It’s How We Wednesday, and I am linking up with Mix and Match Mama. Today’s topic is one of my favorites- planning vacations! Planning vacations is one of things my parents trained me to do growing up (along with decorating for holidays and entertaining).

So I’ll take you back to the year 2003, I was nine years old and looking forward to my first Disney World Vacation. I would say this was my first exposure to vacation planning. Yes, I was only nine, and while my dad did the “big” planning of the vacation: dates, flights, hotels, etc. he had bought the Birnbaum’s Disney World Guide Book and my sister and I were to choose the rides, activities and restaurants we were interested in. I think I read that book from front to cover. I was so excited in learning about all the things you could do, choosing what I wanted to do and making a game plan for getting it all accomplished.

Here’s me on that very first Disney Trip:

Since then I’ve been to many other places, with my Dad (the expert world traveler by the way) always letting my sister and I have some sort of say in either where we went or what we wanted to do. We usually scheduled our summer vacations about a year in advance, so there was plenty of time to plan what we wanted to do.

Then when I was 21, I traveled to Spain for three weeks on my own (it was a study abroad program but I didn’t know a soul who was part of the program prior to arriving). And I spent months researching everything there was to do in the city (Bilbao) I was staying. I planned out everyday what I would do after class so I wouldn’t miss a thing. I crossed everything off of my “bucket list” and felt I really got to know and appreciate the city. This was my first time planning all of my activities on my own.

Now let’s get to more present day, I graduated from college and started living with my now husband. I was young with a new job and planning a wedding but I didn’t want to sacrifice my traveling. It was time to start planning entire vacations all on my own (and pay for them too!).

In the last two years I have planned a road trip to Colorado Springs, my bachelorette party in Disney World, our honeymoon in Hawaii and am currently planning a cruise later this year and a trip to Disney next year!

So let’s get to the good part, how do I actually do all of this? Here the steps I take for planning and staying organized, stress free and being able to relax and do everything I want!

Plan out where you would like to go in the future. Miguel and I have a running list of places we would like to travel in our lives.

Focus on the next two years or so and consider the following things: how much vacation time can I take, how much can I afford, what other big events are coming up?

Take destinations from your list and price them out, including how many days are required.

Fill in your two year calendar with places that fit! Miguel and I did a rough plan for the next five years actually. But our next two years are pretty solidly figured out.

-Create a budget plan and start saving! Planning far in advance gives you time to save enough money but also gives you plenty of time to plan what you want to do and book things! I’m currently pricing our vacation for next year and planning how much I need in savings each month to make it happen!

-Create a timeline of when things need to be booked. Picking where you want to go and starting to save can happen before you even book anything. But you should be aware of when you should be booking flights, hotels, activities, reservations and write them down so you don’t miss out.

-Book Hotels: This is usually first for me since the prices tend to go up closer to the date or don’t change at all so I feel it’s better to get these booked as soon as you can.

-Book Flights/Rental Cars: For flights, they usually aren’t the cheapest when they first come out for the dates, so I watch these until the price drops. (Look at what prices are for about 6 months in advance, don’t pay more than those prices).

-List out activity and dining must do’s: DO YOUR RESEARCH. I utilize google, pinterest and travel books and write down all of things I want to see and do for where I am going. Just keep a running list of things. Do a similar list for restaurants (I like to use trip advisor for reviews).

-After your initial list, make a list by area so you know what things are close together and you can maximize your time.

So you know when you are going to be there, you have your transportation and lodging down, you know what you want to do on this vacation so now it’s time for the fun part!

-Day by day activities and restaurants: I like to list out each day we will be there and then start filling in with my activities list! Be realistic and put activities that are close by next to each other. Don’t over book either. Be conscious of how long each thing will take you (and how long it will take you to get there) and make sure you have some wiggle room and down time everyday. Then fill in with near-by restaurants.

-Book activities and make reservations! This is usually the last thing to do before packing that is (and that is a post in itself).

Not everything you listed may make it on the itinerary and that’s okay. You want to enjoy yourself as well! I like to type out the itinerary and bring it with me and make sure we are staying on track. It’s okay to deviate from the plan a little, but remember why you made one in the first place. I like to have my plan because then when I am on vacation, there is no thinking, because I already did all the thinking so I can just get up and see what I have planned for the day! I get to relax, have fun and still feel fulfilled from my trip because I got to see/do everything I wanted. (No wasting time or feeling frustrated!)

How much you plan will vary by the type of vacation you are going on but these are some general guidelines and tips to follow!

I hope these tips help you for you next trip – thanks for catching up!

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