During my last “Ask Me Anything” poll on Instagram, the most popular questions I received were around travel and activity planning. How far in advance do we plan? How do we budget for trips? And a few other questions. I love planning our family activities and trips so I thought I’d address all these questions and more in a blog post!
Before I dive in, I want to cover two quick things!
First, I am the primary travel and activity planner for our family (which Matt also prefers) and I am almost always working on multiple (big and small) plans at any given time. Similar to blogging, there is something about planning out activities, parties or trips that truly excites me. So once I have everything nearly finalized I’ll loop Matt in for his thoughts and stamp of approval before taking it to the finish line.
And second, if you’ve been following me for a long time you may recall that we did NOT bring our babies on big trips with us. While we still did lots of kid-friendly, age appropriate activities throughout the year and enjoyed family mountain or beach trips, we opted to budget more of our pennies to parent-only vacations. It wasn’t until maybe 2-3 years ago that we began traveling to cooler destinations as a family and now that our kids are 6 and 7, it is SO MUCH EASIER and WAY MORE FUN to take them places — and they actually appreciate them!
Family Planning Meeting
All of our holiday plans and bigger trips are loosely planned and budgeted for during our End of Year Family Planning Meeting. During this meeting, Matt and I sit down together and discuss any big trips we want to take as a family over summer break, as well as timing and destinations for our annual trip away as just the two of us. We also start tossing out ideas for Spring Break plans and discuss any re-occurring traditions we plan to continue (cabin weekend, camping weekend, snow tubing weekend, river tubing weekend, etc.).
We have a separate vacation bank account that we contribute to throughout the year — usually monthly. Depending on other expenses we incur, each month the amount fluctuates. Additionally, while it may be an unpopular way to manage money, we put every penny we can on our credit cards and pay them off each month. It’s amazing how many points we can quickly accumulate just from daycare payments alone! If something can be paid for with a credit card (and there’s no fee for using that payment method), we always choose that option. We use the Chase Freedom credit card as our primary card and a second Chase Marriott credit card that I use for business expenses (although I am considering switching to an Amazon credit card since I don’t travel as much as I used to). The Marriott card comes with a free night award each year but can only be applied towards really low hotel categories (like near airports) and there is also an annual fee (I think it’s $99).
So what do we do with our points? We apply them towards our flights for bigger trips and also cash them in for hotel stays throughout the year (we stay at the Ritz for our anniversary every year on points) and most recently we used some points to stay in Asheville with the kids. So while Dave Ramsey and probably many of you would disagree with this approach, credit cards work really well for us.
Planning Bigger/Expensive Trips
We usually plan and budget for two bigger trips each year — one as a family and one trip as just the two of us (usually Turks & Caicos). These are the two trips I do NOT plan on my own and we usually lock in anywhere from 8 months to a year in advance. If it’s a destination outside of the US or requires a plane, I turn it over to our wonderful Travel Advisor, Christine Serio. She has planned almost every trip we’ve taken out of the country. 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. I should also mention how easy she made it for us to travel out of the country with the constantly changing COVID restrictions. She was on top of every single thing from forms that needed to be completed to testing requirements so I could focus on more fun things like planning excursions, restaurant reservations, etc.
I also do NOT plan any Disney trips and instead rely on Kim Ellison with Marvelous Mouse Travels. She is truly a Disney expert and made our Disney Trip SO easy and magical. She also just helped us plan our big family vacation for next summer — a Disney cruise!
Summer Activity Scheduling
Starting in late January (Yes, January. And I know, it’s wild.) I begin working on our summer plans — mostly summer camps. Some of the bigger full-day camps open their registration in January and it fills up extremely fast, and as a working mom who relies on almost 13 weeks of full day summer programs, I have got to be on top of camp registrations!!! We also start reserving weeks during summer for family beach trips as early as possible. You can find my summer scheduling template HERE.
Our camps are usually nailed down by March/April. Then closer to the end of the school year is when we create our Summer Bucket List! The list is ambitious but it’s nice to have all of the things the kids want to do down on paper so I can start planning all the activities. From there, I look at all the summer weekends on the calendar and start slotting in placeholders for the bucket list activities like renting a boat, river tubing, etc.
Holiday Breaks & Annual Traditions
Since school breaks are a unique beast to tackle, I wanted to carve out a separate section for these and our annual traditions as we approach planning these a little different. At the beginning of the year, I look at all of the school holiday breaks and try to plan fun little weekend getaways. For me, if my office is closed for a holiday (MLK, Labor Day, etc.) giving us a 3 day weekend, I am absolutely going to take advantage of the extra long weekend by planning something fun. This may be a quick trip to Florida, a weekend in the mountains, a camping trip or a few days at the beach.
As the kids have gotten older, we’ve really loved creating new traditions around the holidays too. For these trips, I almost always book it as soon as I return home from the previous trip so I’m not fighting the crowds for inventory around the holidays or paying super inflated prices. As my dad would always say, “early bird gets the worm!” — and that is so true! For example, last year we had so much fun tacking on a quick mountain getaway the day after Thanksgiving to go ice skating and cut down our Christmas tree that I booked our 2021 cabin a few days after we got home. Yes, that is a YEAR in advance, but since we were so far out we were able to find the coolest place at a shockingly low rate. Additionally, for me it’s way more fun to plan the next trip when I am still on the high from the previous one, versus planning winter trips when it’s 90 degrees outside.
The other weekend tradition we’ve learned to book a year in advance is our Labor Day Weekend Camping Trip! Now there are plenty of places you can snag a last minute campsite at, but the really cool ones book waaaaay out. When I reserved our 2020 tent site last year, I was given a tip that if we wanted to try beach camping that the reservations for a year out were already booking up so I went ahead and booked our 2021 tent site right after we returned from our 2020 camping weekend and knew we wanted to do that again and again!!
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!!!
Oh my gosh- so impressed by how organized you are!! Love hearing this insight into your planning process.
Love this my friend – obsessed with the organisation and I love all your family trip photos and memories!
Thank you for sharing x
Are your travel planners local to Charlotte or they online travel planners?
Kristin W says
This is wonderful. I love planning trips and I always like hearing how others do it. We also use our credit cards to maximize points and paying them off every month. Whatever works!
I’d love to hear about some of the couples bucket list trips that you and Matt would like to take!
This is a fantastic guide! Thank you for putting this together and sharing!
Susan Halvatzis says
Amazing post!!! Thank you for sharing and TOTALLY using all of your methods – wow! Go mama!!!
We plan our vacations very similar. Our children are now 5 and 10 so we have just started this year to take bigger family vacations rather than saving those trips for just the two of us. We sail so we did a bareboat sailing charter in the Exumas this year and it was our best vacation to date (I highly recommend this for a family vacation even if you don’t sail because you can do a crewed charter)! We also maximize credit card rewards and loyalty programs and I think it is a fantastic way to travel! I just booked 11 nights in Anguilla and St. Barth for next summer using miles for airfare and hotel points for the Anguilla portion so the trip is a total steal for a family of 4! We have also visited T&C and since you love that destination I really think you should look into Anguilla and St. Barth! Anguilla would be most similar to T&C as it’s a flat island with beautiful beaches but St. Barth is very special-truly a bit of France in the Caribbean!
Carolyn H says
Thank you for this post, I love reading about stuff like this and it was so helpful! I would love a part 2 with trips you have in mind for the family down the road and if you’re saving them for the kid’s to reach specific ages and any bucket list trips on your radar for you and Matt.