Custom Travel Planning Services for Every Escape, from Madison, WI to anywhere in the World

Your Beach Vacation Starts here.

We believe your vacation should be stress-free. Our approach centers on understanding your unique desires, crafting personalized itineraries, and managing every detail with meticulous care. We provide unparalleled support and expertise, ensuring your investment delivers not just a trip, but cherished memories that last a lifetime.

Start Planning My Trip

The Caribbean & Mexico

Discover Your Tropical Haven

From luxurious all-inclusive resorts to hidden island gems, we specialize in curating exceptional experiences in the Caribbean & Mexico. Our services range from intimate romantic escapes to lively family adventures, all meticulously planned to your desires.

All-Inclusive vacations

Honeymoons

Disney

Group Adventures

"Katie takes the worry out of planning so you can just go prepared and have fun!"

I’ve used Katie for multiple vacations. One was my honeymoon and another was an anniversary. I won’t use anyone else but her!”

- Travis & Rachel

"10/10 would recommend Katie! She made everything a breeze.

She made everything a breeze. She helped us figure out what we were looking for, considered our budget, and found us the right fit! She made booking so simple, and provided us with all the details the entire time leading up to our trip. We will absolutely be booking through her again in the future.”

- Joe & Brenda

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Client Love

Why Choose Us for Your Next Adventure?

Unrivaled Expertise

Caribbean travel is our heartbeat. We’ve personally toured resorts, sampled excursions, and studied the islands, so the guidance you get is grounded in real, firsthand experiences – not just Google searches.

Meticulous Attention to Detail

We think of everything so you don't have to. From advising on the best room categories and dining reservations to subtle itinerary optimizations and local insights, our meticulous planning ensures no detail is overlooked, elevating your entire travel experience.

Your Dedicated Travel Partner

Planning travel can be overwhelming, but with us, you have a compassionate and resourceful partner every step of the way. We anticipate your needs, offer solutions before you even ask, and are always there to support you, ensuring peace of mind throughout your journey.

Personalized Planning Experience

The internet is loud and full of mixed reviews. We quiet the noise by learning what you care about — whether it’s the best value, a VIP experience, or something in between and match you with the perfect resort.

Disney

Magical Disney Experiences, Made Easy

Desiree specializes in enchanting Disney vacations, ensuring every moment is filled with wonder and joy. From choosing the perfect park and resort to navigating Genie+ and dining, we handle all the intricate details.

We help clients choose the ideal Disney destination and resort, whether it's Walt Disney World, Disneyland, a Disney Cruise, or an Aulani Resort adventure. But then somehow you find us. 

Our destination planning services include personalized itinerary creation, dining reservations, Genie+ strategies, and continuous support, making the entire process smooth and enjoyable, no matter where the magic happens.

Let's go to disney

Honeymoons

Your First Trip as Newlyweds, Perfected

Wedding planning is exhausting enough. Your honeymoon shouldn’t be.

We’ll help you choose the perfect destination, craft an itinerary that feels effortless, and handle every detail so you can focus on enjoying your first adventure as newlyweds. From champagne to sunsets, we’ll make sure your honeymoon feels as magical as your wedding day.

Your Caribbean Expert

I’ve spent over 15 years immersed in all things Caribbean. First as a curious traveler, then these past 8 years as a full-time travel advisor helping countless clients plan their dream getaways.
This isn't just a hobby; it's my dedicated focus. My expertise comes from extensive firsthand exploration—visiting resorts, experiencing excursions, and navigating the nuances of various islands. I've spent hours diving into the specifics of everything from family-friendly resorts to secluded honeymoon hideaways, understanding the subtle differences that make one destination perfect for you and another not quite right. 

That is where we, the Heart of the Caribbean Team, come in for you.

The internet can be loud, overwhelming, and honestly, a little misleading. Reviews clash, opinions differ, and suddenly you’re not sure what to trust. Some people just want a good value, and others want top-notch. What is important to you? Let us cut through the noise and help match you with a destination and resort that is the perfect fit for your vacation desires.

Let's Find Your Perfect Destination

Questions before you hit the beach?

We’ve got the answers before you get the sand between your toes.

How does the deposit work? Are there payment plans available?

Typically there is a small deposit due to lock in the cost of the trip with the remaining balance due anywhere between 30-60 days prior to travel. You are able to make smaller payments leading up to the final due date. Please reach out with any specific questions regarding payment plans!

How far in advance should I book my all-inclusive vacation?

We recommend booking all-inclusive vacations at least 6-9 months in advance, especially for peak travel seasons or specific resorts, to ensure the best availability and pricing.

Can you help with travel insurance?

Yes, we strongly recommend travel insurance and can guide you through various options to protect your investment and provide peace of mind during your trip.

How do I start planning my honeymoon with you?

Simply reach out through our contact form or give us a call to schedule a complimentary consultation. We'll discuss your vision and begin crafting your perfect romantic escape.

Do you only plan Disney World trips, or can you help with other Disney destinations?

We specialize in planning magical experiences across all Disney destinations, including Walt Disney World, Disneyland, Disney Cruise Line, and Aulani, A Disney Resort & Spa in Hawaii.

Ready to Make Your Travel Dreams a Reality?

Don't just dream about your next getaway—let's make it a reality. Reach out today to start planning the unforgettable trip you deserve, tailored perfectly to your desires.

Take me to paradise