Family & Multigenerational Travel Specialist

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Stacey Iskovitz, Travel Agent in Mount Kisco, NY

Stacey Iskovitz

Mount Kisco, NY Travel Agent
Super Agent

Stacey Iskovitz

Mount Kisco, NY · 8 Years of Experience

Stacey Iskovitz, Key to the World Travel, an independent agent with Key to the World Travel LLC, a Travel Leaders Network Affiliate Agency
5.0
(18)
100% Recommended
Stacey helped us to plan the most incredible Disney trip - it was the first time for my family of three children and going back to... Read More >
About
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Areas of expertise

Destinations:

Florida, Riviera Maya, Caribbean

Interests:

Family Vacations, Disney Vacations, All Inclusive, Cruises, Luxury Hotels

Suppliers:

Disney, Disney Cruise Line, Universal Parks & Resorts Vacations, Funjet Vacations, Inclusive Collection – World of Hyatt

About Me

Three generations, one golden hour
Three generations, one golden hour

Grandma wants dinner at five. The teens want to sleep until noon. The seven-year-old wants the pool, the castle, and the ice cream place, in that order, before 9 a.m. That's the trip I plan most: one family, three generations, and a plan that works for every one of them.

I plan these trips the way I travel with my own family. I've sailed Disney Cruise Line with my boys and again with my mom, taken my teenagers to London, and been to Walt Disney World more than 50 times. I know where multigenerational trips tend to break down: one family's room is a ten-minute walk from the other's, the schedule works for the kids and wears out the grandparents, or the teens are bored by day two. I fix those things before you leave.

The hotel decides most of the trip, so that's where I start. For a bigger group, that might mean connecting rooms, a two-bedroom suite instead of two standard rooms, a villa, or a club level where everyone has a place to gather. I look at walking distances, pool setup, kids and teen clubs, dining that works for picky eaters and serious food lovers in the same group, and how long the transfer is from the airport.

I plan family and multigenerational trips to Walt Disney World and Universal Orlando, all-inclusive resorts across Mexico and the Caribbean, family cruises, and Europe. Whether it's a milestone birthday, a reunion, or the trip your family has been talking about for years, it starts the same way: who's traveling, and what each of them needs out of it.

From there, I build the plan around your group. Pacing that leaves room to rest, a few things everyone does together, time for each generation to do their own thing, and one person (me) tracking every reservation, so nobody in your family has to be the trip planner.

I've spent eight years planning trips like these, and today I'm Senior Travel Advisor and Education Coach at Key to the World Travel. As a Travel Leaders Network advisor, I also have access to partner perks and amenities that can add real value to your stay.

Tell me who's traveling, their ages, and when you're thinking of going, and I'll tell you where I'd send you.

REVIEWS

Rating: 5.0
18 reviews
100% Recommended
Your trust is our priority. Every review is submitted by verified travelers after they have booked and completed their trips. Learn more about our review guidelines.
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Showing 18 reviews

Incredible trip
Reviewed By Lizm1390 - NY | Traveled to Kissimmee | Florida | USA
Stacey helped us to plan the most incredible Disney trip - it was the first time for my family of three children and going back to see Disney through their eyes was so magical. Stacey not only gave excellent tips but she also woke up very early (during the holiday season) to book our dining and make sure we got all the restaurants we wanted. We can’t wait for Stacey to plan our future trips to Disney!
✓ I would recommend this agent to my family and friends.
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Guided Me Through the Entire Planning Process
Reviewed By BrooklynMom - Brooklyn, NY | Traveled to Walt Disney World | Florida | USA
Stacey helped me plan my trip from start to finish- she was very responsive and did a wonderful job of breaking down information into bitesize pieces so the planning process felt way less daunting!
✓ I would recommend this agent to my family and friends.
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The Wild West
Reviewed By V. Hallett - Westchester, NY | Traveled to Wyoming | USA
My boys 8 and 10 at the time wanted to experience the historical sites associated with the Wild West- pioneers, cowboys, and Native American tribes. I also wanted to add a few days at a Dude Ranch and my husband wanted to include some National Parks. Stacey listened and put together the most amazing itinerary inclusive of hotels, historical sites and the driving times between each location. We had two rounds of discussion and our 10 day dream vacation was set. Stacey created an itinerary that took us through Wyoming that included all our requests along with Rodeos, Native America traditional ceremonies, sites of the famous outlaws such as Butch Cassidy and the Sundance Kid and the trip ended with Yellowstone and Grand Teton National Parks. I am very thankful for her skills! I have enlisted her services multiple times since.
✓ I would recommend this agent to my family and friends.
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Best Travel Planner!
Reviewed By Rebecca G - Millwood, NY | Traveled to Walt Disney World | Florida | USA
Stacey helped us plan 2 trips (and one pending next year!). She made understanding the Disney ecosystem so much easier and gave us all of the tools we needed for a great trip. We had such a great time in 2025 that we are going back in 2026! She also booked an all inclusive at Dreams Macao in Punta Cana, Dominican Republic and was so helpful in narrowing down our options and choosing our resort. We loved it! Stacey is so knowledgeable and truly available and supportive throughout all stages of the planning process. Can’t wait to book more trips with her in the future!
✓ I would recommend this agent to my family and friends.
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Best spring break at Dreams Flora in Punta Cana!!
Reviewed By MelissaW - White Plains, NY | Traveled to Punta Cana | Dominican Republic | Caribbean
Stacey has booked our family vacations to Disney before, so she already knew what we’d like and she absolutely nailed it with our spring break at Dreams Flora in Punta Cana! We loved the resort! It's conveniently close to the airport, the food was delicious, and we were able to truly relax even with three kids! We already want to go back for next spring break!
✓ I would recommend this agent to my family and friends.
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My Places

When it comes to travel planning, real-world experience makes a huge difference. Check out the map below to see all the places I have personally visited or booked for my clients. I know these destinations well and can give you reliable guidance.

My Photo Albums and Videos

Disney Cruise with Mom
View Album

    My Travel Stories

    Nose to nose with a new friend.

    Atlantis: Three Generations and Some Rapids

    When Matthew went to Italy with my in-laws and my nephew, Jordan wanted to know what he got to do. Fair question. So we planned Atlantis. Seth and I let Jordan bring a friend, and my mom came too. She'd always wanted to go back to Nassau. We stayed on the concierge level in the Royal Towers, and the lounge became our home base. We grabbed...
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    Flew 3,400 miles to watch the Jets lose.

    London With My Boys: A Jets Game Across The Pond

    The night before the Jets played the Vikings, we came back to our room at Four Seasons Park Lane and found chocolate strawberries dressed up as footballs waiting for my boys. The staff left a treat every night, but that one was timed perfectly. Details like that are why the hotel matters so much when kids are along. Seth and Matthew have ...
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