support and thoughtful touches, like surprise welcome gifts, made the trip stress-free and special. I highly recommend their services for a perfectly planned and memorable adventure.

-Stephanie