Your Personal Travel Planner for Disney Vacations, Cruises & Beyond

From First Idea to Final Boarding—Your Journey Starts Here

Custom travel planning for families, couples, solo travelers, and adventurers 50+

An Affiliate Of Main Street Travel

Kathleen Hesketh, travel agent/advisor dressed in red striped shirt, sits at her desk, ready to book travel

Your Journey Deserves More than a Booking

It deserves a personal travel partner who listens, guides, and cares. That’s where I come in.

I’m Kathleen Hesketh, a Connecticut based personal travel planner, lifelong explorer, and Disney enthusiast with more than a decade of experience designing meaningful trips for families, couples, solo travelers, and those embracing travel in the over-50 stage of life. I'm also a proud agent with Main Street Travel, LLC (dba Mickey World Travel), where personal service meets expert guidance. From magical theme park adventures to relaxing cruises and custom-tailored destination experiences, I help you turn travel dreams into reality.

Serving clients from Connecticut and Massachusetts to Ohio, Texas, Oregon, Idaho, Utah and everywhere in between.

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Why Work With Me

Travel Planning that Goes Beyond the Booking

Planning a vacation should feel exciting — not overwhelming. As your dedicated travel planner, I handle the details so you can focus on the joy of the journey ahead. Whether you’re dreaming of a Disney World family vacation, a cruise through the Mediterranean, or a guided tour of Europe’s most iconic cities, I bring the expertise, connections, and personal attention to make it happen.

My service is available at no additional cost to you. I’m compensated by travel suppliers, which means you get expert, personalized planning without paying extra for it.

My Certifications and Credentials

Member of CLIA (Cruise Line International Association) and certified with Viking

Kathleen-hesketh-College-of-Disney-Knowledge-Home2

Graduate Disney College of Knowledge

Travel writer and Travel Agent, Kathleen Hesketh on a mountain with her Golden Retriever, Nemo.

Travel Writer and Member of Travel Writers Alliance

Disney Vacation Planning

As a travel agent specializing in Disney vacations, I offer expert planning for Walt Disney World, Disneyland, Aulani Resort in Hawai’i, Adventures by Disney, and Disney Cruise Line — backed by the resources of Main Street Travel, LLC (dba Mickey World Travel), a Platinum Authorized Disney Vacation Planner.

Disney vacations have a lot of moving parts. I guide you through every decision — from your first question to the day your vacation starts.

Resort Selection: The right resort sets the tone for your entire trip. I'll help you choose the best fit for your group size, budget, and travel style — whether that's a value resort for families on the go, or or a deluxe property steps from the park.

Ticket Types & Park Strategies: With so many ticket options, it's easy to overspend or underplan. I'll guide you to the right tickets for your group and help you make the most of every day in the parks.

Lightning Lane Strategies: Knowing which attractions to prioritize — and when — can make or break your park day. I'll share tips and strategies to help you skip the longest lines and spend more time on what matters most.

Dining Reservations: Disney dining books up fast — sometimes months in advance. When your reservation window opens, I'm up early securing your top restaurant picks so you don't have to set an alarm.

Discount Monitoring: I continuously monitor for new discounts and automatically rebook your reservation to a lower rate when one becomes available for your travel dates and room type.

Cruise Travel Agent Services

Whether you’re a first-time cruiser or a seasoned sailor, there’s a lot more to a great cruise vacation than simply picking a ship and a date. I guide you through every step of the process — from that very first question to the moment you step onboard.

Selecting the Right Cruise Line: Finding the right fit is essential. Every cruise line has its own personality, onboard experience, and energy. I’ll help you navigate the options so you sail with a line that truly suits you.

Choosing the Right Stateroom: Where you sleep onboard matters more than most people expect. I’ll help you select the right cabin category, location, and configuration for your comfort, budget, and travel style.

Pre- and Post-Cruise Planning: Your cruise experience starts well before you board. I can assist with pre- and post-cruise hotel accommodations, flight arrangements through the cruise line, and ground transportation — so the logistics are seamless from start to finish.

Shore Excursions: With so many options at each port, booking shore excursions may feel overwhelming. On most lines, I can book your excursions for you, providing you with peace of mind that bookings are completed correctly.

First-Time Cruiser Guidance: New to cruising? I love helping first-timers feel confident and excited. From how dining onboard works (yes, there’s more than one restaurant!) to how check-in and boarding day unfolds, I walk you through what to expect so there are no surprises — only great ones.

Custom Destination & Group Travel

For travelers who love discovering the world in the company of others — or who want a perfectly curated experience just for their group — I offer expert planning for escorted group tours, semi-private tours, private tours, and river cruises.

I work with leading tour providers like Collette, Tauck, Kensington Tours, Viking and AmaWaterways to connect you with:

Bucket List Destinations — All the highlights, none of the stress, with guided tours through the world’s most sought-after places.

Culturally Enriching Group Itineraries — Led by seasoned guides with deep local insight. Join an existing tour or create your own group experience.

Private or Tailored Group Tours — Customized experiences for your club, family group, or circle of friends, with guides and transportation included.

River Cruises — Discover art, culture, and cuisine along some of the world’s most storied waterways, with the intimacy and elegance of small-ship travel.

Whether you’re joining an existing itinerary or building something entirely your own, I’ll help you find a travel experience that’s meaningful, well-paced, and worry-free.