ABOUT the AGENCY

Travel isn’t just about where you go.
It’s about how it feels when you arrive.

Wandering With Kay is a boutique travel advisory founded by Kaylee Carreiro, created for travellers who care deeply about where they stay. Specialising in character-led hotels, Mediterranean destinations, and thoughtfully tailored itineraries, the agency focuses on experiences that feel intentional and carefully curated from start to finish.

the founder

our values

INSPIRATION

KIND WORDS

founder story

Kaylee Carreiro

Kaylee Carreiro founded Wandering With Kay from a genuine appreciation for places with character. She finds boutique stays that feel like you’ve discovered something special rather than simply found somewhere to sleep.

Inspired by the effortless style of the Mediterranean and a love for design-forward hotels, she believes the right atmosphere sets the tone for an entire trip.

With over three years of experience, Kaylee specialises in crafting thoughtfully designed journeys for travellers seeking something more personal. As an independent advisor, she draws on global travel connections and firsthand experience to recommend only the places she would choose for herself.

travel advisor, founder

our philosophy

A thoughtful approach to travel planning.

Curated over crowded

Boutique hotels, villas, and stays thoughtfully selected for their atmosphere, design, a sense of place.

Personal, Always

Every recommendation is shaped by you. Your preference and the way you want to feel while traveling is priority.

Travel with Intention

From where you stay to how your days unfold, your trip is designed to feel effortless with space to enjoy the details.

the

Wandering With Kay

INFLUENCE

boutique living

sun-washed

slow mornings

natural materials

design-led

wander:ing

wander:ing

discover:ing

explor:ing

stay:ing

savour:ing

unwind:ing

reminisc:ing

return:ing

KIND WORDS FROM OUR CLIENTS

Kaylee is not only the sweetest but she was SO helpful. She helped my husband and I plan the most beautiful and luxurious honeymoon! It felt so overwhelming during the peak of wedding planning and she helped relieve us of that stress and took care of everything! She is the best!

KASS

KIND WORDS FROM OUR CLIENTS

Kaylee helped me book travel to Ft Lauderdale and made the entire process super simple. I was able to get a flight and hotel booked at a great price and completely without headaches. She was an absolute pleasure to work with!

TIM

KIND WORDS FROM OUR CLIENTS

Thank you Kaylee for coordinating an amazing trip to Barcelona and Paris! We had a fantastic trip and you made sure everything ran so smoothly!

maria

KIND WORDS FROM OUR CLIENTS

I usually get overwhelmed planning trips, but Kaylee made everything so easy. She listened to exactly what we wanted and turned it into an amazing experience. I felt confident and excited instead of stressed—10/10!

JULIA

Ready to start Wandering With Kay?

The right stay changes everything.
Let’s start planning something memorable.

OUR SERVICES

WORK WITH US

Wandering With Kay is a boutique travel advisory founded by Kaylee Carreiro. Specialising in boutique hotels, Mediterranean destinations, and personalised itineraries, Kaylee works with travellers who value design and atmosphere when they travel.


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