Disney Vacations
Disney, planned by someone who's done it before.
Walt Disney World Resort is roughly the size of San Francisco. Most families plan it once every few years. I plan it constantly.
Four theme parks, two water parks, more than twenty-five resort hotels, and a booking system with at least six moving parts that all open on different dates. It is genuinely a lot — and the difference between a good Disney trip and an exhausting one is almost entirely decided before you leave Connecticut.
The dates you pick matter more than everything else combined.
What I actually do for a Disney trip
Get the dates right
This is the biggest lever, and it's where Connecticut families have a specific problem: February break and April break send half of Fairfield County to Orlando in the same two weeks. I'll tell you honestly what those weeks cost in both money and crowds — and if you have any flexibility at all, exactly where to move to.
Pick the right resort
"Deluxe" and "Value" describe price, not suitability. A family with a stroller-aged child and a 7am park plan needs something specific. So does a multigenerational group that wants to split up during the day and regroup for dinner.
Handle the booking windows
Park reservations, dining and the paid line-skipping systems all open at different points, and the good ones go quickly. I'm awake for those. You don't have to be.
Build a plan you can abandon
A day-by-day that gets you onto the big rides early and then lets you stop caring by lunchtime. Rigid Disney plans make people miserable.
Watch for promotions after you book
Disney releases discounts on a schedule nobody publishes. If one applies to your trip, I reapply it and your price drops. Nobody is doing that for you if you booked direct.
The part nobody warns you about
Getting to the parks is the easy half.
What actually wrecks trips is logistics — and this is where having an advisor stops being a nice-to-have. I book all of this:
- Airport transfers — Mears Connect, the Sunshine Flyer or private car, depending on your party and arrival time
- Stroller and wheelchair rental — delivered to your resort, not queued for in a park
- Groceries in your room before you arrive — water, breakfast, snacks. This single item saves most families several hundred dollars
- Scooter and accessibility rental, arranged in advance
- VIP tours and private guides, when the trip warrants it
- In-room childcare through vetted providers, if you want an evening out
Almost no agent lists this. It is the difference between arriving and arriving ready.
Beyond Walt Disney World
From Connecticut, specifically
Most Fairfield County families fly to Orlando from LaGuardia, JFK, Newark or Bradley. They are not equivalent — the fare, the drive, the parking cost and the schedule reliability all vary, and the cheapest fare is frequently the most expensive trip once you total it up. I'll run the real comparison for your dates and your party size.
It costs you nothing
Disney pays my commission. Your price is the same as booking direct, and you get the planning, the promotion monitoring, and someone to call when a flight cancels.
And often, it costs you less. When I book a trip, I often have access to savings and promotions, and when I do, I pass them on to you. In many cases I can book the very same trip, still earn my commission from the supplier, and get you in for less than you'd pay booking it yourself.
Before you go
More ways I can help.
February break, planned honestly
Why the week most Connecticut schools break is one of the busiest of the year, and how I'd plan it if your dates are fixed.
Read the post →
Cruises
Sailings you can drive to from Fairfield County, planned around the cabin that makes the week.
Explore →
All-Inclusive & Caribbean
Warm-weather beach resorts, matched to your family and the way you actually like to spend a week.
Explore →Tell me where you want to go.
No fee, no obligation. Most first conversations take twenty minutes and end with a couple of ideas worth thinking about.
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