You’ve found someone who wants to visit the same destination you do. You’ve exchanged a few messages, enjoyed your conversations, and are beginning to think, Maybe we could travel together.
Wonderful!
But sharing a destination is only the beginning. The person who makes a delightful dinner companion may not necessarily make the right travel companion.
Before booking a trip together, spend some time talking about how each of you likes to travel. There are no “right” answers. The goal is simply to discover whether your expectations and travel styles are compatible.
1. What Does Your Ideal Travel Day Look Like?
This may be the most revealing question you can ask.
Are you an early riser who wants to be out exploring by 8:00? Or do you prefer a leisurely breakfast and a later start?
Do you like a full itinerary, or would you rather choose one activity and leave the rest of the day open?
Some travelers return to the hotel exhausted but delighted after twelve hours of sightseeing. Others want time for an afternoon rest, a cup of coffee at a café, or simply sitting in a park and watching local life.
Neither style is better.
They’re just different.
2. How Active Do You Like to Be?
Be specific.
“I like walking” can mean two very different things to two people.
One traveler may happily walk five miles over cobblestones and hills. Another may enjoy a leisurely mile through town but prefer transportation for longer distances.
Talk honestly about:
- How far you comfortably walk
- How you feel about stairs and hills
- Whether you enjoy hiking
- How often you like to stop and rest
- Whether you prefer public transportation, taxis, rental cars, or walking
Knowing this beforehand can prevent frustration for both travelers.
3. What Do You Like to Do When You Travel?
You may both want to visit Paris—but what does “Paris” mean to each of you?
For one person, it may mean spending hours at the Louvre and Musée d’Orsay.
For another, it means neighborhood markets, cafés, gardens, and wandering along the Seine.
Talk about what excites you:
Museums? History? Shopping? Food? Architecture? Nature? Photography? Theater? Local markets? Guided tours?
And don’t worry if your interests aren’t identical. Compatible travel companions don’t have to spend every minute together.
In fact, that leads to an important question.
4. Are You Comfortable Doing Things Separately?
A good travel companion doesn’t necessarily have to be your companion every hour of every day.
Perhaps you want to spend three hours in an art museum while your companion would rather explore a market.
Great.
Meet for dinner and tell each other about your day.
Being comfortable occasionally separating can make traveling together much easier—and much more enjoyable.
5. What Kind of Budget Do You Have?
Money can create tension very quickly if expectations aren’t discussed beforehand.
You don’t need to reveal your financial situation. You do need to discuss what you’re comfortable spending.
Do you prefer luxury hotels, comfortable mid-range accommodations, or simple locally owned guesthouses?
How much do you normally spend on meals?
Would you happily splurge on an extraordinary experience?
Do you prefer organized excursions or exploring independently?
And how will you handle shared expenses?
Talk about money before the trip so you don’t have to argue about it during the trip.
6. Would We Share a Room?
Never assume.
Some travelers are perfectly happy sharing a room to reduce costs. Others strongly prefer having their own space.
If you’re considering sharing, discuss the realities of it.
Are you a light sleeper?
Do you snore?
Do you stay up late reading or watching television?
Do you need complete darkness?
Do you like the room warm or cool?
Are you comfortable sharing a bathroom?
These may not be glamorous travel questions, but at 2:00 in the morning, they can suddenly become very important ones!
7. How Do You Feel About Food?
Food is a wonderful part of travel—and another area where travelers can have very different expectations.
Do you enjoy trying unfamiliar foods?
Do you prefer casual restaurants or fine dining?
Do you have dietary restrictions?
Do you like long, leisurely dinners or quick meals so you can get back to sightseeing?
And here’s one of my favorites:
Would you rather eat at a restaurant filled with tourists or walk a few streets away and find the little place where the locals are eating?
The answer can tell you quite a lot about someone’s travel personality.
8. How Much Do You Want to Experience Local Life?
For many of us, travel isn’t simply about seeing famous attractions. It’s about experiencing how people live.
Would you enjoy staying in one place for a week rather than visiting four cities in seven days?
Would you wander through a neighborhood market, take a cooking class, use local transportation, return to the same café each morning, or strike up a conversation with someone who lives there?
If you love slow travel and getting to know a place, you may be frustrated traveling with someone whose goal is to check as many attractions as possible off a list.
Again, neither approach is wrong.
But it’s worth knowing which kind of traveler you’re considering sharing your journey with.
9. How Much Planning Do You Like?
Some travelers want every hotel, train, restaurant, and museum reservation arranged months before departure.
Others prefer:
“Let’s get there and see what happens.”
Most of us fall somewhere in between.
Also discuss who enjoys doing the planning.
If one person expects the other to organize everything and neither realizes it until two weeks before departure, your first disagreement may happen before you’ve even packed.
10. How Do You Handle Problems?
Flights get canceled.
Trains are late.
Hotels lose reservations.
It rains.
People get lost.
Sometimes the restaurant you’ve walked twenty minutes to is inexplicably closed.
Ask your prospective companion about a trip where something went wrong.
What did they do?
Someone’s reaction to an unexpected problem may tell you more about their travel compatibility than their favorite destination ever could.
A sense of humor is one of the best things you can pack.
11. How Do We Make Decisions When We Disagree?
You want Italian.
Your companion wants Thai.
You want the 9:00 train.
Your companion wants the 11:00.
You want another day in Florence.
Your companion wants to move on to Rome.
Disagreements are inevitable.
Talk beforehand about how you’ll handle them.
Sometimes you compromise.
Sometimes you take turns choosing.
And sometimes you simply say, “Have a wonderful afternoon. I’ll meet you back here at six.”
12. What Are Your Non-Negotiables?
This is an excellent question for both people to answer.
Maybe you need your own room.
Perhaps you won’t travel without comprehensive travel insurance.
Maybe you need an afternoon break.
Perhaps you’re uncomfortable driving in another country.
Or maybe there is one particular experience that is the entire reason you’re taking the trip.
Say it now.
A prospective travel companion can’t respect a boundary or preference they don’t know about.
Before You Book the Big Trip
If possible, don’t make a three-week international vacation your first experience traveling together.
Meet in person first if you can.
Spend a day together.
Better yet, take a short weekend trip together.
You’ll learn things in 48 hours that you may never discover through weeks of emails and telephone calls.
If distance makes that impossible, have several video conversations. Don’t rush. Give yourselves time to get acquainted, discuss expectations, and decide whether traveling together feels comfortable.
And remember: deciding not to travel together doesn’t mean either of you has done anything wrong.
You simply may not be compatible travel companions.
That’s useful information—not failure.
The Most Important Question
After you’ve discussed itineraries, budgets, rooms, meals, walking, museums, schedules, and everything else, there’s one final question to ask yourself:
Do I feel comfortable with this person?
Not impressed.
Not obligated.
Comfortable.
Can you communicate openly?
Can you disagree respectfully?
Can you laugh together?
Can you imagine sitting across from this person after a long, tiring travel day and still enjoying their company?
If the answer is yes, you may have found much more than someone who wants to visit the same destination.
You may have found a wonderful travel companion.
And perhaps, along the way, a wonderful friend.
A Senior Travel Buddies Thought
Finding someone who wants to go where you want to go is the beginning.
Finding someone who travels the way you like to travel is where compatibility really matters.
The world is waiting. You don’t have to explore it alone.