How I Plan Our Family Adventures

During my recent poll for blog topics on Instagram, travel and activity planning for family adventures was one of the most requested topics.

Throughout the year, when I share our trips and vacations, I often get questions like, “How far in advance do you plan?” and “How do you budget for trips?” Since this post was originally published in 2021 and has been one of my most popular, I’ve heavily updated it to reflect where we are now—so much has changed in the last four years!

I love organizing our family trips and activities, and now felt like the perfect time to revisit this topic and share my updated process with you. Also, you can find ALL of our family adventures HERE!

Before diving in, I want to quickly address two things.

First, I am still the primary planner for our family trips and activities (which Matt is totally fine with!). I’m almost always juggling multiple plans, big and small. There’s something about the process of planning—whether it’s a weekend getaway or a bigger family vacation—that really excites me. Once I’ve got things almost nailed down, I’ll loop Matt in for his input and final stamp of approval before it’s a done deal.

Second, if you’ve been following along for a while, you might remember that we didn’t take our kids on big trips when they were younger. While we always made time for family beach days and mountain weekends, we saved our bigger vacations for just Matt and me. But now that our kids are 9 and 10, traveling as a family has become a total game-changer. They’re old enough to appreciate new destinations, and it’s so much more enjoyable to bring them along for the adventure!

Family Planning Meeting

We loosely plan and budget for all of our holiday plans and major trips during our Annual Family Planning Meeting. In this meeting, Matt and I sit down together (with the kids’ school and summer schedules in front of us) and discuss family trips we’d like to take, along with the timing and destinations for our annual getaway just the two of us. We also review our recurring traditions to see which ones we want to continue (like our camping, snow tubing, river tubing, etc.) and brainstorm ideas for new trips or traditions (this year we really want to take the kids to some football games).

Budgeting for Family Adventures

We have a separate vacation savings account where we contribute throughout the year—usually on a monthly basis. The amount we contribute varies depending on other expenses. Additionally, while it may not be a popular approach, we put every penny we can on our credit card and pay them off in full each month. It’s incredible how quickly the points add up! If there’s no fee for using a credit card, we always choose that option. We use the Chase Freedom credit card.

So, what do we do with all those points? We apply them towards flights for our bigger trips and also cash them in for hotel stays throughout the year (like our annual anniversary staycation). While this strategy might not align with the advice of Dave Ramsey or many others, it works really well for us.

Planning Bigger Family Adventures & Travel Advisors

We typically plan and budget for two big vacations each year—one for the family and one just for the two of us. These are the trips I don’t handle on my own, and we usually book them 8 to 12 months in advance. For any destination outside the U.S. or any trip requiring a flight, I turn to a Travel Advisor to ensure every detail is taken care of.

Travel Advisors

• Christine Serio has planned many of our international trips over the years — most of which have been to Turks & Caicos! Not only does she take care of all the details that are not fun to plan (like resort transfers), she has relationships and connections that come with extra perks (like upgrades) and has extensive travel knowledge.
• Megan Halberstadt of MH Custom Travel planned our Costa Rica vacation last year (after she was recommended to me as a planner with lots of Costa Rica experience) and we loved her so much we are using her again for several trips this year!
• For anything Disney related, I highly recommend Kim Ellison with Marvelous Mouse Travels. She is truly a Disney expert and made our Disney Trip and Disney Cruise SO easy and magical.

International Family Adventures by Age

Traveling internationally with our kids has been such a fun experience, especially as they’ve gotten older! We didn’t start taking them on international trips until a few years ago, but as they’ve grown, we’ve learned what works best at different ages. I’m sharing some of our favorite trips by the kids’ ages to give you a glimpse into what destinations worked really well for us!

• Beaches Turks & Caicos (Ages 6 & 7)
• Disney Wish Cruise (Ages 7 & 8)
• Rosewood Mayakoba Riviera Maya Mexico (Ages 8 & 9)
• Costa Rica (Ages 9 & 10)
• NEXT TRIP: Hotel Xcaret Mexico

Summer Activity Scheduling

Believe it or not, I start planning for summer as early as January (yes, January—wild, right?). That’s when I begin working on our summer plans, mainly focused on securing spots for summer camps. Some of the larger, full-day camps open their registration in January, and spots fill up fast! We also start reserving our family beach trip weeks as early as possible. You can find my summer scheduling template HERE.

By March or April, most of our camps are locked in, though sleepaway camp is usually booked months in advance. As the school year winds down, that’s when we dive into our Summer Bucket List. It’s usually pretty ambitious, but it’s so helpful to get everything the kids want to do down on paper. From there, I start slotting in activities like renting a boat or river tubing, looking at the available summer weekends on the calendar, and adding placeholders for everything we want to fit in.

Holiday Breaks & Annual Traditions

School breaks are a unique challenge to plan for, so I wanted to dedicate a separate section to how we approach them and our annual traditions. At the start of the year, I review all of the school holiday breaks and try to plan fun weekend getaways—whether it’s a mountain weekend, a camping trip, or a few days at the beach.

As the kids have gotten older, we’ve really enjoyed quick trips around the holidays. For these trips, I almost always book them as soon as I return from the previous one. This way, I avoid fighting the crowds and paying inflated prices around the holidays. As my dad always said, “The early bird gets the worm!”—and it really rings true! For example, a few years ago we had such a great time tacking on a quick mountain getaway the day after Thanksgiving to go ice skating and cut down our Christmas tree. As soon as we returned home, I went ahead and booked a cabin for the next year. Yes, that’s a year in advance, but booking early meant we got an amazing spot at an unbeatable price. Plus, I find it way more fun to plan the next trip while still riding the high from the previous one, instead of planning winter trips during the heat of summer.

Another tradition we’ve learned to book in advance is our Labor Day Weekend Camping Trip. While there are plenty of campsites you can snag last minute, the most popular spots book up far in advance. When I reserved our 2020 tent site, I was told that beach campsites were already filling up for the next year, so I booked our 2021 site right after we returned from our 2020 trip. We knew we wanted to do it again, and now it’s become a tradition we plan for a year in advance!

Another tradition we’ve learned to book far in advance is our Labor Day Weekend Camping Trip. While there are plenty of campsites you can snag last minute, the most popular spots book up far in advance. After reserving our tent site one year, I was told that beach campsites were already filling up for the following year, so I went ahead and booked our site right after we returned from our trip. We knew we wanted to do it again, and now it’s become a tradition we plan for a year in advance!

Family Tent Camping Trips

• 2024 Bandits Roost, North Carolina
• 2023 Hunting Island, South Carolina
• 2022 Hot Springs, North Carolina
• 2021 Edisto Island, South Carolina
• 2020 Table Rock, South Carolina

I think that covers everything! If you have a question, drop it in the comments! And if you have any fun destination or activity recommendations, please share those too!!!

You can find all of our Family Adventures HERE!