Choose a friend that you have similar interests
You don't have to completely like the same things but it is important to have some common interests to enjoy your time. If you choose a friend of yours who has different interests, you will have difficulties in deciding. Ex: He may love to see museums but it may be super boring for you. And you will either go with him and get bored or you two will see around seperately. If you go there with him, you won't enjoy it and If you choose the second one, there will be no point on going there with your friend.
Talk about the details before going there
What's your aim? To have fun or to have a rest? Or something else? Do you have the same expectations? Talk about these things.
Have a short trip first
If you have never had a trip together before, try a short one first to see if you can get along or not.
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