A brief guide to hassle-free travel planning with friends

How to simplify the process of getting people you care about to come meet you

Planning a trip for just your immediate family can come with its own challenges, but add a few friends or other family members into the mix, and it might feel like years until you finally figure out whether you’ll be able to travel together. Between various work schedules, personal commitments, departure cities, airfare costs, and plenty more, somehow even the simple act of agreeing on locations and dates — oh, and even the kind of travels —  seems to have only gotten harder as we’ve all aged and added more responsibilities and complexities. We haven’t had to deal with school schedules for Eliza yet, but I imagine that adds another layer of complexity when traveling with kids!

Well, after a few false starts, we’ve stumbled our way into ensuring how to take a trip we want that also clarifies the planning process for extending a welcome to friends or family too. Seriously, it’s almost too simple:

  • Decide where you want to go.
  • Plan the basics of your travels of your own trip (location, dates, type of trip).
  • After you’ve booked the essentials like flights (or trains or car rentals) and lodgings, let friends know your exact plans and how welcome they are to join you.

….That’s it. Of course, this method is not meant to replace careful travel planning with extended family, for example. Instead, it’s intended to bypass the days or weeks of text or email threads in the planning phase, then the eventual spreadsheets, where you find yourself trying to move beyond “I’d love to come!” assertions to coordinate availabilities before ultimately determining who, if anyone, is able to commit.

Case in point: We recently met up in Edinburgh, Scotland with two great friends, Meggie and Pat, who currently live in Paris. We told them about our travels plans as soon as we made them, knowing it might be difficult for them to join us; however, a couple of weeks later they emailed to say they had booked their flights to spend 48 hours spread across three days with us. Because we had mentioned the hotel we booked, they chose the same one, which came with the added bonus of knowing we’d be able to have breakfasts together both mornings they were there.

Victoria Street in Edinburgh

Before they arrived, we set up a WhatsApp group chat between the four of us while we had good Internet access. This made it simple for them to text when they landed and when their bus would arrive in the city, so we could meet them right on time — and waste no time — for a late lunch before Eliza’s nap time. We booked separate tickets for the same entry time at Edinburgh Castle, ate and drank like royalty (though based on our sample size of two orders, we would recommend against ordering nachos when in Edinburgh), and marched all around the city, regardless of rain or shine (mostly cloudy, which still looked great in photos). By the time Meggie and Pat left late on Sunday morning, Eliza chanted their names as we waved goodbye and realized how much we’d miss them until our next (as of now unplanned) rendez-vous. Even though we wish they had longer, we made at least a week’s worth of memories within 48 hours.

Yes, we know not everybody will be as quick and able to book a trip. So before embracing this approach, acknowledge it’s risky in the sense that there’s a good chance that no one will be able to join you, or a smaller group than you hoped for. But you’ll be on the trip instead of on an endless back-and-forth about ideas but no resolution while airfares climb and big ideas get cut down to more “reasonable” options. If you plan a trip you don’t mind taking on your own and get comfortable with the prospect that it might just be you (whether singular you or plural you, as in: your immediate family), you’ll probably still end up quite happy.

Some of the best intentions for skip trips, beach getaways, or city explorations alike can all too often lead one couple to jump at that perfect Airbnb that sleeps 10, only to find out that your non-refundable booking is a little larger than necessary for just the two of you. Unless you know your group is on board and locked in, it can be better to hold fully refundable lodging that works for you and your family, then add onto it or cancel and look into that larger space only once you know who else is able to join. And if friends surprise you at the last minute, they probably won’t be upset about figuring out their own place to stay — hopefully at the same spot as you or somewhere nearby.

This isn’t the first time Meggie and Pat made plans to overlap with ours; last year, they booked an Airbnb down the street from our apartment in Paris. (They lived in New York at the time.) This way, they were able to have their own vacation together, while also ensuring we saw each other lots.

Over the years, we’ve been grateful to have had similar adventures with friends around the world. We went to Puerto Rico (from New York) in 2016 thanks to our friends Teressa and Dillon (traveling from Michigan) wrangling all of the details as travel planning leads. We coordinated with our friends Tanya and Magnus to ensure we crossed paths for a few days in Hong Kong in 2018 when they were first settling in to their new home. And perhaps the friends who kicked off this grand idea in the first place were Christie and Julian (who live in Bonn, Germany) who joined us in Copenhagen back in 2013. They didn’t seem to mind sleeping on a tiny couch together off the kitchen of our apartment rental we’d already booked. Needless to say, we walked literally dozens of miles together and managed to have one of the most memorable long weekends I can remember, despite the tight living quarters — or even because of it?

A view from Lamma Island in Hong Kong

Don’t get me wrong: a well-planned group trip can be wonderful, and there’s nothing quite like getting everyone’s input and making decisions with the aim of accommodating and delighting all, but there’s also no question that this approach can often slow things down to the point the trip may never happen due to conflicting schedules and divergent vacation ideas. Don’t be afraid to take the reins, plan a trip out of the blue, and see which friends or loved ones end up joining. And if they can’t join, enjoy your time alone  and start all over again in hopes of having another trip together.

As for us, we’re already beginning to think about when we can get back to Scotland next. Dates to be determined, but friends will be most welcome!



3 Comments Add yours

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s