You know when people comment, “I really like him, but I could never live with him?” At some level, that’s the thought process you need to use when choosing travel companions. How compatible are you with friends, given the type of trip you are planning? Or, better yet, what does a trip look like with specific friends—including destination, activity level, and daily experiences—that everyone will enjoy?

You’ll spend a lot of time with co-travelers in a compressed time and space. As a result, you’ll get to know them on a different level than you would if you were going out for dinner together or spending the day with them in your backyard. Compatibility is important, so even if you really like them as friends, ask yourself, “Can I travel with them, or are we better off traveling separately?”

This is true not only for friends you know pretty well but also for those friends you think you know very well.

Once you confirm basic compatibility, here are some tips to consider as you make plans and while you are traveling:

1. Communicate Honestly

What does each person like and dislike? For example, do you like visiting cities or is the countryside more your style? What activity level do you feel comfortable with? Do you prefer to hike or spend the day around a pool? Do you want to go to a familiar place or try something new? 

Once you communicate honestly about what you like and don’t like, and everyone brainstorms ideas, you can hone in on those places that interest everyone going on the trip. And, the decisions you make about the trip will fit the group’s preferences.

2. Confirm Budgets Early

Let’s get the terrible topic of money and spending out of the way before we get to the fun stuff. Confirming a budget early in the planning process is an essential evil. Do it before any reservations are made.

How much do you want to spend in total on this trip? Everyone has to be comfortable with the cost and corresponding value of the trip. Estimate the total cost of the trip by including your transportation (flights, train rides, and a car rental if you need one); lodging; 3 meals a day; tours you plan to take; trip insurance; and any miscellaneous items you can think of that don’t fit into these main buckets. Incomes and spending comfort levels differ by individual. Don’t make any assumptions.

3. Add a Cost Buffer

Adding a 10-20% buffer to the total cost of a trip is always a good idea. Even the best estimating can be thrown off by last-minute price increases. Also, a buffer will give you the wiggle room to support decisions ‘on the ground’. For example, a fellow hotel guest mentions a great restaurant that you’d love to try, but it exceeds your daily food budget, or you discover an additional tour you want to take once you arrive at a destination. A buffer gives you the added flexibility to enjoy opportunities as they arise.

4. Include Individual Preferences in Your Itinerary

This is one of my favorite tips. Have everyone make a prioritized ‘wish list’ of what they want to see and do on a trip. The more specific, the better. Wish lists might include a day in a particular city or town if you’re planning a lengthy trip, a tour or class highlighting a personal interest (cooking class, whale watching, wine tour), a landmark or museum, a restaurant, etc.

Each person must be able to experience one or two of their top five ‘wish list’ items on a trip. Sometimes this involves a bit of juggling, but most of the time, items are repeated on multiple lists, and it’s easy to get a consensus to include them on an itinerary.

Someone may want a free day to recoup from multiple days of sightseeing. Work the itinerary so that one person’s free day can be another person’s time to see something of personal interest others want to pass on.

This type of itinerary benefits everyone on the trip. Not only does each individual see or experience a top interest of their own, but they also see a few things they had not considered seeing or perhaps knew nothing about. Happy little surprises are everywhere.

5. Be Open to New Ideas

An extension of Tip #4: Travel requires flexibility and an openness to new experiences. Sometimes the best ideas come from others. So give a new idea a chance to sprout and take root before nixing it. And keep in mind that sometimes Plan B is better than Plan A.

6. Find Lodging that Works for Everyone

This may sound simple, but often it’s not. Some people feel comfortable with Airbnb, while others don’t. Some love a particular hotel chain, while others don’t. Some may want a quiet location, whereas others want to be central to all activities. Lodging may be the first compromise you’ll make.

Additionally, before deciding where you stay, nail down your itinerary. You don’t want to book lodging clear across the city from where you will spend most of your time.

7. Book Transportation Between Home and the Destination Independently

Tip #7 focuses on the first and last legs of your trip: getting between your home base and your travel destination.

Friends often live in different cities. Additionally, many people earn Frequent Flyer Miles on specific airlines or will only fly with certain carriers. In these situations, it often makes sense to book flights (or train tickets) separately to get to the initial destination. Booking seats on the same flight or train simplifies things, but friends arriving separately is very common. For some groups of friends, it’s the norm.

Just agree to arrive at the hotel on a specific day (ideally the day before any tours or ‘must-see’ sites are visited) and by a particular time (ideally within a few hours of each other). Allow for delays.

Once you are ‘on the ground’ at your destination, travel as a unit on the same trains, buses, etc.

8. Pick the Right Dates to Visit

If you want to see the tulips bloom in The Netherlands, book your trip during the month of April. Any other month won’t guarantee the full tulip experience.

Other travel experiences will offer more flexibility. For example, you have more options when visiting the beaches in Algarve, Portugal. You can visit during the peak summer months (July and August) when it is crowded, and pricing is highest, but the weather is picture-perfect. Or, with fewer crowds, you can visit during the shoulder season in June or September when the weather is similar to peak season (but not a guarantee).

Crowds can negatively affect travel experiences in a big way. Over-tourism in a few cities and countries is particularly bad. Going at peak can make a bad situation worse.

I’d instead take my chances on the weather (within reason). If you have the flexibility, I strongly recommend going during non-peak periods for most trips. Shoulder seasons are a great option. One destination that comes to mind as the worst at its peak is Rome. Why visit the Roman Ruins and Colosseum during the summer when it is boiling and humid, and the crowds are ridiculously high unless you have no choice? I once visited the Roman Forum in October. It was lovely. Our tour guide admitted Rome is miserably hot and crowded in the summer months and recommends staying clear of the city from June through August.

9. Make the Trip an Appropriate Length

The length of your trip deserves more thought than some people give. Americans are very accustomed to one-week (7-day) vacations. However, if you are flying to Europe or across the entire U.S., at least two days will be eaten up at airports, on flights, and on hotel transfers. That means your week of vacation is only five days of R&R or adventure.

Some weekly trips require eight or even nine days. Don’t try to cram seven days of sightseeing into five days. Instead, cut back the itinerary or add a few days for travel during your planning process. Your body and mind will thank you.

10. Be flexible

Chances are, something on your itinerary will need to be adjusted during your trip. For example, you get a late start, there’s a museum strike (some are planned in Italy), or you enjoy one of your stops for a few more hours than planned. Be flexible! Go with the flow! Let each day unfold as it may.

You’re on vacation! And, as mentioned earlier, sometimes Plan B is better than Plan A anyway!

11. Decide to Have a Good Time

Travel requires a positive state of mind. You can still have fun with friends if the weather is uncooperative, you have a terrible experience at a restaurant, or some aspect of your trip doesn’t meet your expectations. 

Don’t trash the trip. Just decide to have fun. A poorly prepared meal is not enough reason to ruin a day--for yourself and those with you. Move on—quickly. Some of the most fun days can be filled with unexpected moments. You don’t want to miss them because of a lousy meal distraction.

12. Think Like a Team Member First and an Individual or Couple Second

This is the glue that keeps everything and everyone together. Suppose you think like a team member when deciding where to go, where to stay, what to include on the itinerary, the activity level that works for everyone, how you’ll react when something unplanned happens, and every other decision. In that case, it’s a win for everyone.

Your mantra should be, “I am an individual, but more importantly, on this trip, I am part of a team.” Why travel with friends unless the goal is for everyone to have a great time? 

If you’ve traveled with friends recently, what was your experience? Do you have any additional tips to share with our readers?