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Let's start wandering.

We'd love to hear about your upcoming trip and explore how we can make it your reality. Complete the form below and we'll be in touch to discuss.

contact

kaylee@wanderingwithkay.com

(508) 644-0845

office hours

Mon - Fri: 9am - 6pm EST

Saturday: 1pm - 6pm EST

currently booking summer '26

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THANK YOU FOR GETTING IN TOUCH!
AFTER SUBMITTING YOUR INQUIRY:

Review.

Your enquiry will be carefully reviewed within 2–3 business days to ensure we're a great fit.

Next Steps.

Kaylee will be in touch to confirm availability, gather any additional details, and, if you’d like, arrange a discovery call.

Proposal.

From there, a tailored travel proposal will be created, outlining recommended stays, experiences, and next steps for your trip.

To ensure every trip is planned with care and attention to detail, Wandering With Kay takes on a limited number of bookings at a time. This allows for a more personalised experience and thoughtful recommendations.

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

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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