How to Plan for a Vacation

I often have people ask me how we accomplish so much on our trips and vacations. And my best answer is I do a lot of pre-planning! My feeling is that I have paid a lot of money to get somewhere, and I should experience and enjoy as much of it as possible while I am there. This doesn’t mean that I run myself ragged every day, but it means that I know what I want to experience while I am there and plan to make it happen, and hopefully as inexpensively as possible.

  1. Decide where you want to go first. Sometimes this is pretty easy – there are other factors that help determine your location – whether it is a family gathering, a place that you have wanted to go for a long time or adding onto a work-related trip. Sometimes it is not so easy – you want to go somewhere but don’t know where. In this case I have often used Kayak Explore to see what flights are cheapest at the time I want to travel, and I pick somewhere with an inexpensive flight! I once booked a round trip flight from Chicago to Zurich, Switzerland for $119!
  2. Finding and Booking Flights: I usually use to compare flights for the cheapest ones. I then usually see what those flights cost on the airline’s own websites. They are often the same price and come with the convenience of being able to pick a seat or have a direct confirmation number with the airline.
  3. Finding somewhere to Stay: I usually use to book hotels. But you can also use vacation rentals like and Part of what I like about using is you can earn points towards free hotel stays (usually 10 paid nights equals 1 free night). This means that I normally end up with about 2 free nights per year depending on what I am doing.
  4. Decide about Transportation: In the past few years options have improved tremendously due to rideshare app companies. I always used to rent a car as I didn’t want to get trapped waiting for a taxi, but now with and you do not have to wait long, and you know how much it is going to cost ahead of time. You can also book trips in advance, which is important if you are needing transportation early in the morning. I also like the fact that you can have your app tell you if you are on the correct and shortest route. Rideshares are the best options if you will not need a lot of transportation during your trip, and if the location is close to the airport. However, if you are going to do a lot of moving on the trip, or the hotel is far from the airport, it may be more economical to rent a car. I usually do this through as I have found that the have the best comparison tool. One thing that I have found is that if you book your rental car way in advance and pay in advance you get much better rental rates. I once rented a convertible in California for less than a standard car, by paying for it a year in advance. We had a blast!
  5. Explore Entertainment Options online ahead of time: I always use to see what there is to do in the area ahead of time and make a list of the things that I wish to do. I have never purchased tickets through the ads on TripAdvisor because I have found that they usually bundle more items together than I would want to do and I would have spent more money that just finding individual discounts on the items that I want to do.
  6. Find Discounts on Entertainment and Food: Once I have decided on the things that I want to do I then go to and to see what kinds of discounts I can get on them. This is usually how I pick my restaurants for the trip, and sometimes I even find new things to do that were not on TripAdvisor.
  7. Plan ahead for your scrapbook: Create a habit of taking pictures and collecting ephemera on the trip. This way you will have the things you want when it comes time to scrapbook. I have written a special How to Organize Ephemera on a Long Trip blog that will help you prepare before your trip or vacation.
  8. Go on the Trip and Enjoy Yourself: And then when you get back, organize all of your photos and ephemera and relive your experience through scrapbooking.
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