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How To Have Unbelievable Vacations

When you have time off work, you should be going on epic vacations. You work hard, you should enjoy your life.

Epic vacations mean different things to different people. For some that means climbing a mountain or cities all the sites Rome. For others, it means staying in a nice hotel room binge watching Netflix and eating great food.

There is a specific time and place for each vacation.

    1. Begin with the end in mind

    What does your ultimate vacation look like?


    Mountains with snow.

    Relaxing in Paris at the Ritz Carleton.

    Everyone has a different idea of what a great vacation look is.

    I like to explore new cities and countries. But that can also be really exhausting. There is a lot to see in Rome and if you try to do it all you will wear yourself out. Sometimes it is best to just rent a hotel room in a nice location and stay in and watch Netflix or play video games and recharge.

    Make sure everyone is on the same page about what this trip is going to be. The last thing you want to do is get into arguments with other people about what the trip is supposed to be.

    2. Forget about technology

    I love social media as much as the next person. But social media is not vacation, it is work. It is ok if you post some things from your trip. But enjoy the actual landscape. The people you are going to interact with. Put the technology away as much as possible.

    My advice would be to plan things to be posted automatically while you are gone and then post your trip stuff when you return.

    That way you give yourself time to just enjoy and capture the moments and worry about posting/editing later. Life hits you hard when you return from a vacation and so will social media. That beast will always be there even when you take a step back.

    3. Plan to have special moments

    A special moment is not taking a picture to post on Instagram. That is work.

    A special moment is watching a sunrise/sunset.

    Or laughing with people you are traveling.

    The best moments I have had have been small things. Like buying flowers for another person. Or finding a great hike to do with someone. Get creative. It is worth it.

    4. Roll with the punches

    Something is always going to change. You may have to change restaurants. Or the weather closes some activity you were going to do.

    Or you just do not feel like doing what you had on the schedule. There is nothing wrong with changing plans. Just make sure you communicate with your travelers what you are doing.

    Have a list of alternatives for those people and then do whatever you want. It is your vacation.

    5. Plan the food

    High and low.

    There are many times where the best food is not the fancy restaurant. Sometimes it is. But then sometimes it is just expensive. Mix and match your food.

    Eat a pizza at a local place or order food and have it delivered to your room.

    And then plan for one night at the fancy restaurant that you know is going to be nice. You are paying more for the service and location rather than the food.

    If you are traveling around the world, then eat the local food. I'm not saying go crazy eating spider or crickets, but try some of the local menu items. The food might actually be better, because the ingredients may have been purchased the same day. Restaurants can over prepare food.

    The experience can be as fun as the actual food.

    I like to plan out where I am going to eat. I do not want to waste a bunch of time trying to decide a local place and if they speak English, reservation etc.

    Even if you don't eat at all the places on your list or change the days of what you are going to eat it makes it easier.

    Don't forget the drinks.

    I probably enjoy drinks more than the actual food.

    I love drinking and chatting with someone.

    Find a great location that has good drinks, atmosphere or bar. Ex: The Smith Tower Observatory Bar.

    Tip: Book a hotel with a nice lounge. They often have food, cocktails, views that you can take advantage of if you do not want to go out to a place.

    6. Skin in the game

    If you take a vacation with people makes sure they put some skin in the game. Make them choose a restaurant or one event. If they even slightly invested in the planning of the trip the should not complain as much.

    If someone does nothing and shows up for a trip that will complain that something is not perfect. But if they choose a restaurant and what food everyone is going to have then it becomes a reflection of their choices. They do not want to be seen in a bad light. They want to be seen as being competent.

    This will make your life easier.

    7. Who are you going with?

    You do not have to go with someone. Sometimes the best vacations can be solo trips.

    But most often we take other people with us on our travels.

    If you take the right person or people it might not matter where you go. You just enjoy spending time with them.

    8. Get out of your comfort zone

    Do something unexpected.

    I have jumped out of plane.

    Kayaked next to the Lincoln memorial.

    Helicoptered in New York.

    Hiked up Mt. Rainier.

    There is alway so unique experience that you can do that will push you outside of your comfort. Something unexpected with make your remember your trip. It will make your heart race. It will be a great story to tell. And you can bond with other people that you do it with.

    The same is true of work. Always be pushing yourself out of your comfort zone.

    That could also mean talking to new people.

    I am an introvert so meeting new people is a lot of effort. Vacation is the perfect time to meet new people, because you will never see them again and being from out of town will make you seem exotic.

    9. Get the logistics right

    Where are you going to stay? Airbnb, hotel, hostel, friend's house?

    The better the accommodations the better the travel. It does not have to be fancy. Maybe it has a great location. A great view. It is comfortable.

    Make sure that the accommodations match the intention of the vacation.

    10. Some tools that I recommend - Greatest tool for day trips

    Skyscanner - Great app for airfare - Build American Airlines points for taking quick surveys

    AskSebby - Youtube channel for building CC points

    iPad - Must have for watching programs on the plane and in your hotel room

    TSA Precheck - Worth every penny if you are flying

    Miralax - keep yourself regular

    Gmail calendar/iPhone notes app

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