Kids swimming in a poolDo you ever come home from “vacation” exhausted? In February, we took our family to Orlando. We stayed at a kid-friendly resort and took our oldest to Magic Kingdom for a day. For the most part, we had near-perfect weather (high 60s, low 70s with sunny days) and a convenient location. We were able to walk almost everywhere we needed to go, and we had family traveling with us who could help with the kids so that we could get an occasional break. But I learned that family trips are not the same thing as a vacation, and that it’s important to prepare accordingly.

Now that we’re back, I can safely say that conquering my first week-long vacation with our young family is something I’m happy to have experienced, but also happy to have behind me. There are no regrets on my part and I’m so glad we went (the kids had a blast!). However, I now know several things I would do differently next time, and you might also be able to learn from them for your future family trips.

Now that I’ve had the experience, next time, we’ll aim to prepare for our family trip by:

Going for a shorter amount of time

Being away for eight days was far too long for me. I think four to five days might be a sweet spot. Since having our twins, we’ve gone away for three days a couple of times. So eight days was a giant leap for us. Four to five days feels like just the right amount of time, not too short and not too long.

Planning something to do every day—for everyone

As I mentioned, we had one day planned for Disney. We’d planned to spend the rest of the time at different pools at the resort with my husband’s family. It ended up being a little harder with my twins since we didn’t want to keep them out in the sun for too long, so we ended up splitting up a lot. My husband and I joke that I have a hard time sitting still and relaxing, which is 100% true. I think planning something to do other than the pools would have helped everyone.

Approaching meals and snacks differently

We were lucky that our hotel room had a full kitchen, but my husband and I also felt like we didn’t get a break from making food and cleaning up after our three little ones. Next time, I would meal plan and meal-prep when we first get there (I did a little before we left, but not enough for the week), and then plan specific days to get takeout. My husband and I have also discussed looking for hotel options that includes some or all meals, as well as more activities geared towards little kids.

Looking back, the time we got to spend together as a family was invaluable. Watching our three kids smile and play is such a gift that we get to experience. Now that we’re planning to do things a little differently next time, I’m already looking forward to planning our next family trip.

In search of more travel tips? Check out Flying with Two Toddlers: A Success Story. You can also read Traveling With Toddlers :: Can We Talk About the Good Stuff Too? for another take!

Ashley Flanagan
Ashley Yehl Flanagan has lived in Dennis, MA since 2017, when she and her husband Chris moved from Washington, DC. While on Cape, Ashley has been an active part of the Cape community, including participating as board member of Friends or Relatives with Autism and Related Disabilities (FORWARD) from 2020-2022, member of Cape Cod Young Professionals, and as a parishioner of Our Lady of the Cape. Ashley met her husband Chris Flanagan in 2014, and after four years of dating, tied the knot in 2018. Ashley and Chris are raising three children on the Cape, their daughter and twin boys. During Ashley’s senior year of college, she started a career in the federal government, which led her to travel to 106 countries doing public affairs work. For the past six years, Ashley has been a senior member of press operations at a federal agency, where she leads public communications on global issues. Growing up, Ashley aspired to be a journalist and while in middle school, wrote movie reviews for her local paper, The Hill Country News. She graduated from American University in Washington, DC and lived in London during her junior year.


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