I recently did a three-week trip with friends who had two kids under the age of two across four countries and six different cities.
I learned a lot.
To kick things off: Create a shared note and invite everyone to it. Doesn’t matter if it’s an Apple Note, Google Doc, or Notion doc, as long as everyone can easily access and edit it.
Sit down and talk with your travel mates about these topics in this order:
Destination(s)
Is this a sightseeing trip or a drink and be merry by the pool trip? Or a mix of both? And if you’re choosing multiple cities or countries, try to pick places with similar weather at that time so you don’t have to pack your whole closet.
Duration
Allocate at least 3-4 days per city to ensure you have enough time to explore without feeling rushed. For every hour of time change, plan for at least a day to adjust.
Travel time
Factor in travel time. It doesn't make sense to travel somewhere that's an 8-hour flight away if you're only staying for 3 days. Longer flights and significant time zone changes mean you need more time at the destination to fully enjoy it.
Interests
Some people are early risers, ready to fill every minute with a place to go and something to do. Others are night owls and want a slow morning, with one thing on the agenda, before spending a long night decompressing over a bottle of wine. You can have a blend of both, but make sure everyone’s on the same page about the expectations for the itinerary.
Personally, I like to see the major landmarks, walk around and roam, and eat good food. I could care less about most museums and art galleries. I also hate hikes. I’m gonna have a bad time if I plan a trip with hiking and art enthusiasts. I’ve found that getting everyone to actually look ahead of time at what they’re interested in doing or seeing and then getting it all down in one place saves a lot of time and headache on the trip. This way, no one’s pissed they didn’t get to see the one thing they had top of their list and it also doesn’t all fall on one person to pick things that everyone else isn’t excited about.
Daily planning
Have a general idea of daily plans. If traveling with kids, factor in nap times and the logistics of moving around with a stroller. What time do you want to leave the house each day? Are there certain things to do that are better done in the morning or the afternoon? What scheduled tours are on the agenda? I find it most helpful to have a rough agenda for each day. For example, what time to wake up, what time to leave, the things to do or see throughout the day, dinner plans, and expected time to be back.
Flexibility
Build in buffer time. It’s easy to overcommit when you’re typing in words to a note. But when you’re there and the reality of everyone’s mood and energy sets in, you’ll realize it’s all just a rough plan anyway. Don’t get married to the schedule. You can switch things around and adjust accordingly.
Accommodation
Decide between Airbnbs and hotels. Airbnbs can offer a more homely atmosphere, while hotels provide convenience and services. If you’re just staying somewhere a night or two, I’d recommend a hotel. If you’re staying 3+ nights, I’d recommend an Airbnb.
Location
Choose a location that’s walking distance to main attractions or public transport hubs to minimize travel time within the city. For example, if you’re going to be relying on the subway for the city you’re staying in, when looking at places to stay, have a map in another tab open with the major subway stops.
The last thing you want is to be a 30 minute walk away from the subway just to save $10/day on a cheaper Airbnb option. Or if you’re going to use ride shares often, it’ll be cheaper to take shorter rides close to the main area than to have to take long rides to save a buck by staying somewhere further away. One mistake we made in Edinburgh was we stayed took the train in and our Airbnb was about a mile walk walk from the nearest bus stop, so we (and by we, I mean I) had to lug all our suitcases for a mile over cobblestone streets. Never again.
Meal preferences
Be aware of how everyone eats. Some may skip breakfast, while others need their morning coffee. I don’t normally eat breakfast, but if we’re at a cafe, I might get a pastry or breakfast sandwich if I know we’re going to have a late lunch. I like to have a rather quick but quality lunch to maximize time out and about, and then have a nice hearty dinner. Not everyone’s the same, so tensions will rise if someone feels like they’re always doing something the way they wouldn’t do it, and don’t really know why.
Dining in or out
Do you plan to make food for any meals or pack to eat on the go? The worst thing you can do is try to improvise on the go when everyone is hangry. If some pack a lunch and others don’t and no one talked about it, someone’s going to be annoyed when they either have to stop somewhere or go hungry until dinner. At the very least, plan out which meals you’ll dine in and out so everyone’s on the same page. For Michelin-star restaurants, make reservations well in advance.
Finding quality local food
As a rule of thumb, the places directly around big landmarks are over priced and over rated — another reason to plan ahead. Google Maps is your friend. Look for places with high ratings and lots of pictures. “Michilin recognized” are often the best value options as the quality is top notch but it’s still affordable.
Transportation
Discuss whether you’ll rent a car, use public transportation, or rely on trains. Each option has its own benefits depending on your destination and group size. You also have to account for what the best option is for where you’ll be going. Renting a car is pointless in Manhattan or London. But you’ll be stranded in Tuscany without one.
Navigation
Google Maps is really the only option you can trust abroad. These days, I bring my own car mount so I don’t have to worry about holding my phone or making someone else call out directions. If you’re renting a car, ask for one with CarPlay ideally.
Not everyone needs a role, but you might find that it’s best to agree ahead of time who will be responsible for what.
You could play this two different ways:
For example, I did a lot of the food planning, luggage carrying, and marked the major daily activities. I didn’t drive much and or do anything related to transportation for that matter. But maybe if you’re planning to hop across a few different cities, someone could be in charge of planning for one of those cities and be the curator of everyone’s input.
After talking this over with friends you’re planning on traveling with, you might find that it’s hard to get on the same page. In which case, should you travel with them? Travel stresses relationships. It either makes you closer or pulls you apart. Choose wisely.
