1. Take a trial trip
Before taking a long vacation (e.g. for two whole weeks) why not organize a trial weekend trip first? It doesn’t have to be something big. A nearby destination, a nice hotel and in this way, you will get an idea of what to expect.
2. Do your best on planning the trip
Instead of getting into arguments about what each of you has to do, separate your responsibilities, depending on what you are good at. For example, if you are better at planning, you can book the reservations, and if your loved one has an appeal to languages, let him/her do the communication part.
3. Check beforehand that both of you like the destination
When choosing a destination for your vacation, it is important to meet both partners’ needs and expectations. It isn’t about who makes the reservations, but before your final decision, do a careful investigation and, above all, be fair. For example, if one of you is a golf fanatic and the other one loves sightseeing, then don’t book a whole week of vacation just in a golf resort. If you are thinking about surprising your partner with a vacation gift, consider his/her interests first.
4. Avoid planning a very tight schedule
If your program is too tight, then it can easily become boring. One of you may have a hangover and want to sleep a little more or he/she wants to relax strolling around instead of visiting a museum. It is better to adopt an easy-going program, rather than a tight schedule. Accept that you can’t both like the same things/activities/food and everything will go just fine!
There must be no leader during your vacation, no matter who did the planning for the trip. You are both equal. Therefore, every decision must be common. If you are very strict on your taste preferences, become bold by trying different new tastes. In the same way, if you hate doing sports, but your loved one can’t leave without them, agree to join her/him in a game.