How to Have the Best Mother-Daughter Trip

Spoiler alert! My daughter and I create a curated itineraries when we travel together. It has a little for her, a little for me, and a little for both of us. And when we’re living the itinerary – boots on the ground – we’re flexible and accommodating. Can’t take another step? Must stop for wine? Walk across what bridge?

Yep, we make changes on the fly, rearrange the schedule, and cut if we need to. It comes down to planning, a little compassion, and grace. That’s how we make it work now but we didn’t always. We learned the hard way.

When we started traveling together we didn’t plan. I was newly divorced and floundering, Hilary was a recent college grad. Great combination – what could go wrong? We started small, renting a tiny cabin over a major holiday weekend in Lake Tahoe, California. We’d spent summers there as a family so it was familiar territory.

The unfamiliar part was just the two of us, and we handled that by packing books, food, and wine. We planned to consume it all in hooded sweatshirts as we followed the sun around the deck. That was our only plan. We certainly didn’t plan the best time to leave San Francisco to avoid a traffic-choked drive. But as long as we could roll the windows down (which we did) and sing Adele at the top of our lungs (which we did) we were good.

It was also bad many times that weekend, too. We didn’t plan for the jammed restaurants with multi-hour waiting lists and over-crowded beaches. There was more driving and walking than doing anything. We got stressed and hangry, leading to harsh, teary words.

When the weekend ended we knew we’d do it again and somehow it would work out better. I wish we’d realized sooner that our lack of planning caused the wheels to fall off our wagon and avoided the cringe-worthy moments. It took time and more trips before we began creating a plan, and then more time (plus a remarriage and a daughter now in her 30’s) to get to where we are now.

Let me share with you how we plan for, and around, things when we travel today. I can’t promise that following these tips will create a trip without a hitch, but there’s a good chance they might.

Start with Two Perspectives

The elephant in the room is the difference in your ages. Seems pretty obvious, but before you plan your trip – take a minute and wallow in that fact. Your age difference can mean different fitness and energy levels, different bio-rhythms (morning person mom versus night owl daughter or vice versa), and different economic realities.

In our case, as much as Hilary hates this fact, we’re very alike. Patty Duke alike (if you’re old enough to get that reference.) We both get excited about seeing certain historical places and love finding unique situations to be in the culture of whatever city we’re visiting.

But one of us has more energy, lives in Manhattan, and walks everywhere every day. What sounds doable to Hilary (“So we can walk about 20-30 minutes to the train station…”) translates into hell to me (I’m going to get blisters, sweat like a steelworker, and my hair will flatten into a sculpture of my head. Yay.)

The great thing is, you don’t have to get to know each other every time you travel together. Once you embrace each others’ reality the first time continue to incorporate them into future itineraries. I’m just sayin’ – cabs and occasional wine breaks go a long way.

Talk About the Money

Money. Yikes. It can be a non-issue if one of you has so much of it that you can, and will gladly, pay for everything. HA. Not happening in our mother-daughter travels. (But I’m not giving up. She’s still young.)

Seriously, there’s a good chance your financial situations aren’t equal. So take some basic steps up front to keep money issues from ruining everything. Start your trip planning by being transparent with each other about your budget and spending expectations. When you put together your plans for tours, museums, food, and transportation you can make sure it works for everyone.

Also, consider creating a kitty that you each contribute equally to and use it to pay for the cabs, meals, or museum tours. This saves calculating who owes what and who paid for it the last time. Those types of conversations can impact your relationship and the kitty might help eliminate the drama.

Be Open to Opt-Outs

You know that too much togetherness can be a problem when you’re traveling with anyone, let alone a family member. And, true fact, you might not be interested in seeing, doing, and eating all the same things all the time (unless you’re uber Patty Duke alike.)

There’s no reason for either of you to miss something or feel guilty about going alone. If there are two things on the list and one person wants to see one of them, while the other person is interested in the other one – that’s what you should do. Set up a time and place to meet later and head off, promising to take good pictures to share (yes, I’m going to say over a glass of wine, but order whatever you like.)

And if jet-lag or a low energy day strikes one of you, don’t hold your companion back. If they want to go exploring while you rest – let them. It won’t take anything away from your experience – and you have to know your limitations. Maybe there’s room in the itinerary for you to go back and visit something you missed, or you can catch it on your next trip.

Collaborative Packing

Sharing is caring. Everybody doesn’t have to bring their blow dryer!

Before you start working on your pre-trip to-do list or create your packing list (who does that? I don’t do that!), talk to each other. But don’t just talk – brainstorm! What are the things you both use that can be shared? Go through your list of toiletries to eliminate duplicates – toothpaste, hair products, or whatever you both use. With plug adaptors and device plugs/chargers – split the weight and bring one or the other.

If you can share clothes – so much the better – but that doesn’t work for everyone. Hilary and I live on opposite coasts and yet often buy the exact same shoes, top, or sweater. We’re lucky that we can pack lighter by shopping in each others’ suitcase on a trip. If you can take advantage of this – great, but there’s one rule – whoever owns the item has first right of refusal on wearing it.

Ultimately, my most important advice for having the best mother-daughter trip is to take one. Yes – plan, but take it, take it, take it. Have grace for one another while you travel. Expect little bumps and be flexible. And realize how incredibly lucky you are to have that time to see the world together.

Have any Mother-Daughter travel questions for Cindi? Let us know in the comments below!

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Cindi Conley

Cindi Conley is the traveler behind the TravelingLater blog. She’s a non-nomadic, non-backpacking traveler and proudly packs her blow dryer before she checks her bag. She started traveling in earnest a tiny bit later in life and now it’s a regular part of her life. You can read more of her travel tips + adventures on travelinglater.com and check out her personal finance freelance writing at cindiconleywriter.com.