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Wendy-Ann Maillard
(407) 376-8995
Winter Garden, FL
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I specialize in curating tailor-made Destination Weddings and Romantic Escapes that reflect your unique love story

As a Certified Destination Wedding and Honeymoon Specialist, I’m known for planning unforgettable family vacations and amazing cruises—but my heart truly beats faster when I’m curating romantic escapes. From destination weddings and honeymoons to proposals and anniversary getaways, I help couples create meaningful experiences across the Caribbean and beyond, each one planned with precision and heart.


Let’s bring your dream trip to life.

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Wedding venue on the beach

Memorable Moments

I craft romantic escapes filled with love and meaning—from beachfront “I do’s” to secluded honeymoons and milestone anniversaries. If you’re dreaming of a special getaway, I’d be honored to help bring it to life.

  • Destination Weddings
  • Honeymoons
  • Anniversaries
  • Buddy-Moons & Group Getaways

Certifications & Expertise

I take care of every detail. My clients trust me to remove the guesswork, simplify complex logistics, and deliver dream-worthy moments—whether it’s a seaside vow renewal or a luxurious resort escape.

Logo certification

Certified Destination Wedding Specialist

Logo certification

Proud Member of the Destination Wedding & Honeymoon Specialist Association (DWHSA)

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Wedding Planning FAQs

When should we start planning our destination wedding?
You should start planning 12 - 18 months in advance to secure your venue, date, and group travel rate.
How much does a destination wedding cost?
The cost of a destination wedding varies and depends upon location, venue, guest count, inclusions such as flowers, video, photography, and more.

Pro-tip – Many couples spend less than on a hometown wedding and enjoy a built-in Honeymoon.
What is the difference between a legal and symbolic ceremony?
A legal ceremony is officially recognized in the US and results in a marriage or official document signed by a judge, officiant, or clergy. A symbolic ceremony has no legal weight but feels just as meaningful.
What is the advantage of booking through a Certified Destination Wedding Specialist instead of doing it ourselves?
You gain stress-free planning, vendor connections, exclusive perks, and one-on-one support.
How can you assist with family and guests who will be attending?
I help with travel arrangements, accommodations, and transfers. I also send reminders, updates, checklists, and work through the logistics of planning your wedding.

Kind Words from Happy Couples

Proudly Rated 5/5 on Google

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I have recently returned from an amazing vacation to Montreux Switzerland booked through Dream Vacations and Wendy as our agent. The trip and accommodations were excellent. Great hotels, our transfers were smooth. International travel can be intimidating, it’s essential you have a knowledgeable agent to work with. Wendy also put together our trip to Ireland and Wales back in the fall. Great job there also. Highly recommend her for superior vacation planning.

Steven Flewellyn

Wendy was amazing! She took all of the stress out of planning our trip. Me and my fiancé had an amazing and all of her recommendations were spot on! Definitely will be booking with Wendy in the near future!

Elijah Lewis

Where can I start, professional, available, and accommodating. Wendy assisted me with planning my vacation as if she was planning for her own. She provided many options and ideas but not pushy. I’m glad I went with her and my wife was amazed with the surprise trip Wendy and I planned. Men, if you’re planning that special trip for that special person in your life and don’t where to start like me. Contact Wendy,, you won’t be disappointed

Cedrick Kelly
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Let’s create something unforgettable together.