The Itinerary | 5 Tips for Planning a “Split” Family Vacation

I am here to tell you that it is possible. Some of you have read in other posts that my parents divorced when I was very young, and so growing up my brother and I adapted early on to a “split” schedule; alternating holidays, vacations with either side of the family at different periods of time throughout the year, and we were able to do it without any holidays or special events being ruined - instead, we learned how to plan trips and holidays so that everyone could be involved and we got to see family on either side just as often!

In this post I will highlight some of the things we learned as kids that I have carried into my adult life. Being engaged, almost married, means that I now have another “side” to see, and I don’t mean to brag, but I think we do a pretty good job making the most of a week back in the Lakes Region or Maine all while keeping these things in mind before, during and after!


1. Get everyone’s schedules, and plan out the “day trips” or larger events in advance.

Whenever Bryer and I have locked in some vacation time, we come up with our “itinerary” before we even get to our destination; sometimes even months in advance. This will consist of things we have been aching to do for a while or places we have wanted to visit or re-visit since the last time we were visiting family. Once that “wish list” is created, or we have factored in a birthday party or wedding shower etc., we will touch base with ALL the family members - I’m talking brother and his girlfriend, dad, mom, sister, best childhood friends, in-laws; anyone you want to see. Leave no stone unturned.

Coordinating ahead of time will make it so that there are no feelings hurt when someone can’t make it to something, that same thing can be avoided in most cases so that everyone can be together, and you can better make decisions about who to see first etc. based on availability and work schedule.

Our personal experience is that locking in the plan ahead of time is a great way to keep everyone happy, included, and also off your back when all you want to do is relax. They know what to expect and how long they will get to see you. It’s a win-win.

2. A week is NOT a year - you can’t do everything, so be okay with that before you leave.

That itinerary I just talked about? Yeah, good luck getting to everything! Actually, before you go, get comfortable with the idea that half of it won’t happen.

I sound like a hypocrite, but while it is a great planning tool when deciding who you can see when, it isn't the best for “keeping you on schedule” while you’re actually visiting.

For example, every time I plan a trip to see my family in NH, I fill the itinerary with all of my favorite things to do; I’m going to kayak on Squam Lake, mini golf at Pirates Cove, play ski ball at Funspot, hit ALL the thrift stores, and drink all the Wayfarer Coffee, etc., and though at the time I’m planning I feel like its a great plan, more than half of my trip ends up filled with time sitting at home on the couch watching movies, sitting out at the fire just having a laugh, or playing board games with family... which truly ends up being better than running around trying to hit every store and outside destination I had listed in the first place.

Those moments are ones that you will hold closest to your heart in 20+ years - roll with it and see the beauty and comfort in it. Trust me! Plans change, and that is okay.

3. Pack comfortably AND light.

I’ll be honest, I still haven’t mastered this one, so do as I say, not as I do. But really, this is just one of those things that I have learned over the years... no matter how many new summer outfits I want to bring for when we “go out” etc. the majority of the time I am on vacation I am sporting cloth shorts, unwashed hair, pajamas, and plastic flip flops. Comfort is key here. After all, this is a time for you to be unwinding and decompressing from whatever it is that winds you tight during your norm.

Also... if you are like my sister and I, you will go back home with a suitcase (or more) of clothes and other things that you didn't come with. Account for shopping and gifts by packing light and leaving room for those new items you’ll be lugging around. It will help you stay organized.

4. Be okay with not taking photos, and just live in the moment.

I am over the idea in this stage in my life that if there isn’t a picture of it, it didnt happen. I definitely got caught up in that for a long time, and though I look back at all of those photos very fondly now, I do sometimes catch myself wishing I had been more of a part of the experience; a part of the present moment. My Mom and I have maybe two pictures together in the last five years and that is because we are always the ones to pick up the camera to document what’s going on.

I own a BEAUTIFUL Canon camera that is finally paid off in full, I have a polaroid, and I have a cell phone which I carry with me always, but still somehow leave a week long vacation period with a couple of pictures of my Mom’s cats, my Dad’s backyard and some food I ate. What I have come to realize is that all the moments that stand out, will stand out later on for the same reasons - pictures or not. The photo doesn't make it a great memory, you being there for it does!

5. Factor in your home base.

When planning a trip where you will have to travel multiple places, over a short period of time, always be considering where you are starting and where you have to get back to when it comes to location.

Where we live in Worcester, we are two and a half hours from both my family in Laconia and Bryer’s family in Maine. We luck out here because no matter where we go first, we are only one hour from the other family and two and a half hours back home. In your case, you may have family 4 hours from home and other friends or family an hour from you. In that case, I always say do the big chunk of traveling first - no one truly hates a road trip when you have something to look forward to when you get there, but after a week’s worth of day trips or even just lots of visiting, it can be mentally exhausting to think about traveling four hours home, unpacking and getting everything ready for work the next day. Give yourself that extra time to get acclimated back into your space instead!


Especially in the world we are living in now, I feel like my urge to travel elsewhere and be on my own in any capacity possible has faded a bit, and instead the urge is to go back where I know it is safe and familiar - which is okay.

It means more to me to spend time with my sister cleaning out her closet, my brother cooking a meal in my Mom’s kitchen, my Dad outside of his house he just built, sitting by a fire and roasting marshmallows, or with my Mom playing badminton out in the street or sewing a t-shirt quilt.

I urge you during this period of all of our lives to adopt the idea of simplicity, and think hard about the things you take for granted on the daily. If this pandemic has taught me anything it is that you can’t always have a plan that works out perfect. You can’t always do everything or say the right things. You can’t have all the expensive things in life. But you can have your family - no matter if that means your biological family, your animals or your truest friends. Family is a truly remarkable and unbreakable normality for me, and I think this period of time has just reinforced that.

Happy travels, friends! Stay safe!

XOXO Autumn