Family Vacation Planning Services
whimsical wishes travel concierge
WHAT WE PLAN
Here are the six things we do more than anything else.
If your trip isn't on this list, ask anyway.
You already know the trip you want your family to have. The hard part is the six weeks of open tabs, contradictory forum advice, and second-guessing that sit between here and there.
That's the part we do. Whimsical Wishes plans family vacations end to end - the destination, the resort or the ship, the timing, the reservations, and the hundred small decisions that separate a good trip from one your family still talks about years later.
You work with one advisor who knows your family. Not a call center, not a booking engine, not a chat window. A person who remembers that your youngest melts down in the heat and your oldest will not be separated from the teen club.
WALT DISNEY WORLD
Our deepest specialty, and the one families come back for. We handle resort choice, tickets, park days, dining, and Lightning Lane strategy - planned around how your family actually travels rather than how the internet says it should be done. Rope drop is not for everyone, and we'll tell you if it isn't for you.
DISNEY CRUISE LINE
& DISNEY BEYOND THE PARKS
Disney Cruise Line, Disneyland, Aulani, and Adventures by Disney. Cruising is where a lot of park families end up once they realize they can unpack once and still get the same care - and picking the right ship, itinerary, and stateroom matters far more than picking the right week to book.
UNIVERSAL ORLANDO RESORT
We are a Universal Preferred Travel Agency, which means we plan Universal Orlando the way we plan Disney - hotel choice, Express Pass strategy, and which days to spend where. Especially useful for families splitting a trip between both, where the order of the days changes the whole week.
FAMILY CRUISES
Royal Caribbean, Norwegian, Celebrity, Princess, and the rest. Cruising with children is its own sport, and the right ship matters more than the right price - a ship that suits a family with toddlers is not the ship that suits a family with three teenagers. We match the ship, the itinerary, and the stateroom to the crew you're actually traveling with.
ALL-INCLUSIVE RESORTS
Mexico, the Caribbean, and beyond. Not every all-inclusive is built for families, and the differences are almost impossible to see from a website. We know which resorts get young kids right, which get teenagers right, which have the quiet adult corner worth paying extra for, and which ones photograph better than they live.
EUROPE WITH KIDS
Italy, Greece, the UK, France, and the places families assume are too complicated to attempt with children. They usually aren't - it's the logistics that stop people, and the logistics are the part we do. Our favorite version is the one that looks like the vacations you already love: somewhere beautiful on the water, slow mornings, long dinners, and the culture just there rather than scheduled.
What it looks like to plan with us
Tell us about the trip. Fill out the Get Started form with as much or as little as you know - some families arrive with a spreadsheet, others with "somewhere warm, February, help." Both are fine.
We talk. A real conversation with the advisor you'll be working with, about your family, your budget, and what you're actually hoping this trip feels like.
We plan it, and you go. We build the itinerary, handle the reservations and the timing, and stay with you through the trip - including the day something doesn't go to plan, because occasionally something doesn't.
Why families trust us with the planning
Whimsical Wishes Travel Concierge is a women-owned agency based in Massachusetts, working with families across the country.
We are EarMarked by Disney as an Authorized Disney Vacation Planner and a Universal Preferred Travel Agency. We are members of ASTA, the American Society of Travel Advisors, and we are affiliated with Travel Leaders Network, one of the largest travel agency networks in the world.
Those are the credentials. What they mean in practice is that our advisors have stayed at the resorts, sailed the ships, and walked the parks - and that when we tell you something is worth it, we're telling you from experience rather than from a brochure.
Questions families ask before they get started
Do travel advisors at Whimsical Wishes charge a planning fee?
Many of our advisors charge a planning fee, and we encourage it. Planning a family trip well takes real expertise - knowing which resort fits your family, which ship, which week, and the hundred details that are hard to see from a website. A planning fee reflects that work. Your advisor will tell you what theirs is before any planning begins, so you always know upfront. What you get for it is judgment you can trust and a lot of hours back.
Will the trip cost more than booking it myself?
Generally no. Most of what we book is priced the same whether you book it or we do, because our commission is paid by the resort, cruise line, or supplier rather than by you. What changes is what you get for that same price - someone watching for price drops and promotions, handling the reservations, and fixing things when they go sideways. Where a planning fee applies, your advisor tells you before any work starts.
What if we've already booked part of the trip?
That happens often and it's usually fine. Depending on what you've booked and how, we may be able to take it over and manage it alongside the rest of your trip, or we may leave it as-is and build around it. Tell us what's already in place when you get in touch and we'll be straight with you about what we can and can't help with.
What happens if something goes wrong while we're traveling?
You call us. A canceled flight, a room that isn't what was promised, a closure, a family member who gets sick - this is the part of the job that never shows up in a brochure and matters most when it happens. You are not filing a ticket or waiting in a chat queue. You're calling the advisor who planned the trip and knows exactly what you booked.
How far in advance should we start planning?
Earlier than most families expect. For Walt Disney World, nine to twelve months out gives you the best resort availability and the widest choice of dining. For cruises, twelve to eighteen months for the sailings and staterooms people actually want, longer for holiday weeks and Alaska summers. All-inclusive resorts and Europe are more forgiving, though the best weeks still go early. That said, we plan trips on six weeks' notice regularly - if the trip is sooner than that, ask rather than assuming it's too late.
Do you only plan Disney trips?
No. Disney is our deepest specialty and it's where many families meet us, but we plan Universal vacations, ocean and river cruises, all-inclusive resort stays, and family travel through Europe. If it's a meaningful family vacation, it's probably something we do. Tell us about the trip you're thinking about. There's no obligation and no script - just a conversation about where you're going and what would make it worth the trip.
Tell us about the trip you're thinking about.
There's no obligation and no script - just a conversation about where you're going and what would make it worth the trip.