Jen

Guthrie

CRAZY IMAGINATION TRAVEL
Planning Extraordinary Vacations since 2004
Planning your dream vacation can feel overwhelming, but that’s where I shine. With personalized itineraries, insider tips, and stress-free planning, I make every step effortless — so you can focus on the magic.
Personalized Itineraries
Insider Tips & Hidden Gems
Stress-free Planning
Personalized Itineraries
Insider Tips & Hidden Gems
Stress-free Planning

Every Great Adventure Has a Beginning

Every family, every trip, every dream looks a little different — and that’s exactly why I follow a proven process. From your very first ideas to the final farewell, I walk you step by step through planning, reservations, and all the magical details in between. The result? A smooth, stress-free journey that feels effortless from start to finish.
Step 1. Dream & Discover

I start with you — your family, your favorites, and your must-do moments. Whether it’s castles, cruises, island escapes, or global adventures, I shape the trip around what matters most to you.

08 Feb, 2022
Step 2. Reserve the Magic

From staterooms and dining to special events and behind-the-scenes tours, I handle the reservations that bring your dream vacation to life. You’ll enjoy the magic without the stress of juggling the details.

05 Feb, 2022
Step 3: Navigate Like a Pro

Every destination has its own systems and shortcuts — and I know them all. From Lightning Lanes in the parks to excursion bookings on the ships, I guide you through the logistics so you spend less time waiting and more time exploring.

12 Jan, 2021
Step 4: Stay & Play

Relax knowing I’ve matched you with the right resort, cruise, or adventure, complete with dining, entertainment, and hidden gems tailored to your style. All you need to do is soak in the magic.

Step 5: Support All the Way

Questions pop up? Plans change? I'm with you before, during, and after your vacation — making sure every moment is as seamless and memorable as you imagined.

12 Jan, 2020

About Me

My love for travel started when I learned how to stretch every dollar to give my own family unforgettable vacations. Over the years, that passion has grown into helping others plan stress‑free, meaningful getaways - whether it’s a thrill‑packed theme park adventure, a relaxing cruise, a romantic all-inclusive escape, or a bucket‑list rail journey. I believe travel should feel magical, memorable, and perfectly tailored to you.

Where My Expertise Shines

As a Disney Destinations specialist, I provide thoughtful recommendations, personalized itinerary planning, and concierge-level support from start to finish. In addition to my Disney expertise, these are the areas where my experience, knowledge, and passion shine brightest.

Caribbean Cruising

My experience with Caribbean cruising helps me know how to match travelers with the right cruise line, ship, itinerary, and stateroom. I know what to consider when comparing ports, private islands, dining, onboard atmosphere, excursions, and the balance of relaxation and adventure. I can provide recommendations and help secure the details that make your Caribbean cruise feel sunny, seamless, and perfectly suited to your vacation style.

Celebration Trips

My experience with celebration travel helps me understand how to match the destination and details to the reason you’re traveling. I know what to consider when recommending resorts, cruises, room types, dining, activities, and special experiences for birthdays, anniversaries, graduations, retirements, and other milestones. I can help secure the pieces that make the trip feel personal, meaningful, and easy to enjoy.

Holiday Trips

My experience with holiday travel helps me understand how much timing, availability, pricing, and seasonal demand can affect the trip. I know what to look for when recommending destinations, resorts, cruises, room types, activities, and holiday experiences. I can help secure the right details early and thoughtfully so your holiday getaway feels festive, smooth, and worth celebrating.

Multigenerational Trips

My experience with multigenerational travel helps me understand how to balance different needs, budgets, mobility levels, interests, and vacation styles. I know what to consider when recommending destinations, accommodations, cruises, activities, transfers, and pacing for multiple generations. I can help organize and secure the details so the trip feels comfortable, inclusive, and memorable for the whole family.

World Wide Travel

My experience with worldwide travel helps me turn broad vacation dreams into a clear, thoughtful plan. I know how to compare destinations, travel styles, resorts, cruises, tours, transfers, timing, and itinerary flow based on what matters most to you. Whether you know exactly where you want to go or need help narrowing the world down, I can help recommend and secure the details that make your vacation feel personal, exciting, and well cared for.

Everything I Handle for You

From reservations to hidden extras, my complimentary services cover every detail of your trip so you can focus on the fun, not the logistics.
Travel Reservations & Payments

I book directly with all our partners and manage deposits, payments, and insurance options on your behalf.

Expert Recommendations

From parks to cruises to guided adventures, I craft itineraries that match your family’s style and highlight the best experiences.

Technology & App Guidance

I help you set up and navigate apps and tools like My Disney Experience, Lightning Lane, Virtual Queues, and more.

Priority Reservations

Hard-to-get dining, VIP tours, cabanas, spa services, or special events—I know how to secure the must-dos that make your trip magical.

Dining Planning

From character breakfasts to signature dining, I handle reservations and recommend hidden gems tailored to your tastes.

Transportation Guidance

I simplify airport transfers, port connections, and local travel so you know exactly how to get where you’re going.

Special Events & Extras

Seasonal festivals, themed parties, and one-of-a-kind experiences—I help you fit them into your plans without the stress.

Accommodations & Stays

Whether it’s a resort, villa, cruise stateroom, or pre- and post-trip hotels, I’ll find the right fit for your group and budget.

Travel Documentation

I provide clear guidance on passports, IDs, and any required paperwork so you’re prepared long before departure.

All the Little Details

From stroller rentals to grocery delivery to cribs in your stateroom, I cover the extras that make your trip feel seamless.

What My Clients Are Saying

A well-planned vacation speaks for itself—but my clients are happy to speak up too. Here are a few magical moments, in their own words:
The Hilt Family

We recently returned from a cruise onboard the Disney Treasure. Jen G. with Crazy Imagination Travel helped us plan our trip. She was able to get us 2 staterooms with excellent locations and helped with travel insurance. Working with her made the trip planning and preparations easy and we are looking forward to planning our next trip with her.

The Trent Family

Jen at Crazy Imagination Travel, Inc. took care of us from start to finish helping us create the perfect vacation. Couldnt have asked for a better experience!

The Conners

My wife and I had a wonderful time in Hawaii and enjoyed the recommendations and planning provided by Jen Guthrie. She was quick with responses and recommendations. Just before travel, one excursion needed to cancel due to equipment failure (the boat broke) and Jen was quick to reschedule with a different provider. As well, Jen worked within our budget and followed up with our experience. We will certainly be using Jen Guthrie again to plan trips.

The Mayer Family

I want to share my story and tell you exactly why you need to use Crazy Imagination Travel: Jen Guthrie to book your next vacation. We booked a week at the Wilderness Lodge (my dream resort) and I was officially able to start counting down the days. When we were just under the 80 day mark, my husband sent me a text saying that his employer was not going to approve that week of vacation for him. Needless to say, I had a full blown panic attack/meltdown. But I called Jen Guthrie, our travel agent and through sobs told her what was going on. She said she was going to "work her magic" and would call me back as soon as she knew something. Within the hour, our reservations had been changed to the following week (which I made sure was approved) and we even got a better room for a lower rate. I'm not sure how she did it, but she "worked her magic" and made it happen. THIS IS WHY YOU NEED A TRAVEL AGENT, specifically Jen Guthrie!!! I will never book another Disney trip without her!!!

Your Disney
Dream is Waiting

Let’s turn your wish list into a plan and your plan into an unforgettable vacation. From the first idea to your final day, we’ll make every moment effortless and magical.

Your Magical Journey Starts Here